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Siesta Key Holiday Rentals

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    Travellers to Siesta Key are booking July dates now. Secure your holiday rental today, and have the perfect trip.
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    2 Bedroom  2 Bath  Home in Siesta Village1 / 9
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Beachy Chic Condo in Siesta Key - Waterfront - Free wifi - Sleeps 4 !1 / 31
    (16)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Siesta Key 2 BR, 2 1/2 Bath - *Across From Beach - Pool-view* - Newly Renovated1 / 49
    (3)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Siesta Key Beach Condo, 2Br/2Ba Direct Beach Front1 / 20
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Reviewed 10 October 2017
    We absolutely loved this little condo on the beach. Our foursome vacations together at least once a year. We love the Gulf coast and are only interested in beachfront rentals...
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    Description Details Features Inquires Similar Listings google-map-thumb Siesta Key Beach Condo, 2Br/2Ba Direct Beach Front USD 160 Per day 6312 Midnight Pass Rd., Siesta Key slider PreviousNext Property Description Relax in this beautiful fifth floor beach front Condo...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Bay Views - Private access to Beach. Enjoy Tennis, Heated Pools, Fishing1 / 50
    (11)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
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    Reviewed 28 December 2017
    Beautiful beach and spacious condo with all amenities at your doorstep, enjoyed tennis , pool and exercise room and outdoor gas grill right across street yet still very private...
    Reviewed 20 November 2017
    We had a wonderful vacation stay in this condo. It was spacious, clean and had beautiful views of the waterway. We really enjoyed having our morning coffee watching the boats go...
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    About this property
    Gulf & Bay Club Bayside is a gated resort community is across the street from our private access to - Siesta Key Beach with the world renowned white sands - rated one of the top ten in the US! FREE High Speed Wireless Internet ! - just bring your Laptop. Watch the boats float by! Just steps from...
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    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    NEW EVERYTHING  Luxury 1 king Bedroom  Villa #4  Siesta Key Pool  JAN SPECIALS1 / 12
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Luxury King 1 bedroom condo King Size - Double pillow top bed Ground floor Air conditioning Daily, Weekly, Monthly rates. Everything new 2017 Kitchen Coffee maker Toaster Microwave Stainless Steel fridge with ice maker Adults only 21 Years and over Heated swimming pool Free parking...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    About this property
    The Beach Place is a small group of tropical garden Floridian beach cottages located at Siesta Key Beach - 30 seconds to the sand and 10 - 15 minute walk to Siesta Village. We have a heated pool, tiki cabana wet bar for the guests to entertain at, beachfront picnic and BBQ, poolside BBQ, plenty...
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    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    8 Steps to the Sand of Siestas Best Beach! - Old Man and the Sea Inn (1)1 / 29
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Air Conditioning
    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 July 2017
    Wonderful, relaxing, perfect location! On the quiet side of the key, easy close access to gorgeous crescent Beach. Easy quick walk to bus stop and local market, restaurants as...
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    About this property
    Old Man and the Sea Inn - 1 marlin to the sand! 2BR (sleeps 8). Brought to you by Gertrude Rentals! Perfect for travelers in search of uncomplicated seclusion. Located in the most “private” non-private beach neighborhood in Siesta Key, The Old Man and the Sea Inn can accommodate up to 24 guests...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Reserve now!  Beautiful Siesta key Beach1 / 24
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Housekeeping Included
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    • Waterfront
    • DVD Player
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 July 2017
    This is such a beautiful condo! Very comfortable and beautifully decorated. The beach is so nice and close. Wonderful time, highly recommend!!!
    Reviewed 18 June 2017
    Had a wonderful stay. The condo was located right off the beach and lots of restaurants nearby. Nice place
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    About this property
    I have tried to make this apartment as comfortable as your own home only at the beach. This unit has two bedrooms and two baths. It can accommodate six people with a king bed and two double beds. There are plenty of closet and dresser space, a fully-equipped kitchen, color TV's, VCR and/or DVD and...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Balcony
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    • Grill
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Siesta Dunes gated complex directly on the Gulf of Mexico. Beautiful complex with gated security. Parking next to the front door of this first floor garden unit with easy access to unit. Unit has everything you need for your stay. Washer and dryer in the unit for your use. Master suite with king...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Beachfront Getaway in Siesta Key1 / 28
    (13)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 March 2018
    Dior's home was just like the photos listed. Great modern interior with a full kitchen and very comfortable bed. A 1 minute walk to the best beach I've been to was an amazing...
    Reviewed 21 August 2017
    A 1950's condo with all new upgrades inside. They don't make places like this anymore. Single floor condo, big pool, with private beach access. Kids toys for the beach...
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    About this property
    This luxurious one story townhouse was newly renovated and has its own private access to the #1 beach in the US merely steps away from the front door. It boasts all the luxury you'd expect from a beach house! Modern kitchen, contemporary bathroom with walk in rain shower, luxurious bedroom and...
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    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Gulf Side Siesta Key Villa~Peaceful 1st Floor Villa, 3 pools-Jamaica Royale #1001 / 35
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 days ago
    Unit 100 was very nice. An updated older condo with a modern touch. A great location 100 yards from a private section of beautiful Siesta Key beach.
    Reviewed 1 August 2017
    This unit at Jamaica Royale provides everything and a whole lot more to make your vacation exceptional! The owner is very friendly and easy to communicate with. Her response...
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    About this property
    Unlike many rental properties on Siesta Key, Unit #100 was recently renovated! This condo is a 2 bedroom, 2 bath garden view unit located in the quiet area of Jamaica Royale Condominiums! If you want peace and quiet, a relaxing environment to enjoy, this is the condo for you. Jamaica Royale is...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    A Tropical 1Br Retreat on a Florida Isle1 / 24
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Siesta Palms by the Beach . . . where we invite you to relax, unwind and enjoy our casual way of life. Resting just one block from the powdery-white sands of Siesta Key's world famous, award-winning Crescent Beach is our tropical Siesta Palms by the Beach. With no busy streets to cross,...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Hot Tub
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
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    • Patio
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy an incredible sunset on Siesta Key's Crescent Beach and walk back to your private villa on Siesta Key in Polynesian Gardens. Plan your get-a-way at our two bedroom, two bath villa where you have a screened-in lanai looking into the grassy back yard with your own personal BBQ grill. The...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Eight Steps to the Sand of Siestas Best Beach! - Old Man and the Sea Inn (4)1 / 52
    (34)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Grill
    • Parking
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    • Washer
    • Waterfront
    • Air Conditioning
    • Balcony
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 April 2018
    Great location. Steps away from beach, short walk to restaurants, free shuttles to the village. Clean condo.
    Reviewed 12 September 2017
    We stayed for a long weekend and couldn't have been more pleased. Their team has thought of everything- all you need to do is sit back and enjoy the amazing location and town...
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    About this property
    A Gertrude Rentals Property! Rated 'The World's Finest, Whitest Sand' at the Great International Sand Challenge. Perfect for travelers in search of uncomplicated seclusion. Residing in Siesta Keys most 'private' non-private beach neighborhood and just one marlin's length (5 steps) from yard to...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Updated Townhouse!  Private access to Beach. Enjoy Tennis, Heated Pools, Fishing1 / 38
    (12)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Cable/satellite TV
    • Sauna
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Balcony
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 January 2018
    It was more than I expected.I stayed with my whole family.Fully equiped, nice decoration, comfortable, peaceful, neat. The weather on the first week was not the ideal one to...
    Reviewed 29 September 2017
    I booked this condo for the dates of 9/21/17 through 9/28/17 and cannot express my thoughts enough to the point I have already referred 2 friend's. I'm pretty hard to please guy...
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    About this property
    Across the street is our Private Access to one of the BEST beaches - Siesta Key Beach with the world renowned white sands - rated one of the top ten in the US! Gulf & Bay Club Bayside is a gated resort community of Key West style Town Homes all with one car attached garages. Gulf & Bay Club...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Newly Renovated Waterfront Condo w/Beach Access1 / 21
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Waterfront
    • Cable/satellite TV
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    • Air Conditioning
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 May 2017
    A really lovely apartment, very well equipped. location is perfect if you want a peacful beach holiday.Turtle beach is stunning and great for fishing, swimming and collecting...
    Reviewed 17 April 2017
    This is a wonderful 2-bedroom, 2 bath condo overlooking the bay. The nicely decorated lanai is a great place to relax with your morning coffee. The kitchen is wonderfully...
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    About this property
    Our 2nd floor, end unit condo was completely renovated over the winter of 2012– 2013. The floor plan was opened up to provide a nice airy feel and to enjoy the water view. All furniture, flooring and fixtures are new. The entry hall has a bench to store your flip-flops and other beach gear and...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    NEW EVERYTHING Luxury King Villa #2 on Siesta Key! Walk to the beach Pool1 / 13
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    About this property
    Everything is new in our 1 bedroom condo. Inside and out King size double pillow top bed Kitchen, Coffee maker, Microwave, Toaster. 55 inch HDtv in lounge 50 inch HDtv in bedroom New heated swimmimng pool Free internet Free parking A short walk to Siesta Key beach 2 night Minimum retals
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    8 Steps to the Sand of Siestas Best Beach! - Old Man and the Sea Inn (2)1 / 23
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    • Waterfront
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 February 2017
    What a wonderful stay! To start, Daniel is a very down-to-earth guy....ALWAYS responded promptly to phone calls and emails, and always was always courteous and complete in...
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    About this property
    1BR (sleeps 4)- Perfect for travelers in search of uncomplicated seclusion. Brought to you by Gertrude Rentals! Located in the most “private” non-private beach neighborhood in Siesta Key, The Old Man and the Sea Inn can accommodate up to 24 guests and is a four unit Key West style home located...
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    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    SIESTA KEY! Tranquil Gulf-side 2 Bed/2 Bath in Jamaica Royale  #1041 / 19
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Patio
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 March 2017
    Truly awesome experience. Quiet garden sid. A home away from home. Nice sheets & new towels. Everything we needed. Very responsive & helpful owner Beach side, 3 pools...
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    About this property
    Jamaica Royale Condominiums are located directly on the Gulf of Mexico along the white sands of world-famous Siesta Key Beach in Sarasota, Florida. A barrier island on Florida’s West coast, considered the most beautiful of Florida’s barrier islands, Siesta Key’s beach boasts “the world’s finest...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Siesta Key, Heated pool, Gulf and Bay, Cute Siesta Key Condo, Gated1 / 21
    (2)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Air Conditioning
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    • Housekeeping Included
    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 April 2018
    The Sea Club condo was fabulous!! The location, being on the inner coastal, watching the boats every day and night go by, was perfect. Loved to watch the others fishing off...
    Reviewed 16 June 2017
    The apartment is on the waterway side of the key and is great if you want to fish. The walk to the beautiful beach is only a 10 minute walk away. The apartment is clean and...
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    About this property
    Our condo has just been remodeled with granite counter tops, stainless steel appliances, dishwasher, cabinets, new tile, new bathroom, and new furniture. It is a second floor unit. We have included all the essentials for a family that likes to have the flexibility to make meals at 'home' or...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Secure Parking
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    1st floor condo/ 40 yards from the beach/ go out lanai door directly to the beach. Condo was completely re-furbished just a few years ago/ considered one of the very best siesta key condos/ guest need food that is all/ the condo is fully equipped. Considered the best condo for the price on siesta...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sunset Point Siesta Key FL  AWESOME RENTAL !!1 / 27
    (9)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Patio
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    • Sauna
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 August 2017
    Could not have a better location. Steps from the sand with the village in walking distance. The beach house is a great place to stay. Everything you need. We very much enjoyed...
    Reviewed 7 July 2017
    This location is absolutely perfect! It is on the most beautiful beach and steps to an adorable village with several restaurants, shops and all the amenities you could need. It...
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    About this property
    Beach and water front on Gulf Of Mexico. A block from Siesta Key Village for lite and fine dinning, fun, shopping and nightlife. Two Master Suite King Bedrooms with Master Bath for each. Sauna, four Mexican tiled decks with panoramic views of the Gulf and beaches. Fishing Pier. Leather, stone...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Spacious Beach Get -A- Way1 / 16
    (4)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Reviewed 2 days ago
    The space was great. Very close to Siesta Key Beach. The only thing is that it is a 3 floor duplex and it makes it kind of difficult bringing your stuff up the stairs.
    Reviewed 10 April 2017
    Loved the location. No, this is not right on the beach but it was just a short walk. We spent most of our time just north of the public beach where there were very few people...
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    About this property
    Spacious Beach Getaway (sleeps 6), Calle del Otoño unit D, a 3 bedroom / 2.5 baths townhouse of 2,000sq/feet which is located right next to Gumbo Limbo. It offers 1 king, 2 twins and 1 queen size bed, brand new carpeting (January 2016), a balcony with partial Gulf view and a heated pool. This...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Jamaica Royale #92 on the #1 Beach in the USA!1 / 12
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Porch
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 February 2018
    After reading some of the reviews we were somewhat nervous. The resort was clean and staff was friendly. Our condo in Tower II was found clean and had a great view of the gulf...
    Reviewed 12 August 2017
    We came in around 5pm. I thought its ok not to call because they said in the email that the key will be left in the lockbox. No key when we got there. We had to call and after...
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    About this property
    Jamaica Royale condo #92. Located at the #1 BEACH IN THE USA, this 2 bedroom, 2 bath garden view unit has everything you need! It is located in the garden area of our beautifully landscaped property. It has new furniture and is freshly painted, with tile floors in the living areas and carpet in...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Siesta Key Condo, Crescent Arms, unit 605 South1 / 24
    (14)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Cable/satellite TV
    • Balcony
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    • Air Conditioning
    • Ocean Views
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 March 2018
    Karen was very thorough and very easily to communicate with. The condo is exactly as you see in the pictures. There are some beach chairs provided in the condo, but we didn't...
    Reviewed 27 March 2018
    The condo (605S) is clean and has an updated kitchen. There is a new refrigerator, stove, dishwasher and oven. The screened in deck with new furnishings is small but...
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    About this property
    Split floor plan with each bedroom having a private full bath, tv and access to the lanai. New bathroom floors installed in October 2016 and new tile in master bath/tub. New king size mattress as of May 2017. New stainless steel microwave and range November 2017. Free Siesta Breeze open air...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    NEW EVERYTHING Luxury 1 Bedroom King Villa 3 Pool Walk to beach JAN SPECIALS1 / 13
    (2)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 January 2018
    It was very nice on a quiet street only a few minute walk from crescent beach. It's an older building, although they have refreshed it with all new interiors and furnishings...
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    About this property
    A Luxury 1 bedroom ground floor condo King size double pillow top bed 55 Inch HDtv in living room 50 Inch HDtv in bedroom Kitchen, Microwave, Coffee maker, Toaster. Stainless Steel fridge with ice maker. Adults only 21 years and up Heated swimming pool. Free internet (high speed WIFI) Free parking...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Hibiscus Suite -Best Beach Location of Siesta Key-1 / 16
    (1)Very good
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 November 2017
    We were there for 5 days for our honeymoon and the place were very nice! Looks just like the picture and was very clean. The first two days were a tues and Wednesday so it was...
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    HIBISCUS SUITE # 662B (sleeps 4, ground level, sqft 580.00) - Spacious 1 bedroom studio apartment(580sq/ft) ground floor, with 1 King size bed plus and a luxury self-inflatable Queen size Air-bed and 2 flat screen TV’s Bath features a walk-in rain-forest shower and washer and dryer. This...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Housekeeping Included
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    • Hot Tub
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    1st Floor Large Corner Unit Newly Painted & Furnished This is a large corner unit 1280 sq. ft in the center of private Crescent Beach which is deeded just for the Palm Bay Guests. This is a gulf to bay resort which gives you access to a pool , fishing pier & hot tub on the bay side along with...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    A Tropical 2Br Retreat on a Florida Isle1 / 41
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Washer
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Siesta Palms by the Beach . . . where we invite you to relax, unwind and enjoy our casual way of life. Resting just one block from the powdery-white sands of Siesta Key's world famous, award-winning Crescent Beach is the tropical Siesta Palms by the Beach. With no busy streets to cross,...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Central Heating
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    Pet friendly
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    Smoking allowed
    About this property
    Imagine Yourself At (Tiny) Home: Beach life is best! Enter through the bright yellow, life-sized replica of a Siesta Key lifeguard stand, and drop your beach bags on the two stools beneath our surfboard-shaped breakfast bar. Passing through the living room, decorated with just a touch of...
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    Location Information
    Siesta Key, Florida 34231
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Palm Bay Club  Private Beach 3 min. - Pool, jacuzi1 / 84
    (25)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • DVD Player
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    • Air Conditioning
    • Sauna
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    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 March 2018
    As two couples who were seeking a fantastic beach. a very comfortable condo with all amenities, a beautiful pool, hot tub & fishing pier we were not disappointed! Nancy’s...
    Reviewed 3 February 2018
    We enjoyed staying in this condo. It was very clean, up to date, safe, quiet, and had everything we needed—even beach supplies. The beds were comfy and the living room has a...
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    About this property
    Our condo is on the second floor and is only 3 doors from the lovely pool, jacuzzi and fishing pier. The private Cresant Beach which is deeded just for the Palm Bay Guests and is just across the street from the Bay side. It is raked every a.m. and loung chairs set out and also has a charcole grill...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sandy Toes Siesta Key Florida   (6798)1 / 37
    (18)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Grill
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    • Balcony
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 March 2018
    Short walk to the best beach ever! Perfect sunsets. Easy walk to restaurants and bars. Our dog was a happy camper too! It was nice to have our own washer and dryer. Garage...
    Reviewed 17 January 2018
    What a great find Sandy Toes was. Everything we needed is here, including two bikes to ride to breakfast at Mongo's or just to see the Key. Heated pool (84), was a community...
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    About this property
    A short stroll down a private road to the #1 Beach in the US. You will love the location - you are located in the Resorts of the SaraSea community and can walk to everything you might need or want... Grocery, restaurants, ice cream, pizza, sports rentals, drugstore or boat rental. You have your...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Siesta Key Townhouse across from Pristine Sand & B1 / 30
    (17)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Air Conditioning
    • DVD Player
    • Grill
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    • Secure Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 September 2017
    Beautiful townhouse overlooking a small lake. Turtles swam by below the balcony and popped up their heads to say hello! Everything you could want for a wonderful stay was...
    Reviewed 29 July 2017
    Spent a lovely 10 days in Michelle's condo.......couldn't have asked for much more, from the very beginning of the booking Michelle was always on hand to answer any queries we...
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    About this property
    “Pristine sand, blue skies - 'Number 1 Beach'” The Best Thing to Come Home to after a Day on the Beach Is... ...a vacation home as comfortable as your own home. Just a walk across the street to Siesta Key's world famous #1 Beach. This split-level townhouse, has 2 bedrooms (King in Master...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Location! Location! Location! Walk out the door, across the street and onto the # 1 ranked beaches in America! This beautiful condo is on the ground floor, no steps, with a tropical enclosed lanai. It features 3 televisions, Tommy Bahama furnishings, a barbecue grill and high speed internet for...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beachfront- Gulf View! 2 BR/BA Crescent Arms 603S, #1 Beach in the US.1 / 24
    (9)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
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    • Waterfront
    • DVD Player
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    • Ocean Views
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 March 2018
    Such a well appointed condo, with a fabulous location right on the beach.Easy walking distance to some great restaurants. Our owner was very attentive and answered all...
    Reviewed 13 November 2017
    We loved this condo. The beach was wonderful. Siesta Key Village was so close with great restaurants to choose from... Pavan was very nice to work with. What more can you ask...
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    About this property
    - Expansive, panoramic gulf view from every room of this 6th floor condo. -Crescent Arms is a quiet, beach front, high rise condominium building that is ideally located for maximum fun and relaxation. -Right on the beach with lounge chairs provided. As close as you can get to the Gulf without...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Key West Suite next to Siesta Key Beach1 / 32
    (6)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Balcony
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 May 2016
    Spacious enough for 3 little ones and 2 adults. My wifeet and I stayed in the makeshift room next to family room. Very clean and well kept. We were spoiled and had the property...
    Reviewed 27 June 2015
    The suite 5610 was on the ground level, perfect for kids. The suite and outside areas were very clean and offered a lot of amenities. The pool was very clean and just the right...
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    About this property
    2 apartments to choose from: Key West Suite A relaxed beach experience. This cozy two bedrooms & den apartment, full 2 baths (1 King bed + 2 Twins + 1 Queen) 1,200 sq/ft. suite on second level with two private balconies and partial Gulf view from the den. This apartment is fully furnished and...
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    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sea Shell Condo-Right On Crescent Beach-Siesta Key1 / 24
    (9)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Air Conditioning
    • Terrace
    • Wi-Fi
    • Grill
    • Ocean Views
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 weeks ago
    Clean, roomy, well-stocked with all kitchen amenities that you could think of. Master bedroom very roomy. Extra space for your bathroom essentials in medicine cabinet...
    Reviewed 24 August 2017
    We stayed in unit 207. The property is very nice. The condo was clean, modern and well equipped with all your kitchen needs and wants. We like to cook and were pleased with the...
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    About this property
    If you are looking for the perfect spot for a family vacation, to escape the cold and snow, or a quiet romantic getaway this is the place for you. Recently updated throughout, this 2 bedroom 2 bath condo sleeps 6 comfortably all in real beds. Just outside your door is Crescent Beach, consistently...
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    Location Information
    Siesta Key, Florida 34243
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Luxurious 2 BR Condo - Short Walk to Siesta Beach1 / 14
    (18)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Sauna
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    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 April 2017
    We stayed at the apartment for 2 weeks during Easter holidays with our 2 girls (aged 1 and 4). We had a lovely holiday. We felt there was some positives and negatives with the...
    Reviewed 31 January 2017
    Everything about this condo was fantastic! The beautiful two bedroom/ two bathroom, spacious, quiet, the large swimming pool and two gas grills which we used often, we will...
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    About this property
    Newly furnished, newly renovated 2BR (one king size & 2 single beds) + convertible sofa bed, 2 Bathrooms 2nd floor condo (sleeps 4-6), and with all the amenities of a comfortable home. Located in White Sands Village with 7 acres of lush tropical surroundings, our air-conditioned condo offers two...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Stay on Siesta,Beach Bungalow PET Friendly1 / 16
    (6)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 November 2016
    Very cozy but good for 1-2 people. Walk to private beach and pool. Only thing - can be quite noisy at night with the bar across the street but otherwise great
    Reviewed 5 July 2016
    Old Florida vibe, love it. Short walk to beach! Perfect size place for my husband and I and our 60 lb lab. The private fenced grassy area in backyard was perfect for our dog...
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    About this property
    PET Friendly! This one bedroom and one bathroom beach bungalow is located 150 yards away from the beach. You can walk to restaurants, shops and a great pool area. Queen bed and a sleeper sofa make it possible to sleep four. Enjoy your morning coffee on your private screened porch or while you walk...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Amazing Beachfront Condo, Siesta Key, 100ft+ Beach1 / 33
    (4)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Waterfront
    • Ocean Views
    • Patio
    • Wi-Fi
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 days ago
    Siesta Key is our favorite domestic vacation spot. However, it has become a very popular, crowded, and loud spring break spot, especially at the public beach and the Village...
    Reviewed 1 July 2017
    We had the best vacation ever at this condo. Everything was clean and comfortable. The beach was beautiful an almost private. We enjoyed all The surrounding activities. Kayaking...
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    About this property
    Great first impressions are evident from the moment you enter this lovely condo and enjoy the breathtaking ocean views from our private oversized lanai. We know you'll adore our comfortably decorated oceanfront condo and have the relaxing vacation you've been dreaming of. This unit unfolds as you...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    8 Steps to the Sand of Siestas Best Beach! - Old Man and the Sea Inn (3)1 / 23
    (20)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    • Patio
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    • Balcony
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 April 2018
    Great location! Only steps to beach access. Our unit was very clean and had all we needed for 2 people. The owner Daniel, was great to work with. He always replied to any...
    Reviewed 22 November 2017
    The rental was perfect for my husband and I with our 2 dogs. Everything you could possibly need is in the cutely decorated unit. A plethora of towels, dishes, cups and even a...
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    About this property
    1BR (sleeps 4)- Perfect for travelers in search of uncomplicated seclusion. Brought to you by Gertrude Rentals! Located in the most “private” non-private beach neighborhood in Siesta Key, The Old Man and the Sea Inn can accommodate up to 24 guests and is a four unit Key West style home located...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Luxury Villa, Sleeps 6 Comfortably Located on Siesta Key Beach, Sarasota Florida1 / 26
    (6)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Secure Parking
    • Grill
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    • Air Conditioning
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 January 2018
    The house was beautiful, lots of updates throughout and you can tell it's really well cared for. It's so nice staying in the villa as opposed to one of the hotel-room...
    Reviewed 9 October 2017
    This was the 2nd time we stayed at this villa. It was even more beautiful than last time. It was very clean, new beds, couch and love seat, fully stocked kitchen if you want to...
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    About this property
    ZERO HURRICANE DAMAGE IN OUR AREA - This is a Luxurious Villa on Siesta Key Beach Florida on Crystal Sands - Experience why Siesta Key, Sarasota Florida has been rated the #1 beach in the USA (#5 in the world by TravelAdvisor) for so many years. Siesta Key is one of the only beaches in the world...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Siesta Key -  2bdrm on the beach - amazing views!!1 / 54
    (25)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Secure Parking
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    • Ocean Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 April 2018
    The condo was perfect for us. Loved being on Turtle Beach. Location was great. Very close to lots of activities and restaurants. The beautiful sunsets right off the screened in...
    Reviewed 2 April 2018
    The setting is wonderful and the condo had everything you could need or want. The elevator, laundry and parking spot are just steps away. We spent several afternoons at the pool...
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    About this property
    The condo benefits from its own private pool. The living room, master bedroom, and lanai (balcony) all have stunning ocean views. The lanai, with over $10,000 of new doors and windows, is furnished with a table and chairs to enable you to dine al fresco. There is also a comfortable couch to...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 bedroom/1 bath Contemporary Beach Cottage1 / 10
    (2)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
    • DVD Player
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 February 2017
    It was like home away from home. Glad we were able to take our dog and cottage was fully equipped with everything necessary for our stay.
    Reviewed 31 May 2016
    The space seems bigger than the pictures lead it on to be which is a plus! We really enjoyed our stay as the master bedroom was very spacious. We visit Siesta Key almost every...
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    About this property
    Half Mile to the Beach This recently remodeled Beach house has both inside and outside living spaces. There is a combination Kitchen/dining/living area with windows on every wall allowing in loads of the wonderful Florida natural light. The kitchen is all white with stainless appliances and...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Adorable condo steps from the #1 Siesta Key beach1 / 18
    (1)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 July 2017
    Booking process was great! Owner was very responsive and helpful. Super comfy king-sized bed, comfortable bathroom, and close to the beach. Great for a couple; a little tight...
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    About this property
    Adorable, quiet, and clean home away from home on the South end of Siesta Key. Only a short five minute walk to beach at access 13, a more secluded area and away from the more crowded beaches. The king sized bed is extra comfortable with a flat screened tv, dressers, nightstands, fan, and walk in...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Private Siesta Key House - Walk to Village & Beach - Heated Pool/Spa - No Stairs1 / 26
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Patio
    • Grill
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    • Air Conditioning
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 January 2018
    I stayed over the winter holiday with my husband and other adult family.It was the perfect place to have a pleasant vacation. Close to all shops and downtown and also a short...
    Reviewed 5 September 2017
    What a beautiful modern and superbly located house. Immaculate and well maintained with everything you could possibly need. Our host Randy was excellent and answered our...
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    About this property
    Steps from the islands best restaurants, shops (in the Village area) and a short walk to the #1 beach in the USA! Great home with 2 car and 1 car private garages. Recently renovated including a screened in patio, hot tub and pool. Brand new appliances making this home a great place for monthly...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Villa Palma - The Best Mid-Century-Modern Siesta Key Villa1 / 21
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Patio
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • DVD Player
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 November 2016
    We had a great time at Villa Palma. The villa is very clean and it has everything you need for your stay. It is very close to the beach, we ended up only going to the beach. The...
    Reviewed 10 August 2016
    What a LOVELY place to stay!!! Sean was flexible, attentive and accommodating, and there was even fresh fruit, sparkling water and a personalized welcome sign waiting on the...
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    About this property
    Villa Palma is a stand-alone single story villa located in the beautiful Polynesian Gardens community, on the beautiful barrier island of Siesta Key, Fl. The home is chic and hip in its mid-century modern beach cottage decor and schictyle. The newly renovated kitchen is sleek in design and...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    The Top Siesta Key Location, The Village Studio - Eat Shop Beach!1 / 14
    (15)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Waterfront
    • Outdoor Dining Area
    • Internet Access
    • Patio
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 March 2017
    We loved walking everywhere - the beach, especially every sunset; shops, great food. The condo was lovely, and the setting enriched by the other owners in the complex.
    Reviewed 24 March 2017
    We enjoyed our 3 day stay. A longer stay would require a larger place but it was perfect for this time. Our host was very helpful and had a nice gift awaiting our arrival :)
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    About this property
    A Gertrude Rentals property. Enviable location just steps away from everything! The Siesta Key Village Studio is an accommodating ground floor, one-room efficiency apartment perfectly nestled on a quiet tropical street between the best beaches, shopping and dining on the island. Wander one...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Stay on Siesta - Beach House Bungalows 21 / 12
    (2)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • Balcony
    • Waterfront
    • Washer
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 July 2016
    What a perfect location in Siesta Key! Just a quick walk to gorgeous Crescent beach. Directly across the street from our favorite restaurant Captain Curt's and ice cream spot...
    Reviewed 21 September 2015
    We stayed at the property from 9/11 thru 9/15. The apartment was clean and comfortable and about 5 minute walk to the beach. We fished almost every night from the complex's...
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    About this property
    Tastefully decorated in pastel colors, reflecting the relaxing ambiance of a Florida beach bungalow. As you gaze out the picture window the umbrella tables on the tropically landscaped patio come into view. The back of our bungalow is a private patio great for relaxing and taking in the sun. The...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    1
    Siesta Key Holiday Rentals

    Looking for world class powdery white quartz sand beaches, a relaxed low-rise life style, and about 100 nearby golf courses on Florida’s South Gulf Coast? This plus bay- and ocean-side views can be yours with a money-saving Siesta Key holiday rental. From Siesta Key cross Roberts or Little Sarasota Bay to Sarasota for museums, art, wildlife, circuses, opera, ballet, symphonies, theatre, film festivals, botanical gardens, baseball spring training, and polo, cricket, and lawn bowling clubs.

    Lions, Tigers & Circuses

    When you need a break from basking in the sun or seashell collecting around Siesta Key, it’s Ringling Brothers and Barnum & Bailey Circus time at Circus Sarasota (Feb., March) and the Museum of the Circus (year-round) at the old Ringling wintering grounds. Visit the Ringling’s bayside winter mansion, Ca d'Zan, and savor their extensive art collection at the recently expanded John and Mable Ringling Museum of Art. The nearby Big Cat Habitat is a sanctuary for lions, tigers, bears and other animals. Hike or take a swamp buggy eco-tour with the kids at Babcock Wilderness in Punta Gorda, and see Florida’s native plants and animals in their natural habitats.

    Gardens & Aquariums

    Let the whole family enjoy the mazes, pirates ships, colorful flowers, and tropical birds at the Sarasota Children's Garden. Marvel at the orchids, bromeliads, and Sarasota Bay views at Selby Gardens. Enjoy the Parker Manatee Aquarium, plus the Bishop Planetarium’s digital projections of the heavens with Dolby surround sound at the South Florida Museum, near the Manatee River in downtown Bradenton. Schedule a Monday, Wednesday, or Friday morning for Mote Aquarium’s Narrated Shark Training Sessions; and visit Molly the Mollusk, a 27-foot pickled New Zealand giant squid.

    Locomotives & Science

    Learn some science and technology with the family at downtown Sarasota’s bay-front G.WIZ (Gulfcoast Wonder & Imagination Zone). In the evening, treat the family to Broadway theatre, dance, or a jazz, pop, or rock concert at the Van Wezel Performing Arts Hall, next door to G.WIZ. Make a weekend visit to the Florida Railroad Museum, 45 minutes north of Siesta Key in Parrish, where you can get hands-on-training, take over the controls, and even rent a locomotive.

    History & Baseball

    From your money-saving Siesta Bay holiday rental home, apartment or condo, take Stickney Point Road across Little Sarasota Bay to the Tamiami Trail (U.S. 41) and Historic Spanish Point. This unusual museum and archaeological site has an intact prehistoric village with middens, as well as a pioneer home, citrus packing house, and old boatyard. In 1924, the New York Giants began a spring training tradition in Sarasota that is being continued by the Baltimore Orioles and the Grapefruit League in Ed Smith Stadium.

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