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Siesta Key House Rentals

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    Travellers to Siesta Key are booking April dates now. Secure your holiday rental today, and have the perfect trip.
    94 Matching Rentals in Siesta KeyView all 886 rentals
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    Rates reduced on the adorable condo.  Beach Access to the most beautiful Beaches1 / 14
    (5)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Fido Friendly, Saltwater Pool, Only 1 mile to SK Beach, Close to the Village, Sh1 / 42
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Private Siesta Key House - Walk to Village & Beach - Heated Pool/Spa - No Stairs1 / 26
    (4)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    8 Steps to Sand Path of Siesta's Best Beach! - Old Man and the Sea Inn (4)1 / 47
    (35)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Patio
    • Balcony
    • Washer
    • Cable/satellite TV
    • Waterfront
    • Wi-Fi
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 January 2019
    Property is extremely well maintained and contains what you will need for your trip. I would say our suite was best for about 4 people. It would sleep more, but I like my...
    Reviewed 12 April 2018
    Great location. Steps away from beach, short walk to restaurants, free shuttles to the village. Clean condo.
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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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    8 Steps to the Sand of Siestas Best Beach! - Old Man and the Sea Inn (3)1 / 84
    (21)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • Waterfront
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    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 June 2018
    This place was amazing and could not have been more perfect to stay at for an extended vacation!!!! The unit was cozy and comfortable- it had everything that you could possibly...
    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...
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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 Beach Condo, 2Br/2Ba Direct Beach Front1 / 20
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Waterfront
    • Air Conditioning
    • Grill
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    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 August 2018
    This condo is right on the beach. If you are looking for a family friendly place this is it. We absolutely loved this place and the view ..OMG is AMAZING!!! The place was well...
    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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    About this property
    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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    The Shells Villa - Next to Beach & Village1 / 41
    (67)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Washer
    • Cable/satellite TV
    • Patio
    • Waterfront
    • Air Conditioning
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 October 2018
    We booked this vacation home for our family reunion. It was absolutely perfect. All the amenities anyone could ask for were provided. GREAT location...steps away from a...
    Reviewed 26 March 2018
    My family and I just returned from a week at the Shells Villa. We had a wonderful time there and hope to return in the future. Our group consisted of our three grown daughters...
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    About this property
    3 Bedroom, 2.5 Bath Beach Villa (Sleeps 8-10) What makes us different than other homes you may be considering: · The Beach - The home is located on the ocean side of Beach Rd., so you just walk out your door and through our private access path. It’s literally 230 feet to Siesta Key Beach....
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Sandy Toes Siesta Key Florida  (6796)1 / 40
    (23)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Patio
    • Waterfront
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 April 2018
    Everything was great. The condo was updated, clean and spacious. It had what we needed to really enjoy our week. It was a quick walk to the beach, restaurants and shops. We...
    Reviewed 25 March 2018
    We had so much fun. It was so nice that the kids had their own space , own TV, own bathroom. The beach is amazing. The owner provided beach towels, chairs and umbrellas. I...
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    About this property
    A spacious 2 bedroom 2 bath Townhouse, with a 2 car garage and extra guest parking. Stroll down a private road (about 300 yards) to the #1 Beach in the U,S. You are in the Resorts of Sara Sea and just a couple of blocks from restaurants, grocery, sports rentals and ice cream ! The Great room has...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    The Top  Location on Siesta Key - Gertrude's Village House1 / 50
    (30)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Waterfront
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    • Balcony
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 May 2017
    My son booked this for his whole family. There were nine of us. The beach was just a half block away. It was beautiful with cool white sand, aqua water with warm rolling...
    Reviewed 24 September 2016
    Stayed there, the location is great. Everything in walking distance. The kitchen was supplied with everything you need. The positives beyond location varied, quiet, lots of room...
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    About this property
    A Gertrude Rentals property! Our Top Location! Leave the car behind. Richly furnished, perfectly nestled between the best beaches, shopping and dining on the Island, and sure to provide a combination of fun and rejuvenation you won't find in other getaways. Our living room, master bedroom and...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Sarasota-Siesta Key Coastal Five Bedroom with Pool and Spa1 / 38
    (8)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 January 2019
    My family of 7 adults thoroughly enjoyed our stay here from 12/22-1/2! I booked the house in March 2018 & from that time even until NYE day, I had excellent communications...
    Reviewed 31 July 2018
    My family with extended family(total of 8) shared this large home with 5 bedrooms and we had plenty of room and at same time all had our privacy when we wanted it. The kitchen...
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    About this property
    Excellent location at only 120 Yards To The Cool White Quartz Sand Of Siesta Beach! ?This Home Has Water Frontage, Pool, Hot Tub And BBQ Area Within A Screen Enclosure. There Is A Nice Sized Sunning Patio As Well With Views Down The Waterway. This Home Entertains Excellent Because The Pool Area Is...
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    Siesta Key, Florida 34242
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 13
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    8 Steps to the Sand of Siestas Best Beach! - Old Man and the Sea Inn (2)1 / 43
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Grill
    • Air Conditioning
    • 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 Beachfront 3 Bedroom Home, Sarasota1 / 46
    (4)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • DVD Player
    • Wi-Fi
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 September 2018
    We had a wonderful stay at Siesta Keys Florida. David ‘s home is beautiful and well maintained. It does have several bests of steps if you have any kind of handicap. My husband...
    Reviewed 29 January 2018
    This is a very nice three story three bedroom house. The first floor includes two separate garages with the house entrance in between. The second floor includes a spacious...
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    About this property
    Description:Walk out the back door to the clean white sand of Siesta Key Beach. This home has private Siesta Key beach frontage on the prime section of beach, there are no homes between you and the beach. Nearly every room has a full view of the Gulf & beach. The entire back of this house opens...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    8 Steps to the Sand of Siestas Best Beach! - Old Man and the Sea Inn (1)1 / 47
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Balcony
    • Patio
    • Cable/satellite TV
    • Washer
    • Grill
    • Waterfront
    Suitability
    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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    Walk to Village, Heated Saltwater Pool,  Bike/Walk to Beach, WiFi/Cable, Custom1 / 38
    (1)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • DVD Player
    • Patio
    • Air Conditioning
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Blue Mermaid is located less then 1/2 mile and less than a 10 minute stroll from Siesta Key Village. It's a 12 minute walk to the beach and the crystal sands and sparkling waters of the Gulf of Mexico on Siesta Key. Walk to our local gourmet grocery store for freshly prepared sushi, or for a...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Palm Oasis - Relax in Comfort - 1 Month Minimum1 / 35
    (3)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Cable/satellite TV
    • Parking
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 August 2018
    This was a family vacation that had been planned for months. We were unaware of the red tide until a few weeks before leaving for our trip. Not spending any time at what was...
    Reviewed 6 August 2018
    For a large family that has not been on vacation sometime, this was ideal. Walking distance to beach and to village as well as the amazing salt water pool. With 3 children under...
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    About this property
    The Palm Oasis is a 4-bed single family home with 2,000 sq. ft. located only 1 block away from Siesta Key Beach. This home is on one level and has all the amenities including a brand new salt-water pool which is the center of the backyard and a outdoor BBQ grill with a bar to enjoy your fabulous...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Sandy Toes Siesta Key Florida   (6798)1 / 74
    (22)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Grill
    • Internet Access
    • Air Conditioning
    • Balcony
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 August 2018
    The house was nice and spacious along with a garage for your car. You are walking distance to restaurants and stores. And just a couple minute walk to white sand beach. They had...
    Reviewed 22 June 2018
    Had everything we needed. We appreciate Joe the maintenance guy checking on us. He was very helpful. Would stsy here again.
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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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    April 26-May 3 Available Stay in Siesta Key Village and Walk to the Beach1 / 9
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Patio
    • Grill
    • DVD Player
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Fabulous location! 1 block from the beach and 1 block from the Village. Very clean! Returning again next year
    Reviewed 2 September 2017
    This was by far the best place we have stayed at in Siesta Key. The house was clean and had everything we needed to have a great vacation. We could not have ask for a better...
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    About this property
    This charming tropical 1,320 sq.ft. 2 bedroom 2 bath home is located within the heart of Siesta Key Village and a block away from the famous Siesta Key Beach. Walk to everything, yet have privacy of a home. It is newly renovated with all new furniture and beach house décor. This home is equipped...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Best in Siesta Village! 1.5 blocks to best beaches! - Casa Van Lopik (Canal)1 / 96
    (19)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Grill
    • Cable/satellite TV
    • Balcony
    • Wi-Fi
    • Waterfront
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 April 2018
    This was the perfect place for eight fabulous women who were celebrating life. The beds were comfortable and the rooms spacious. The hot water plenty. It was a plus to have...
    Reviewed 6 March 2017
    Location is the best thing about this condo -- short walk to beach and to Siesta Key Village. Very convenient. Another big "pro" was Daniel. The owner is very...
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    About this property
    A Gertrude Rentals property! Large 3BR home perfectly located between the best beaches, shopping dining and entertainment on Siesta. Leave the car behind. After the beach, you could wander to town for fresh oysters and seafood, drinks, live music or ice cream, or just relax in a tropical garden...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Our Beach House1 / 17
    (4)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    Reviewed 6 November 2018
    Nice place on Siesta Key. Little smaller than some previous places we’ve rented. Everything clean and comfortable. Pool and grill in back was great. Kitchen was fine with...
    Reviewed 28 June 2016
    Just back from our trip to Siesta Key with my Husband and 4 kids where we spent a lovely relaxed week at 'our beach house'. The house was fully equipped with everything a...
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    About this property
    OUR BEACH HOUSE (right behind the Cottage) (sleeps 6) Fully renovated in the late summer of 2013, this spacious, enchanting 3 bedroom/2 full baths ground-level property of 1,100sq/feet offers 1 King, 1 Queen and 2 Twin beds. You will be in close proximity to Siesta Beach and to Siesta Village. The...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    NEW POOL! 3 Bed 2 Bath on Siesta Key   Walk to beach   POOL  Great location1 / 18
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
    • Wi-Fi
    • Air Conditioning
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 February 2019
    I loved that we were just a 2 block walk from the beach, less than a block from Siesta Key Village filled with restaurants, bars, grocery store, etc. Everyone in the Village was...
    Reviewed 22 March 2017
    This three bedroom two bath house is located on Siesta Key near the South Bridge. It has great beach access near several fun restaurants. The owners were very supportive and...
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    About this property
    SIESTA SUN VILLAS - BRAND NEW POOL! 3 Bed 2 bath home on Siesta Key in Sarasota, FL Sleeps 6 people in beds. We are on the beautiful Island of Siesta Key. Walking distance to the number 1 beach in the USA. Full kitchen with oven, microwave, fridge, freezer, coffee maker & toaster. Large HDTV in...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    The Banyan - A Tropical Retreat in Paradise1 / 25
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Grill
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 April 2018
    The Banyon is a remarkably beautiful and comfortable home. There are many private seating areas inside and out. The kitchen is fully equipped; the beds are very comfortable and...
    Reviewed 12 August 2017
    We loved this place! It was so private you felt like you were in your own world with the surrounding trees and tropical landscaping, yet close to most everything. The home was...
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    About this property
    View of Roberts Bay / Near Beaches / Great Shopping & Dining Get lost in the intoxicating relaxation of Siesta Key, in this luxurious private home. This tropical retreat is a single-family residence located at the end of a secluded dead end street in the opulent neighborhoods of northern Siesta...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Lovely Siesta Key & Sarasota 3 bedroom home - Less than 3 miles to Siesta Key1 / 23
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Parking
    • Private Garden
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 July 2018
    There couldn't be a better house or location to stay at! It's only a short 10 minute drive from Turtle Beach and Siesta Key Beach and dead in the middle of everything that you'd...
    Reviewed 6 July 2017
    Perfect location for SIESTA KEY and THE Greater SARASOTA area. Shopping Centers, Restaurants , and The Beach are nearby. The Home is Great and Modern . Perfect for Families...
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    About this property
    From the beautifully landscaped front yard with the unique Rainbow Eucalyptus Tree to the spacious living areas, and the fantastic layout. As you enter this home, you will be impressed with the lovely touches this home has. It is tastefully updated, with recently installed new laminate floors, new...
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    Location Information
    Siesta Key, Florida 34231
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Top in Siesta Village at Best Beaches, Food & Entertainment! - Casa Van Lopik(J)1 / 49
    (17)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Waterfront
    • Balcony
    • Patio
    • Wi-Fi
    • Porch
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 June 2016
    While ratings and reviews are subject to personal taste, we found this property average at best. The positives included a nice size home, 3BR, 2BA, 2 blocks to the beach and...
    Reviewed 4 December 2015
    Our extended family of 7 with 4 adults and 3 children, stayed 4 nights at this property. We were thrilled to see that the grocery store was at the end of the street, as were all...
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    About this property
    Casa Van Lopik (jardin), our garden facing suite, is a large 3BR home. Brought to you by Gertrude Rentals! Perfectly located between the best beaches, shopping dining and entertainment on the island. It was named for our father who was a ships captain and sailed the world for 30 years but always...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Luxury Condo Ground Floor Across the Street1 / 18
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 June 2018
    This condo was perfect. It had everything we needed to feel right at home. It was clean and well-maintained and the owner was very responsive. Beaches were within walking...
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    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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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Block to the Beach on Siesta Key Vacation Rental Home with Swimming Pool1 / 28
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Kid friendly
    Smoking allowed
    About this property
    Welcome to Cape Aqua! This single family vacation rental home on Siesta Key has 3 bedrooms 2 1/2 baths and pool. Located on the closest private street to America's #1 named.The two large double doors with decorative frosted glass welcome you into this spacious home. The floor plan offers a very...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    8 Steps to Sand Path! Best Value on Siesta Key! - The Siesta Key Poor Boy1 / 44
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
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    About this property
    A Gertrude Rentals Property! Rated 'The World's Finest, Whitest Sand' at the Great International Sand Challenge! Just 8 steps from the yard to the sand of the beach path! The Poor-Boy unit is perfect for travellers in search of all the best the island of Siesta Key has to offer but on a limited...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Grill
    • Ocean Views
    • Central Heating
    • Waterfront
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 Bedrooms, 2 Bathrooms, Private Suites Sleeps 6. Ocean views private lanai Relax with your morning coffee with beautiful white sand and ocean breeze, so peaceful. Condo complex is right on the beautiful white sands of the #1 beach in the USA. So convient walk right out and put toes in the sand....
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Air Conditioning
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ocean Beach Gleason home rests on Siesta Key near Siesta Key Beach and Siesta Key Village. This is a stunning 4 bedroom or 3 br w/den, 2 bath updated and custom home all on one level with a saltwater pool (heat optional) and spa that over looks a small lake. Bring your well-behaved Fido with...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    The Palm Island House - a Shangri-La! 1.5 blocks to Siesta Keys best beaches!1 / 34
    (14)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Waterfront
    • Balcony
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 July 2017
    Palm Island was a DREAM home for us!! My bf and I were the only ones that went on this vacation so we had the WHOLE house to ourselves!! It was amazing!! A perfect location...
    Reviewed 4 December 2015
    We loved this home! We had a large group and it never felt crowded. The house is lovely and very convenient to everything! Highly recommend this rental!
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    About this property
    Prominently featured in the 2013 and 2014 in NYJL House Tour Magazine and winner Spring of 2014 Top Auction Item. Brought to you by Gertrude Rentals! This Spanish revival home is located on Palm Island, the heart shaped island within the island of Siesta Key, just steps from the beach and one...
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    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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    Lakefront Oasis 3 Bdrm House with Heated Pool minutes from village and beach1 / 42
    (4)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Grill
    • Private Outdoor Pool (Heated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 days ago
    From the magazine worthy interior decor to the outside oasis this home is a gem. We truly loved our stay at your Siesta home. The sunshine spills inside to brighten all the...
    Reviewed 11 August 2017
    I travelled to Florida with my fiancee for work and decided to extend our stay to enjoy a little R & R. We have used AirB&B in the past and we found this gorgeous home to...
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    About this property
    Surrounded by lush, tropical garden, our private villa is situated on a quiet cul-de-sac bordered on two sides by Lake Nancy. A birdwatchers and nature lovers delight! Sip your coffee in your PJs on the private, sunny terrace, feed the ducks in the lake in our backyard or enjoy a dip in the...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    PALM'S HOUSE1 / 24
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Unheated)
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    • DVD Player
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 June 2015
    As soon as we arrived we knew were going to have a happy stay at Palm's House! Our 5 person party was aged from 16 to 80 and we ALL had a wonderful time! The house itself is...
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    About this property
    Fabulous home on Siesta Key (Sarasota)( two weeks minimum stay ). Just 2 minutes drive to the beach & village. This home features 3 bedrooms and 2 baths with a large kitchen that opens to the family room. Great pool with southern exposure,and enclosed in a screen lanai for mosquito protection...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Washer
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This renovated POOL HOME WITH WATER VIEW is located in a wonderful family neighborhood just a few miles from the beautiful #1 Siesta Key Beach and is close to shopping, restaurants. Light and bright with 3 bedrooms, 2 full bathrooms, 2 car garage, a Family and dining/living room, this home has it...
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    Location Information
    Siesta Key, Florida 34231
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Waterfront
    • Wi-Fi
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    • Hot Tub
    • Children's Pool
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Treat yourself to an exquisite getaway at this Sarasota condo, part of the high-end Harbor Towers Yacht & Racquet Club. Boasting a variety of upscale community amenities - including three lighted Har-Tru tennis courts, an on-site fitness center, a pool and hot tub, and an unbeatable location right...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Luxury Siesta Key Four Bedroom,Five Bathroom Pool Home,180 Yards to Siesta Beach1 / 23
    (2)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Parking
    • Private Outdoor Pool (Heated)
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    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 October 2018
    We had 4 adults, 5 children and a small dog. What a magnificent home. We were very impressed with the cleanliness, the beauty, and all the amenities the home offered. A...
    Reviewed 7 August 2018
    Our family looked at several homes in Siesta Key and settled on this one due to its convenient location to the public beach entrance along with direct access to the canal. We...
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    About this property
    This Luxury Four Bedroom, Four and a Half Bathroom Home will leave you breathless as you enter. There are not many large rental homes, this close to Siesta Beach, that live like this home. Most Rentals by the beach have their living area 16 feet above the ground level and the pool below, which is...
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    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
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    • Children's Pool
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Snowbirds are welcome at this charming bayside condo complete with a full kitchen and a furnished patio, plus an on-site fitness center, tennis courts, and pools. Visit Siesta Key Village for fantastic shopping and dining, less than two miles from your rental, or take a short stroll over to...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    PRISTINE SIESTA KEY VILLAGE HOME1 / 28
    (6)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Air Conditioning
    • DVD Player
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Hot Tub
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 October 2018
    It was a perfect week for us in a perfect House.Great style and interior and we could use the bikes and kayak. Walk distance to the nice restaurants and the beach. We will...
    Reviewed 29 August 2017
    Beautiful accommodation, superbly located and very well equipped. The new swimming pool is the jewel in the crown, and Cydney was a pleasure to deal with. We would hope to go back.
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    About this property
    Hidden behind a contemporary privacy wall, enter into our front yard oasis. The perfect setting for tanning, dining and entertaining alongside the waterfall feature. Extensive renos offering a stunning gourmet kitchen, updated bathrooms, flat screen tv's in bedrooms and the most appealing Lanai...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Balcony
    • Patio
    • Waterfront
    • Ocean Views
    • Cable/satellite TV
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    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    DIRECTLY ON NUMBER ONE RATED BEACH IN THE USA SIESTA BEACH!!! Included with your stay: Complimentary Bicycles, Beach chairs, Beach-Towels, Free-rides around Siesta and a 7-day week office for your convenience and guest needs. Beachfront home on Siesta Key Sunset Point. Siesta Key Beach is the...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Wi-Fi
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    • Private Garden
    • Private Outdoor Pool (Heated)
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    lovely house in the private yard.The deck is covered by a lanai and is surrounded by tropical plants including key lime, coconut, and banana giving complete privacy, the pool enjoys the sun all day, shady areas can be sought on the large deck. There is a full sized double garage and driveway...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    • Internet Access
    • 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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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Our Tropical Island Home1 / 14
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Patio
    • Private Outdoor Pool (Heated)
    • Balcony
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 July 2018
    This makes our second time staying here. Everything has been perfect! Great location to beach and kayaking launch. Nice pool to relax in at end of the day. Beach chairs...
    Reviewed 22 July 2016
    We stayed for three weeks in this beautiful house. Great location between Siesta Key Beach and mainland. Also calm neighbourhood, clean house, fully equipped kitchen that had...
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    About this property
    This wonderfully updated island vacation home has a spacious floor plan. There are tropical views from every window. The beautiful, heated private pool includes a spa and a waterfall. You can open the large patio doors to the screened in lanai that overlooks the pool and bring in the sound of...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Heated)
    • Waterfront
    • Patio
    • Ocean Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4 Bedroom Beachfront Pool Home. Closest house to the beach on Siesta Key! Included with your stay: Complimentary Bicycles, Beach chairs, Beach-Towels, Free-rides around Siesta and a 7-day week office for your convenience and guest needs. Siesta Key Paradise is nestled within walking distance of...
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    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Amy was the first house to arrive at Tiny House Siesta. She is one of our smallest as she comfortably sleeps 3 people. Second floor master bedroom private from the rest of the house. She has all the amenities of being at home, so there is no reason for a boring hotel room. She has a sitting area,...
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    Siesta Key, Florida 34231
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    SEA HORSE VILLA 1 bedroom, 1 bathroom on Siesta Key Your own private entrance. Outside sitting area with a table and chairs. Perfect for a couple. 1 bedroom and a futon in the living room. Large HDTV & Free WiFi Microwave, Fridge, Coffee maker, & sink in the kitchen. Fully furnished. Daily rentals....
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    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    6 Bedroom 4 Bathroom house   New pool  Siesta Key Florida  Walk to the Beach1 / 32
    (1)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 July 2017
    Excellent all-around. Owner was very responsive and friendly. House was clean and in great condition upon arrival, and even bigger than expected! To top it all off, it was...
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    About this property
    Siesta Sun Villa Our home is one large house that has a 3 bed 2 bath unit. A 2 bed 1 bath unit and a 1 bed 1 bath unit. All with connecting doors so you can rent the whole house to sleep 12 guests all in beds. It is perfect for large familys, Weddings and reunions. Private back yard, Overlooking a...
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    Siesta Key, Florida 34242
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located just over the bridge from Siesta Key and minutes away from Sarasota’s thriving dining and arts districts, our sunny and cheerful tiny house, Red Lifeguard Stand, sleeps four. With the convenience of a hotel, the comfort of a vacation home, and the cool factor of a tiny house, make staying...
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    Siesta Key, Florida 34231
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    New 6 Bedroom, Luxury Home in Gated Community1 / 22
    (1)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Waterfront
    • Air Conditioning
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 April 2017
    View from master bedroom was fantastic. Plenty of room for the 14 of us. Will defiantly book again. Kitchen had all appliances needed. Grill was old and had to light with a...
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    About this property
    Perfectly located, New, 6 bedrooms 4 1/2 bathrooms private home,in a gated community, combines luxury with convenience of location. We offer you a large 6000sf+ home within a short distance to the pristine beaches of Siesta Key and walking to the Village, Restaurants, shops and nightlife. Privacy...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 14
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You need a vacation and we've got just the place! Not only are we a 5 minute walk to beach, but we're only 2 blocks to the famous Siesta Key Village with all the shops, restaurants and bars. If you don't want to eat out, you have a grocery store right in the village. They have already made...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Beach, Village, Dock, Private Heated Pool... Fantastic Location, No Car Needed!1 / 44
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Waterfront
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • Housekeeping Included
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 days ago
    This is a fabulously decorated beachy feel cottage. Beautifully renovated indoor lay out. Updated, stainless steel kitchen with huge island buffet. Located minutes (walking...
    Reviewed 7 August 2018
    What a gem! This house was perfect for our family vacation. Just steps from both the beach & village - everything is close by. Great care has been taken to transform this...
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    About this property
    HERE IT IS! This “one of a kind” property is uniquely situated between the beach, canal, village with a private heated pool & dock, one of the best spots on Siesta Key! This charming 1,500 sq. ft. cottage beach home is being offered for the 1st time. If you want a cute, private original bungalow...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Three bedroom house directly on beach with gulf vi1 / 26
    (2)Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    • Cable/satellite TV
    • Ocean Views
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We have a 2 week minimum rental period. Tiffany Sands is a group of 9 townhouses directly on Crescent Beach. Our beach house is a stand alone unit(unattached). We have gulf views with 2 decks facing the Gulf of Mexico. It is a spacious 1,800 sq. ft. and newly decorated with a fully appointed...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 7
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Secure Parking
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to your own secluded tropical oasis. Lush island landscaping surrounding the property makes this home a unique and private setting. Private dock on protected cove 2 minutes from Sarasota Bay/ICW. Rent a boat at neighboring marina if you choose. Breathtaking large private pool, with numerous...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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