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Gulf Gate Estates House Rentals

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    Gulf Gate Estates is popular with travellers just like you. Don’t let them get your perfect place first—book today!
    130 Matching Rentals in the Gulf Gate Estates AreaView all 663 rentals
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    Gulf Gate Estates
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Gulf Gate Estates
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    About this property
    Welcome to Cass Pool Home! Only a 6 minute drive to the beach on Siesta Key. Want to leave your car in the driveway? No problem, rent bikes if you like; it's only a 13 minute bike ride to the Beach Access #12! This is a lovely updated 2 bedroom (King, Queen) 1 full bath with two separate TV...
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    Gulf Gate Estates, Sarasota 34231
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Gulf Gate Estates
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    About this property
    Gulf Gate Getaway *Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions. Perfect for families and groups of friends, this sunny home has everything (including a scenic pond!) you need to enjoy some...
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    Gulf Gate Estates, Sarasota 34231
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Gulf Gate Estates
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Grill
    • Central Heating
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Kingston Lake is situated in beautiful and tranquil surroundings on a large plot, only 4 miles from the beaches of Siesta Key. On a floor space of 160 sqm are 3 bedrooms and 2 bathrooms, a fully equipped kitchen with breakfast bar, which opens to the living and dining area. The spacious...
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    Gulf Gate Estates, Sarasota 34238
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Gulf Gate Estates
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Outdoor Pool (Heated)
    • Private Garden
    • Grill
    • Air Conditioning
    • Secure Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Lake View is located in the quiet subdivision of Gulf Gate Woods on a large lot with plenty of privacy. The distance to Siesta Key and the beaches is only 2 miles. The cozy home features an open floor plan with a spacious living area and a Florida room, also two Bedrooms and two bathrooms, a...
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    Gulf Gate Estates, Sarasota 34231
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Gulf Gate Estates
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Washer
    • Grill
    • Wi-Fi
    • Patio
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to this exquisite spacious 3 bedroom and 2 bathroom home with a pool in the renowned Gulf Gate Estates community. The open floor plan grants all the space any amount of guest could ask for. Enjoy the large living room with a flat screen TV or the newly remodeled fully equipped kitchen with...
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    Gulf Gate Estates, Sarasota 34231
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Gulf Gate Estates
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
    • Patio
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Single family house located in quite and safe Golf Gate community, 10 min. drive to #1 in America Siesta beach, close to everything ( restaurants, shopping centers, library, grocery stores, beaches, etc...). Full electrical house has 1 car garage, laundry (washer and dryer), patio with gas grill,...
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    Gulf Gate Estates, Sarasota 34231
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    The following rentals are within 10 kilometres of Gulf Gate Estates.
    Island Time Beachside. Beach Access #13 in 5-10 minutes!  Near everything!1 / 12
    (5)Excellent
    Siesta Key, FL
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Washer
    • Grill
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    • Air Conditioning
    • Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 March 2019
    The unit was so clean and lovely to stay at. The walk to the beach is quick and very beautiful. Angel was always quick to response and hospitable. I would definitely come again!
    Reviewed 17 July 2018
    Great home feel, cute place! Very clean and great accommodations. Comfortable bed and furniture, just like home, except at the beach! Love that it is a short walk to the beach...
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    About this property
    Upper floor. Walk to Siesta Key beach, only 0.2 mi from beach access 13. Clean, updated, with all the amenities you have at home. Fully equipped kitchen. Quiet and peaceful getaway and close to shopping, dining, grocery, pharmacy, bars, pubs, bike, boat, & kayak rentals. Park your car and use free...
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    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Fido Friendly, Saltwater Pool, Only 1 mile to SK Beach, Close to the Village, Sh1 / 38
    (1)Excellent
    Siesta Key, FL
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Grill
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 August 2018
    The house was beautiful and very spacious. Great proximity to the beach and town center, and the kids loved Glebe Park, which was located a short walk down the street. We are...
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    About this property
    On Siesta Key we offer a high-end gorgeous, Fido friendly with Prior Approval, Key West style 3 bedroom, 2.5 bath custom home. Desire a private saltwater heated pool while vacationing on Siesta Key? Then this vacation home will be your home away from home in tropical paradise…..just minutes from...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Siesta Key, FL
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Hot Tub
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Vacation on Siesta Key in this newly built 4 bedroom custom pool & spa home just a 600 ft. away from Shell Beach. Across the street and down the small drive is the gulf. Shell Beach has a very small sandy beach. It's on Big Pass and looks out to Lido Key. Here the water has a current so little...
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    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Private Siesta Key House - Walk to Village & Beach - Heated Pool/Spa - No Stairs1 / 26
    (4)Excellent
    Siesta Key, FL
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Patio
    • Grill
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 February 2019
    We had such a great experience with this rental. The house was beautiful, perfect for a family with a small child (ours was about 15 months old). And you can't beat the location...
    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...
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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, 3 Bathrooms, Sleeps 6
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    Canal Home on Siesta Key w/ Pool, Wifi, Renovated 1950 Style Sarasota School of1 / 33
    (1)Excellent
    Siesta Key, FL
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 November 2018
    This house is perfect for your Siesta getaway!Close to Village and #1 beaches great pool on the CanalI would defiantly stay here again!
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    About this property
    We help make the most of your vacation by providing Free Admission to some of the area’s top attractions each and every day including a choice of a free, bike rental, free kayak rental, or free dolphin fun cruise! Round-trip airport transportation provided for up to 3 passengers from SRQ or TPA...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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    Lovely 2 BR Beach Cottage at Lido Key Villas across from Lido Beach1 / 21
    (5)Excellent
    Lido Key
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Private Garden
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 October 2018
    I highly recommend vacationing here and staying at this charming Villa. We stayed seven days for the F18 Worlds Regatta that David and Mark were in! We enjoyed the cleanliness...
    Reviewed 21 October 2018
    We had an excellent time at this rental which is convenient to everything Lido Key has to offer. While there we enjoyed a kayak tour around the corner, dined at the local...
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    About this property
    Our spacious fully furnished two-bedroom cottage is directly across the street from the beach (600 ft, a 2 min walk). It offers everything you need to enjoy a memorable beach vacation. It features all the conveniences – full kitchen, full bath and a lovely tree-shaded back yard. There is also a...
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    Location Information
    Lido Key, Sarasota 34236
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    The Shells Villa - Next to Beach & Village1 / 41
    (69)Excellent
    Siesta Key, FL
    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 2 weeks ago
    We stayed here with our family, seven of us all together, including 3 children (5, 8 & 11). Big place! Lots of rooms and never felt crowded at all. Lots of stairs too but...
    Reviewed 16 May 2019
    This was a lovely place to stay! Very spacious and charming place. It was well stocked with towels and we loved having a washer/dryer on site. There were 5 beach chairs that...
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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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    Siesta Key Beach Condo, 2Br/2Ba Direct Beach Front1 / 20
    (4)Very good
    Siesta Key, FL
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Waterfront
    • Air Conditioning
    • Grill
    • Balcony
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 May 2019
    The location and views were great. The shuttle is easy to catch and the beach is pristine. The condo itself was not very clean when we arrived. We found candy wrappers on the...
    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...
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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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    Sandy Toes Siesta Key Florida  (6796)1 / 40
    (23)Very good
    Siesta Key, FL
    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
    (31)Very good
    Siesta Key, FL
    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 6 June 2019
    2min from the best beach in the world... 2min from restaurants and hot spots. Perfect location. Quiet at night fun during the day... Siesta in the afternoons. Very comfortable.
    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...
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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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    Walk to Village, Heated Saltwater Pool,  Bike/Walk to Beach, WiFi/Cable, Custom1 / 34
    (1)Excellent
    Siesta Key, FL
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • DVD Player
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    • Air Conditioning
    • Washer
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    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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    Sarasota-Siesta Key Coastal Five Bedroom with Pool and Spa1 / 38
    (10)Excellent
    Siesta Key, FL
    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 18 April 2019
    David was very helpful and responsive, the house was clean and the beds comfortable. The pool was a dream for kids with easy visibility for parents.
    Reviewed 18 March 2019
    A block from the most beautiful beach, plenty of room for multiple people and ages, plus an awesome screened in pool, hot tub, grill and eating areas. Couldn't ask for more. We...
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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 Sand Path of Siesta's Best Beach! - Old Man and the Sea Inn (4)1 / 47
    (36)Very good
    Siesta Key, FL
    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 8 June 2019
    The rental was great. The place was very clean. I do have to say the walls are thin so you can hear your neighbors and vice versa. Pets are allowed in the rental, but not...
    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...
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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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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Sandy Toes Siesta Key Florida   (6798)1 / 37
    (22)Excellent
    Siesta Key, FL
    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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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2BR/2BA House Just Steps to Siesta Village & Siesta Key Beach1 / 13
    (5)Excellent
    Siesta Key, FL
    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 8 March 2019
    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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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 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 / 84
    (21)Excellent
    Siesta Key, FL
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • Waterfront
    • Patio
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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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    Location Information
    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 / 47
    (1)Excellent
    Siesta Key, FL
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Balcony
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    • Cable/satellite TV
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    • 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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    Palm Oasis - Relax in Comfort - 1 rental per calendar month1 / 35
    (3)Very good
    Siesta Key, FL
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Cable/satellite TV
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    • Private Outdoor Pool (Heated)
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    • 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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    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Family friendly house with pool/spa1 / 29
    (2)Very good
    Lido Key
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • DVD Player
    • Washer
    • Air Conditioning
    • Housekeeping Included
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 August 2016
    The owners are great, very friendly and helpful. The house was clean and almost everything needed was supplied. The rooms are nice and clean. The pool was the main focus of the...
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    About this property
    We want you to enjoy, staying here this year & be back with your friends/family. Beautiful house on 1 acre lot, close to everything located in one of the best and desirable area in south Sarasota. This property offers easy access to all local attractions and beaches. Only a short drive to the...
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    Lido Key, Sarasota 34233
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Our Beach House1 / 17
    (4)Excellent
    Siesta Key, FL
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    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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    Siesta Key, FL
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Grill
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    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In the middle of Siesta Key, tucked away on a shaded and quiet canopy lane is this bright and open air 3 bedroom 3 bath home less than one mile from the world famous Siesta Key beach. Plenty of space to spread out and enjoy your vacation, whether it be out on the pool deck, in the hot tub,...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Luxury Condo Ground Floor Across the Street1 / 18
    (1)Excellent
    Siesta Key, FL
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    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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    NEW POOL! 3 Bed 2 Bath on Siesta Key   Walk to beach   POOL  Great location1 / 18
    (3)Excellent
    Siesta Key, FL
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
    • Wi-Fi
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    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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    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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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    8 Steps to the Sand of Siestas Best Beach! - Old Man and the Sea Inn (2)1 / 43
    (2)Excellent
    Siesta Key, FL
    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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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Best in Siesta Village! 1.5 blocks to best beaches! - Casa Van Lopik (Canal)1 / 48
    (19)Excellent
    Siesta Key, FL
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Parking
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    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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    Siesta Key, FL
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We help make the most of your vacation by providing Free Admission to some of the area’s top attractions each and every day including a choice of a free, bike rental, free kayak rental, or free dolphin fun cruise! Round-trip airport transportation provided for up to 3 passengers from SRQ or TPA...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Siesta Key, FL
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    • Private Outdoor Pool (Heated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Discover Siesta Key at this three bedroom two bathroom vacation rental home located in the heart of Siesta Key tucked away in a quiet neighborhood. Hire one of the many free ride services on the key for a quick trip to visit Siesta Key village where you can find a multitude of restaurants,...
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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
    (3)Excellent
    Siesta Key, FL
    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 19 April 2019
    We loved this house and it was stocked with all the amenities that any renter will need for the beach. We especially loved the screened in porch and the cosy set-up of the house.
    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...
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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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    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
    Siesta Key, FL
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    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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    Siesta Key, FL
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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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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    Siesta Key, FL
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Grill
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spread out and enjoy this wonderfully appointed and tastefully decorated 3/2 home with private pool just steps away from powder white sands of Siesta Key Beach. Not far from Siesta Key village too where you can eat out in one of the many restaurants, have a drink and dance the night away, grab a...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Siesta Key, FL
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    • Grill
    • Ocean Views
    • Balcony
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    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 Bedrooms, 2 Bathrooms, Private Suites Sleeps 6. Ocean views on 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 convenient, walk right out and put your toes in...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Top in Siesta Village at Best Beaches, Food & Entertainment! - Casa Van Lopik(J)1 / 49
    (17)Very good
    Siesta Key, FL
    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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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Luxury Siesta Key Four Bedroom,Five Bathroom Pool Home,180 Yards to Siesta Beach1 / 23
    (6)Excellent
    Siesta Key, FL
    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Parking
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    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 April 2019
    This beautiful house is just the ticket for a large group. The location is within walking distance of the beach and village. It has a nice sized pool and the porch overlooking...
    Reviewed 8 April 2019
    This was our first visit to Siesta Key and we really didn’t have a very good sense of the Island before booking our rental. We were really fortunate to find this place. It was a...
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    About this property
    This Luxury Four Bedroom plus den with a sleeper sofa bed has Four and a Half Bathrooms and 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...
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    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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    Luxury Siesta Living On The Water *New Property*1 / 47
    (1)Excellent
    Siesta Key, FL
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Reviewed 29 May 2019
    Have you ever been to a place that just feels right? A place where you don’t want to leave and can’t wait to come back again on Siesta Beach? A place where you dream of going...
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    About this property
    The Property Live your travel lifestyle in the luxury stylings of The Henry. This one of a kind private accommodation on Siesta Key, features immaculate hand-picked designer furnishings staged to maximize the comfort, utility, and aesthetic appeal of each living space. From playing cards in the...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Lakefront Oasis 3 Bdrm House with Heated Pool minutes from village and beach1 / 42
    (4)Excellent
    Siesta Key, FL
    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 18 March 2019
    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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    PRISTINE SIESTA KEY VILLAGE HOME1 / 83
    (6)Excellent
    Siesta Key, FL
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
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    • DVD Player
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    • 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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    Siesta Key, FL
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Patio
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you are looking for a private home on Siesta Key that's only 460 feet from the Siesta Key Beach Access; then this is your vacation home to come to! It rests on a quiet street in a beautiful upscale neighborhood on Siesta Key just steps from playing in the sand with your kids, or reading a...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 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
    Siesta Key, FL
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Pet 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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    The Palm Island House - a Shangri-La! 1.5 blocks to Siesta Keys best beaches!1 / 34
    (14)Very good
    Siesta Key, FL
    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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    Siesta Key, FL
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Hot Tub
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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 7
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