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Holiday Rentals in Siesta Key, FL

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    Travellers to Siesta Key are booking March dates now. Secure your holiday rental today, and have the perfect trip.
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    5 of 5 stars (8) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • DVD Player
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    About this property
    Spacious 1 bedroom, 1 bathroom, turn key furnished condo at Harbor Towers on Siesta Key. The unit has been totally remodeled, kitchen with granite counter tops, new cabinets, new lighting and stainless steel appliances. Bathroom has new shower and granite counter tops. Ceramic tile flooring... View all property information
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    Siesta Key, Florida 34242
    1 / 26
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    NEW PAINT AND CARPET! Canal front and tropical garden view from this 2 bedroom/1.5 bath first floor unit. Step out the back door of the spacious screened lanai to walk along the beautiful grounds and boat dock. Living room has sofa bed, TV, VCR, & CD Player. Master bedroom has queen size bed.... View all property information
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    Siesta Key, Florida
    1 / 22
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    If your specific dates are not available, please ask about our other 2015 renovated waterfront villa Our SF Villa has been completed remodeled in the Fall of 2013 and includes custom Italian Kitchen Cabinetry, Travertine Tile, Glass Backsplash with under mount lighting, quartz countertops, and... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 1 August 2015
    I was quite impressed with the condo the minute I walked in! The photos of the rental are very accurate. It has a beautiful kitchen, an open living space (complete with a sleeper...
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Enjoy this 1st floor, gulf view condo located just steps from the pool. You'll find everything you need to enjoy your beach vacation. New king size bed, living room furniture, as well as various kitchen supplies. Freshly painted in September 2013. You will not be disappointed! Additional amenities... View all property information
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    Siesta Key, Florida
    1 / 13
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    *** NEWLY RENOVATED!*** Gorgeous 2 bedroom/1.5 bathroom Bay Side unit. Tile throughout. Extended living room area. King bed in the master bedroom and two twins in the guest bedroom. Walk out your back door to the heated pool and the boat docks. Only about a 5 minute walk to your private beach on... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 19
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    This unit offeres wireless high speed internet connection. Beautifully decorated fifth floor end unit overlooks the bay and only a few minutes walk to the pure white sands of our own private beach! Water views from all main rooms in this bright and sunny spacious 1800 sq ft. unit. Step out from... View all property information
    Location Information
    Siesta Key, Florida
    5 of 5 stars Reviewed 4 June 2015
    My wife and I have just returned from Siesta after a week in this great unit. Siesta Key is everything advertised, beautiful beaches, funky village and awesome weather. What made...
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    1 / 12
    4.5 of 5 stars (10) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Island House Beach Resort - Siesta Key Florida, Crescent Beach - This large 2 bedrooms, 1 1/2 bath villa is appox. 1000 sq. ft. It has a large living area, dining area, fully equipped kitchen, all appliances, central ac/heat, covered parking, screened lanai, free wi-fi in unit! The unit is... View all property information
    Location Information
    Siesta Key, Florida
    5 of 5 stars Reviewed 12 March 2014
    Because of husband's illness, it was first time returning after six years. It was very comforting and peaceful. Condo was immaculate and well updated/decorated. Staff and...
    4 of 5 stars Reviewed 17 December 2013
    The place was nice.. We stayed from Thursday - Monday. They don't supply beach towels, and won't replenish you with bath towels if you are there less than a week.. If you need...
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    1 / 39
    5 of 5 stars (6) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • DVD Player
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    • Porch
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    About this property
    Newly upgraded ( September 2015 ) with new kitchen, new vanities, newly painted and with the tiles steam cleaned this Siesta Key villa is a gem. It comes with a with a lovely heated community salt water pool and private access to the beautiful white sanded Crescent Beach! Crescent Beach on Siesta... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 2 July 2015
    Loved this place! The whole place is clean neat and well kept. The amenities are up to date and the rooms are very comfortable. The owner(s) are very helpful and great...
    5 of 5 stars Reviewed 6 June 2015
    It was perfect was nice and clean and walking distance to a private less crowded beach where we rented a kayak and stayed on the water all day. The water is so clear you can see...
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    1 / 24
    4.5 of 5 stars (13) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Waterfront
    • Balcony
    • DVD Player
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    • x
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    About this property
    Welcome to a bit of heaven! Newly udpdated throughout including large flat panel HDTV with PREMIUM CABLE including HBO, DVR and WIRELESS INTERNET FREE! A gorgeous gulf-front vacation awaits you as you come and enjoy this enchanting condo! Located directly on beautiful Turtle Beach in Siesta Key... View all property information
    Location Information
    Siesta Key, Florida 34242
    4 of 5 stars Reviewed 18 June 2015
    Use the map provided to select the location of your unit, I.e. View of beach(towers 1&2), poolside units, short walk to beach etc. Clean towels and linens are as available as...
    4 of 5 stars Reviewed 14 February 2015
    The view is beautiful from the front(ocean) and the back (channel) . Area is very quiet as is the condo. we actually found ourselves whispering the first day! Roar of the ocean...
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    1 / 25
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Owner takes pride in this beautifully decorated 2nd floor unit. 2 bedroom 1 1/2 baths. Newly remodeled! Very cozy and comfortable with amazing tranquility and peacefulness courtesy of the laid back, canal-front setting. The unit features ceramic tile floors and a den-like sitting room off of the... View all property information
    Location Information
    Siesta Key, Florida
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    5 of 5 stars (11) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Washer
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    • Waterfront
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    About this property
    We have a beautiful two story beach house on the best beach in America! The sand is 99% quartz and white like powdered sugar, it's so perfect for sandcastles that every year The Crystal Classic is held with most beautiful sand sculptures. Our home is situated directly on the sand with 3... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 1 June 2015
    I have stayed in Siesta Key well over 25 times, and this house is truly unique! It's spacious, well-appointed, clean, and has a lot of extras (baby walker, baby gate, tons of...
    4 of 5 stars Reviewed 16 November 2014
    Stopped there with my wife and 2 sons, plus their partners for my 60th birthday, had a truly great time. You are on the beach and I mean on Siesta Beach, you open the door and...
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    1 / 10
    5 of 5 stars (6) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Ocean Views
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Patio
    • Washer
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    This vacation rental offers a full view of Siesta Key Beach/ The Gulf upon entry; relax and enjoy from your lanai or master bedroom. The property has been newly transformed to accommodate our guests best welcome to Siesta. From the comfort of the home décor to your fully stocked kitchen: cookware,... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 5 March 2015
    What an awesome condo. Unit was furnished beautifully and very up to date. Couldn't have has asked for more. Location was great. Great views of the ocean and less than 20 minute...
    5 of 5 stars Reviewed 3 March 2015
    My 92-yr. old mother and myself stayed at this "Calm at Siesta" condo. Couldn't have stayed at a better place. As for Mom who uses a walker, everything was convenient for her in...
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    1 / 6
    2.5 of 5 stars (2) Poor
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Washer
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    • Balcony
    • DVD Player
    • Grill
    • Waterfront
    • Satellite TV
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Newly remodeled with a tiled kitchen and bath and new furnishings. Includes: King bed Pullout queen sleeper fully equipped kitchen Laundry facilities VCR/DVD Wifi Dishwasher/Micro Patio/gas Grills NOTE: PLEASE CONTACT US FOR AVAILABILITY. We do NOT always keep this calendar current. Thanks.... View all property information
    Location Information
    Siesta Key, Florida 34242
    4 of 5 stars Reviewed 25 September 2014
    This was our second stay at Sand Box and we have booked for April 2015. All staff were very friendly and went out of their way to make us feel at home. Property was very clean and...
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    1 / 29
    5 of 5 stars (35) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Elder access
    • x
    About this property
    This bright, cheerful and newly redone condo is located on Siesta Key which is renowned for its powdery white sand beaches and gorgeous sunsets. We have our own private, gated access to Crescent Beach and a lovely, large, heated pool. Both the pool and the beach are just a 2 or 3 minute walk from... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 5 November 2015
    Sue made us feel very welcome as she greeted us upon arrival . Our room was stocked with everything you need from the kitchen to beach supplies and everything in between what a...
    5 of 5 stars Reviewed 27 July 2015
    This place was perfect! The beach was so close and the pool was so warm! We had a few days of rain, which everyone kept saying was so unusual for that area, but the place was...
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    1 / 14
    4 of 5 stars (6) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Sauna
    • Terrace
    • Balcony
    • DVD Player
    • Parking
    • Air Conditioning
    • Satellite TV
    • Internet Access
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    Do you want to avoid crossing the street to get to the beach, or carrying your beach chairs with you? Then this is the place you've been looking for! Just open the gate and a beautiful stretch of sugar white sand awaits you. Loungers are already set up for you and there are also tiki shade... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 4 November 2015
    Unit was spotless and well equipped. Nice private beach with chairs. Easy walk to restaurants stores and shops.
    4 of 5 stars Reviewed 26 August 2013
    Great Condo. Stayed 5 nights and everything was as stated. Condo was very clean and large. Loved the hot showers. Beach was beautiful and loved the use of beach chairs. Such a...
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    1 / 18
    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
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    • Pet-friendly
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    About this property
    Island House Beach Resort - Siesta Key Florida, Crescent Beach - This large villa is approx. 1000 sq. ft., non-carpeted, has a large living area, dining area, fully equipped kitchen, all appliances, screened lanai, central ac/heat, and covered parking, 3 tvs, dvd, free wi-fi in unit!. It has a king... View all property information
    Location Information
    Siesta Key, Florida
    5 of 5 stars Reviewed 15 October 2010
    Villa 9 was newly redecorated; therefore, it was a pleasure to spend 10 days in a clean, updated, and comfortable villa. The comfort of Villa 9 was worth a little bit of a walk...
    5 of 5 stars Reviewed 17 April 2009
    We lost our precious husband and daddy about a year ago when he died very suddenly and unexpectedly. We decided shortly after that happened to come back to Island House for...
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    1 / 13
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    THIS THREE BEDROOM/TWO BATH CORNER UNIT HAS BEEN COMPLETELY REMODELED, REDECORATED AND UPDATED! Over 1600 sq. ft. of spacious living space and ceramic tile throughout; beautifully decorated--everythinhg new! The living area features a large flat screen TV and DVD player, the kitchen is adorned... View all property information
    Location Information
    Siesta Key, Florida
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    1 / 26
    5 of 5 stars (37) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Grill
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    About this property
    Very clean, bright & airy 1 bedroom, single- story cottage. Ebb Tide #1 offers all you need for a wonderful vacation at the beach. - Beautiful, large, heated, saltwater pool. - Private, gated access to world renowned Crescent Beach, famous for its powdery, white, quartz sand and gorgeous sunsets!... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 1 December 2015
    Thanks Sue for thinking of every single detail. I have nothing but positive things to say about the Cottage. Sue has thought of everything you need for your stay. The only...
    5 of 5 stars Reviewed 17 October 2015
    Upon arrival, We were greeted by Sue (The owner). She informed us of all the area had to offer, and gave us advice on where to eat, and party! We had a wonderful time, and enjoyed...
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    1 / 34
    4 of 5 stars (1) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Villa Fiesta at 1115 Crescent Street is another beautifully decorated, exciting new 4BR/4BA/2Kit home recently added to The Cottages collection of fine vacation homes. Villa Fiesta and its sister home, Villa Margarita are two beautiful 4-BR pool homes offering unique sleeping combinations to larger... View all property information
    Location Information
    Siesta Key, Florida 34242
    4 of 5 stars Reviewed 28 December 2015
    The location of this unit is great. It is truly walking distance to the beach. The units provide beach chairs, beach "wagons", beach towels and even some beach toys and boogie...
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    1 / 1
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Pet-friendly
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    • ?
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    • x
    About this property
    Newly remodeled -Queen Murphy Bed -Convenience Kitchen -Laundry Facilities on site -Patio / Grill -VCR/DVD -WiFi -Microwave NOTE: PLEASE CONTACT US FOR AVAILABILITY. We do NOT always keep this calendar current. Thanks. Visit our site to see more photos and descriptions:... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 20
    5 of 5 stars (7) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Washer
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    • Outdoor Dining Area
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    • Pet-friendly
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    • Child-friendly
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    About this property
    We offer a boutique style property with just 4 units. Close enough to the beach without the congestion of larger properties. Enjoy this newly renovated (2014) apartment, located less than a mile from beautiful Siesta Key Beach. We've fully remodeled in the 'Beach Chic' style, with a touch of... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 3 weeks ago
    Our family of teenagers and one toddler, traveled for Christmas break. The house was exactly as the photos depicted, great living room/dining room space. the three bedrooms were...
    4 of 5 stars Reviewed 6 May 2015
    Just returned on Sunday from a week long stay in Siesta Keys at this three (3) bedroom apartment. The communication was great with easy arrival and clean accomodations. We were...
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    1 / 22
    4.5 of 5 stars (8) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Private Outdoor...
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    • DVD Player
    • Terrace
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    The Perfect Place to Stay When You Need to Get Away! Free Wi-Fi access, Fully Furnished, Gulf Beach Views, Screened Balconies, Cable TV, A/C/H, Free Local Calls, Elevators, Large Heated Swimming Pool, Shuffle Boards, Covered Parking, Laundry Facilities, all units Non-Smoking Rec-Room: pool table,... View all property information
    Location Information
    Siesta Key, Florida 34242
    4 of 5 stars Reviewed 14 July 2015
    The unti was very clean and all essentials provided. Management staff were visible daily and during the July 4th holiday - the grounds were protected with security guards to...
    5 of 5 stars Reviewed 28 July 2013
    We stayed in 402. It was great! Very nice and comfortable unit. AWESOME view from the screened in patio. Plenty of beach chairs and an umbrella to use on the best beach ever...
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    About this property
    On the waterfront / Fireplace / Great Shopping / Near a Mountain Get lost in the intoxicating relaxation of Siesta Key, in the luxurious private home of Camp Paradise. Camp Paradise is a single-family residence located at the end of a secluded dead end street in the opulent neighborhoods of... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 17
    4 of 5 stars (1) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
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    • Private Outdoor...
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    • Child-friendly
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    About this property
    Island House Beach Resort - Siesta Key, Crescent Beach, Ground Floor unit! This unit is located at Island House Beach Resort on sunny Siesta Key. It is 2 bedrooms, 2 baths, 1300 squart feet.King, full, futon. It has a large living room, fully equipped kitchen, all appliances, dining area, lanai... View all property information
    Location Information
    Siesta Key, Florida
    4 of 5 stars Reviewed 5 May 2014
    Island House was the perfect spot for a vacation in Siesta Key. The condos are comfortable, fully furnished and their location on the beach is spectacular. We actually stayed in...
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    1 / 20
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Nestled on the southern tip of Siesta Key is our ground-floor condo, Bay Tree Club 106. Located in an oceanfront complex, it will pamper you with brand-new HDTVs, spacious and well-appointed rooms, and a sunny lanai overlooking grassy grounds. The Gulf of Mexico is just steps away from Bay Tree... View all property information
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    Siesta Key, Florida 34242
    1 / 19
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Not owned by Gumbo Limbo. Only steps to the Siesta Key BEACH! Spacious and enchanting 3 bedroom/2 full baths ground-level property (sqft 1,322) offers 1 King, 1 Queen and 2 Twin beds. The Beach House features central A/C, a lanai, a full kitchen with stainless-steel appliances, a dishwasher,... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 1 October 2015
    We really enjoyed our stay in the property. It had all the amenities to make our short vacation enjoyable. We had a small complication with the TV and the staff was quick to...
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    1 / 41
    5 of 5 stars (21) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Spacious, vaulted 3 bedroom beach townhouse located among the resort community of Sara Sea Circle with direct, private beach access to the world famous (rated #1 in USA) Crescent and Siesta Key Beaches. This large townhouse very comfortably sleeps eight in 1 King / 3 Queen beds. There is a large,... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 3 weeks ago
    The townhouse is beautiful. We had 6 women for a girls trip and this was the perfect place. Well appointed. Bikes and toys in the garage. Beach and pool very short walk. Close to...
    5 of 5 stars Reviewed 4 weeks ago
    We have been coming to Sarasota and Siesta Key for 30 years. Most years we have to pack up or buy things that make for lots of errands on the first day or two of the holiday, but...
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    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Lovely top floor tropical condo sits directly on beautiful Sarasota bay. breathtaking views and breezes from the top floor balcony. Gulf views from the kitchen window. just steps to beautiful turtle beach. Condo has been recently updated and decorated. Has one of the best and largest lap pool on... View all property information
    Location Information
    Siesta Key, Florida 34275
    1 / 19
    5 of 5 stars (7) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    GULF FRONT - GROUND FLOOR UNIT!! This spectacular 2 bedrooms, 2 baths unit is 1300 sq. ft. as is located on Crescent Beach. This condo offers a view of palm trees, white sand and turquoise waters of the Gulf of Mexico.Fully equipped kitchen, all appliances. The unit has a king size bed and 2 twins.... View all property information
    Location Information
    Siesta Key, Florida
    5 of 5 stars Reviewed 18 July 2013
    We stayed in 1 North this past april,and enjoyed every minute of our stay. This unit has many wonderful updates,(even nicer than the photos portray!) and is very clean,with plenty...
    5 of 5 stars Reviewed 20 September 2012
    Great Condo and time had by the family, despite the sea being too rough to swim in due to Irene.
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    1 / 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Spacious 2 bedroom, 2 bath, 2nd floor unit on #1 ranked Siesta Beach. Fantastic gulf, beach and pools views from the lanai & master bedroom allow you to leave your cares behind. Owner’s completed a major renovation in August 2015. New kitchen, bathrooms and flooring throughout. Master bedroom &... View all property information
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    Siesta Key, Florida
    1 / 8
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    VILLA CHAMPAGNE: Welcome to “Villa Champagne”, one of the most fabulous vacation homes in Siesta Key. It’s also one of the most popular favorites among our many guest families. The magic begins as you enter the foyer of this beautiful villa and gaze across the expansive living area, then... View all property information
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    Siesta Key, Florida 34242
    1 / 32
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Love sunsets? How about white sand, plush beds, a choice of three pools, swans ... and a little shuffleboard? If this sounds like a month or more of paradise, you’ll immediately love life at Siesta Key Gulf and Bay Club #108D. Book now for a stay of 28 or more days. This ground floor condo is... View all property information
    Location Information
    Siesta Key, Florida
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Quiet and serene, but close to local attractions, you will love this large 4 bedroom, family friendly home with 2 kitchens, new appliances, modern furnishings, and beach buggy with all the gear! Separate living areas can accommodate one large family or two smaller ones. Each living area has its... View all property information
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    Siesta Key, Florida 34242
    1 / 17
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Two 2 BR / 2 bath beautifully furnished units with fully equipped kitchens, cable TV, WiFi, and washer/dryer. Relax by the pool, stroll to shopping and dining in the Village, or enjoy an afternoon at Siesta Beach only a short stroll away! Pets welcome. MORE UNITS AVAILABLE. VISIT OUR SITE FOR... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 3 November 2015
    I don't write many reviews but Scott and his business partner(s) did such an amazing job with all their countless renovations/upgrades to this property. Its easy to see the...
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    1 / 6
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Relish in the Florida sun on Crescent Beach! Relax & kick back in this attractive two bedroom condo with a stunning view!! Our condo is a two bedroom and two bathroom renovated unit (2011). Some new furniture and granite & marble kitchen counter tops. High speed wireless internet, free local & long... View all property information
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    Siesta Key, Florida
    1 / 5
    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Newly remodeled with a tiled Kitchen & Bath and new furnishings. -TWO Full Baths -King Bed -Queen Bed -Pullout Queen Sleeper -Fully Equipped Kitchen -VCR/DVD -CATV -WiFi -Dishwasher/Micro -Patio/Gas Grills- -Laundry Facilities on site NOTE: PLEASE CONTACT US FOR AVAILABILITY. We do... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 4 weeks ago
    I was looking for a place on or near the beach for a little get away with my daughter while she was home on break. Came across the Sandbox and decided to give it a try. It was a...
    5 of 5 stars Reviewed 6 December 2015
    We stayed here with my son and his family for I believe the 6th year in a row. My son used to come here every year with his girlfriend. We come here for Thanksgiving and I've...
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    1 / 23
    5 of 5 stars (24) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Siesta Key, Sarasota upscale vacation rental unit within a few steps of the water or a gorgeous pool. Lush, tropical landscaping in well maintained Bay Oaks. Breathtaking views of the intercoastal with fully appointed fishing dock. Accross the street from the beach and there are no beach charges... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 30 June 2015
    Bay Oaks is a great place to stay on Siesta Key! When we arrived our Condo was very nicely decorated, clean and comfortable. It worked perfect for 2 adults and 2 kids. This condo...
    5 of 5 stars Reviewed 21 May 2015
    The unit was very well furnished and clean with a wonderful kitchen area,the property was very bueatiful and I enjoyed relaxing on the peer in my free time,the beach is stunning I...
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    1 / 6
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    About this property
    Convenient first floor unit. Direct access to the pool, deck and beach. Comfy furnishings with an eye appealing style. The perfect location to kick-back while watching for the elusive 'green flash' at sunset. Additional amenities include: tile flooring, bathtub in the guest bathroom, 2 twins in... View all property information
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    Siesta Key, Florida
    1 / 35
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Centrally located in the heart of Sarasota, and only minutes away from our world famous Siesta Key Beach, the completely renovated Villa Trinidad offers a cool and soothing retreat with a heated swimming pool and a spectacular view of one of the most beautiful canals off of the Sarasota Bay.... View all property information
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    Siesta Key, Florida
    1 / 6
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Enjoy sunsets from this 2 bedroom, 2 bathroom, 4th floor gulf view unit. This unit features cathedral ceilings and recent updates including a new kitchen, bathrooms, and 6 speaker surround sound system. Additional amenities include: carpet and tile flooring, internet available in rec room only, 2... View all property information
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    Siesta Key, Florida
    1 / 15
    4 of 5 stars (1) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Island House Beach Resort - Siesta Key Florida, Crescent Beach - This lovely 2 bedroom, 1 bath villa is located on the widest part of Crescent beach. It is approx 1000 sq. ft and has a large living area, dining room, fully equipped kitchen, screened lanai, covered parking, central ac/heat, free... View all property information
    Location Information
    Siesta Key, Florida
    4 of 5 stars Reviewed 2 December 2009
    Clean house, quiet area, easy access to the beach. Fun place for kids to play and swim.
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    1 / 17
    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Island House Beach Resort! Crescent Beach, Siesta Key Florida. This beautifully maintained complex is located on one of the best beaches in central Florida. This 3rd floor, 2 bedroom, 2 bath condo offers views of palm trees, white sand and the turquoise waters of the Gulf of Mexico. The view is... View all property information
    Location Information
    Siesta Key, Florida
    5 of 5 stars Reviewed 12 July 2015
    This place was great and the staff was always available and helpful. We drove down from Ohio for a short three day adventure. Everything was great. very clean short walk to beach...
    5 of 5 stars Reviewed 28 February 2011
    This was a lovely property. Fully remodeled with nice finishes. True to pictures. Very confortable for a family vacation. The beach is incredible.
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    1 / 19
    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Island House Beach Resort! Siesta Key Florida, Crescent Beach. Ground floor unit. This 2 bedroom, 2 bath condo is 1300 sq. ft. It has a large living area, dining area, fully equipped kitchen, all appliances, lanai. It has a king, 2 twins. Central heat/ac. Free Wi-Fi in unit. This beautifully... View all property information
    Location Information
    Siesta Key, Florida
    5 of 5 stars Reviewed 19 June 2011
    We stayed in the 10 South unit and my family loved the pool and the beach access! We have vacationed at Siesta Key over the past 25 years and stayed at most of the available...
    5 of 5 stars Reviewed 9 June 2010
    My husband and I stayed at Island Beach House, Unit 10a. From the minute we checked in, the service was great, Scott was very friendly and knowledgeable of the area. Our unit was...
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    1 / 30
    5 of 5 stars (26) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Smoking allowed
    • Elder access
    • x
    About this property
    Siesta Key, Sarasota upscale vacation rental unit within a few steps of the water or a gorgeous pool. Lush, tropical landscaping in well maintained Bay Oaks. Breathtaking views of the intercoastal with fully appointed fishing dock. Across the street from the beach and there are no beach charges on... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 13 July 2015
    very nice and comfortable accommodation. Apartment is great and look better than in photos. You will find apsolutely everything you need in it. From all kitchen appliances...
    5 of 5 stars Reviewed 24 June 2015
    Barbara did an excellent job answering any questions I had before, during, and after my stay. Her place is spotless and well equipped to make your stay comfortable! Public beach...
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    1 / 46
    4 of 5 stars (23) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    3BR Oceanview Townhome 3BR/2.5B, Heated Pool, Private Elevator, Crescent Beach - Siesta Key, FL BEACHWALK; Three bedrooms, two and a half baths, garage, private pool, private elevator, en suite Jacuzzi tub, beach view, sleeps up to eight, steps to world famous Siesta Key - Crescent Beach... and... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 17 May 2015
    This is our second year staying at Beachwalk, a Sunnyside property. Siesta Key Beach is literally a block away! You can't beat the location and price. Great views of the beach...
    3 of 5 stars Reviewed 11 May 2015
    The Condo is just across the road from the beach and a few blocks from shops and food. It was as advertised and the photos are a good indicator of the furnishings. This could be a...
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    1 / 27
    5 of 5 stars (5) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    FREE High Speed Wireless Internet ! - just bring your Laptop. Watch the boats float by! Just steps from the Pool, Club House, and picnic area with gas Weber grills. Across the street from Crescent Beach!! Our three bedroom two story townhouse in Gulf & Bay Club Bayside is in a complex of Key... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 18 December 2015
    The unit was clean, beautiful and had everything we needed to cook Thanksgiving dinner. We enjoyed watching the boats go by on the waterway and also enjoyed the private access to...
    5 of 5 stars Reviewed 7 July 2015
    This rental is top notch. We have stayed there several times, and plan on returning for years to come. The rental is up to date, nicely furnished, updated kitchen, close to the...
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    1 / 13
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    NEW TILE CERAMIC TILE THROUGHOUT UNIT! Spacious 2 bed/1.5 bath first floor unit with extended living room. Walk right out your back door to the canal and boat docks. Living room offers comfortable leather seating & TV, DVD, VCR. Master bedroom features king size bed with TV. Master bath has tub... View all property information
    Location Information
    Siesta Key, Florida
    Siesta Key Vacation Rentals

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

    Lions, Tigers & Circuses

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

    Gardens & Aquariums

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

    Locomotives & Science

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

    History & Baseball

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