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Siesta Key Rentals with Pools

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    Travelers to Siesta Key are booking July dates now. Secure your vacation rental today, and have the perfect trip.
    606 Matching Rentals in Siesta KeyView all 723 rentals
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    Beachfront Getaway in Siesta Key1 / 28
    (16)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Updated Townhouse!  Private access to Beach. Enjoy Tennis, Heated Pools, Fishing1 / 114
    (12)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Gulf Side Siesta Key Villa~Peaceful 1st Floor Villa, 3 pools-Jamaica Royale #1001 / 35
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Beachy Chic Condo in Siesta Key - Waterfront - Free wifi - Sleeps 4 !1 / 62
    (16)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Patio
    • Waterfront
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 15, 2017
    My wife and I visit Siesta Key at least once a year, usually for the sand sculpture competition. We had stayed at one particular place every time, but had a bad experience...
    Reviewed August 16, 2017
    We had a great experience staying at this place!! It was a short walk to the beach and fairly close to everything. Make sure you read the emails before you arrive, (i missed...
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    About this property
    Welcome to our Condo in Siesta Key ! Located on the inter-coastal Waterway and a short walk to the whitest sand and the # 1 beach in the USA. This 1 bedroom Condo is a great retreat for anyone looking for a beautiful Island getaway! Our condo is on the 2nd floor (sleeps 4) We are on Siesta...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    -Hide-A-Way Suite- next to Siesta Key Beach1 / 18
    (3)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Cable/satellite TV
    • Waterfront
    • Patio
    • DVD Player
    • Air Conditioning
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    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 21, 2017
    Great location to beach and town. Well maintained and attention to your needs. Onsite pool and outdoor space is beautiful. Great stay.
    Reviewed April 12, 2017
    Very happy with choice, across the street from beach, and very close to the village! Found some wonderful bars and retaurants!
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    About this property
    HIDE-AWAY SUITE # 664B (sleeps 4, ground level, sqft 580.00) this apartment has been completely remodeled July 2015. This 1 bedroom / 1 bath apartment, offers a king bed plus and a luxury self-inflatable Queen size Air-bed and 2 flat screen TV’s. This suite offers a full size new kitchen and...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Hot Tub
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy an incredible sunset on Siesta Key's Crescent Beach and walk back to your private villa on Siesta Key in Polynesian Gardens. Plan your get-a-way at our two bedroom, two bath villa where you have a screened-in lanai looking into the grassy back yard with your own personal BBQ grill. The...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Key West Suite next to Siesta Key Beach1 / 32
    (6)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Washer
    • Air Conditioning
    • Balcony
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 20, 2016
    Spacious enough for 3 little ones and 2 adults. My wifeet and I stayed in the makeshift room next to family room. Very clean and well kept. We were spoiled and had the property...
    Reviewed June 27, 2015
    The suite 5610 was on the ground level, perfect for kids. The suite and outside areas were very clean and offered a lot of amenities. The pool was very clean and just the right...
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    About this property
    2 apartments to choose from: Key West Suite A relaxed beach experience. This cozy two bedrooms & den apartment, full 2 baths (1 King bed + 2 Twins + 1 Queen) 1,200 sq/ft. suite on second level with two private balconies and partial Gulf view from the den. This apartment is fully furnished and...
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    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    15 min. walk/3 min. drive/free shuttle to Siesta Key! Best rates for a 2bdr/2bth1 / 30
    (11)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 28, 2017
    Very clean and updated rental. Had everything we needed and more, nice screened in patio to relax on as well. Even though it’s not on beach, very close to everything to enjoy...
    Reviewed November 16, 2017
    This place was exceptional clean and well maintained. Beaches are literally right around the corner. I would recommend anyone visiting the Seista Keys area to check this place out!
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    About this property
    All new! This spacious, 2 bedroom/2 bath has everything you need for a relaxing and fun vacation in Sarasota, just minutes to Siesta Key. Relax in comfort with all the amenities: - Fully equipped Kitchen with all new appliances, dishes, glassware, etc. - Top quality, brand new queen size beds -...
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    Siesta Key, Florida 34231
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Jamaica Royale #92 on the #1 Beach in the USA!1 / 12
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Porch
    • Patio
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 16, 2018
    After reading some of the reviews we were somewhat nervous. The resort was clean and staff was friendly. Our condo in Tower II was found clean and had a great view of the gulf...
    Reviewed August 12, 2017
    We came in around 5pm. I thought its ok not to call because they said in the email that the key will be left in the lockbox. No key when we got there. We had to call and after...
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    About this property
    Jamaica Royale condo #92. Located at the #1 BEACH IN THE USA, this 2 bedroom, 2 bath garden view unit has everything you need! It is located in the garden area of our beautifully landscaped property. It has new furniture and is freshly painted, with tile floors in the living areas and carpet in...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Ebb Tide #8 1 Bdr/2 Bath Fall Openings1 / 46
    (27)Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Patio
    • Wi-Fi
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Great location on Siesta Key. Easy walk to the best beach and lovely pool. Melinda was very accommodating and easy to work with. Thanks!
    Reviewed 3 weeks ago
    This is located on the beach side of Midnight Pass, a detail that is enormously helpful. As with most of the condos along the beach this one is dated as well. The unit itself is...
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    About this property
    Fall Openings !! Season 2019! 1 Bdr- (2) BATH! PRIVATE 2ND floor END unit! No one walking past door !! QUEEN SEALY in Bedroom, Leather QUEEN SLEEPER in living room, two comfortable leather RECLINERS that lay---- sooooo---flat you will wake up in often!! Plenty...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Siesta Key -  2bdrm on the beach - amazing views!!1 / 54
    (27)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Secure Parking
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Ocean Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    I can't imagine a better, more convenient location! Not only is the beautiful, expansive beach a few steps away, but there is bay right behind the condo, and a (free!) shuttle...
    Reviewed 4 weeks ago
    This condo is in the perfect location to start... private yet close to downtown with a free shuttle service that is timely and convenient. The views from sunrise to sunset will...
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    About this property
    The condo benefits from its own private pool. The living room, master bedroom, and lanai (balcony) all have stunning ocean views. The lanai, with over $10,000 of new doors and windows, is furnished with a table and chairs to enable you to dine al fresco. There is also a comfortable couch to...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Spacious 4bed air-con villa on Siesta Key1 / 26
    (2)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Parking
    • Grill
    • Patio
    • Washer
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 28, 2016
    This lovely 4-bed villa was well proportioned and kitted out for our party of 6 adults but deciding who should get the biggest and best bedroom with the only en-suite could have...
    Reviewed July 21, 2015
    We stayed two weeks here and had a wonderful time. The villa was very spacious with large bedrooms, eat-in kitchen and living rooms. Most impressive was how well equipped it...
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    About this property
    Very spacious, air-conditioned 4 bed detached ranch-type Villa on Siesta Key Bayside. Sleeps 8, 1 King, 1 Queen, 2 Full and 2 twin beds. 1 month minimum Jan-March, 2 week minimum April -Dec. Maximum 3 cars . Large Heated Communal pool, Own Outdoor patio area with BBQ , Table, seating and sun...
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    Siesta Key, Florida FL34242
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Honeymoon Suite - Gulf views - next to Siesta Key Beach1 / 21
    (6)Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Waterfront
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Grill
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 30, 2018
    The suite was lovely, and the bed was very comfortable. The grounds and pool were very well maintained. Great Beach access.
    Reviewed August 2, 2016
    Me and 2 friends booked this wonderful appoartment very short-term (the day before) and the owner Virginia was just amazing. She helped us with the booking, welcomed us...
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    About this property
    Gumbo Limbo Vacation Rentals: Honeymoon Suite, 60 steps to the BEACH. NEWLY REMODELED AND REFURBISHED. Spacious 1 bedroom / 2 full baths townhouse (850sq/ft) over 2 floors, with 1 King size bed, and a luxury Queen self inflating air bed for max. comfort. This townhouse also offers 2 balconies...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Private Siesta Key House - Walk to Village & Beach - Heated Pool/Spa - No Stairs1 / 26
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Patio
    • Grill
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 29, 2018
    I stayed over the winter holiday with my husband and other adult family.It was the perfect place to have a pleasant vacation. Close to all shops and downtown and also a short...
    Reviewed September 5, 2017
    What a beautiful modern and superbly located house. Immaculate and well maintained with everything you could possibly need. Our host Randy was excellent and answered our...
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    About this property
    Steps from the islands best restaurants, shops (in the Village area) and a short walk to the #1 beach in the USA! Great home with 2 car and 1 car private garages. Recently renovated including a screened in patio, hot tub and pool. Brand new appliances making this home a great place for monthly...
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    Siesta Key, Florida 34242
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beachfront- Gulf View! 2 BR/BA Crescent Arms 603S, #1 Beach in the US.1 / 24
    (9)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Washer
    • Ocean Views
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 25, 2018
    Such a well appointed condo, with a fabulous location right on the beach.Easy walking distance to some great restaurants. Our owner was very attentive and answered all...
    Reviewed November 13, 2017
    We loved this condo. The beach was wonderful. Siesta Key Village was so close with great restaurants to choose from... Pavan was very nice to work with. What more can you ask...
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    About this property
    - Expansive, panoramic gulf view from every room of this 6th floor condo. -Crescent Arms is a quiet, beach front, high rise condominium building that is ideally located for maximum fun and relaxation. -Right on the beach with lounge chairs provided. As close as you can get to the Gulf without...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    A Tropical 1Br Retreat on a Florida Isle1 / 24
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Patio
    • Balcony
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Siesta Palms by the Beach . . . where we invite you to relax, unwind and enjoy our casual way of life. Resting just one block from the powdery-white sands of Siesta Key's world famous, award-winning Crescent Beach is our tropical Siesta Palms by the Beach. With no busy streets to cross,...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Beach Walk Townhouse1 / 16
    (4)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 20, 2018
    The space was great. Very close to Siesta Key Beach. The only thing is that it is a 3 floor duplex and it makes it kind of difficult bringing your stuff up the stairs.
    Reviewed April 10, 2017
    Loved the location. No, this is not right on the beach but it was just a short walk. We spent most of our time just north of the public beach where there were very few people...
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    About this property
    Spacious Beach Getaway (sleeps 6), Calle del Otoño unit D, a 3 bedroom / 2.5 baths townhouse of 2,000sq/feet which is located right next to Gumbo Limbo. It offers 1 king, 2 twins and 1 queen size bed, brand new carpeting (January 2016), a balcony with partial Gulf view and a heated pool. This...
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    Siesta Key, Florida 34242
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Sea Shell Condo-Right On Crescent Beach-Siesta Key1 / 24
    (9)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Air Conditioning
    • Terrace
    • Wi-Fi
    • Grill
    • Ocean Views
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 17, 2018
    Clean, roomy, well-stocked with all kitchen amenities that you could think of. Master bedroom very roomy. Extra space for your bathroom essentials in medicine cabinet...
    Reviewed August 24, 2017
    We stayed in unit 207. The property is very nice. The condo was clean, modern and well equipped with all your kitchen needs and wants. We like to cook and were pleased with the...
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    About this property
    If you are looking for the perfect spot for a family vacation, to escape the cold and snow, or a quiet romantic getaway this is the place for you. Recently updated throughout, this 2 bedroom 2 bath condo sleeps 6 comfortably all in real beds. Just outside your door is Crescent Beach, consistently...
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    Siesta Key, Florida 34243
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Newly Renovated Waterfront Condo w/Beach Access1 / 21
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Waterfront
    • Cable/satellite TV
    • Balcony
    • Washer
    • Parking
    • Air Conditioning
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 25, 2017
    A really lovely apartment, very well equipped. location is perfect if you want a peacful beach holiday.Turtle beach is stunning and great for fishing, swimming and collecting...
    Reviewed April 17, 2017
    This is a wonderful 2-bedroom, 2 bath condo overlooking the bay. The nicely decorated lanai is a great place to relax with your morning coffee. The kitchen is wonderfully...
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    About this property
    Our 2nd floor, end unit condo was completely renovated over the winter of 2012– 2013. The floor plan was opened up to provide a nice airy feel and to enjoy the water view. All furniture, flooring and fixtures are new. The entry hall has a bench to store your flip-flops and other beach gear and...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Siesta Key, Heated pool, Gulf and Bay, Cute Siesta Key Condo, Gated1 / 21
    (2)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Housekeeping Included
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 9, 2018
    The Sea Club condo was fabulous!! The location, being on the inner coastal, watching the boats every day and night go by, was perfect. Loved to watch the others fishing off...
    Reviewed June 16, 2017
    The apartment is on the waterway side of the key and is great if you want to fish. The walk to the beautiful beach is only a 10 minute walk away. The apartment is clean and...
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    About this property
    Our condo has just been remodeled with granite counter tops, stainless steel appliances, dishwasher, cabinets, new tile, new bathroom, and new furniture. It is a second floor unit. We have included all the essentials for a family that likes to have the flexibility to make meals at 'home' or...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Grand accomdation on USA #1 Beach  - Siesta Key Fl1 / 32
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Sauna
    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    • Children's Pool
    • Washer
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Harbor Towers Yacht and Racquet Club Unit 503 provides one of the best views in the building (fifth floor facing south/east). The glass enclosed Lanai with floor-to-ceiling sliding glass doors provides bright sunlight during the morning and afternoon with excellent views of the intercostal water...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Palm Oasis - Relax in Comfort -1 / 35
    (1)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Cable/satellite TV
    • Parking
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Wi-Fi
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Palm Oasis is a 4-bed single family home with 2,000 sq. ft. located only 1 block away from Siesta Key Beach. This home is on one level and has all the amenities including a brand new salt-water pool which is the center of the backyard and a outdoor BBQ grill with a bar to enjoy your fabulous...
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    Location Information
    Siesta Key, Florida 34242
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Patio
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    • Shared Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Got Paradise!? Well now you do..... This oasis on Siesta Key is just that. The condo is only a block or so away from famous Siesta Key beach and rests in Siesta Key Village where you will find lots of great dining, amazing shops, coffee houses and more, all a short walk away. With everything you...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Siesta Key 2 BR, 2 1/2 Bath - *Across From Beach - Pool-view* - Newly Renovated1 / 49
    (3)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Balcony
    • Washer
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    • Patio
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 27, 2017
    Lovely condo - great for a Ladies' Weekend Away! Very spacious and clean. It was easy to get to town and the beach using the Frog Hopper FREE taxi service! Washer and dryer was...
    Reviewed August 11, 2017
    The location is family friendly and close to everything . Very nice pool and very clean condos. Excellent management team . Very eager to help you to have the best experience...
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    **** Newly Renovated (Jan 2018) **** Steps to Siesta Beach and a Gorgeous Condo, Bring the Entire Family! #1 Beach in the US (2017) : Siesta Key is the United States #1 Beach Boasting Miles of Powder White Sand and a Charming Village loaded Shopping, Dining and Ice Cream :) Our 2 bedroom 2.5...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 7
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    New furnishings (11/17) complete an already fabulous condo! Be the first to enjoy this newly painted, newly furnished adorable & quaint ground floor two bedroom, one bath condo with water views and all of the amenities you are looking for in a fun yet relaxing atmosphere. This particular unit is...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Children's Pool
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    About this property
    This is a large, bright and clean 2 bedroom and 2 bath first floor Condo. Being first floor gives you extra entrance through patio or lobby. Also one of the few condos with a private patio with new furniture to enjoy the beautiful weather and view. Condo clean and bright and beautifully decorated....
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Crescent Arms 703S, Beachfront Penthouse, Gulf View from Every Room! 2BR-BA1 / 40
    (11)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Pet friendly
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    Reviewed 1 week ago
    Pavan and Tracy are very attentive and accommodating. During our stay we needed nothing. the Condo is well appointed, nicely furnished and had everything we needed, including...
    Reviewed June 12, 2017
    The location is amazing. Walking distance to Captain Curts and other great restaurants and ice cream shops. The view of the beach is amazing. The owner checked in with is before...
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    -Accommodations: Condo, 2 Bedrooms + Convertible Bed, 2 Baths (Sleeps 4-6) -Expansive, panoramic gulf view from every room of this 7th (top) floor condo. -Crescent Arms is a quiet, beach front, high rise condominium building that is ideally located for maximum fun and relaxation. -Right on the...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Got Paradise!? Well now you do..... This oasis on Siesta Key is just that. The condo is only a block or so away from famous Siesta Key beach and rests in Siesta Key Village where you will find lots of great dining, amazing shops, coffee houses and more, all a short walk away. With everything you...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Gorgeous Direct gulf Front 2 Bedroom Condo on Siesta Keys... JUST REMODELLED1 / 31
    (11)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 3, 2018
    Fishermans cove condo was perfect. It was located at the lower end of the key so it was quiet. The unit allowed for views of the sunrise and sunset. We have booked it for next...
    Reviewed November 26, 2017
    We loved the condo, loved the location. The staff was very friendly and helpful. I cant say anything bad about it, it was GREAT!! I cant wait to go back!
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    About this property
    Our Fisherman's Cove condo description Paradise awaits - GORGEOUS, totally renovated in 2016, two bedroom, beach front condo on the Gulf of Mexico with sunset views overlooking the and sunrise views of the lagoon, expansive water views from every window. Beach was restored so it is large...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    About this property
    1st Floor Large Corner Unit Newly Painted & Furnished This is a large corner unit 1280 sq. ft in the center of private Crescent Beach which is deeded just for the Palm Bay Guests. This is a gulf to bay resort which gives you access to a pool , fishing pier & hot tub on the bay side along with...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sandy Toes Siesta Key Florida   (6798)1 / 37
    (20)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
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    Reviewed 2 weeks ago
    Firstly, let me say we've never booked a place which wasn't a hotel or a resort. So this was new for me. I found tripadvisor very helpful and Sandy Toes Siesta Key was a...
    Reviewed 3 weeks ago
    We loved this place. Lots of space in a private community with a pool and private beach access. They really do have everything you’ll need at the house: beach chairs, bikes...
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    About this property
    A short stroll down a private road to the #1 Beach in the US. You will love the location - you are located in the Resorts of the SaraSea community and can walk to everything you might need or want... Grocery, restaurants, ice cream, pizza, sports rentals, drugstore or boat rental. You have your...
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    Siesta Key, Florida 34242
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Luxury Villa, Sleeps 6 Comfortably Located on Siesta Key Beach, Sarasota Florida1 / 26
    (6)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 16, 2018
    The house was beautiful, lots of updates throughout and you can tell it's really well cared for. It's so nice staying in the villa as opposed to one of the hotel-room...
    Reviewed October 9, 2017
    This was the 2nd time we stayed at this villa. It was even more beautiful than last time. It was very clean, new beds, couch and love seat, fully stocked kitchen if you want to...
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    About this property
    ZERO HURRICANE DAMAGE IN OUR AREA - This is a Luxurious Villa on Siesta Key Beach Florida on Crystal Sands - Experience why Siesta Key, Sarasota Florida has been rated the #1 beach in the USA (#5 in the world by TravelAdvisor) for so many years. Siesta Key is one of the only beaches in the world...
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    Siesta Key, Florida 34242
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Charming Siesta Key Condo, Walk to Beach, Pool1 / 29
    (5)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 21, 2017
    The location is perfect, the beautiful white beach of Siesta Key is on your doorstep. If you feel energetic it is a brisk 25 minute walk into the village from the condominium or...
    Reviewed July 10, 2016
    Very short walk to the beach! Sue is so friendly! The condo was in excellent condition! We will definitely stay here again!
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    About this property
    Spacious Condo on Siesta Key with 2 Queen Beds is beautifully furnished, all new, and super clean! WALK RIGHT OVER TO THE #1 BEACH IN AMERICA, you do not need a car on this vacation stay. And if you want to see the rest of Siesta Key you can take the free shuttles, and the new Siesta Key Trolley...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    NEW EVERYTHING Luxury King Villa #2  JUNE 16TH 6 NIGHTS  Walk to the beach Pool1 / 13
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    About this property
    Everything is new in our 1 bedroom condo. Inside and out King size double pillow top bed Kitchen, Coffee maker, Microwave, Toaster. 55 inch HDtv in lounge 50 inch HDtv in bedroom New heated swimmimng pool Free internet Free parking A short walk to Siesta Key beach 2 night Minimum retals
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    The Banyan - A Tropical Retreat in Paradise1 / 25
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
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    Smoking allowed
    Reviewed April 26, 2018
    The Banyon is a remarkably beautiful and comfortable home. There are many private seating areas inside and out. The kitchen is fully equipped; the beds are very comfortable and...
    Reviewed August 12, 2017
    We loved this place! It was so private you felt like you were in your own world with the surrounding trees and tropical landscaping, yet close to most everything. The home was...
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    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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Siesta Key Townhouse across from Pristine Sand & B1 / 30
    (17)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    Pet friendly
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    Reviewed September 6, 2017
    Beautiful townhouse overlooking a small lake. Turtles swam by below the balcony and popped up their heads to say hello! Everything you could want for a wonderful stay was...
    Reviewed July 29, 2017
    Spent a lovely 10 days in Michelle's condo.......couldn't have asked for much more, from the very beginning of the booking Michelle was always on hand to answer any queries we...
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    “Pristine sand, blue skies - 'Number 1 Beach'” The Best Thing to Come Home to after a Day on the Beach Is... ...a vacation home as comfortable as your own home. Just a walk across the street to Siesta Key's world famous #1 Beach. This split-level townhouse, has 2 bedrooms (King in Master...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Villa Palma - The Best Mid-Century-Modern Siesta Key Villa1 / 21
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Patio
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    Pet friendly
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    Reviewed November 7, 2016
    We had a great time at Villa Palma. The villa is very clean and it has everything you need for your stay. It is very close to the beach, we ended up only going to the beach. The...
    Reviewed August 10, 2016
    What a LOVELY place to stay!!! Sean was flexible, attentive and accommodating, and there was even fresh fruit, sparkling water and a personalized welcome sign waiting on the...
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    About this property
    Villa Palma is a stand-alone single story villa located in the beautiful Polynesian Gardens community, on the beautiful barrier island of Siesta Key, Fl. The home is chic and hip in its mid-century modern beach cottage decor and schictyle. The newly renovated kitchen is sleek in design and...
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    Siesta Key, Florida 34242
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    SIESTA KEY! Tranquil Gulf-side 2 Bed/2 Bath in Jamaica Royale  #1041 / 19
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Reviewed March 7, 2017
    Truly awesome experience. Quiet garden sid. A home away from home. Nice sheets & new towels. Everything we needed. Very responsive & helpful owner Beach side, 3 pools...
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    About this property
    Jamaica Royale Condominiums are located directly on the Gulf of Mexico along the white sands of world-famous Siesta Key Beach in Sarasota, Florida. A barrier island on Florida’s West coast, considered the most beautiful of Florida’s barrier islands, Siesta Key’s beach boasts “the world’s finest...
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    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Siesta Key Condo, Crescent Arms, unit 605 South1 / 24
    (16)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    The tropical storm didn't stop us. We loved it. The home was amazing. Everything was there you would ever need.
    Reviewed 3 weeks ago
    This condo is by far one of the cleanest and most beautifully decorated on the island. Comfortable beds, great living area, well equipped kitchen... and the view from the lanai...
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    About this property
    Split floor plan with each bedroom having a private full bath, tv and access to the lanai. New bathroom floors installed in October 2016 and new tile in master bath/tub. New king size mattress as of May 2017. New stainless steel microwave and range November 2017. Free Siesta Breeze open air...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Bay Views - Private access to Beach. Enjoy Tennis, Heated Pools, Fishing1 / 50
    (11)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    Reviewed December 28, 2017
    Beautiful beach and spacious condo with all amenities at your doorstep, enjoyed tennis , pool and exercise room and outdoor gas grill right across street yet still very private...
    Reviewed November 20, 2017
    We had a wonderful vacation stay in this condo. It was spacious, clean and had beautiful views of the waterway. We really enjoyed having our morning coffee watching the boats go...
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    About this property
    Gulf & Bay Club Bayside is a gated resort community is across the street from our private access to - Siesta Key Beach with the world renowned white sands - rated one of the top ten in the US! FREE High Speed Wireless Internet ! - just bring your Laptop. Watch the boats float by! Just steps from...
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    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Siesta Villa Laughing Gull - Boutique Chic Villa. Steps From Pool, Dock, & Beach1 / 21
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 14, 2017
    We just got back from our stay at the Siesta Villa Laughing Gull. It is a wonderful 2 bedroom home. Everything is as pictured and stated in description. We stayed with a family...
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    About this property
    Siesta Villa Laughing Gull Find yourself in the relaxing comforts of Siesta Villa Laughing Gull. A single-story stand-alone villa, located in the beautiful private community of Polynesian Gardens, on the tropical barrier island of Siesta Key, Fl. The peaceful tranquility of Villa Laughing Gull is...
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    Siesta Key, Florida 34242
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    Discover the beauty of Siesta Key at Siesta Villa Whispering Palms. Our recently renovated 3-bedroom, 2-bathroom stand-alone villa is your new home-away-from-home. Featuring 1700 sqft of air-conditioned living space, an open floor plan, large living spaces, spacious bedrooms, and well-manicured...
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    Siesta Key, Florida 34242
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    NEW EVERYTHING  Luxury 1 king Bedroom  Villa #4  Siesta Key Pool JUNE 19TH 3 DAY1 / 12
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    About this property
    Luxury King 1 bedroom condo King Size - Double pillow top bed Ground floor Air conditioning Daily, Weekly, Monthly rates. Everything new 2017 Kitchen Coffee maker Toaster Microwave Stainless Steel fridge with ice maker 21 Years and over Heated swimming pool Free parking Free...
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    Siesta Key, Florida 34242
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    You will Never Want to Leave this Upscale, Mid-Century Modern, 4 bedroom Pool home with Salt-Water Canal Views and Boat Dock on Siesta Key!!! This unique 1950's built, renovated, 4 bedroom, 3 full bath, 'Sarasota School of Architecture style' pool home is conveniently located...... only a 6 minute...
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    Siesta Key, Florida 34242
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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    Luxurious 2 BR Condo - Short Walk to Siesta Beach1 / 14
    (18)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 20, 2017
    We stayed at the apartment for 2 weeks during Easter holidays with our 2 girls (aged 1 and 4). We had a lovely holiday. We felt there was some positives and negatives with the...
    Reviewed January 31, 2017
    Everything about this condo was fantastic! The beautiful two bedroom/ two bathroom, spacious, quiet, the large swimming pool and two gas grills which we used often, we will...
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    About this property
    Newly furnished, newly renovated 2BR (one king size & 2 single beds) + convertible sofa bed, 2 Bathrooms 2nd floor condo (sleeps 4-6), and with all the amenities of a comfortable home. Located in White Sands Village with 7 acres of lush tropical surroundings, our air-conditioned condo offers two...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sarasota-Siesta Key Coastal Five Bedroom with Pool and Spa1 / 76
    (6)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 1, 2018
    Perfect location. Very close to the beach and downtown. The sliding kitchen windows opening to the counter bar in the screened in pool and hot tub area made eating in so fun...
    Reviewed March 4, 2018
    The location is fantastic. Literally one short block to worlds greatest beach. Short one mile walk into the quaintest town with lots of restaurants, bars, shops. The house was...
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    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
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 13
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed 2 weeks ago
    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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    Location! Location! Location! Walk out the door, across the street and onto the # 1 ranked beaches in America! This beautiful condo is on the ground floor, no steps, with a tropical enclosed lanai. It features 3 televisions, Tommy Bahama furnishings, a barbecue grill and high speed internet for...
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    Location Information
    Siesta Key, Florida 34242
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Siesta Key Condo w/Private Beach Access, Wifi Included,  Heated Pool, Tennis & B1 / 30
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 29, 2018
    Loretta's place was clean, comfortable, and beautifully kept. It's on the second story with private balcony and a short walk to the beach and an even shorter walk to a nice pool...
    Reviewed March 11, 2018
    Condo was very comfortable, great location, Nice view from balcony. Complex was well-maintained resort like on the bay. Owners were always available to speak with any hours...
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    About this property
    Step out onto your private balcony and watch the boats docked in a small cove just off the intercoastal. - Completely redone 2 bedrooms, kitchen, baths, living room in a beautiful beach theme with predominantly white colors with pops of turquoise, teal and calming sea blue. - Enjoy...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Patio
    • Air Conditioning
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy your vacation in this beautifully renovated two bedroom 1.5 bath condo that sleeps 6. Step into the unit and immediately notice the warm open feel, the beautifully tiled floors and the sweeping panoramic views of an inlet off of the intracoastal waterway. The view goes on for acres and...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Newly Renovated & Modern, Wifi, Gulf Facing Harbor Towers, 3 bedroom with den1 / 30
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 22, 2018
    What an amazing property! Everything is brand new. Condo is equipped with everything you could possibly want/need! Loved that everything we needed for the beach was provided...
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    About this property
    Newly remodeled, modern and beautiful 3 bedrooms, plus a den, 3 full bath condo right on Siesta Key, in a complex overlooking the intracoastal waterway and close to the beach!! Fabulous powdery white sands of Siesta Key Beach are just a short stroll away!! You won't be disappointed! Take a look...
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    Location Information
    Siesta Key, Florida 34242
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    1
    Siesta Key Flight and Weather Info
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    83° 68°
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    84° 69°
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    85° 70°
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    Additional Siesta Key Info

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    • Local time: 01:15 AM (EDT)
    • Peak travel: February - April
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