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Holiday Rentals in Siesta Key, FL

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    1 / 42
    5 of 5 stars (11) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 29
    5 of 5 stars (7) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    5 of 5 stars (8) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
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    About this property
    For the most up to date availability and pricing please visit our subscription listing on Flipkey I39II38 Leave your worries behind... If you're looking for a relaxing beachfront condo that's been totally remodeled you've come to the right place. (all new photos coming later this month) Our... View all property information
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    Siesta Key, Florida 34242
    1 / 27
    4 of 5 stars (9) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Internet Access
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    About this property
    Welcome ! Sea Club II is Located steps away from the whitest sand and the # 1 beach in America, Siesta Key. Our location 200 yards away has an easement for private beach access. We are located on the intercoastal waterway of Little Sarasota Bay on the island of Siesta Key . Whether you are keen... View all property information
    Location Information
    Siesta Key, Florida 34242
    4 of 5 stars Reviewed 3 days ago
    We arrived on January 9 and stayed 21 days. The property was lush with trees and hanging miss. After unpacking our car we went into the condo. And, we were greeted by a colorful...
    4 of 5 stars Reviewed 12 August 2015
    I was very nervous about using this site, due to the great prices and fake looking pictures. I just don't trust anything on the internet. My girlfriend showed me the site, I...
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    1 / 16
    5 of 5 stars (8) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    About this property
    BIG FALL SALE !!! Oct 10 to Dec 19 GREAT Value !!! MVPROPERTIES AT SIESTA KEY Recently renovated and very conveniently located duplex villas at beautiful Crescent Beach on Siesta Key. We have (2) 2 bedroom 1 bath apartments. Each apartment sleeps up to 5 persons. Rent 1 apartment or both. The... View all property information
    Location Information
    Siesta Key, Florida 34242
    4 of 5 stars Reviewed 15 August 2015
    Ideally situated 2 minutes from the beach, restaurants,shops and 7 eleven. Very clean accommodation has everything that you need but does need a little refurb ie furniture...
    5 of 5 stars Reviewed 10 August 2015
    We had a great stay here. The owners were VERY pleasant. Everything that you would need for a beach vacation with a toddler was included and readily available. The place was...
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    1 / 20
    5 of 5 stars (7) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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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 / 16
    5 of 5 stars (21) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Porch
    • Parking
    • Patio
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This lovely 2BD/1BA apartment is located just 1 mile from beautiful Siesta Key Beach. Siesta Key was rated the #1 Beach in the United States by Dr. Beach (2011) and the #2 Beach in the U.S. in the 2013 TripAdvisor Travelers Choice Awards. Siesta Key was listed in 2014 by Smarter Travel.com as... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 16 October 2015
    Our family had another wonderful stay in Siesta Key!! We were here two years ago (I forgot to write a review.), and everything was a great now as it was then. Kathy and Dan...
    5 of 5 stars Reviewed 11 August 2015
    My family and I stayed in this 2 bedroom, one bath apartment from 8/1 - 8/7/15 and from the moment we arrived, we fell in love with the place, the décor, the location and all of...
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    1 / 26
    5 of 5 stars (37) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    €108
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    • Grill
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    • x
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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 / 23
    5 of 5 stars (32) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Patio
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    • Washer
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    • Satellite TV
    • DVD Player
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
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    About this property
    Ebb Tide #3 is waiting for you: All quality furnishings & linens, fully equipped with everything you need for a fun and relaxing beach vacation! This cottage-style condo has been redone with your comfort in mind. Rated the #1 Beach in the USA: Crescent Beach on Siesta Key is literally a 3 minute... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 28 December 2015
    Loved everything about the place. sue was very hospitable and the place was spotless. Loved the proximity to the beach and the great restaurants within walking distance. Loved...
    5 of 5 stars Reviewed 13 December 2015
    Very seldom does a place live up to and exceed expectations, but this local gem is amazing! The yard is lovely, with comfy place to sit and grill, if you want to eat in. Our...
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    “Pristine sand, blue skies - 'TripAdvisor's best beach in the U.S. in 2015' The Best Thing to look forward to after a Day on the Beach Is... ...Another Day on the Beach : ) 1001 Beach Rd unit W502, Siesta Key Fl 34242 Just a walk across the street to Siesta Key's world famous #1 Beach. This... View all property information
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    Siesta Key, Florida 34242
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    €538
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    • Sauna
    • Internet Access
    • DVD Player
    • Satellite TV
    • Waterfront
    • Patio
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    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... View all property information
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    Siesta Key, Florida 34242
    2 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    €139
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    • Air Conditioning
    • Shared Garden
    • Grill
    • Ocean Views
    • Satellite TV
    • Wi-Fi
    • Secure Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
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    About this property
    Stay at our newly renovated open and relaxing vacation rental... Welcome to Sunspot at Sea Club II located on the Intracoastal Waterways and across the street from the world famous Siesta Key Beach. A perfect short or long term getaway. Enjoy the Fishing Pier, Day Boat Dock, Pool, Keyed Beach... View all property information
    Location Information
    Siesta Key, Florida 34242
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    €1,071
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    • Ocean Views
    • Porch
    • DVD Player
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Washer
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Leave your worries behind... If you're looking for a relaxing beachfront condo that's been totally remodeled you've come to the right place. (all new photos -just uploaded!) Our ground-level oceanfront condo is the perfect place to unwind unplug and recharge the batteries. Fisherman's Cove is a... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 19
    4 of 5 stars (15) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Patio
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Grill
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This Siesta Key Studio was renovated and refurbished in November 2013 it has all new furnishings throughout and is accompanied by a secluded outside area with table and chairs, BBQ and reclining sun loungers surrounded by tropical plants and foliage. Easy access - no stairs. Fully equipped... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 1 week ago
    Derick & Marina were a pleasure to work with as far as response time and availability. My husband and I stayed at the Ebb Tide, unit 7, for a short 5 day stay. It was exactly...
    3 of 5 stars Reviewed 29 November 2015
    This rental will meet your needs as a couple if you plan on spending the bulk of your time at the beach and pool which were close by with easy access an plenty of room. The unit...
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    1 / 39
    4.5 of 5 stars (6) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
    • Balcony
    • Air Conditioning
    • DVD Player
    • Waterfront
    • Internet Access
    • Satellite TV
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • x
    About this property
    -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... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 12 November 2014
    What a breathtaking view to walk into when you step inside the condo! This place is just heavenly and we relaxed from the moment we stepped inside. It was perfect for our family...
    4 of 5 stars Reviewed 15 February 2014
    Room is great. View is outstanding. We really enjoyed our stay. Room is quiet no outside noise. We recommend
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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
    • Washer
    • Air Conditioning
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Elder access
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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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
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    • Terrace
    • Private Outdoor...
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    About this property
    *** NEW PROPERTY *** Stay directly across from Siesta Key beach at this beautiful lakeside condo. Stepping through the front door you are greeted with an open floor plan in this two bedroom two bathroom condo. The living room is equipped with flat screen TV and seating for the whole family. Step... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 38
    4.5 of 5 stars (6) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    €901
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    • Waterfront
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    • Secure Parking
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    • DVD Player
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Elder access
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    About this property
    A mere stones throw from the Gulf from this beachfront vacation paradise! Located on Siesta Key in Sarasota, Florida, this vacation home has the best of both worlds -- the beach in front and the Intercoastal and boat docks in back with a heated swimming pool in the middle. This beachfront vacation... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 6 January 2015
    Our family of 5 (kids: 11, 13 & 15 yrs) just LOVED this place. The condo was great and in a beautiful area and had everything we needed...beach toys, lawn chairs, fishing poles...
    4 of 5 stars Reviewed 10 April 2014
    This is the fifth time we have had the pleasure of vacationing at El Galeon. We love the location with the beautiful beach access and walking to restaurants. We love the Manasota...
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
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    • x
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    About this property
    Enjoy this upscale townhouse located within walking distance of Siesta Key Village and beaches. This 3 bedroom 3 bath Mediterranean style townhouse is the perfect escape for rest and relaxation. It features a private swim spa, is located in a quite neighborhood, and is just around the corner from... View all property information
    Location Information
    Siesta Key, Florida 34242
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    1 / 28
    4.5 of 5 stars (9) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Take to the water or stick to the shore - the world is your proverbial oyster while staying at Siesta Key’s Palm and Bay Club G88. Enjoy great comfort and value in this gulf-view suite, with all the resort amenities you can imagine. Two pools and a fantastic hot tub, a large fitness center and lit... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 8 September 2010
    Palm Bay club is a beautifully maintained property located on the best section of Siesta Key Beach. The view from Grand Tower 88 is spectacular.
    4 of 5 stars Reviewed 23 June 2010
    Excellent vacation location! Definitely will come again. The view is very good - we liked very much where the side where the balcony was - nice beach view, relaxing and not too...
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    1 / 29
    5 of 5 stars (6) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Ocean Views
    • Grill
    • Wi-Fi
    • Waterfront
    • Washer
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    About this property
    Fisherman's Cove condo description Lovely 2 bedroom, beach front condo on the Gulf of Mexico with sunset views overlooking the gulf and sunrise views of the lagoon, expansive water views from every window. . Watch the sunset, the birds and ocean wild life swim by. Swim, snorkel, fish, surf or... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 4 December 2015
    Nice, clean, well equipped condo unit. Everything working properly. Buildings are located at end of the street, so no through traffic. It was very quite. There is even a public...
    5 of 5 stars Reviewed 19 November 2015
    If you are looking for ocean and beach views this is the place. The condo is decorated well and clean, the staff here is friendly and helpful and close to good restaurants. I...
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    1 / 52
    4.5 of 5 stars (8) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Roll into the lap of luxury and enjoy a unit that’s still sparkling new. Siesta Key Gulf and Bay Club is known to be the finest long-stay resort in the area - and this newly renovated unit with a new air conditioning and heating system, Gulf and Bay Club 305C, trumps the competition. Sleeping 6,... View all property information
    Location Information
    Siesta Key, Florida 34242
    4 of 5 stars Reviewed 17 July 2013
    Quite satisfied with our condo unit. Plenty of room for family of 6. Very happy with the condition (cleanness) of the kitchen. All plates, dishes, silverware, coffee maker very...
    4 of 5 stars Reviewed 2 January 2013
    Close to beach, nice and clean place. Found it slightly over- priced though. There are other decent places available at lower rates.
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    1 / 37
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    €1,000
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    • Internet Access
    • Satellite TV
    • Patio
    • Washer
    • DVD Player
    • Sauna
    • Air Conditioning
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Smoking allowed
    • Elder access
    • x
    About this property
    This gorgeous Siesta Key luxury beach view condo is directly on world famous Crescent Beach located mid-Key, just south of the south bridge and right across the street from South Village with fast access on/off the island. This Siesta Key vacation rental condo is located in the Siesta Breakers... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 26 July 2015
    Very nicely decorated, and well-stocked, condo right where 72 hits the main north/south street on the key - so a few miles south of the Village. A terrific location! Really good...
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    1 / 26
    5 of 5 stars (1) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    €176
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Elder access
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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... View all property information
    Location Information
    Siesta Key, Florida FL34242
    5 of 5 stars Reviewed 21 July 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 was...
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    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Gorgeous 2 bedroom condo across the street from #1 voted beach Siesta Key. We have everything for your home away from home. The beauty of Sarasota will get your attention on your first visit. Siesta Beach is one of the top ranked beaches in the world! Its fine quartz white sand has a silky,... View all property information
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    Siesta Key, Florida 34242
    1 / 39
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Our House on Siesta Key is located on one of the most beautiful streets on Siesta Key 'Sunset Point'. You are literally a few feet from the cool, white sandy beach and a few feet from 'The Village'. No need to use your car to get to a grocery store, bank, restaurants, nightlife, boutique... View all property information
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    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 3 January 2016
    After vacationing in Florida every year for over 30 years, this property on Siesta Key was by far one of my top overall visits. The accommodations were similar to a five-star...
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    1 / 18
    4.5 of 5 stars (9) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Gertrude's Twin Banyan - Oasis at Pool & Beach - Study the water in the pool or wander to the beach and village. This relaxing oasis is framed by 70 year old banyan trees and rests on a quiet tropical street just one and one half block from the best beach and two and one half blocks from the best... View all property information
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    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 10 December 2015
    Fabulous, clean and comfortable condo. Short walk to beach and to the village. Lovely clean pool, great for cooling down in the heat!, I asked for an iron and board and they were...
    5 of 5 stars Reviewed 3 December 2015
    Property: Gertrudes Twin Banyan, 446 Canal Rd - 2BR/1Bath; sleeps 7 This condo was a great place. Nice pool. Convenient to beach, restaurants and shopping. The walk to town...
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    1 / 35
    5 of 5 stars (32) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    About this property
    Siesta Key, Sarasota upscale vacation rental unit with a direct view of the intercoastal water. Lush, tropical landscaping in well maintained Bay Oaks.Breathtaking view of the intercoastal with fully appointed fishing dock. Across the street from the beach and there are no beach charges on Siesta... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 2 December 2015
    When we arrived at the condo, Barbara was there to greet us and gave us the tour. The location faces the intercostal waterway with great scenic views from the screened in lanai...
    4 of 5 stars Reviewed 22 November 2015
    We stayed at the apartment for 3weeks. Beautifully decorated and furnished, kitchen fully stocked with whatever utensils/crockery/cutlery you might need. Shower was excellent, AC...
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    1 / 22
    5 of 5 stars (8) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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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 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 own... View all property information
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    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 5 weeks ago
    The condo exceeded our expectations from amenities to beach location. There was not 1 item we needed that the condo did not have, including a very convenient outside shower for...
    5 of 5 stars Reviewed 26 December 2015
    The townhouse had everything needed for a comfortable stay. There was even a Christmas Tree set up for us to enjoy and gourmet popcorn left under the tree. The beach is only a...
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    1 / 16
    5 of 5 stars (4) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    • Hot Tub
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    • Pet-friendly
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    • ?
    • ?
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    • Elder access
    • x
    About this property
    Cortez Cottage is located within five minutes easy walk of Siesta Key beach, always rated in the top beaches in USA and world, powdery white sand and gorgeous Gulf of Mexico gentle waves and stunning sunsets. The cottage is just a couple of minutes walk from the heart of Siesta Village, with... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 3 June 2014
    Couldn't have asked for a better place to stay. Having never been to Siesta before, I initially wasn't sure where the location was, in comparison to the beach and commercial...
    4 of 5 stars Reviewed 24 June 2013
    we stayed here with my whole family in May 2013. The place is great, close to everything e very clean. I have a newborn, so it was great to go home earlier when the sun was too...
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    1 / 24
    4.5 of 5 stars (9) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • x
    • x
    About this property
    A spacious 2 bedroom 2 bath Townhouse, with a 2 car garage and extra guest parking. Stroll down a private road (about 300 yards) to the #1 Beach in the U,S. You are in the Resorts of of Sara Sea and just a couple of blocks from restaurants, grocery, sports rentals and ice cream ! The Great room... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 2 January 2016
    The condo exceeded our expectations from amenities to beach location. There was not 1 item we needed that the condo did not have, including a very convenient outside shower for...
    5 of 5 stars Reviewed 23 September 2015
    We had a great time at Sandy Toes. We stayed with our children and they had a great time on the beach and riding bikes. Very clean and just a few steps away from the beach!
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    1 / 14
    5 of 5 stars (9) Excellent
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    €74
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    • Air Conditioning
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    • Outdoor Dining Area
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    • Patio
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Elder access
    • x
    About this property
    Our favorite location on Siesta Key, The Siesta Key Village Studio, an accommodating ground floor one-room efficiency apartment perfectly nestled on a quiet tropical street between the best beaches, shopping and dining on the island. Wander one block to your beach, appropriately named “Sunset... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 30 September 2015
    We had a little over a week gap between selling our home and closing on our new home and had no place to stay. Easy enough to find a place to stay unless you have three dogs. The...
    5 of 5 stars Reviewed 6 May 2014
    My husband and I have been married for two years now, but with his deployments, we haven't been able to have our honeymoon until now. We stayed here from april 20 - 27th. First...
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    1 / 28
    5 of 5 stars (14) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Porch
    • DVD Player
    • Grill
    • Waterfront
    • Air Conditioning
    • Washer
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Siesta Key, Sarasota upscale vacation rental unit with a direct view of the inter-coastal water. Lush, tropical landscaping in well maintained Bay Oaks. Breathtaking view of the inter-coastal 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 5 July 2015
    The place was amazing and even better than imagined. It was equipped with amazing leather couches to relax, full laundry service, an amazing shower, and a great kitchen with all...
    5 of 5 stars Reviewed 30 June 2015
    We absolutely loved this place - it feels like your home as soon as you arrive , and has the most wonderful setting , looking out to the trees and jetty . The setting is ideal for...
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    1 / 14
    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    • ?
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    • x
    About this property
    PLEASE BOOK THRU ME, CARRIE CAUDILL, FLORIDA, DO NOT SEND MONEY TO ANOTHER PERSON OR STATE. PLEASE CONTACT THE OWNER FOR PRICES AND DATE'S, DON'T GO BY FLIPKEY'S, CARRIE 941-587-4794 siestakeycarrie@gmail.com My ground floor rental is directly on the beach on the Gulf of Mexico, with... View all property information
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    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 7 September 2015
    Had Anything And Everything That A Family would use on there stay from sewing kit to surf toys and boards. Easy to reach if needed, but all was Great Thanks
    5 of 5 stars Reviewed 15 August 2014
    My family and I stayed at Fishermans Cove unit 102 from August 1-13. We found the pictures and description of the condo online to be accurate. The condo included many amenities...
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    1 / 5
    4.5 of 5 stars (22) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Welcome to your tropical getaway. Everything you need is right here or within walking distance. Lovely one bedroom condo is comfortably furnished with your relaxation in mind. The beautiful heated pool is right out your front door. A gorgeous sandy beach with warm, azure water is only steps... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 12 April 2015
    My sisters and I had a wonderful time staying at Peter and Linda's condo. It was so perfectly, neat and fully supplied of everything one would need to enjoy the beach. The kitchen...
    4 of 5 stars Reviewed 9 January 2015
    1) Excellent location, one house over from the beach, 2' to restaurants, café, stores... 2) Did not use the swimming pool. 3) Condo is small (400sf) but has everything you need...
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    1 / 42
    5 of 5 stars (46) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    €202
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    • DVD Player
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    • Air Conditioning
    • Internet Access
    • Grill
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Elder access
    • x
    About this property
    3 Bedroom, 2.5 Bath Beach Villa (Sleeps 8-10) What makes us different than other homes you may be considering: · The Beach - The home is located on the ocean side of Beach Rd., so you just walk out your door and through our private access path. It’s literally 230 feet to Siesta Key Beach.... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 30 December 2015
    I stayed at Shells villa five nights with my family and everyone enjoyed their stay so much we want to go back again soon. The villa is very comfortable and lovely decorated.
    5 of 5 stars Reviewed 11 December 2015
    We stayed four nights at the Shells Villa and had a wonderful time. The house had everything that we needed for a relaxing vacation. The home was very close to the beach and it...
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    1 / 40
    5 of 5 stars (19) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    €762
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    • Satellite TV
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    • Air Conditioning
    • Sauna
    • Washer
    • Grill
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Our condo is on the second floor and is only 3 doors from the lovely pool, jacuzzi and fishing pier.In the summer months from May 1 - Nov 1 I offer a low rate of $850 .00 per week. In the mid winter rate goes up to $1200.00 per week and for the months of March and april the rate is $1600.00 per... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 1 December 2015
    My husband and I had a wonderful stay in this apartment. It offers everything you could want, well equipped, clean, comfortable, near the pool, excellent pier for fishing and...
    5 of 5 stars Reviewed 10 August 2015
    My husband and I stayed in this awesome condo with three teenagers and we had the most fabulous time. I had some concerns about not being beach front and having to cross the...
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    5 of 5 stars (11) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    €275
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
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    • Elder access
    • x
    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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    4.5 of 5 stars (23) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    €81
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    • Satellite TV
    • Air Conditioning
    • Washer
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    • Wi-Fi
    • DVD Player
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This condo is the perfect getaway from the bustle and noise of everyday life. No need to stay in crowded and boring hotels. Relax and enjoy in comfort, a clean, beautiful, and updated condo on the gulf/beach side of world famous Siesta Key a short minute walk from the studio to the white sands of... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 3 August 2015
    This was by far the cutest place in town to stay. We were right where we could rent bikes and walk to restruants and stores. The beach well I know now why they say it is the...
    5 of 5 stars Reviewed 3 May 2015
    I was a great week, steps away from the beautiful beach, The arrangements and the condo were perfect.
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    1 / 19
    4 of 5 stars (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    €1,609
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    • Internet Access
    • Waterfront
    • Sauna
    • DVD Player
    • Balcony
    • Terrace
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    This is world famous Siesta Key where the sand is compared to powder. The sunsets over this gorgeous beach are breathtaking! This Condominium is fully-equipped, with a large wrap-around deck, overlooking a beautiful pool and sauna. The master bedroom has a king-size bed. The spare bedroom has two... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 3 November 2014
    I recently stayed at the Seashell in this unit on a vacation with my girlfriend and fell in love with the place. The surrounding area is fantastic! Forgetting the perfect scene on...
    5 of 5 stars Reviewed 19 August 2014
    I think this is our fourth year to stay here. Once again we had a wonderful time. Can't wait to come back.
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    1 / 29
    5 of 5 stars (35) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    €108
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    • Air Conditioning
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    • DVD Player
    • Wi-Fi
    • Parking
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    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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 / 34
    4.5 of 5 stars (6) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    €107
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    • Patio
    • Washer
    • Air Conditioning
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    • Wi-Fi
    • Grill
    • Satellite TV
    • Porch
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    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 13 August 2015
    We had a relaxing time and the kids had a blast. Nice place with access to the beach and a private pool. Restaurants and shops within walking distance and a quick drive to the...
    5 of 5 stars Reviewed 14 June 2015
    We stayed for 2 days after a 4 day cruise. The bungalow was very nice and clean. It was inviting and seemed like a home away from home. It seems like the owners do keep items left...
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    1 / 24
    4.5 of 5 stars (2) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    €807
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    • DVD Player
    • Shared Outdoor Pool...
    • Grill
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    • Terrace
    • Balcony
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Spacious and clean, this 2 two story condo at Midnight Cove II has 3 bedrooms and 2.5 baths to accommodate you and your guests. The main living area has large family room with 65' flat screen TV, 6 person dining room, full kitchen, and half bath. Upstairs the large master suite with king-size bed... View all property information
    Location Information
    Siesta Key, Florida 34242
    4 of 5 stars Reviewed 31 October 2013
    Easily locatable vacation home with lots of space for 6 people. Nice porch on the top floor, spacious living room and kitchen. Very close to parking place (15 meters). Excellent...
    5 of 5 stars Reviewed 4 February 2013
    This 3 bedroom, 2 1/2 bath condo was in a superb location on the property and in the Siesta Key area itself. The pool was a very short walk away. The beach was across the...
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    1 / 24
    5 of 5 stars (1) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    €1,076
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    • Private Outdoor...
    • Satellite TV
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Upscale town home with private heated pool in superb location. Find yourself just around the corner from Siesta Key village and a short walk or bike ride to Siesta Key beach. Situated on a quite street with lush landscaping, this town home can sleep up to 6 guests. On the first floor you will... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 16 December 2014
    We rented this town home for 1 week to get away from the brutal winter we have been having back home. We were looking to come down as a last minute trip and found this property...
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    1 / 39
    5 of 5 stars (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    €1,345
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    • Satellite TV
    • Private Outdoor...
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    • Waterfront
    • DVD Player
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Take a look at this spacious canal front home on Siesta Key with heated pool. This home is great for a large family or even two families with its open floor plan. Enter the home through the double French doors and down the foyer into the heart of the home; the open family room, living room w/... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 3 March 2014
    The property was as pictured, most everything is brand new when my family and I had stayed here. There is more than ample room for everyone to convene in the living spaces. We...
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    1 / 23
    3.5 of 5 stars (2) Average
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Terrace
    • Satellite TV
    • Grill
    • Balcony
    • Internet Access
    • Waterfront
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Come in and enjoy this spacious condo with water views of the intercostal in the quite and tropical community of Bay Oaks. This 2 bedroom 2 bath unit has plenty of space for 4. The generous kitchen is equipped with everything you would need when staying 1 week or a month. The living space is open... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 12 March 2014
    We stayed one week this March and had a great experience. The unit is tucked away at the end of the street with a covered parking spot for the unit. Check-in was as simple as...
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    1 / 30
    4.5 of 5 stars (12) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    €179
    / Night
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    Amenities & Details
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    There's plenty of room for everyone here at Our House. We have a split-level living/dining area, with a large living room made for a crowd! The huge sectional sofa faces our new HDTV with DVD player, so anytime you need a little downtime from all the outdoor fun, settle in with your favorite movie,... View all property information
    Location Information
    Siesta Key, Florida 34242
    3 of 5 stars Reviewed 31 July 2015
    We arrived on a Sunday and our 3-person family stayed for a week. PROs: Room enough for a small family Across the road from Siesta Key Beach park - 10-15 minute walk...
    4 of 5 stars Reviewed 7 September 2011
    Master bed was fine with me, but wife felt it was too firm for her. Of course, I could sleep on a tile floor.
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    1 / 23
    4.5 of 5 stars (8) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    €179
    / Night
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    Amenities & Details
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    So what if you don’t have a beach house of your own? When you stay at Our House at the Beach, you’ll feel right at home. Our House at the Beach 504W is located on the barrier island of Siesta Key, home to parrots, pelicans, and a beach that residents and visitors alike say has the finest and... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 31 May 2010
    Very nice accomodation. Pool and BBQ facilities outstanding. Would definitely recommend and revisit.
    4 of 5 stars Reviewed 2 March 2010
    The Excelsior is a very nice condo complex. We were a little disappointed with the condo unit as far as cleanliness. It also could use some updating and had loose floor tile in a...
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    1 / 19
    4 of 5 stars (31) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    €112
    / Night
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    Amenities & Details
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Do you have children who’ll delight in the geckos and insects they can discover in the garden? Or do you love nature and the sight and scents of tropical flowers? An idyllic ocean side condo perfect for energetic kids or families seeking added privacy, Siesta Dunes Beach 38A is your perfect... View all property information
    Location Information
    Siesta Key, Florida 34242
    5 of 5 stars Reviewed 13 October 2014
    Nice unit. Loaded. Parking ids a few steps away with storage room with a lot of different stuff. Walking distance to the beach is about 5-7 mins. About 5 mins walking distance to...
    4 of 5 stars Reviewed 22 August 2012
    Siesta Dunes is a great place for families with the location of the pool and the beach, however 38a is the farthest unit from the pool, so if you have small children it is a good...
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    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.