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Siesta Key Apartment Rentals

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    Travellers to Siesta Key are booking March dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 25
    5 of 5 stars (4) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    5 of 5 stars (14) Excellent
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    5 of 5 stars (2) Excellent
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Very cheerful, updated and professionally decorated 2 bedroom/2 bathroom, 1400+ sq. ft unit on 4th floor in elevator building. Ceramic tile throughout invites a cool and clean feel. King Bed in Master Bedroom. Two Twins in Guest Bedroom. Maximum of no more than 4 people. Spacious screened-in glass... View all property information
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    Siesta Key, Florida 34242
    1 / 30
    5 of 5 stars (26) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Siesta Key, Sarasota upscale vacation rental unit within a few steps of the water or a gorgeous pool. Lush, tropical landscaping in well maintained Bay Oaks. Breathtaking views of the intercoastal with fully appointed fishing dock. Across the street from the beach and there are no beach charges on... View all property information
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    Siesta Key, Florida 34242
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    Centrally Located in Building 4 on the 3rd floor with a very nice Gulf View. Elevator. Living room has new leather sofa sleeper 11/09 TV, with new Sony DVD player. Screened in Lanai. Master bedroom has king size bed with TV. Master bath has step up to large tub with shower head & shower curtain.... View all property information
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    Siesta Key, Florida
    1 / 41
    4.5 of 5 stars (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Condo, 2 Bedrooms + Infl bed(s), 2 Baths, (Sleeps 4-6) Fisherman's Cove condominium. Walk directly into the beautiful azure waters of the Gulf of Mexico at Turtle Beach or onto your own boat at the private lagoon entrance to the Intra-coastal. Spacious ground floor unit with spectacular views and... View all property information
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    Siesta Key, Florida 34242
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Updated and beautifully decorated 2 bedroom/2 bath 4th floor unit. Overlooks gulf side pool, Crescent Beach and Gulf of Mexico. Washer and dryer in unit. Living room includes a sofa sleeper, TV, DVD player. Master bedroom offers Queen bed, TV, DVD. Master bath has walk-in shower with seat. Guest... View all property information
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    Siesta Key, Florida
    1 / 18
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    VERY SPACIOUS 5th Floor corner unit overlooking the tranquuil waters of the intra coastal waterway. The glass enclosed lanai stretches from the living room to the master bedroom. Living room is adorned in Florida decor and has TV, DVD, portable stereo w/CD player. Off the kitchen is an additional... View all property information
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    Siesta Key, Florida
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    Cozy Cove is a small condominium complex of six total units, located on the south end of Siesta Key in Sarasota, Florida. The complex sits on the Gulf side of the Key along Blind Pass. The complex itself is on the inlet with a dock at the back of the property where you will often see fish jump and... View all property information
    Location Information
    Siesta Key, Florida 34242
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    THIS 2 BEDROOM/2 BATH 2ND FLOOR WALK UP UNIT HAS BEEN REMODELED!! Light ceramic tile throughout; updated kitchen with granite counter tops and stainless steel appliances! Beautifully decorated with leather sofa and reclining chair. Flat screen TV in living area; flat screen TV with DVD players in... View all property information
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    Siesta Key, Florida
    1 / 13
    3 of 5 stars (1) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Do you need a paradise vacation? We've got the perfect vacation rental for you..You will enjoy a two bedroom first floor condo located in the plush, rolling 14 acres of greenery of Midnight Cove ii that provides a tranquil serene atmosphere. You will be able to eat breakfast on our lanai as you... View all property information
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    Siesta Key, Florida 34242
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    About this property
    Gorgeous intra coastal waterway view from this fifth floor two bedroom/two bath unit. Tastefully decorated, light and bright. Over 1400+ s.f. with tiled glassed in lanai over looking the tropical gardens, boats and waterway. Only a five minute walk to our private piece of world famous Crescent... View all property information
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    Siesta Key, Florida
    1 / 30
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    If you are looking for a place to unwind and decompress, this is the ideal place for you. Experience Siesta paradise with incredible sunsets and balmy breezes directly on the Gulf of Mexico with its beautiful white sand beaches stretching for miles. And not to brag, but the number one beach in the... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    This cozy efficiency apartment is located less than a mile from the beach. Our private building boasts just 4 units, allowing for a boutique style setting in a residential area. Come relax in this newly offered efficiency apartment on the second floor (walk up). Not only is this unit Turnkey... View all property information
    Location Information
    Siesta Key, Florida 34242
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    I have tried to make this apartment as comfortable as your own home only at the beach. This unit has two bedrooms and two baths. It can accommodate six people with a king bed and two double beds. There are plenty of closet and dresser space, a fully-equipped kitchen, color TV's, VCR and/or DVD and... View all property information
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    Siesta Key, Florida 34242
    1 / 35
    3.5 of 5 stars (12) Average
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    The Cottages at Siesta Key offers totally renovated vacation cottages on Siesta Key off the coast of sunny and beautiful Sarasota, Florida! 13 Villas only a 2 minute walk from the beach! Studios up to 4BR's! We rent daily, weekly or monthly and there is no minimum stay, except for weekends,... View all property information
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    Siesta Key, Florida 34242
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    New to rental program. View all property information
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    Siesta Key, Florida 34242
    1 / 29
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    About this property
    NEW UPDATES AND BEAUTIFULLY DECORATED 2 BED/2BATH; over 1400 s.f. located on the first floor. Ceramic tile floors in living areas. Dine al fresco or sip a margarita on the spacious screened lanai at the table or high top bar overlooking the lush tropical grounds, crystal white sands of the beach... View all property information
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    Siesta Key, Florida
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    About this property
    Island House Beach Resort! Crescent Beach, Siesta Key Florida. This beautifully maintained complex is located on the widest part of one of the best beaches in Florida. This condo offers a view of palm trees, white sand and the turquoise waters of the Gulf of Mexico. The view is picturesque and the... View all property information
    Location Information
    Siesta Key, Florida
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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
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    • Pet-friendly
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    • x
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    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
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    Siesta Key, Florida 34242
    1 / 17
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Beach front and fabulous! Everything is new and remodeled in this unit! Sun yourself on the open balcony and enjoy this 2 bedroom/2 bath in style. The living room is furnished with a LCD TV/VCR, leather sofa and decorated with brilliant colors! The master bedroom offers a king bed and a flat panel... View all property information
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    Siesta Key, Florida
    1 / 15
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    About this property
    Direct Beach front! Step out your back door to Crescent Beach and the Gulf of Mexico. Updated two bedroom/two bath 1100 s.f. unit w/ceramic tile floors, upgrades in kitchen - granite counter tops, custom cabinetry. Master bedroom has BRAND NEW King bed and guest bedroom has two twin beds.... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 26
    4.5 of 5 stars (7) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    PLEASE NOTE: The Price displayed here is NOT ACCURATE! (It does not take the 'Seasonal Rate' into consideration) - Sorry - this is Flipkey's policy, not ours. This luxury third floor condo #308 is bright and airy with its extra long Lanai! The Lanai (screened porch) overlooks the Gulf,... View all property information
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    Siesta Key, Florida 34242
    1 / 10
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Beautiful, newly renovated, beach front apartments on Siesta Key. One bedroom, one bathroom with jacuzzi tub, all linens, full size modern kitchen, living room with full size futon couch, flat screen tvs in the living room and bedroom with Verizon Fios, NBA League Pass, all premium channels, free... View all property information
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    Siesta Key, Florida 34242
    1 / 18
    4.5 of 5 stars (9) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    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
    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
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    Siesta Key, Florida 34242
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    About this property
    Look at the fabulous intercoastal waterway view from this spacious 3 bedoom/2 bath bayfront unit! Step out back lanai door to the tropical grounds and bay. Only a few minutes to walk to our own little private piece of world famous Crescent Beach! No need to bring your own beach chairs...we have... View all property information
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    Siesta Key, Florida
    1 / 17
    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Island House Beach Resort! Crescent Beach, Siesta Key Florida. This beautifully maintained complex is located on one of the best beaches in central Florida. This 3rd floor, 2 bedroom, 2 bath condo offers views of palm trees, white sand and the turquoise waters of the Gulf of Mexico. The view is... View all property information
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    Siesta Key, Florida
    1 / 39
    4.5 of 5 stars (6) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
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    Siesta Key, Florida 34242
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    NEWLY REFURBISHED 2 BR, 1.5 BA !! New floors, paint, furniture, decor & appliances in 2012. This light and bright ground floor condo is the closest Bay unit to the pool, office, laundry and beach. The newly furnished screened lanai offers views of the beautiful tropical grounds. Living room has... View all property information
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    Siesta Key, Florida
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    *** NEW *** Never miss a beach-scape sunset when you are just a couple hundred meters from Americans #1 beach, Siesta Key Beach. Enjoy this two bedroom two bathroom condo style unit in a great location: a short walk to the beach on a quite street but just minutes from shops, bars, and restaurants.... View all property information
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    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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    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
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    Siesta Key, Florida 34242
    1 / 17
    5 of 5 stars (41) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Find your vacation getaway on the island paradise of Siesta Key, Florida! SIESTA KEY BEACH HAS BEEN RATED THE #1 BEACH IN AMERICA BOTH BY TRIP ADVISOR (2015) AND DR. BEACH in 2011. Our condo is located on this beautiful beach, known as 'The World's Finest, Whitest Sand'. A tropical vacation... View all property information
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    Siesta Key, Florida 34232
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    Perfect for guests looking for a rental of one month or longer, your time spent at Siesta Key Gulf & Bay Club #409 is guaranteed bliss. Confirmed to be the “Best Sand Beach in America” by the Travel Channel, Siesta Key’s residents and renters alike know they’ve got a very good thing. On Florida’s... View all property information
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    Siesta Key, Florida 34242
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    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    2nd Floor with stairs walk up. Living room has sofa bed, TV, VCR, & DVD. Glass enclosed Lanai with great views of canal. Master bedroom has king size bed with TV. Master bath has tub with shower head & glass doors. Guest bedroom has two twin beds. Guest bath is half bath. Complimentary Wi-Fi in... View all property information
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    Siesta Key, Florida
    1 / 5
    4.5 of 5 stars (22) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    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
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    Siesta Key, Florida 34242
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    4 of 5 stars (16) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    How long does it take you to walk 100 yards? Not very long at all. While on vacation at Crescent Beach, consider that your morning commute - from bed to pool. Enjoy the great convenience of a ground floor unit at Siesta Key’s Jamaica Royale unit 91. Delight in the great value of this garden view... View all property information
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    Siesta Key, Florida 34242
    1 / 17
    5 of 5 stars (1) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 6 | Quick View
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    Island House Beach Resort, Siesta Key Florida! This is a newly fully renovated one-bedroom, two-bath top floor apartment with a great view of the beautiful Gulf of Mexico. It sleeps up to six with one king bed in the bedroom and two queen-sized sleeper sofas in the apartment. There is a room that... View all property information
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    Siesta Key, Florida 34242
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    2 bedroom, 2 bathroom on 4th floor, lovely view... Enjoy the best that beautiful Bay Oaks has to offer. This 4th floor corner condo has been remodeled. With 1101 square feet, this 2BR/2BA condo has a living room, dining room, kitchen and screened lanai where you can enjoy morning coffee or evening... View all property information
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    Siesta Key, Florida 34242
    1 / 22
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Village West # 101 is the perfect place for your Siesta Key Vacation. With rentals by the day, by the week, or longer this location is sure to please. Our newly Remodeled Siesta Key Ground Floor Apartment is in the heart of the Village of Siesta Key. This apartment is well appointed and... View all property information
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    Siesta Key, Florida 34242
    1 / 30
    5 of 5 stars (8) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
    • Sauna
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    Across the street is our Private Access to one of the BEST beaches - Crescent Beach on Siesta Key.Gulf & Bay Club Bayside is a Resort complex of Key West style Town Homes all with one car attached garages. Gulf & Bay Club Bayside offers:* two heated pools* clubhouse with exercise/workout center and... View all property information
    Location Information
    Siesta Key, Florida 34242
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    beautifull, totally remodeled condo ,fully porcelain tiled, new cherry kitchen cabinets, stainless appliances, granite and lanai overlooks pool with small view of #1 beach in U.S. fully furnished with 3 TV, cable and internet and utilities included. Local area offers fun , swimming , fishing,... View all property information
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    Siesta Key, Florida 34242
    1 / 19
    4 of 5 stars (1) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Only 60 steps to #1 most beautiful Beach in the nation – SIESTA KEY PUBLIC BEACH -. Spacious newly remodeled 1 bedroom studio apartment with (580sq/ft) ground floor, 1 King size bed and a luxury self inflating Queen air bed for max comfort. The bathroom offers a walk-in rain-forest shower. The... View all property information
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    Siesta Key, Florida 34242
    1 / 38
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    WHAT A VIEW! Very updated, tastefully modern, Bay Front Condo with AMAZING views of the water! ALL NEW, absolutely BEAUTIFUL Hardwood floors! Newer, Stainless Steel appliances in the fully equipped kitchen with dishwasher, full-size refrigerator, microwave, oven and stove. GORGEOUS bathrooms,... View all property information
    Location Information
    Siesta Key, Florida 34242
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    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 4 | Quick View
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    • Grill
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    • Terrace
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    About this property
    Our two bedroom condo is a five minute walk to one of the most beautiful beaches in the world. Siesta Key is famous for its pure white sand and crystal clear water. It is always ranked near the top of the best beaches in the country. After a day in the sun you can return to a quiet and lush... View all property information
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    Siesta Key, Florida 34242
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    NEW TILE CERAMIC TILE THROUGHOUT UNIT! Spacious 2 bed/1.5 bath first floor unit with extended living room. Walk right out your back door to the canal and boat docks. Living room offers comfortable leather seating & TV, DVD, VCR. Master bedroom features king size bed with TV. Master bath has tub... View all property information
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    Siesta Key, Florida
    1 / 35
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Beautiful Bayside 3 bed/2 bath 1800+ s.f. 4th floor unit overlooking the sparkling intra coastal waterway. Just watch the boats glide by from your spacious glass enclosed lanai. Spacious floor plan includes cool and light ceramic tile throughout; comfortable and neutral Florida style decor; very... View all property information
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    Siesta Key, Florida
    1 / 42
    4 of 5 stars (1) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    YOUR PRIVATE GETAWAY ON THE KEY ASK ABOUT OUR SUMMER SPECIALS!!!!!!!!! Does not include Weekends or Holidays!!! Looking to relax, Flip Flop Cottages is the place to be for a quaint and private vacation in Siesta Key, Florida. Come and stay at our serene environment and enjoy and visit all the... View all property information
    Location Information
    Siesta Key, Florida 34242