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Holiday Rentals in Osprey

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    The following rentals are within 15 kilometers of Osprey, Florida.

    1 / 7
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    1 / 19
    5 of 5 bubbles (1) Excellent
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
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    • x
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    • x
    About this property
    Enjoy the Florida lifestyle in this 4th Floor, 1400 sq. ft., 2 BDR/ 2 Bath condo overlooking the tranquil waters of the intra coastal waterway. Cross the road and you are just a few hundred feet away from your own piece of the soft white sugary sands of Crescent Beach. Master bedroom is furnished... View all property information
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    Siesta Key, Florida 34242
    1 / 19
    Siesta Key
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    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
    Location Information
    Siesta Key, Florida 34242
    1 / 17
    5 of 5 bubbles (4) Excellent
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Private Outdoor...
    • DVD Player
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    • Terrace
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    • Pet-friendly
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    • x
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    • x
    About this property
    Spectacular view on Crescent Beach, Siesta Key florida. This 3rd floor unit is located directly on the Gulf of Mexico. Enjoy panoramic views from living room, master bedroom, guest bedroom. This unit is 2 bedrooms, 2 bathrooms and is 1300 sq. ft. King, 2 twins, central heat/ac. It has a large... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 23
    5 of 5 bubbles (3) Excellent
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    • Waterfront
    • DVD Player
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    • Pet-friendly
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    • x
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    • x
    About this property
    Totally renovated during the summer of 2012, this all-new 2 bedroom, 2 bath Penthouse unit directly on the Gulf of Mexico has North Carolina pine wood and Portuguese Carrara marble floors, LG stainless steel kitchen appliances, granite counter tops and three state-of-the-art Samsung 'Smart TVs'... View all property information
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    Siesta Key, Florida 34242
    1 / 42
    5 of 5 bubbles (21) Excellent
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    • Sauna
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    • Pet-friendly
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    • x
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    • x
    About this property
    Our condo is on the second floor and is only 3 doors from the lovely pool, jacuzzi and fishing pier. The private Cresant Beach which is deeded just for the Palm Bay Guests and is just across the street from the Bay side. It is raked every a.m. and loung chairs set out and also has a charcole grill... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 24
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
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    • Secure Parking
    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    The gated Sea Shell complex sits directly on our #1 Crescent Beach with unit #105 easily accessible from the 1st floor just above the ground floor parking area. Sea Shell is a secure community centrally located at the heart of south end of Siesta Key across from the world renowned Captain Curt's... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 38
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    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
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    1 / 24
    Siesta Key
    8 Bedrooms, 3 Bathrooms, Sleeps 16 | Quick View
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    • x
    About this property
    This is a wonderful Siesta Key Waterfront Home just steps to the main Siesta Key beach!!!! ( only 1 BLOCK away) An expansive 2700 sq ft residence, this home contains 8 bedrooms, 3 baths and situated directly on the water. This perfect location is right in the middle of siesta key; between the... View all property information
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    Siesta Key, Florida 34242
    1 / 17
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Newly redecorated 5th floor unit overlooking the Gulf of Mexico. Ceramic tile throughout, leather sofas in living room with queen size sleeper, large flat panel TV and DVD. Step out on the spacious screened lanai from the living room or master bedroom and watch the Florida sunset. Kitchen is well... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 16
    4.5 of 5 bubbles (2) Very good
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
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    • x
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    • x
    About this property
    Island House Beach Resort - Siesta Key Florida, Crescent Beach - This large villa is approx. 1000 sq. ft. It has a large living area, dining area, fully equipped kitchen, all appliances, screened lanai, central ac/heat, covered parking, 3 tvs, dvd, free wi-fi in unit!. It has a king size bed,... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 14
    4.5 of 5 bubbles (13) Very good
    Siesta Key
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Air Conditioning
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    • Pet-friendly
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    • Smoking allowed
    • x
    About this property
    Our favorite location on Siesta Key, The Siesta Key Village Studio, brought to you by Gertrude Rentals! 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... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 20
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    2 BR. - 2 BA -- 6 Person Max. -- High Rise -- Pond/Cityscape View 1080 - 601 is a Gulfside Highrise unit, located approximately 125 yards away from Crescent Beach 2 Bedroom / 2 Bath unit. Approx. 1250 Sq. Ft. (1375 including the lanai) Bedding: Master Bedroom: King Guest Bedroom: King... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 16
    Venice
    1 Bedroom, 1 Bathroom, Sleeps 1 | Quick View
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    • Patio
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    • x
    About this property
    Great house - newly tiled, freshly painted, very clean. It has everything you need, just show up and relax. The street is very quiet so there's no traffic noise. There is an empty lot across the street which increases the privacy. The back yard is completely fenced with privacy fencing. There's a... View all property information
    Location Information
    Venice, Southwest Gulf Coast 34295
    1 / 25
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Beautifully decorated 2/2.5 overlooking the serene canal waters and boat docks. Only a short walk to your own private piece of the white sands of Crescent Beach. No need to drag beach chairs...we have lounge chairs and umbrellas for our guests. Living areas are ceramic tiled and walk out to the... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 38
    Siesta Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    ONLY A BRIEF 5 MINUTE WALK TO OUR PRIVATE PIECE OF CRESCENT BEACH!Gorgeous, updated 3 BD/2.5 BA two story townhouse overlooking the tranquil canal and tropical greenery. Located on the ground floor is the spacious living room with 50" flat panel TV,DVD,VCR, CD stereo and high speed internet access.... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 25
    5 of 5 bubbles (3) Excellent
    Venice
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Ocean Views
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    • Grill
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    • Pet-friendly
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    • Smoking allowed
    • x
    About this property
    Villa Grande is a light, bright and sunny split-design single family home which is located just minutes away from the popular Sharky's restaurant, downtown Venice and several fabulous beaches. A single story home, it is fully updated with ceramic tile floors throughout and features a split design... View all property information
    Location Information
    Venice, Southwest Gulf Coast 34293
    1 / 24
    Venice
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Outdoor...
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    • Private Garden
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    • ?
    • ?
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    • x
    About this property
    Enjoy our roomy 2 bedroom, 2 bath vacation home in beautiful Venice, FL. This ultra cozy home is exceptional because it is situated on five lots (your average home has one lot). You'll have privacy and “room to breathe”. The residence has a private pool and patio, which adjoin the lanai. The pool... View all property information
    Location Information
    Venice, Southwest Gulf Coast 34293
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    1 / 30
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
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    • x
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    • x
    About this property
    Fantastic Bay side unit on the 3rd floor with an elevator. 2 bedroom 2 full bath with washer and dryer. Beautiful tile thru out the unit looks like wood flooring. Living room has large flat screen TV, unit also has wireless internet. Great "Cooks" kitchen everything a cook would need, New granite... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 8
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Central property, 1st & 2nd floor garden style unit with 2 Bedrooms and 2 Bathrooms. All rental properties are turn-key furnished and include washer & dryer. Internet access, beach access, tennis courts and exercise facilities available, access to two swimming pools. No pets are permitted on the... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 19
    4.5 of 5 bubbles (25) Very good
    Siesta Key
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    The Royal Palm Suite (sleeps 6) is a 3 bedroom luxury townhouse of 1,850 sq/feet over 3 floors, 2 kings and 1 queen size bed, 3 balconies (each has a Gulf View), almost all rooms have a Gulf view, a kitchen with granite counter tops, master bathroom offers a bathtub with Gulf view and a bidet.... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 21
    Siesta Key
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • x
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    • x
    About this property
    Siesta Villa Coralline is a stand-alone single story villa located in the beautiful community of Polynesian Gardens. Villa Coralline has been designed & decorated as an upscale beach cottage featuring two bedrooms, one with a queen bed and the second with two twins. The villa’s tropical beach theme... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 28
    Siesta Key
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Cute ground floor 2 bed / 1.5 bath unit just steps to pool and boat docks from back door of unit. Extended living room makes this over 1000 sq. ft. of living space. New carpet and wood laminate in living area. Florida decor with sleeper sofa, TV and DVD player in living area. Master bedroom has... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 24
    4.5 of 5 bubbles (18) Very good
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • ?
    About this property
    Siesta Key - Gulf-Front Retreat - 2 BR – Free Boat Docks Located Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views.  The building is one of the closest condos to the Gulf... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 22
    Siesta Key
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    NEWLY FURNISHED!! Ground floor unit Bay side. Extended living room area. Unit has large tile throughout. The unit will comfortably sleep 6 people. Master has a King bed , guest bedroom has two twin beds and a new queen sofa sleeper in the living room. Kitchen has been updated as well with newer... View all property information
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    Siesta Key, Florida 34242
    1 / 26
    5 of 5 bubbles (1) Excellent
    Venice
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Ocean Views
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    • x
    About this property
    Sandcastle Cottage is a comfortable one story open floor plan 2 bedroom single family home located only minutes away from popular Sharky`s restaurant (and the newly opened Fin's) and the Venice Fishing Pier. It features two bedrooms and two baths with a tile floor, breakfast bar that seats three... View all property information
    Location Information
    Venice, Southwest Gulf Coast 34293
    1 / 38
    Siesta Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Magnificent 6th floor, quiet, end/corner unit with over 1600 sq. ft. of spacious living space. The unit is a 3 bedroom 2 full baths. Master bath has large walk in shower with dual sinks. Guest bath is tub/shower combo. Tile flooring through the entire unit except the larger guest bedroom with queen... View all property information
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    Siesta Key, Florida 34242
    1 / 22
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    Beautifully decorated first floor 2 bed/2 bath 1400+ sq. ft. bay front unit. Glassed enclosed lanai makes an extra family room and overlooks the intra coastal waterway. Step out the back door to stroll the lush, tropical grounds of island paradise! Living room offers TV, VCR, DVD, Stereo,... View all property information
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    Siesta Key, Florida 34242
    1 / 17
    Siesta Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Spacious 1600+ sq. ft. 3/2 ground floor unit. Step out lanai and back door to pool and beach! New flat screen tv's in living room and all bedrooms, king bed in master bedroom. Step-in shower/roman tub in master bath. Guest bedroom has queen bed and guest bath has a tub/shower combination. 3rd... View all property information
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    Siesta Key, Florida 34242
    1 / 26
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    NEWLY PAINTED AND CARPETED IN MAY '07. Step right out your back door to the soft, white sugary sand of world famous Crescent Beach! You are so close to the Gulf of Mexico in this 2/1.5 unit. Tastefully decorated and you can watch the sunset right from your screened lanai! The living room offers a... View all property information
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    Siesta Key, Florida 34242
    1 / 15
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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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
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    Siesta Key, Florida 34242
    1 / 15
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    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 / 17
    4.5 of 5 bubbles (6) Very good
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Island House Beach Resort - Siesta Key Florida, Crescent Beach - This NEWLY REMODELED, 2 bedrooms, 2 bath unit is appox. 1000 sq. ft. It has a large living area, dining area, newly remodeled kitchen, all new tile floors, screened lanai, covered parking, central ac, free wi-fi in unit. It has 3 tvs,... View all property information
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    Siesta Key, Florida 34242
    1 / 16
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Beautifully remodeled and redecorated unit with granite countertops and stainless steel appliances in the kitchen; ceramic tile throughout and updated baths! Gorgeous decor! This 2 bed/2 bath second floor 1400+ s.f. unit overlooks the tropical gardens and Gulf of Mexico! Enjoy the lazy days in... View all property information
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    Siesta Key, Florida 34242
    1 / 25
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    This condo unit is just minutes from the World Famous Siesta Key Beach! It is located on the Intracoastal waterway with full use of the clay tennis courts, lounge chairs and gorgeous outdoor areas. It is a ground floor unit with private exterior entrance from it's private patio with hammock and... View all property information
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    Siesta Key, Florida 34242
    1 / 42
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Many recent upgrades and enhancements with more to come! All new carpet as of 2017! Beautifully decorated, 2 level, 2BR/2.5BA townhome! Split level, with living room, lanai, kitchen, dining and half bath on the main level and 2 bedrooms, (master has open-air patio) 2 full bathrooms and washer/dryer... View all property information
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    Siesta Key, Florida 34242
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    Nokomis
    4 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    • Central Heating
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    • Waterfront
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    Enjoy a slice of Florida paradise for your large group at this newly renovated beach house! Perfect for multiple families vacationing together, family reunions, or snowbirds wanting extra bedrooms to accommodate the visiting grandkids. The property is located West of Route 41, minutes to Casey... View all property information
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    Nokomis, Florida 34275
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    5 of 5 bubbles (1) Excellent
    Siesta Key
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Patio
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    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
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    Siesta Key, Florida 34242
    1 / 13
    Siesta Key
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Everything is new in our 1 bedroom condo. 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 Adult only 21 years and older A short walk to Siesta Key beach 2 night... View all property information
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    Siesta Key, Florida 34242
    1 / 20
    Siesta Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    3 BR. - 2.5 BA -- 6 Person Max. -- Townhouse -- Greenbelt View 1207 is a Bayside Townhouse unit, located approx. 100 Yrads away from the Intercoastal waterway. 3 Bedroom / 2 1/2 Bath unit. Approx. 1400 Sq. Ft. (1500 including the lanai) Bedding: Master Bedroom: King Guest Bedroom: 1... View all property information
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    Siesta Key, Florida 34242
    1 / 38
    Siesta Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    • Pet-friendly
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    • x
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    • Smoking allowed
    • x
    About this property
    3BR Unit with over 1800 sq. ft of living space! Unique kitchen layout optimizes gulf viewing and includes stainless steel appliances, granite countertops, new cabinets, and a Keurig coffee maker. New flatscreen tv's throughout and wireless internet. Fabulous 180 degree view of the white sands of... View all property information
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    Siesta Key, Florida 34242
    1 / 12
    Siesta Key
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    • x
    About this property
    Sea horse Villa Is in our beach house on Siesta Key Your own prive entrance. Outside sitting area with a table and chairs. Perfect fpr a couple. I bedroom and a futon in the lounge. Microwave, Coffee maker, Sink, Fridge. Fully furnished. Daily rentals. Located a short walk from the number 1 beach... View all property information
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    Siesta Key, Florida 34242
    1 / 7
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Relish in the Florida sun on Crescent Beach! Relax & kick back in this attractive two bedroom condo with a stunning view!! Our condo is a two bedroom and two bathroom renovated unit (2011). Some new furniture and granite & marble kitchen counter tops. High speed wireless internet, free local & long... View all property information
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    Siesta Key, Florida 34242
    1 / 11
    Lido Key
    1 Bedroom, 5 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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    • x
    About this property
    Large 1 bedroom fully furnished condo (981 square feet) includes 1 bedroom, 1.5 baths, featuring an open kitchen with island, dining room, living room and an office. 10th floor.<BR><BR>Fully equipped, brand new kitchen with granite countertops, sofa sleeper, cable TV, telephone, and WiFi. Laundry... View all property information
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    Lido Key, Sarasota 34236
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    Siesta Key
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Spacious, newly furnished, 3 bedroom, 2 bath, top floor, Gulf waterfront, unit on #1 ranked Siesta Beach. Expansive views of the Gulf, beach, and pool from the open patio, the Florida Room porch, the living room, the master bedroom and the guest bedroom will relax and delight you. Open the sliding... View all property information
    Location Information
    Siesta Key, Florida 34242
    1 / 24
    5 of 5 bubbles (1) Excellent
    Siesta Key
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
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    Welcome to Cape Aqua! This single family vacation rental home on Siesta Key has 3 bedrooms 2 1/2 baths and pool. Located on the closest private street to America's #1 named.The two large double doors with decorative frosted glass welcome you into this spacious home. The floor plan offers a very... View all property information
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    Siesta Key, Florida 34242
    1 / 18
    Nokomis
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
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    • Private Outdoor...
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    • Grill
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    About this property
    Beautiful Florida waterfront home dock for your boat minutes to beaches,tiki bars,islands by boat or car fenced in yard well behaved pets welcomed hot tub and wet bar on pool deck to watch beautiful sunsets kayaks and stand up paddle board on site great fishing large and roomy home.jump on... View all property information
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    Nokomis, Florida 34275
    1 / 7
    Siesta Key
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    1-403 has a new kitchen, updated baths and updated interior with an extended living space. The living area has a cathedral ceiling and partial Gulf view. Wireless internet is available. All window treatments are new. Additional amenities include: bathtub/shower in guest bathroom, 2 twin beds in... View all property information
    Location Information
    Siesta Key, Florida 34242