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Holiday Rentals with Pools in Osprey

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    Osprey is popular with travellers just like you. Don’t let them get your perfect place first—book today!
    31 Matching Rentals in the Osprey AreaView all 48 rentals
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    Osprey
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Welcome to the Paradise1 / 17
    (1)Excellent
    Osprey
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly paradise with heated pool close to Sarasota-Osprey-Nokomis-Venice1 / 17
    (2)Very good
    Osprey
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    2 BR / 2 BA Condo in Stoneybrook Golf & County Club - Sarasota & Siesta Key1 / 15
    (2)Excellent
    Osprey
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Hot Tub
    • Grill
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • Sauna
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 June 2018
    The location is amazing! The condo was super clean and very family friendly. I loved the community with multiple pools and the awesome clubhouse. It was just a short drive or...
    Reviewed 25 May 2018
    There was not a single unmet need the entire week. This unit is clean, comfortable, and serene. The kitchen has everything, so we cooked a lot. From the beach towels, cooler...
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    About this property
    Stoneybrook Golf & Country Club is a gated community on Palmer Ranch with a fully renovated clubhouse with fine and casual dining, close proximity to Siesta Key's world-famous beaches, shops, restaurants, and Sarasota's active arts communities. This unit is a ground-floor end/corner unit with extra...
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    34238, Osprey, Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Osprey
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Patio
    • Grill
    • Washer
    • Wi-Fi
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Dear Renter, I am Beya, the owner and I'm offering authentic villas in the natural environment on Palmer Ranch. The villa is a spacious house with stunning garden with palm and pine trees. The location is just perfect, Mall, restaurants, and park are located just minutes drive, sparkling Siesta Key...
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    34238, Osprey, Florida
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Osprey
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Parking
    • Internet Access
    • Terrace
    • Air Conditioning
    • Balcony
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully re-modeled 2nd floor unit on Turtle Beach! Sit on your lanai and enjoy the amazing views of the Gulf of Mexico. Complex offers shuffle board, heated pool, boat docks by application and a prime location on Turtle Beach. Enjoy Sunday Brunch at O'Pheila's on the water just a short walk...
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    34242, Osprey, Florida
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Osprey
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Wi-Fi
    • Private Garden
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Idyllic beachfront home located on exclusive, unique Casey Key in Sarasota, Florida. Set in lush tropical greenery including 61 palm trees, sea grapes, and Hibiscus plants, just a few backyard steps to a white sand beach and spectacular sunsets on the Gulf of Mexico. Walk to historic Casey Key...
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    34229, Osprey, Florida
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Osprey
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Begin your sunkissed adventures at this 2-bedroom, 1-bathroom vacation rental condo that sleeps 4 in Siesta Key. This coastal condo boasts all the amenities of home with the luxuries of an upscale resort. Spend your days lounging around the heated community pool or take a short stroll to nearby...
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    34242, Osprey, Florida
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    The following rentals are within 10 kilometres of Osprey.
    LUX CONDOs near beautiful, sparkling Siesta Key Beach.1 / 27
    (1)Excellent
    Gulf Gate Branch
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Washer
    • DVD Player
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 October 2017
    The location is great. Really close to the beach. The host is very friendly and helpful. We enjoyed our vacation.
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    About this property
    Dear Renter, I am Beya, the owner with more a decade experience in the vacation rental field. I have been offering authentic condos in the beautiful natural area of the Vintage Grand community. I would be happy to host you in one of my condos.I have down and upstairs floor condos with lake-view or...
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    34238, Gulf Gate Branch, Florida
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Gulf Gate Branch
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    • Private Garden
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Amazing 2 bedrooms, 2 bathroom, with private backyard in a quiet neighborhood. This bright and fully remodeled home is tastefully decorated and well stocked. Conveniently located close walk to Publix and Walmart. Restaurants, cafeterias, spas, beauty salons, bars are around downtown area and only...
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    34233, Gulf Gate Branch, Florida
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4/3 Pool home 4 miles from Siesta Key Beach1 / 24
    (1)Excellent
    Gulf Gate Branch
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Private Garden
    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 January 2018
    This was an amazing place and we couldn't have been happier with our selection. Having a screened in pool attached to the house allowed us easy access everywhere without going...
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    About this property
    U-shaped home surrounding a private pool in the center. 4 bedrooms, living and dining area overlook pool. 40' of glass doors make this true indoor/outdoor living. House sits on a corner lot with 2 driveways. There is room for 2 cars in the rear driveway. House also has a washer/dryer. Split plan...
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    34233, Gulf Gate Branch, Florida
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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    Gulf Gate Branch
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Cable/satellite TV
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    • Patio
    • Grill
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Walk the soft sandy shores of Siesta Key beach from this 1 bedroom1 bath vacation rental on Siesta Key. The unit offers an open floor plan with full kitchen, dining area, and living room with flat screen TV. Through the large sliding doors you can sit out and enjoy the pool area on the screen...
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    34242, Gulf Gate Branch, Florida
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Gulf Gate Branch
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 Bedrooms, 2 Bathrooms, Sleeps 4 1/2 mile from The Gulf Of Mexico WIFI with HDTV in the living area Pets allowed with permission and pet deposit Absolutely no pets allowed in the pool area Short walk to the beach Private condo 8 units on the complex Looking for a tropical winter get-away or...
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    34231, Gulf Gate Branch, Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Gulf Gate Branch
    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Wi-Fi
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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. The unit...
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    34242, Gulf Gate Branch, Florida
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 6
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    Gulf Gate Branch
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
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    Smoking allowed
    About this property
    Only 8 min. to the #1 Beach in the USA 'Siesta Key Beach'!! Our 'SUPER CLEAN' large 3 bedroom / 2 bathroom condo in a beautiful gated complex. This spacious split plan offers a master bedroom with a walk-in closet, central living room, kitchen, dining room room and two bedrooms on seperate wings...
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    34238, Gulf Gate Branch, Florida
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Gulf Gate Branch
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a one bedroom one bathroom unit furnished with king-size bed in the private bedroom and queen-size sleeper sofa in the living room accommodating up to four persons. The living room is furnished with a 40' flatscreen TV with HD programing. The kitchen is equipped with 4-burner gas range,...
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    34242, Gulf Gate Branch, Florida
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Gulf Gate Branch
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a two bedroom two bathroom unit furnished with king-size bed in one private bedroom, two twin-size beds in the other private bedroom, and sleeper sofa in the living room accommodating up to 6 persons. There are two bathrooms one with shower only and the other with tub/shower combo. The...
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    34242, Gulf Gate Branch, Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Gulf Gate Branch
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come and enjoy this two bedroom two bathroom condo style vacation rental located just a short walk to Siesta Key beach. The main living area has an open concept with living room and dining area in the first great room when you enter the unit. There is a full kitchen with breakfast bar opening off...
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    34242, Gulf Gate Branch, Florida
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Gulf Gate Branch
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a one bedroom one bathroom unit furnished with king-size bed in the private bedroom and queen-size sleeper sofa in the living room accommodating up to four persons. The living room is furnished with a 40' flatscreen TV with HD programing. The kitchen is equipped with 4-burner gas range,...
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    34242, Gulf Gate Branch, Florida
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Gulf Gate Branch
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Wi-Fi
    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a one bedroom one bathroom unit furnished with king-size bed in the private bedroom and queen-size sleeper sofa in the living room accommodating up to four persons. The living room is furnished with a 40' flatscreen TV with HD programing. The kitchen is equipped with 4-burner gas range,...
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    34242, Gulf Gate Branch, Florida
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Gulf Gate Branch
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    This is a three bedroom two bathroom single family home furnished with king-size bed in the private master bedroom with beautiful en-suite bathroom equipped with stall shower. Adjacent is the first guest bedroom furnished with two twin-size beds. The third bedroom with pool view is furnished with...
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    34242, Gulf Gate Branch, Florida
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Gulf Gate Branch
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Washer
    • Hot Tub
    • Parking
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    NEW seasonal rental property available in Sarasota Gulf Gate neighborhood with close proximity to Siesta Key Beach, shopping, restaurants, just about everything ! 2 bedrooms, 3 NEW queen size beds, 2 baths, large NEW screened lanai includng a pool and integrated spa/hot tub! 1 car garage with new...
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    34231, Gulf Gate Branch, Florida
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Gulf Gate Branch
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    • DVD Player
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come enjoy the relaxed but vibrant vibe of Sarasota, Florida. The beautiful white sand beaches of Siesta Key, named #1 beach in America, is located just 2.3 miles from this private single family home. Thousands come each year to enjoy the areas beaches, restaurants, and leisure life style. This...
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    34231, Gulf Gate Branch, Florida
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Gulf Gate Branch
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a one bedroom one bathroom unit furnished with king-size bed in the private bedroom and queen-size sleeper sofa in the living room accommodating up to four persons. The living room is furnished with a 40' flatscreen TV with HD programing. The kitchen is equipped with 4-burner gas range,...
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    Location Information
    34242, Gulf Gate Branch, Florida
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Gulf Gate Branch
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    Located just a 5 minute drive to Siesta Key and 10 minutes to Downtown Sarasota, this home is perfect for experiencing the wide array of atmospheres Sarasota has to offer. Step through the front door and be greeted by a bright open living space with skylights throughout. The kitchen is well...
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    34231, Gulf Gate Branch, Florida
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Gulf Gate Branch
    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a spacious studio style two bedroom unit furnished with king-size bed and queen sleeper sofa downstairs and queen bed upstairs Accommodating up to 6 persons. The downstairs bathroom is equipped with tub/shower combo. While the upstairs offers a sky view stall shower. The unit is furnished...
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    34242, Gulf Gate Branch, Florida
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 6
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    Gulf Gate Branch
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Take a look at this well appointed 1 bedroom 1 bath unit just a couple hundred meters from the #1 beach in America, Siesta Key Beach. This vacation rental unit has an open living area with full kitchen, dining area, and living room with flat screen TV. Walk through the large sliding glass doors out...
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    34242, Gulf Gate Branch, Florida
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Gulf Gate Branch
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to this exquisite spacious 3 bedroom and 2 bathroom home with a pool in the renowned Gulf Gate Estates community. The open floor plan grants all the space any amount of guest could ask for. Enjoy the large living room with a flat screen TV or the newly remodeled fully equipped kitchen with...
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    34231, Gulf Gate Branch, Florida
    Condo/Apartment - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Gulf Gate Branch
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Welcome to this exquisite spacious 3 bedroom and 2 bathroom home with a pool in the renowned Gulf Gate Estates community. The open floor plan grants all the space any amount of guest could ask for. Enjoy the large living room with a flat screen TV or the newly remodeled fully equipped kitchen with...
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    Location Information
    34231, Gulf Gate Branch, Florida
    Condo/Apartment - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Gulf Gate Branch
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Balcony
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
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    • Grill
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax in comfort at Sea Winds! The unit offers a king bed and sleeper sofa, open patio space and a garden view, perfect for enjoying an outdoor meal. Take a dip in the community pool or shop the neighboring plazas. Beach accesses are 2 blocks in either direction, just a short walk.. Wireless...
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    Location Information
    34242, Gulf Gate Branch, Florida
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Gulf Gate Branch
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Don't hesitate to book this newly renovated 3-bedroom, 2-bathroom vacation rental condo for your next getaway to Sarasota! A group of 6 and 1 friendly Fido will enjoy lovely accommodations and access to the Sienna Park community pool. This condo is conveniently close to attractions in Gulf Gate...
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    34231, Gulf Gate Branch, Florida
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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