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Holiday Rentals in Longboat Key

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    Travellers to Longboat Key are booking July dates now. Secure your holiday rental today, and have the perfect trip.
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Two Month Minimum Rental Required by Condo Association. This gulf-front Longboat Harbour Towers, sixth floor condo(4401 Gulf of Mexico Drive)has panoramic views of the Gulf of Mexico with NEW KITCHEN, BATHROOMS, AND WINDOWS. The sunny, cheerful interior encourages relaxation from the time you... View all property information
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    Longboat Key, Florida 34228
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    4.5 of 5 bubbles (57) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    ++++++Rated " EXCELLENT" digital badge on TripAdvisor and FlipKey++++++. This exclusive award recognizes outstanding vacation rentals based on reviews of past year so you can rent with confidence. TOP 5 REASONS TO VACATION AT THE... View all property information
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    Longboat Key, Florida 34228
    1 / 22
    4 of 5 bubbles (1) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    We have two beautiful condos at Club Longboat. One is a beachfront condo and the other is a garden unit with a restricted view of the Gulf of Mexico from the living room balcony. Both condos are fully furnished, three bedroom units (one king bed, two twin beds, one queen bed or sofa sofa bed),... View all property information
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    Longboat Key, Florida 34228
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    This newly built waterfront home will take you to another place and time. Tucked away in native tropical vegetation perched on the Bays edge looking out to Longboat Pass, this home is the perfect retreat for a couple or small group. Modern, open floorpan with a Scandinavian feel boasts hardwood... View all property information
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    Longboat Key, Florida 34228
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    5 of 5 bubbles (5) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    At our beautiful low-rise resort, located directly on the beach, our two-bedroom condominium is fifty paces from the pool and a private beach of soft white sand. 15F in popular Casa del Mar provides a spacious living room/home theatre (46 inch plasma TV & BlueRay Player), vaulted ceilings, and a... View all property information
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    Longboat Key, Florida 34228
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Light, nicely decorated and well appointed condo in a small friendly two floor / 12 unit building located on bay side of Island and mere steps from private beach. Everything is provided for your stay. Located mid-island - a walk to nearby shops and terrific restaurants. Heated pool, fishing dock, &... View all property information
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    Longboat Key, Florida 34228
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Two bedroom unit with King bed, 2 double beds, sofa sleeper, and full kitchen This beachfront resort is set on beautiful white sand beaches that meet the sparkling, turquoise waters of the Gulf of Mexico. This is the perfect location for catching the warm Florida sun, swimming, or walking the... View all property information
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    Longboat Key, Florida 34228
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Full Kitchen Weeks are Saturday to Saturday only There is an elevator on site. Longboat Bay Club offers luxurious 1,600-square-foot vacation accommodations steps away from the Gulf of Mexico, overlooking beautiful Crane's Bay. You can enjoy fishing, tennis, bicycling, basketball, and picnics.... View all property information
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    Longboat Key, Florida 34228
    1 / 13
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Ground floor Condo with two steps that lead out the back lanai to the white sands of Longboat Key. You can't get any closer to the beach than in this unit. The private beaches out the back door offer miles of shell collecting, sandcastle making, snorkleing, and dolphin sightings. Silver Sands... View all property information
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    Longboat Key, Florida 34228
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    4 of 5 bubbles (1) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    Perfect holiday apartment that is continually renovated. Building was completely renewed in 2008. With 103 sq. m. and balcony, accommo dation for up to 5. With all imaginable furnishing, e.g. full HD TV, free Pay TV in a great quality in every room, CD stereo system, Blu Ray DVD, High Speed... View all property information
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    Longboat Key, Florida 34228
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Spacious 2400 sqft 3 bedroom Spanish style house with a beautiful huge fully Italian tiled sunken living room. The house has large glass windows making it bright and well lit. The panoramic view of the canal is visible from all the areas including the 2 bedrooms. living room and dining room. You... View all property information
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    Longboat Key, Florida 34228
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    5 of 5 bubbles (8) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    We offer two beautiful Gulf front, renovated 1 Bedroom / 1 Bath apartment in the Beachcomber condo. Unit 303 and 401. See our unit's info on AwayToParadise Condo located right on the beach across the street from shopping malls with Pablix superstore, CVS, Italian restaurant and public... View all property information
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    Longboat Key, Florida 34228
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    4.5 of 5 bubbles (12) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Beautiful 3rd floor 2BR/2BR unit #309, overlooking pool, in Sand Cay Beach Resort on the exclusive island of Longboat Key. South facing balcony. Striking views of the beach from the balcony, and a glimpse of the bay from the bedrooms. Cathedral ceilings throughout, bright open kitchen with corian... View all property information
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    Longboat Key, Florida 34228
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    • Welcoming, distinctive, fully furnished 2 bedroom, 2 bathroom condo in a verdant, tropical environment.<BR>• Very private and quiet first floor, 1600 ft. unit with lush garden views.<BR>• Master suite with office niche, king size bed, walk-in closet and double sinks in bathroom.<BR>• Guest... View all property information
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    Longboat Key, Florida 34228
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    5 of 5 bubbles (9) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Lovely completely new fully equipped 3 bedroom beach cottage beautifully decorated with lush landscaping and outdoor lanai for dining and relaxing. Master bedroom, 2 other bedrooms, and 2 full baths plus lanai dining area. High speed internet and digital TV. Quiet upscale residential... View all property information
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    Longboat Key, Florida 34228
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    You’ll find everything you need for a comfortable extended paradise getaway when you visit Longboat Key vacation rental 671 Old Compass Road. This three bedroom canal front home offers great amenities along with a heated pool and spa for the relaxing Florida vacation you’ve been dreaming of. This... View all property information
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    Longboat Key, Florida 34228
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    ***ONLY ONE RENTAL PER MONTH, SO BOOK FAST TO SECURE YOUR SPOT!*** This 2400 sq ft four bedroom private home located in the exquisite Country Club Shores neighborhood, offers coastal access with its own dock, an enclosed pool overlooking the waterfront, and a gorgeous gourmet kitchen and... View all property information
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    Longboat Key, Florida 34228
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    1 / 23
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Beautiful ground floor beachfront (on Gulf of Mexico) 3 bedroom, 2 full bath condo on Longboat Key. Fully furnished kitchen, washer and dryer (in unit), dedicated parking for 1 car directly in front of unit, with additional guest parking. Master Bedroom has a king sized bed, flat screen TV, en... View all property information
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    Longboat Key, Florida 34228
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    5 of 5 bubbles (5) Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    This spacious 5 bedroom villa is situated directly on the beautiful white sand beaches of Longboat Key. Offering a large outdoor private heated swimming pool and glorious views of the Gulf of Mexico from almost every corner, fully-equipped gourmet kitchen, fireplace, BBQ, and much more - it is your... View all property information
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    Longboat Key, Florida 34228
    1 / 39
    4 of 5 bubbles (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Our gulf front condominium has a beautiful view of the Gulf of Mexico not only from the balcony, but from the living room as well. We also have two other condos in this same resort that rent at lesser rates than shown below. We only recently purchased this condo, but in 2013 we replaced all the... View all property information
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    Longboat Key, Florida 34228
    1 / 14
    5 of 5 bubbles (9) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    NATURAL BEAUTY of Longboat Key RIGHT ON THE BEACH PANORAMIC 2ND FLOOR BALCONY VIEWS Our Studio condo is right on the beach with magnificent panoramic views from its second floor balcony position. ENJOY THE BEACH FROM YOUR BED, LIVING, DINING AND KITCHEN! Our studio sleeps 3 with new in 2016... View all property information
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    Longboat Key, Florida 34228
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Our luxury vacation home will comfortably accomodate up to 12 guests and is located on a deepwater canal and has a dock suitable for a boat up to 30 feet in length. Beautiful Longboat Key beach is less than a 10 minute walk from the house and world-class shopping and dining at the famous St.... View all property information
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    Longboat Key, Florida 34228
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1400 sq ft free standing villa Our villa has 2 bedrooms, 2 bathrooms, living/ dining room, full kitchen and two bonus rooms. It is located on the bay which comes into the center of the community and features a marina - manatees and dolphins have been known to stop by! .Our unit is close to the... View all property information
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    Longboat Key, Florida 34228
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Designer's hidden home: walk to Florida's best secluded beaches. Longboat Key is a tropical paradise. Just bring your yacht, golf clubs, tennis rackets and relax. Wi-Fi & TV Our Venetian Villa is nestled on the placid Longboat Key. With a short drive from the airport, Ringling Museum, St.... View all property information
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    Longboat Key, Florida 34228
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    5 Bedrooms, Sleeps 10 | Quick View
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    This spacious 5 bedroom villa is situated directly on the beautiful white sand beaches of Longboat Key. Offering a large outdoor private heated swimming pool and glorious views of the Gulf of Mexico from almost every corner, fully-equipped gourmet kitchen, fireplace, BBQ, and much more - it is your... View all property information
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    Longboat Key, Florida 34228
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    Million dollar view! Beautiful waterfront bay penthouse condo. Gorgeous panoramic views of Sarasota Bay and downtown Sarasota in this Windward Bay award winning condo complex! This condo has a bay view from every room, makes you feel like you are on a cruise. Starting April 2016 this condo is... View all property information
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    Longboat Key, Florida 34228
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    'Very Welcoming & Peaceful' - several times quoted from our Guests Book. Best value on Longboat Key... Longboat Key is one of the most beautiful and secure barrier islands off of the west coast of Florida. Our townhouse is within a short walk to a nature lovers paradise - a 32 acre park which is... View all property information
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    Longboat Key, Florida 34228
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    About this property
    The home is a cottage located in historic Longbeach Village in the North end of Longboat Key, Florida. The home is near both the beach and the intercoastal waterway, with some water views. The beautiful Longboat Key beach is walking distance, about five blocks away.<BR><BR>We purchased the home... View all property information
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    Longboat Key, Florida 34228
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Our house is located on Longboat Key, outside of the city of Sarasota, on the west coast of Florida. There is an airport in Sarasota, as well as in Tampa, which is a little over an hour away. Longboat Key is pretty and green, and is linked, by bridge, to Anna Maria Island on the north, and to St.... View all property information
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    Longboat Key, Florida 1234
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    We just purchased this property and completely remodeled it. It has a new kitchen with granite counter tops, stainless appliances, and wine cooler. All new furniture and a 48 in TV in the living room and new central A/C. It is located in the middle of longboat key with shopping and restaurants in... View all property information
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    Longboat Key, Florida 34228
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    About this property
    Holiday paradise on the stunning Florida west coast on the island of Longboat Key. Stunning, elegant and luxurious complex. For selfcatering there is the kitchen with all necessities and modern devices. Of course, there is a washing machine and dryer avialable. First-class furnishing. Safe and... View all property information
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    Longboat Key, Florida 34228
    1 / 49
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Located near the historic town of Longboat at the north end of Longboat Key, this Key West-style home is located less than 150 yards from Whitney Beach and the Gulf of Mexico. One of 16 unique homes built by famed architect Frank Folsom Smith, on property formerly owned by the long-time resident,... View all property information
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    Longboat Key, Florida 34228
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    We are able to offer reservations in weekly increments with arrivals and departures Fridays, Saturdays and Sundays only. Gulf Tides of Longboat Key offers a number of recreational opportunities and a superb location near the cities of Tampa, Sarasota, and Fort Myers. At the resort's beach, you can... View all property information
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    Longboat Key, Florida 34228
    1 / 26
    5 of 5 bubbles (5) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Beautifully decorated one bedroom condo directly on the beach. New kitchen with granite counter tops, and a 47in flat screen TV. Watch the sunset from your living room or porch, the sand is only 20 feet from your front door. Contact owner before booking View all property information
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    Longboat Key, Florida 33312
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    LONGBOAT KEY - Beautiful Gulf to Bay. Bayport Beach and Tennis Club is a rare find. This award winning, amenity-rich community at sea’s edge is situated in the middle of Longboat Key. A popular residential enclave of 136 homes on 27 acres of picturesque gardens. Bayport is bordered by the Gulf of... View all property information
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    Longboat Key, Florida 34228
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    3 Bedrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
    About this property
    This luxurious villa on gulf features a heated pool, 3 beautiful terraces, fully-equipped gourmet kitchen & outdoor BBQ grill, fine art & sculpture, high-speed internet, flat screen televisions, video & board games, bicycles, ping pong, & much more. Located near the historic town of Longboat at... View all property information
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    Longboat Key, Florida 34228
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
    • ?
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    • x
    About this property
    Available for 3 MONTH MINIMUM rental with approval from condo association. Beautiful beach front condo located just 1.5 miles from St. Armand's Circle. Very upscale and beach feels very private. Pool, spa, and deck newly renovated. We have 24 hour, 7 days a week, guard gated community and... View all property information
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    Longboat Key, Florida 34228
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    Beautiful, spacious 2/2 condo on Longboat Key available for 2016 season! Newly remodeled with designer kitchen, high-end appliances, and modern furnishings. Completely turnkey stocked with all essentials. Condo offers canal and bay views. Washer/dryer in unit. Community features three pools,... View all property information
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    Longboat Key, Florida 34228
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    5 of 5 bubbles (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Our condo has everything you will need for a relaxing vacation on the beach. The island of Longboat Key... ... is one of the most beautiful places in Florida. Longboat was voted the second most favored island in North America, according to a survey by a nationally recognized travel magazine.... View all property information
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    Longboat Key, Florida 4725
    1 / 25
    4.5 of 5 bubbles (20) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • ?
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    ****Please go to longboatbeachcom .**** for more information. I will email you a quote from my booking program. Condo was updated July 2016, so pictures are current. Beautiful and a great escape! Beach directly across the street about 50 steps. You can hear and see the Gulf from your unit. Best... View all property information
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    Longboat Key, Florida 34228
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Condo is located in Banyan Bay Club which consists of a total of only 44 units arranged in two floors. This condo is located at the Garden level. No stairs. The lanai at the rear of the unit opens onto a private Banyan and Palm tree-filled lawn with views of Sarasota Bay. The lanai contains a table... View all property information
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    Longboat Key, Florida 34228
    1 / 28
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
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    The Blue Pearl has stunning views, surrounded by waterways, the perfect vacation spot on Longboat Key. 2 blocks from the azure blue waters of the Gulf of Mexico with miles of quiet private beaches. Decorated with a beach theme this spacious 1 bedroom has inside washer dryer and granite counters,... View all property information
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    Longboat Key, Florida 34228
    1 / 10
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Private Outdoor...
    • Ocean Views
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    • Pet-friendly
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    • x
    • ?
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    • x
    About this property
    A special address on the Gulf of Mexico beach at the very north end of Longboat Key overlooking a bird sanctuary with views of the sea, sky and our extraordinary sunsets. One of nine contemporary townhomes designed by noted architect Tim Seibert (Sarasota School of Design), this stunning home is... View all property information
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    Longboat Key, Florida 34228
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    We offer our new 2 bedroom, 2 bath Islander Club condo unit 74N. We just finished a complete renovation. Everything is new. See our website AwayToParadise com Experience living at the beach in the active community of Islander Club! This 2 bedroom, 2 bath 1235 Sq.Ft unit is elevated to the 7th floor... View all property information
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    Longboat Key, Florida 34228
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • DVD Player
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    • Terrace
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    NEW: 1375 square foot penthouse corner unit overlooking lagoon/canal on Sarasota bay. The unit is freshly painted and updated throughout with all new beds and linens. The kitchen is an all white original kitchen. One King, one queen bed, and a twin daybed on the lanai. Elevator and parking. The... View all property information
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    Longboat Key, Florida 34228
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Wi-Fi
    • Children's Pool
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    • Pet-friendly
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    • x
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    • x
    About this property
    Wonderful and clean condo that is just steps away from the gulf of mexico and its wonderful beach. Pool and workout facilities right next to condo. Condo has a master suite with a king size bed and a second bedroom with a queen size bed. We want to rent for two months at a time, so we are priced... View all property information
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    Longboat Key, Florida 34228
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • x
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    • x
    About this property
    Beautifully renovated unit with tile floors and granite counter tops. Unit has full washer and dryer. Lanai is enclosed with glass sliders for extra functionality. First floor unit has beautiful bay views and is accessible by stairs or elevator. The master bedroom overlooks the bay and the second... View all property information
    Location Information
    Longboat Key, Florida 34228