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Longboat Key Vacation Rentals

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    Travellers to Longboat Key are booking July dates now. Secure your vacation rental today, and have the perfect trip.
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    Secluded 2-bedroom private home with open floor plan including living room, dining area and well-equipped kitchen. Screened in lanai facing canal, gardens and active wildlife. One king bedded room and one queen bedded room with abundant closet space. Two newly renovated baths, washer/dryer,... View all property information
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    Longboat Key, Florida 34228
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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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    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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    Paradise is not lost. Beachplace is a private gated Gulf front community with 24 hour security located on the famous Longboat Key. Being steps away from the longest stretch of private beach on Longboat Key and 30 acres of manicured grounds makes Beachplace one of the island’s most beautiful Gulf... View all property information
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    Longboat Key, Florida 34228
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    About this property
    This unit is ONLY available from August 19, 2017 - August 26, 2017, only $1200 for the week! Please refer to my website (google white sands of Longboat Key, FL) for more pictures and details! Unit was renovated in 2016! This fully furnished 2 bed/2bath townhouse (bay side unit 113, refer to link... View all property information
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    Longboat Key, Florida 34228
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    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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    4.5 of 5 bubbles (2) Very good
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    Inn1-207 MAY AND JUNE SPECIAL, SAVE $700 PER WEEK. $1,400 per week reduced from $2,100. The perfect island getaway, located on the southern tip of Longboat Key with a beautiful beach and pool area. This deluxe unit features approximately 1700 square feet with a 52' long, open beachfront lanai.... 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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    Amazing totally furnished 5 Star beech front time share rental Property with PARTIAL ocean view. 2-bedrooms and 2-baths. Sleeps six comfortably: king size bed, two twin beds, and queen size sleep sofa. Wonderful free amenities. Check things out on line by looking up the Veranda Beach Club for... 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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    • Balcony
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    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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    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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    About this property
    Beautiful ground floor beachfront (on Gulf of Mexico) 3 bedroom, 2 full bath condo on Longboat Key. NOTE THIS UNIT IS ONLY AVAILABLE BETWEEN jUNE 1 AND SEPTEMBER 20 OF EACH YEAR. CHECK OUR CALENDAR FOR AVAILABILITY ON SPECIFIC DATES IN THAT RANGE. Fully furnished kitchen, washer and dryer (in... 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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    About this property
    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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    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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    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
    1 / 26
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    '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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    5 of 5 bubbles (5) Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    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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    1 / 22
    4 of 5 bubbles (1) Very good
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    About this property
    We have 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. They are fully furnished, three bedroom units (one king bed, two twin beds, one queen bed or sofa sofa bed), full size... View all property information
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    Longboat Key, Florida 34228
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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... View all property information
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    Longboat Key, Florida 34228
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    5 of 5 bubbles (1) Excellent
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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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    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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    About this property
    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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    • x
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    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
    1 / 39
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    • x
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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
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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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    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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    About this property
    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
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    • x
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    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
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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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    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
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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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    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 / 26
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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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    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
    Location Information
    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
    Location Information
    Longboat Key, Florida 34228
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Grill
    • Wi-Fi
    • Patio
    • Satellite TV
    • DVD Player
    • Parking
    • Private Garden
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    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
    Location Information
    Longboat Key, Florida 34228
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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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
    Location Information
    Longboat Key, Florida 34228
    1 / 14
    5 of 5 bubbles (9) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Balcony
    • DVD Player
    • Internet Access
    • Satellite TV
    • Terrace
    • Waterfront
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    1 / 13
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Private Garden
    • Air Conditioning
    • Satellite TV
    • Parking
    • Wi-Fi
    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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
    1 / 10
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Private Outdoor...
    • Ocean Views
    • Air Conditioning
    • Satellite TV
    • Waterfront
    • Washer
    • Patio
    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    1 / 25
    4.5 of 5 bubbles (20) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Patio
    • Washer
    • Balcony
    • Wi-Fi
    • Satellite TV
    • Grill
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    About this property
    ****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
    1 / 28
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Air Conditioning
    • Balcony
    • Satellite TV
    • Grill
    • Internet Access
    • Washer
    • Patio
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    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
    Location Information
    Longboat Key, Florida 34228
    1 / 26
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
    • Air Conditioning
    • Secure Parking
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Longboat Key, Florida 34228
    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Wi-Fi
    • Children's Pool
    • Satellite TV
    • Air Conditioning
    • Secure Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Longboat Key, Florida 34228
    1 / 21
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Washer
    • Patio
    • Air Conditioning
    • Waterfront
    • Porch
    • Wi-Fi
    • Balcony
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • x
    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
    Location Information
    Longboat Key, Florida 34228
    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Amenities & Details
    • Patio
    • Private Outdoor...
    • DVD Player
    • Air Conditioning
    • Washer
    • Internet Access
    • Ocean Views
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    LOOKING FOR RENTERS FOR 1 MONTH MINIMUM Beautiful Quiet Condo for rent On the third floor (top floor) ! Corner unit with stunning views of the water! Elevator Completely renovated with bamboo floors Well equipped kitchen with granite counters, Bathrooms are in marble and granite... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 / 6
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Satellite TV
    • Air Conditioning
    • Parking
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
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