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Holiday Rentals with Pools in Longboat Key, FL

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    1 / 17
    4.5 of 5 stars (3) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    4.5 of 5 stars (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    4.5 of 5 stars (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Groundfloor Beachfront! From large living and dining area with open kitchen just step outside to your private patio and walk right out to the BEACH (25 seconds!) Magnificent condo 1100 sqft with open floor plan. 2 bedrooms, 2 full bathrooms, ceiling fans, full kitchen with stainless steel... View all property information
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    Longboat Key, Florida 34228
    1 / 18
    4 of 5 stars (1) Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    The Outrigger Resort is a quaint 10 unit complex. This unit is equipted with very comfortable furniture and all your needed appliances and accessories. Included in the kitchen is stove, refrigerator, toaster, coffee pot, etc., including all necessary utensils. The unit is designed with front... View all property information
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    Longboat Key, Florida 34228
    4 of 5 stars Reviewed 9 May 2016
    We needed three rooms with three bathrooms. There was one couple with a toddler, one couple and one adult. The unit was clean and spacious. The kitchen could have been better...
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    1 / 18
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    A lovely pet and family friendly private home, located on a private deep water canal with direct access to Sarasota Bay and only a short walk (200 meters) away from the quiet white sand beach perfect for morning beach-combing and end of day amazing golden sunsets. Located in the prestigious yet... View all property information
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    Longboat Key, Florida 34228
    5 of 5 stars Reviewed 10 August 2015
    What a Villa, one of the best I have had the pleasure of staying in during my 15th visit to Florida. Many mod cons, some a little too modern for me, so that's where your teenage...
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Studio unit with King bed, sofa sleeper, and full kitchen 'stove top only, no oven' This beachfront resort is set on beautiful white sand beaches that meet the beautiful turquoise waters of the Gulf of Mexico. Resort with golf courses, 6 restaurants, tennis courts, spa, and deep water marina. Rate... View all property information
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    Longboat Key, Florida 34228
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Florida's SeaHorse Beach Resort on Longboat Key is located on the white sand beaches of the Gulf of Mexico. From the moment you arrive, the friendly and professional staff will welcome you to this Premier property where you can experience a panoramic view of the Gulf from your suite, or while... View all property information
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    Longboat Key, Florida 34228
    1 / 18
    4.5 of 5 stars (2) Very good
    Studio, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    ***OCEAN FRONT SPECIAL*** $295/3 nights , $350/4 nights Monday to Friday July - September . This complex is a two story building with only 15 condos, beautifully landscaped, with sophisticated charm and a casual beach atmosphere. The pictures of the beach and Ocean are taken from the condo,... View all property information
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    Longboat Key, Florida 34228
    5 of 5 stars Reviewed 18 March 2016
    We stayed at this unit for two weeks and found it an ideal place to stay overlooking the Gulf of Mexico on Longboat Key. The studio unit is cozy, but did not feel cramped with two...
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Spacious, bright Bayside PET-FRIENDLY town home with partial Bay view and lush tropical landscaping. Unit has Full Kitchen, 2 LARGE BEDROOMS and 2 1/2 BATHS. Enjoy the fishing pier, large pool, tiki bar/restaurant. Come enjoy our Tropical Paradise! First level is extended parking garage. Second... 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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    Beach Castle Resort BC9 - Condo 2 Bedroom/ 2 Bath on Longboat Key , maximum occupancy of 6 people. Offering a beautiful view of the gulf, but more economical than the other Gulffront condominiums at the Beach Castle Resort, the owners have spared no expense in renovating this condo.BEautifully... View all property information
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    Longboat Key, Florida
    1 / 23
    5 of 5 stars (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    THE BEACH ON LONGBOAT KEY - One Bedroom Gulf Front Condo # 225 ** Ocean Front Special *** July 5 - 7 $195 for 2 nts , July 24 - 31 30% disc . This beautiful brand new beach front condo features a modern motif, designer decor, beautifully landscaped, with sophisticated charm and a casual beach... View all property information
    Location Information
    Longboat Key, Florida 34231
    5 of 5 stars Reviewed 12 April 2016
    The unit is kind of small, but the private balcony made it! Wonderful view, private beach, and the fact that the complex is only 14 units made for a very intimate experience...
    5 of 5 stars Reviewed 29 December 2015
    We thoroughly enjoyed our time in your beautiful condo on Longboat Key. The weather was perfect and the condo was absolutely lovely. You’ve done a beautiful job decorating – we...
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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 / 24
    3 of 5 stars (1) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Beach Castle Resort BC6 - Condo 2 Bedroom/ 2 Bath on Longboat Key , maximum occupancy of 6 people. Beautiful Gulf View unit, all updated. Screened in lanai overlooking the gulf - wake up, take your coffee/tea and gaze out over the pristine waters of the gulf. Awaken each morning to the view from... View all property information
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    Longboat Key, Florida
    3 of 5 stars Reviewed 10 May 2016
    Stayed in unit 6 of at Beach Castle Resort the week of 4th of July. It was a last minute vacation opportunity and this was one of a very few units available on Longboat Key. We...
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Nestled among majestic palms and tropical landscaping, this Country Club Shores home is situated on a deep sailboat water with 113 feet of waterfront, and offers outstanding boating opportunities - all just two houses away from Sarasota Bay! Southern exposure on the canal side provides year-round... View all property information
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    Longboat Key, Florida 34228
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    LOCATION, LOCATION, LOCATION! Beautiful view of Sarasota Bay with private beach access just across the street. Newly renovated open kitchen and breakfast bar with seating for three, upgraded stainless appliances, and quartz countertops. Entire unit is freshly painted and immaculate with new tile... View all property information
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    Longboat Key, Florida 34228
    1 / 43
    5 of 5 stars (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
    4 of 5 stars Reviewed 19 March 2015
    Casa Del Mar is located in a beautiful part of Long Boat Key. The beach is beautiful and F15 condo was only steps away from the beach. There were plenty of lounge chairs on the...
    5 of 5 stars Reviewed 4 July 2014
    This is the first time we stayed at this property, and it was amazing !!! It was everything we were told it would be. Our unit had updated appliances, a TV in every room, a brand...
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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
    1 / 14
    5 of 5 stars (8) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Balcony
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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
    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed 20 January 2016
    My husband and I stayed 2 nights at this mid-key studio condo. It has everything you need and the beach front location is amazing. The property is a former motel that has been...
    5 of 5 stars Reviewed 24 December 2015
    Great place to stay, right on the ocean. Everything was clean and well maintained. The kitchen is modern and provides plenty of pots and pans to use. It feels private and cozy...
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Beautifully furnished 1 bedroom/1 bath condo overlooking the Gulf of Mexico. Stroll for miles on the white sandy beaches of Beautiful Longboat Key or just relax and enjoy the sunsets View all property information
    Location Information
    Longboat Key, Florida 34228
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    637 Norton - Private canal home 4 Bedroom/ 3.5 Bath with private pool, maximum occupancy of 8 people. Live the Florida lifestyle in this beautiful, comfortable 4 bedroom, 3 bath private home located in the Sleepy Lagoon on the quaint end of Longboat key. This home sleeps 8 - 10 people. Offering... View all property information
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    Longboat Key, Florida
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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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
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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 / 28
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    ONE MONTH MINIMUM RENTALS ONLY. NO WEEKLY RENTALS. ONE OF LONGBOAT KEY'S BEST KEPT SECRETS! Longbeach is located at the north end of the island, right on the Gulf of Mexico. This quiet community offers a pool and two tennis courts. This charming 2nd floor walk-up has been lovingly furnished... View all property information
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    Longboat Key, Florida 34228
    1 / 44
    4 of 5 stars (1) Very good
    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
    4 of 5 stars Reviewed 27 April 2015
    I have had my eye on this house for 2 years now. Boy am I glad that I finally pulled the trigger and decided to stay here. Traveled with my wife, two children ages 2&4 and...
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    1 / 49
    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
    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
    1 / 17
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    **ONE WEEK MINIMUM RENTAL HOME** This casual beach home is just the right place to enjoy a laid-back, toes-in-the-sand vacation! Nestled on the shores of the Gulf of Mexico at the north end of Longboat Key, it's the perfect spot for relaxing days on the beach, followed by fabulous sunsets and... 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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    * CONDE NAST VOTED LONGBOAT KEY THE SECOND BEST ISLAND DESTINATION IN NORTH AMERICA * Located on fabulous Longboat Key approximately 3 miles south of Anna Maria island, 6 miles north of Armand's Circle at Windward Bay.This 27 acre condominium complex situated between the Gulf Of Mexico and the... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Welcome to the Longboat Key Sarasota's most enjoyable vacation spot ever. If you are ready to relax and enjoy life our rental home is waiting for you. See my units website: AwayToParadise Up to 4 person private accommodation in our 1 Bedroom / 1 Bath island-side unit completely renovated,... View all property information
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    Longboat Key, Florida 34228
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    We offer two beautiful completely renovated in October 2015 1 Bedroom / 1 Bath apartment in the Beachcomber condo. Unit 303 and 401. Welcome to the Longboat Key Sarasota’s most enjoyable vacation spot ever. If you are ready to relax and enjoy life with our rental apartment is waiting for you.... View all property information
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    Longboat Key, Florida 34228
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Roomy one story villa with views of Bayou , pool and steps to private beach. Private beach conservancy offers tennis, shuffleboard, bocci ball, cabanas, grills and private beach chairs. Large master suite with roomy walk in closet. Bonus small bedroom with twin bed and dresser and hall bath.... View all property information
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    Longboat Key, Florida 34228
    1 / 10
    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    == Up to 25% discount on the regular resort rate == Special rates and discounts are available depending on time and length of stay. 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... View all property information
    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed 14 July 2015
    This was my first stay at Sand Cay Beach Resort and I can't say enough positive things about my experience. I have been to Longboat Key on several occasions and was excited to be...
    5 of 5 stars Reviewed 22 June 2015
    My wife and I stayed at the resort for one week in June 2015. I so wish we'd booked for 2 weeks. The apartment was lovely. No faults from us on the apartment, the pool area or the...
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    • 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
    3 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Seascape 103 - Condo 3 Bedroom/ 2 Bath on Longboat Key , maximum occupancy of 6 people. You'll enjoy the feel of an old-fashioned Florida beach vacation in this quiet, secluded 8-unit complex nestled on the shores of the Gulf of Mexico at the north end of Longboat Key. This is the definition of... View all property information
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    Longboat Key, Florida 34228
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    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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    5 of 5 stars (8) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    WINTER COUPLES SPECIAL 12/1-1 /30 $8000/60 nights + tax and fees. PACK YOUR SWIMSUIT & SMILE - THE REST IS HERE: Take the wooden walkway to swim in warm gentle azure gulf waters Walk softly past sea turtle nests - shell on your own private gulf beach Watch dolphins, shore birds from sun... View all property information
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    Longboat Key, Florida 34228
    5 of 5 stars Reviewed 14 April 2015
    The two balconies and lanai overlooking the fabulous Gulf of Mexico provide a beautiful and ever-changing view of Nature's best work. Condo is large, clean and comfortably...
    5 of 5 stars Reviewed 8 August 2014
    You couldn't ask for anything more in a vacation retreat. Clean, modern, roomy accomodations. Steps to a white sand beach where the umbrellas and beach chairs are set up by the...
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Welcome to Longboat Key! This 2 bedroom one bath ground floor condo offers a full kitchen, with open living and dining area. There is a enclosed patio opening to the community pool. Covert Condominiums are located on the northern part of Long Boat Key on Sarasota Bay. There is deeded beach access... View all property information
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    Longboat Key, Florida 34228
    3 Bedrooms, 4 Bathrooms, Sleeps 5 | Quick View
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    3 MONTH MINIMUM Elegant 3 Bedroom, 3.5 Bath condo, almost 3000 sq. ft with 700 sq ft covered wraparound terrace. Panoramic views of Sarasota bay, golf course, heated pools, hot tub and clubhouse; workout room, saunas, Har-Tru Tennis courts, BBQ area, children's pool. Stunning mirrored and... View all property information
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    Longboat Key, Florida 34228
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    This is the largest two bedroom apartment in the condo complex and is located on the top floor with extra large balconies. It has a great view of the Gulf of Mexico as well as Sarasota Bay. It is only 100m from the Gulf of Mexico beach where there are chairs, chaises and umbrellas for those staying... View all property information
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    Longboat Key, Florida 34228
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2 bedroom deluxe unit with King bed, 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 beach. Plenty... 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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    ***Minimum 30 Day Rental*** Longboat key offers uncrowded beaches, great food and serene accommodations. Bayport Beach and Tennis Club is a beach to bay complex made up of 2 story buildings that offer privacy in a very serene and relaxing environment. This condo is a 2 bedroom 2 bath condo that is... View all property information
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    Longboat Key, Florida 34228
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Spacious 2 Bedroom (King in MBR and Queen in Guest BR) and 2 bath unit with Gulf View (North side) - watch sunset go down over the Gulf. Well decorated and furnished with a screened in lanai. Walk out to pool, hot tub, Har-Tru tennis and Gulf. 2 month minimum rental. Gym on site. 1 mile walking... View all property information
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    Longboat Key, Florida 34228
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Recently upgraded, second floor, Gulf front condo. Open concept kitchen, dining, living and family room with spectacular views of the Gulf. King size bed in Master bedroom with walk-in shower. Amenities include: flat screen televisions in den and both bedrooms, VCR/DVD and free high speed wireless... View all property information
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    Longboat Key, Florida 34228
    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
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Whitney Beach 145 - Condo 2 Bedroom/ 2 Bath on Longboat Key , maximum occupancy of 4 people. Enjoy a relaxing holiday in this lovely two bedroom, two bath ground floor unit at popular Whitney Beach, nestled at the north end of Longboat Key. Located on the bay side of this sought-after resort... View all property information
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    Longboat Key, Florida 34228
    1 / 26
    5 of 5 stars (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
    5 of 5 stars Reviewed 16 April 2016
    We were so excited to have such a beautiful, clean and well equipped suite. Kim has done such a great job. The gorgeous quiet beach was fantastic and the view was fabulous. We...
    4 of 5 stars Reviewed 6 May 2014
    Stayed there for a week and found it close to perfect. Waking up in the morning and being blessed with dolphins swimming about 10 yards from the beach is bril! If you are...
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Studio unit with King bed, sofa sleeper, and full kitchen 'stove top only, no oven' 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
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    One bedroom unit with King bed, sofa sleeper, and full kitchen This beachfront resort is set on beautiful white sand beaches that meet the gorgeous turquoise waters of the Gulf of Mexico. Sun, swim, walk the shoreline on this one of a kind beach with sand that is soft it will soothe your feet.... View all property information
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    Longboat Key, Florida 34228
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    ***PRICE AND AVAILABILITY SUBJECT TO CHANGE WITHOUT NOTICE. CHECK IN DATES FOR THIS RESORT ARE FRI/SAT/SUN*** Longboat Bay Club provides you vacation accommodations that include ample recreation and pampered relaxation. The Gulf of Mexico and Sarasota Bay provide you with several opportunities... View all property information
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    Longboat Key, Florida 34228