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Holiday Rentals and Apartments Longboat Key, FL

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    Travellers to Longboat Key are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 44
    4 of 5 stars (1) Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    6 Bedrooms, 6 Bathrooms, Sleeps 18 | Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    SEA PINES This rarely available premier oceanfront location has one of the best views on Longboat Key looking out over the low dunes to the Gulf of Mexico where you can see the dolphins play, and the most amazing sunsets you’ll see anywhere. Quiet and serene with magnificent views, yet only a ten... View all property information
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    Longboat Key, Florida 34228
    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
    Location Information
    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 / 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 / 52
    5 of 5 stars (8) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
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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
    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
    Location Information
    Longboat Key, Florida 34228
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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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
    Location Information
    Longboat Key, Florida 34228
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    This exclusive beach house is located on the waters edge, directly on the Gulf of Mexico on prestigious Longboat Key. When you open the back door, walk out onto the pristine private beach and into the warm waters of the Gulf. This modern luxury property is newly renovated and has all the amenities,... 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
    Location Information
    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 / 14
    5 of 5 stars (8) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Balcony
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    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
    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
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Includes swimming pool and partial views of the gulf, and only 1/2 block from the incredible beaches of Anna Maria Island, this adorable vacation rental in... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 / 26
    5 of 5 stars (5) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    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
    Location Information
    Longboat Key, Florida 33312
    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
    Location Information
    Longboat Key, Florida 34228
    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
    Location Information
    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, 2 Bathrooms, Sleeps 10 | Quick View
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    Quiet area in Longboat Key Village area, on Broadway. Short walk to white sandy beach, relax in the morning on the patio area. 2 large family rooms with Flat screen TV's, full kitchen with everything you need for making nice meals. Washer and dryer, king, queen, and 2 twins, 2 queen pull out sofa... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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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
    Location Information
    Longboat Key, Florida 34228
    3 Bedrooms, 4 Bathrooms, Sleeps 5 | Quick View
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    • Children's Pool
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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
    Location Information
    Longboat Key, Florida 34228
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    One bath cottage all new beds, Linens, towels etc. Cottage available weekly or monthly in the Lovely North Longboat Key Village where resident peacocks visit daily. Sit out on your porch in the evening and relax or dine out at many of the water front restaurants. Offered FULLY FURNISHED with each... View all property information
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    Longboat Key, Florida 34228
    1 / 22
    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
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Three bedroom cottage available weekly or monthly in the sought after North Longboat Key Village where resident peacocks visit daily. New beds, Linens, towels etc. Also available on VRBO #702686<BR>Offered fully equipped unit reflecting its own unique style of a beach getaway in paradise, full of... View all property information
    Location Information
    Longboat Key, Florida 34228
    5 Bedrooms, 4 Bathrooms, Sleeps 11 | Quick View
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    3 Cottages with grass court yard to enjoy family time together. Relax in our 3 bedroom cottage, 1 bedroom with 2 pull out sleeper sofa's. Gas grill, full kitchens, and patio area. Washer and dryer. Short walk to Gulf of Mexico and white sandy beach. Relax with book in the quiet back court yard. Pet... 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
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Buttonwood Cove 205 - Condo 3 Bedroom/ 2 Bath on Longboat Key , maximum occupancy of 6 people. Enjoy a vacation filled with extras when you stay at this lovely 3 bedroom, 2 bath Buttonwood Harbour condominium. An attractive complex located at the south end of Longboat Key, Buttonwood Harbour... View all property information
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    Longboat Key, Florida
    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
    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
    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 / 24
    5 of 5 stars (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    Set on 2 acres of land on a private island, this new home (completed in 2010) will provide an island vacation experience for you and your family like no other. The house has 4 bedrooms and 4 bathrooms and an outdoor shower. The two upstairs 2-room bedroom suites sleep up to 5 each, and all bedrooms... View all property information
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    Longboat Key, Florida 34228
    1 / 39
    4 of 5 stars (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
    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
    1 / 26
    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
    1 / 30
    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
    Location Information
    Longboat Key, Florida 4725
    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
    1 / 10
    5 of 5 stars (15) Excellent
    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 DO NOT ACCEPT BOOKINGS ONLINE THROUGH TRIPADVISOR*** I will email you a quote from my booking program. Beautiful and a great escape! Beach directly across the street about 50 steps. You can hear and see the Gulf from your unit.... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 / 1
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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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
    Location Information
    Longboat Key, Florida 34228
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
    • Hot Tub
    • Parking
    • Satellite TV
    • Washer
    • Internet Access
    • Balcony
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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
    Location Information
    Longboat Key, Florida 34228
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
    • Wi-Fi
    • Ocean Views
    • DVD Player
    • Porch
    • Waterfront
    • Washer
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Charming 1 bedroom 1 bath canal front unit. On canal with dock in the<BR>Back yard. A beautiful Beach, amazing 35 acre park, great restaurants<BR>All within a five minute walk. Great space in an amazing place! Everything you <BR>Need to relax for a long weekend, a week, a month, or a winter, or... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 / 12
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Private Outdoor...
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Magnificent 3 bedroom, 2.5 bath beach front condominium (3 month minimum stay) The Players Club has all the sophistication and stunning scenery that has made Longboat Key a world class destination. This idyllic location is on the south end of Longboat Key just minutes from downtown Sarasota and St.... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 / 20
    4.5 of 5 stars (18) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Washer
    • DVD Player
    • Private Outdoor...
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Waterfront
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    La Playa is a small 21-unit resort property of privately-owned condominiums available exclusively for weekly rentals twelve-months per year. Located on spectacular Longboat Key, a short drive from Sarasota on the wide sand beaches of the Gulf of Mexico, La Playa offers privacy and direct beach... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 / 16
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
    • Air Conditioning
    • Private Outdoor...
    • Terrace
    • DVD Player
    • Wi-Fi
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Spacious corner unit 2 bedrooms 2.5 bathrooms (3 month minimum stay) The Players Club has all the sophistication and stunning scenery that has made Longboat Key a world class destination. This idyllic luxury beach location is on the south end of Longboat Key just minutes from downtown Sarasota and... View all property information
    Location Information
    Longboat Key, Florida 34228
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Children's Pool
    • Hot Tub
    • Ocean Views
    • Satellite TV
    • Waterfront
    • Sauna
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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
    Location Information
    Longboat Key, Florida 34228
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Waterfront
    • Washer
    • Grill
    • Air Conditioning
    • Wi-Fi
    • Patio
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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
    Location Information
    Longboat Key, Florida 34228
    1 / 31
    5 of 5 stars (12) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
    • Balcony
    • DVD Player
    • Washer
    • Satellite TV
    • Waterfront
    • Grill
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Escape to Paradise with Incredible Sunsets and Balmy Breezes direct on the Gulf of Mexico with its beautiful White Sand Beaches stretching for miles. Private and very quiet, and features two bedrooms with a king size bed in the master suite and a queen size bed in the second bedroom, two full... View all property information
    Location Information
    Longboat Key, Florida 34228
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Air Conditioning
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    ***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
    Location Information
    Longboat Key, Florida 34228
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Washer
    • Air Conditioning
    • Satellite TV
    • Patio
    • DVD Player
    • Grill
    • Wi-Fi
    • Secure Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This unit is ONLY available from August 20, 2016 - August 27, 2016, only $1200 for the week! Please refer to my website (google white sands of Longboat Key, FL) for more pictures and details! This fully furnished 2 bed/2bath townhouse (bay side unit 113, refer to link at the bottom of the page for... View all property information
    Location Information
    Longboat Key, Florida 34228