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Holiday Rentals in Longboat Key

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    Travellers to Longboat Key are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 99 Rentals in Longboat Key
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Little Gull is a small resort located 1 hour south of Tampa Florida on a key. This resort has access to Sarasota Bay and the Gulf of Mexico. The beach is only accessible by the local resorts so it seems private. Unit 11 is a one bedroom condo available for rent during 3-23 thru 3-30 and 4-13...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Longboat Key Bayfront condo in Bay Isles1 / 24
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Beautifully updated 2 bedroom, 2 bath Fairway Bay condo in double gated Bay Isles on South Longboat Key. Sweeping views of Sarasota Bay with downtown Sarasota in the distance from this 3rd floor unit with elevator. Fairway Bay has two heated pools, gym, tennis courts and access to the private,...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    637 Norton1 / 70
    (1)Excellent
    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. Distance to the Beach: 1 block 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...
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    Longboat Key, Florida 34228
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Away to Paradise! Unit 301 with 180 degrees unobstructed Mexican Gulf View. Beachfront condos on Florida's gulf coast. This is a corner condo so you have a more space and side window view. A luxurious experience on the beautiful beaches and emerald waters of the Gulf of Mexico awaits you when you...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    LUXURIOUS 1 BEDROOM ON THE BEACH , $150.00 PER NIGHT. RED TIDE IS GONE!1 / 24
    (8)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
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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
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    Longboat Key, Florida 33312
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
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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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Breakfast bar plus combined living/dining area with spectacular view. Walk directly out to the beach from the screened lanai. Textile art sets the décor of this cheerful unit apart and quiet bedrooms are separated from family activity areas in this 'all-on-one-level' condo. Additional amenities:...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Little Gull Cottages is a small resort located 1 hour south of Tampa Florida on a key. This resort has access to Sarasota Bay and the Gulf of Mexico. The beach is only accessible by the local resorts so it seems private. Unit 13 is a two bedroom condo available for rent during week 12 (Saturday...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Carefree décor brings the beach right inside with the soft blues and yellows of sea and sun. This townhouse has spacious living/dining area with fully equipped corridor kitchen on first level, and two carpeted bedrooms on second level including a private balcony off the master bedroom. Additional...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Little Gull is a small resort located 1 hour south of Tampa Florida on a key. This resort has access to Sarasota Bay and the Gulf of Mexico. The beach is only accessible by the local resorts so it seems private. Unit 10 is a one bedroom condo available for rent during week 14 April 6 - 13...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Light and bright condo directly on the beach, totally renovated in 2014. Walk right out from the screened lanai to sink your toes into the warm sand. Modern kitchen with breakfast bar, open living/dining floor plan with quiet bedrooms set apart from family activity. Additional amenities: Beach...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Tranquility and rejuvenation is what you will find renting this apartment. This is an apartment, located on Longboat Key, between the bay and white sand beaches. With 1 bedroom, 1 bathroom, equipped kitchen and TV equipped living room, it can perfectly accommodate a couple. You do not need to leave...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Gulf Breezes, Soft Sand! Your Place on the beach!1 / 51
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Remodeling is complete! Our beautiful low-rise resort is located directly on the beach, and 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/dining area with 46 inch plasma TV & BlueRay Player,...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Zilli Tower 503 is a family-owned 800 square foot tower apartment on the shores of the Gulf of Mexico. It is part of the Zilli Collection . Each with the Zilli touch of amazing view, decor, ( not typical wicker furniture , silly beach artifacts 40 year old flooring etc 1 SIZE fit all .) We...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Whitney Beach 1451 / 28
    (1)Terrible
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
    • Terrace
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    • Private Outdoor Pool (Heated)
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    Whitney Beach 145 - Condo 2 Bedroom/ 2 Bath on Longboat Key , maximum occupancy of 4 people. Community pool. Distance to the Beach: 500 ft. 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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    This lovely, single-level home boasts a number of great amenities, while also being dog-friendly. It comes equipped with a heated pool, a boat dock, and lift, as well as a golf cart for your use. The back lanai is well furnished, making it the perfect place to relax by the pool while taking in the...
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    Longboat Key, Florida 34228
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Comfortably appointed to reflect the sand and sea view from spacious living/dining area on first level of light and bright townhouse. Laid back, island-style décor with screened lanai beachside. 2nd floor master bedroom features a balcony perfect for sunset watching or star gazing. Additional...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Stunning, newly renovated 3BR/3BTH home on preferred southern end of Longboat Key. Luxury interior design features cozy, oversized Restoration Hardware furniture, high-end linens, fully appointed gourmet kitchen, large master bath with Jacuzzi overlooking canal, and more. Whether it's a fun day a...
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    Longboat Key, Florida 34228
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Bright and cheerful with beach-style decor and pops of color. Tiled throughout, off the open living/dining area you'll discover a secluded lanai under the palm trees just steps from the pool. Relaxation starts here, where everything is all on one level and it's an easy-breezy walk to the beach.
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Bright and cheerful with beach-style decor and pops of color. Tiled throughout, off the open living/dining area you'll discover a secluded lanai under the palm trees just steps from the pool. Relaxation starts here, where everything is all on one level and it's an easy-breezy walk to the beach....
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Beach front condo in Longboat Key1 / 13
    (1)Average
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
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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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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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...
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    Longboat Key, Florida 34228
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beach Castle Resort 61 / 28
    (1)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Shared Outdoor Pool (Unheated)
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    Beach Castle Resort BC6 - Condo 2 Bedroom/ 2 Bath on Longboat Key beach side , 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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beach & Tennis Enthusists Vacation Condo1 / 22
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
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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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Cute 1br condo on the water on north Longboat Key. Small one story complex with only 8 units so very private. Boat dock and kayak launch right outside and great fishing from the dock. Washer and dryer inside the unit. Easy 3-4 minute walk to the beach or easy drive to Holmes Beach and Anna Maria...
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    Longboat Key, Florida 34228
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Children's Pool
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    About this property
    Enjoy your family vacation in the two beds,two baths 1,503 sf spacious condo,fully turn key equipped waiting for you to move-in. All utilities are free including hi speed internet, Wi-Fi, three flat TV's, landline phone, in-unit washer and dryer. Condo unit 203 located on the 2nd floor,...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    This upscale townhouse with luxury conveniences features a streamlined and upgraded granite and tile kitchen and bathroom on the first level. A spacious, open dining and living area leads to the screened lanai facing the Gulf with stairway to the beach. All bedrooms are carpeted. Second level...
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    Longboat Key, Florida 34228
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
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    Smoking allowed
    About this property
    This is a spacious house, located in Halyard Lane on Longboat Key, close to St. Armands Circle (3 miles) and private beach (0.5 miles). With 3 bedrooms, 2 bathrooms, equipped kitchen and TV equipped living room, it can perfectly accommodate a family or group of friends of 6 guests. The house is...
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    Longboat Key, Florida 34228
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Nestled in the palms, this 2nd floor, all-on-one-level condo features elegant decorator touches enhancing this serene tropical hideaway. The private balcony offers a partial view of the Gulf and its sunsets, which can also be glimpsed from the combined living and dining area. Granite in the kitchen...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    House Has 4 Bedrooms sleeps up to 8 people Fully stocked Kitchen with updated appliances across street from Beach and shopping and dining lots of water activities available Also has a bbq and a room in one bedroom that is private 2 tvs and cable are at house also in the summer time you can see...
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    Longboat Key, Florida 34228
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Private Garden
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    On the Beach - Brilliant Sunsets - Balmy Breezes Quiet & secluded - Only three other units in the building. The surf, dolphins, incredible sunsets all from screened balcony! Enjoy warm sunny days and tropical nights while staying in a secluded romantic setting in our two-bedroom villa on your...
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    Longboat Key, Florida 34228
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    This tennis resort boasts gorgeous views of Mangrove wetland and is just a short walk from stunning gulf beaches! The community pool makes this a lovely family-friendly getaway. Find great bird-watching and wildlife viewing from the balcony, or stroll through Mangrove tunnels on the boardwalk....
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    Longboat Key, Florida 34228
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Cool and serenely decorated to reflect a tropical hideaway. Stainless steel kitchen, with plenty of cupboards and spacious granite breakfast bar. Designer bedding in the carpeted king master and queen guest bedrooms which are separated from the family activity areas. Walk directly out to the beach...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Center courtyard unit just steps from the pool, with palm trees and Gulf views from the screened lanai directly off the open living and dining area. Wicker furniture and plump floral cushions make a delightful and comfortable décor. Bedrooms are located away from the family activity areas in this...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    SUMMER- FURNISHED- 2 bedroom/ 1.5 bathroom unit is ready to go! Completely turn key, with bicycles,kayak and beach chairs! Amazing pool right on the Sarasota Bay! Great Kayaking right on the property! Private beach access on the Gulf of Mexico drive. The house has been totally remodeled with...
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    Longboat Key, Florida 34228
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Wonderful Beach front condo in magnificent Longboat key. You will Love the the beautiful private Balcony with sensational beachfront views of turquoise Gulf waters. This unit is on the second floor with an elevator for easy access. The space is a roomy 1175 sqft with a full size kitchen living room...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sand Cay Resort is centrally located on beautiful Longboat Key next to the new Zota hotel, with it's beautiful restaurants and bars. There are other restaurants and shopping close by. The resort has a heated pool, shuffleboard, basket ball and full tennis court, in addition to an immaculate...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Kick your shoes off, put on a pair of flip-flops, and walk down to the sparkling bay during your stay at this 2-bedroom, 2.5-bathroom vacation rental condo in Longboat Key! The condo is ideally located in the Cedars East community. Up to 8 guests can spend days at the beach, swimming in the...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 8
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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...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Wonderful and clean second floor 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 are priced right and ready to negotiate to...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Smoking allowed
    About this property
    • Welcoming, distinctive, fully furnished 2 bedroom, 2 bathroom condo in a verdant, tropical environment. • Very private and quiet first floor, 1600 ft. unit with lush garden views. • Master suite with office niche, king size bed, walk-in closet and double sinks in bathroom. • Guest bedroom with...
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    Longboat Key, Florida 34228
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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