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Cottages in Longboat Key, FL

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    All 76 Rentals in Longboat Key
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    Travellers to Longboat Key are booking January dates now. Secure your holiday rental today, and have the perfect trip.
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    5 Bedrooms / 4 Bathrooms / Sleeps 12
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    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    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... View all property information
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    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    About this property
    Enjoy a terrific holiday at Fairway Bay, one of south Longboat Key's most coveted addresses. It's easy to see why people love to stay at this beautiful, sprawling resort. A friendly guard at the gate will welcome you into a lushly landscaped compound, and will direct you down a winding tree-lined... View all property information
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    1 Bedroom / 1 Bathroom / Sleeps 4
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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 Bay... View all property information
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    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    About this property
    SAVE 15% THIS APRIL - $2550 per week reduced from $3000. The Banyan home is ideally located just four blocks to the beach on the south end of Longboat Key in Country Club Shores. Situated on a large corner lot this spacious home has all new furnishings with a coastal, cottage flair. The... View all property information
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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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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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Spectacular penthouse condo. Additional amenities include: coffee maker, laundry, ice maker. View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    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. Quiet upscale residential neighborhood. Two minute walk to a quiet clean... View all property information
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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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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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    House on canal, 5 minute walk to the Beach. A 3bedroom/ 2 bathroom home on the north end of Longboat Key, Florida. One king bed, 2 Queen beds, and One bath has a walk- in shower and the other has the tub choice. A nice large kitchen to cook for your family and friends, while enjoying the space... View all property information
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    Studio / 1 Bathroom / Sleeps 3
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    About this property
    The Beach on Longboat Key - New Gulf Front Condo # 103 ~ Beach Front Special ~ $350/4nights , $280/3nights - Stay must begin May 26/27 or end June 3/4 , June 16 to June 19 - $99/night This complex is a two story building with only 15 condos, beautifully landscaped, with sophisticated charm and... View all property information
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    3 Bedrooms / 4 Bathrooms / Sleeps 8
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    About this property
    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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    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Water Views
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    • x
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    About this property
    == 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
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    1 / 49
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    • x
    • x
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    About this property
    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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    6 Bedrooms / 6 Bathrooms / Sleeps 20
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    • Fireplace
    • Hot Tub
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    • x
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    About this property
    Looking for tropical seclusion on a private island? Georgous sunsets with blue, blue waters? If so, then look no further. Nestled among the lush vegetation, your private polynesian beach house awaits your arrival! Accessible only by boat,this getaway assures you complete privacy and relaxation.... View all property information
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
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    • Dryer
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    About this property
    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. The views cannot be beat! The beach is great and the pool and hot tub inviting too! The... View all property information
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    2 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Air Conditioning
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    • Gym
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    • x
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    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
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    1 / 24
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    About this property
    Longboat Key 2 Bedroom 2 Bath Condominium at Seaplace (2 month minimum stay) This newly remodeled and updated, 2 bedroom 2 bath, open living area condominium is tastefully decorated and in immaculate condition. A two month minimum stay is required. Luxury vacation rental properties like Seaplace... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • x
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    About this property
    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 star-kissed nights. Built in the... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    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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    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    About this property
    ***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. 843 Bayport way is a 2 bedroom 2 bath upper... View all property information
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    1 Bedroom / 1 Bathroom / Sleeps 4
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    • x
    • x
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    About this property
    Wonderful gulf front one bedroom one bath fully furnished condo with king bed and two sofas for sleeping. Expansive white sandy beach. Private walled garden in back of screened porch and patio and living room, dining room and kitchen face the patio, pool and view of the gulf with most morning... View all property information
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Condo is located in Banyan Bay Club which consists of a total of only 44 units arranged in two floors. This condo is located at the Garden level. No stairs. The lanai at the rear of the unit opens onto a private Banyan and Palm tree-filled lawn with views of Sarasota Bay. The lanai contains a table... View all property information
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    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    About this property
    On beautiful Sarasota Bay in a lush tropical setting, Harbour Bay Club is on Dream Island, only a short walk to the famous beaches of Longboat Key. Comfortably and stylishly decorated, this condo offers stunning views of the Bay from both the living area and the master bedroom. There are two... View all property information
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