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House Rentals in Longboat Key, FL

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    Travelers to Longboat Key are booking March dates now. Secure your vacation rental today, and have the perfect trip.
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    5 of 5 stars (2) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    $4,800
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    About this property
    Large Gated Home on waterway - White Sand Beach only steps away. Our vacation home is spacious and beautifully furnished with 3 bedrooms and a large loft with sleeper-sofa, 3 full bathrooms, sleeps uo to 8 people, Perfect for families or couples. The home has a fully equipped gourmet kitchen with... View all property information
    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed May 28, 2015
    We stayed here from may 9 to 16 with my 2 kids (3.5 and 2 years old), husband and my parents. The house was more than we could ask for. Plenty of room, very nicely decorated...
    5 of 5 stars Reviewed March 4, 2010
    The home was beautiful, all the amenities. Great location. We had no issue at all with the process of renting, made our reservation, paid and went. Everything was smooth, just how...
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    $429
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    About this property
    Set on a 30 acre private island a few hundred yards off North Longboat Key, this new water front home (completed in 2012) will provide an island vacation experience for you and your family like no other. The house has 2 bedrooms, an outside sleeping porch/bunk bed, along with 2 1/2 bathrooms and an... View all property information
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    Longboat Key, Florida 34228
    1 / 8
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    $125
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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
    Location Information
    Longboat Key, Florida 34228
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    $3,895
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    About this property
    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 a private, heated pool. In the back, you have your own private dock on the deep-water canal that will... View all property information
    Location Information
    Longboat Key, Florida
    1 / 17
    6 Bedrooms, 6 Bathrooms, Sleeps 20 | Quick View
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    $829
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    • Pet-friendly
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    • Child-friendly
    • x
    • ?
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    • Elder access
    • 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
    Location Information
    Longboat Key, Florida 34228
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • x
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    • Elder access
    • x
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    About this property
    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
    Location Information
    Longboat Key, Florida 34228
    1 / 49
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    $300
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    • Pet-friendly
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    • Child-friendly
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    • 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
    Location Information
    Longboat Key, Florida 34228
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    1 / 44
    4 of 5 stars (1) Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
    From
    $700
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    • Internet Access
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    • Waterfront
    • Private Outdoor...
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    • Pet-friendly
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    • Child-friendly
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    • x
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    • Elder access
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    About this property
    This spacious 5 bedroom villa is situated directly on the beautiful white sand beaches of Longboat Key. Offering a large outdoor private heated swimming pool and glorious views of the Gulf of Mexico from almost every corner, fully-equipped gourmet kitchen, fireplace, BBQ, and much more - it is your... View all property information
    Location Information
    Longboat Key, Florida 34228
    4 of 5 stars Reviewed April 27, 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 / 17
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    From
    $414
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
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    About this property
    **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
    Location Information
    Longboat Key, Florida 34228
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    • Parking
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    • Patio
    • Outdoor Dining Area
    • DVD Player
    • Air Conditioning
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    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • Smoking allowed
    • Elder access
    • x
    About this property
    Comfortable Turn-Key Tropical Home is just a two-minute walk to the private sandy white beaches and dazzling blue waters of North Longboat Key. There is ten miles of sidewalks for your enjoyment to bike, jog, or walk as well as direct access from your backyard to Durante Park, a gorgeous Nature... View all property information
    Location Information
    Longboat Key, Florida 34228
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    $3,000
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    • Washer
    • Wi-Fi
    • Satellite TV
    • Patio
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    • Air Conditioning
    • Balcony
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Our house is located on Longboat Key, outside of the city of Sarasota, on the west coast of Florida. There is an airport in Sarasota, as well as in Tampa, which is a little over an hour away. Longboat Key is pretty and green, and is linked, by bridge, to Anna Maria Island on the north, and to St.... View all property information
    Location Information
    Longboat Key, Florida 1234
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    From
    $150
    / Night
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    • Satellite TV
    • Private Yard
    • Secure Parking
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    • Internet Access
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    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
    1 / 24
    5 of 5 stars (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    $8,400
    / Week
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    • Washer
    • Grill
    • Satellite TV
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    • Balcony
    • Waterfront
    • Wi-Fi
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    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
    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed September 1, 2015
    The perfect place for a family vacation. The home, the property, the beach, and the location were all top notch. It exceeded my expectations. The owners were very accomodating and...
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    1 / 13
    4.5 of 5 stars (23) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    From
    $195
    / Night
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    • Satellite TV
    • Grill
    • Washer
    • Hot Tub
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    ++++++Rated ' EXCELLENT' digital badge on TripAdvisor and FlipKey++++++. This exclusive award recognizes outstanding vacation rentals based on reviews of past year so you can rent with confidence. TOP 5 REASONS TO VACATION AT THE... View all property information
    Location Information
    Longboat Key, Florida 34228
    4 of 5 stars Reviewed January 1, 2016
    This is a very spacious condo that is fully equipped and easily accommodated the 8 of us. Great AC, 3 tvs, bicycles, bbq pit, etc. Close to the beachand includes access to a...
    5 of 5 stars Reviewed July 19, 2015
    We were really happy to rent Castle in sky after looking at many travel sites. We found nothing that could hold 9 women on Longboat Key unless we wanted to pay twice as...
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    1 / 17
    3.5 of 5 stars (2) Average
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    From
    $132
    / Night
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    • Air Conditioning
    • DVD Player
    • Internet Access
    • Patio
    • Satellite TV
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Pet friendly, Unique Bungalow Canal Home on the North End of Longboat Key. Unique Bungalow Canal Home on the North End of Longboat Key. If you have been putting off writing the next great American novel due to the lack of a peaceful setting then this quaint canal home may be just the place for you.... View all property information
    Location Information
    Longboat Key, Florida 34228
    3 of 5 stars Reviewed April 9, 2014
    This rental was was very clean and had every thing you would need on vacation. Very cute house with huge yard. Loved hanging on the screened in porch. Nice location off the...
    4 of 5 stars Reviewed March 18, 2014
    The cottage was well reflected by the pictures. Everything fairly new and clean. Beds comfortable, has everything. Area quiet but short drive to Bradenton and Holmes beaches, for...
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    1 / 1
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
    From
    $400
    / Night
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • 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 / 10
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
    From
    $267
    / Night
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    • Private Outdoor...
    • Washer
    • Patio
    • Balcony
    • Waterfront
    • Satellite TV
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    A special address on the Gulf of Mexico beach at the very north end of Longboat Key overlooking a bird sanctuary with views of the sea, sky and our extraordinary sunsets. One of nine contemporary townhomes designed by noted architect Tim Seibert (Sarasota School of Design), this stunning home is... View all property information
    Location Information
    Longboat Key, Florida 34228
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Amenities & Details
    • Satellite TV
    • Balcony
    • Washer
    • Terrace
    • Parking
    • Air Conditioning
    • Internet Access
    • Private Indoor Pool
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    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.... View all property information
    Location Information
    Longboat Key, Florida 34228
    1 / 5
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Grill
    • Parking
    • Satellite TV
    • Washer
    • Porch
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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
    Location Information
    Longboat Key, Florida 34228