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Vacation rentals in Longboat Key, Florida

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All 131 Rentals in Longboat Key
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$183
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
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$115
Per Night
Studio, 1 Bathroom, Sleeps 2
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$187
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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Also consider
Almost Paradise! Beautiful 2b/2b on Long Boat Key
2 Bedrooms, sleeps 4
$120 / night
Luxurious Villa with Pool, Gourmet Kitchen & WiFi!
3 Bedrooms, sleeps 6
$508 / night
Luxurious Villa with Pool, Gourmet Kitchen & WiFi!
3 Bedrooms, sleeps 6
$508 / night
Castle in the Sky Near Beach and Tennis
4 Bedrooms, sleeps 10
$214 - $323 / night
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$1,012
Per Week
1 Bedroom, 1 Bathroom, Sleeps 4
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$177
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
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$4,163
Per Month
1 Bedroom, 2 Bathrooms, Sleeps 4
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$145
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
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$196
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 7
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$157
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
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$214
Per Night
Studio, 1 Bathroom, Sleeps 3
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$69
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
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$171
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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$211
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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$181
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1 Bedroom, 1 Bathroom, Sleeps 4
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$1,330
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5 Bedrooms, 5 Bathrooms, Sleeps 10
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$172
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1 Bedroom, 1 Bathroom, Sleeps 4
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$219
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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$3,286
Per Month
2 Bedrooms, 2 Bathrooms, Sleeps 6
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$204
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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$156
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2 Bedrooms, 1 Bathroom, Sleeps 4
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$2,793
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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$159
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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$183
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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$4,382
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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$5,367
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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$82
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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$207
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1 Bedroom, 1 Bathroom, Sleeps 6
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From
$126
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Studio, 1 Bathroom, Sleeps 4
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$192
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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$137
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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$197
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1 Bedroom, 1 Bathroom, Sleeps 4
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$214
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1 Bedroom, 1 Bathroom, Sleeps 6
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From
$1,972
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1 Bedroom, 1 Bathroom, Sleeps 4
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From
$4,157
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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From
$110
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2 Bedrooms, 1 Bathroom, Sleeps 4
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From
$192
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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From
$139
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
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From
$130
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1 Bedroom, 1 Bathroom, Sleeps 4
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From
$97
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1 Bedroom, 1 Bathroom, Sleeps 4
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From
$3,286
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3 Bedrooms, 2 Bathrooms, Sleeps 6
26 photos Details
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Suitability

  • Wheelchair access (10)
  • Elder access (48)
  • Suitable for children (50)
  • Pet friendly (8)
  • Smoking allowed (0)

Amenities

  • All pools (99)
  • Air Conditioning (93)
  • Internet (88)
  • Other outdoor space (87)
  • Public pool (75)
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Beachfront condos and bayside villas – your vacation rental on Longboat Key

Imagine overlooking Sarasota Bay and relaxing in your own villa pool garden … or enjoying crimson sunsets from your Gulf front family vacation condo. Beach and bay rental homes deliver the best of all worlds with spacious living, exceptional kitchens and easy access to Longboat Key parks, shopping and upscale or relaxed dining selections. For fishing excursions or family vacations, select rentals offer flexibility and value for holidays at the beach.

Longboat Key - the upscale coastal vacation destination

This gorgeous Florida key combines serene seashore enjoyment with luxury shopping and dining choices. Families enjoy the many water sport activities from fishing, boating and kayaking to plucking perfect seashells along the shoreline. Couples and friends explore chic dining and shopping spots around St. Armand’s Circle. The aristocratic heritage of the St. Armand and Ringling families resonates through quiet gardens and plush Palm Beach-style shopping. Umbrella-draped cafes and handsome restaurants offer exceptional European fare and inventive coastal specialties. Work off that decadent dessert with a stroll around the circle for leather, jewelry, resort wear and art gallery browsing.

Cultural treasures along Sarasota Bay

Venture just across the bridge over Sarasota Bay for unrivalled cultural treats. The Ringling circus family bequeathed an elegant legacy of art and architecture. The estate includes the acclaimed John and Mable Ringling Museum of Art, the family’s winter Ca’ d’Zan mansion – a Venetian Gothic masterpiece - the Circus Museum and historic Asolo Repertory Theater. With elegant gardens and terraces spread over 20 bayside acres, the complex provides hours of enjoyment.

Waterfront dining

Beyond the eclectic mix of St. Armand Circle restaurants, you’ll want to sample excellent bay front restaurants. The Dry Dock is a favorite of locals and visitors alike, with waterside dining under coconut palms or indoor seating with the same exceptional views. Boasting ultra fresh grouper sandwiches, char-grilled burgers and a host of pasta and chicken selections, the Dry Dock grill is a casual dining treat. Diners arrive by car or boat to enjoy Mar Vista Dockside Restaurant and Pub in the historic village at the North end of the key. With quaint indoor or outdoor dining and spectacular views, try steamer pots of fresh seafood or exotic scallop and crab dishes that wash down quite well with islander mojitos, margaritas and other such flavorful concoctions. Land lovers can choose from the number of chicken, steak and pork dishes.

Visitor reviews aid vacation rental selection

You’ll have no trouble knowing what to expect, as you search for the just-right villa or condo rental. Our unbiased visitor reviews offer clear descriptions and candid evaluations, so you can feel confident in your choice.