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Vacation Rentals in Longboat Key, FL

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All 94 Rentals in Longboat Key
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$193
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1 / 23
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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$157
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1 Bedroom, 1 Bathroom, Sleeps 4
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$179
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2 Bedrooms, 2 Bathrooms, Sleeps 7
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Also consider
Perfect island getaway vacation
1 Bedroom, sleeps 5
$121 / night
Longboat Key Villa steps from the beach!
1 Bedroom, sleeps 4
$67 - $90 / night
House on Canal/ Walk to Beach
3 Bedrooms, sleeps 6
$127 / night
Updated condo in serene setting  beach and bay
2 Bedrooms, sleeps 4
$50 - $167 / night
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$171
Per Night
1 / 29
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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5 of 5 stars Reviewed July 13, 2014
We rented this condo on a recent trip to Longboat Key. We chose this unit as we were able to take our boat with us on vacation and dock it at the condo. We utilized a public...
5 of 5 stars Reviewed July 9, 2014
Loved this rental for 7 days. Location has access to the bay, (manatees visited dock), and across the road with access to the beach for swimming was wonderful. Having a 3...
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$3,795
Per Week
1 / 25
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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$89
Per Night
1 / 20
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1 Bedroom, 1 Bathroom, Sleeps 4
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$1,375
Per Week
1 / 31
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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$110
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1 / 29
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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$3,000
Per Month
1 / 16
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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$110
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1 / 25
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2 Bedrooms, 7 Bathrooms, Sleeps 4
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$3,000
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1 / 19
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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$195
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1 / 23
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1 Bedroom, 1 Bathroom, Sleeps 6
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$169
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1 / 17
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1 Bedroom, 1 Bathroom, Sleeps 6
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$1,800
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1 / 23
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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$3,750
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1 / 24
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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$167
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1 / 41
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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$4,000
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1 / 23
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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$200
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1 / 25
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3 Bedrooms, 2 Bathrooms, Sleeps 8
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$193
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1 / 27
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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$3,000
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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$1,800
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1 / 19
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1 Bedroom, 1 Bathroom, Sleeps 4
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$142
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1 / 6
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2 Bedrooms, 1 Bathroom, Sleeps 4
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$100
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2 Bedrooms, 1 Bathroom, Sleeps 4
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$186
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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$190
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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$70
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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$132
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1 / 7
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1 Bedroom, 1 Bathroom, Sleeps 4
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5 of 5 stars Reviewed September 28, 2014
Don't let the word "Motel" detour you from checking out this fantastic property! There are 4 beautiful units right on the beach. Each is complete with full kitchen and there is a...
5 of 5 stars Reviewed September 27, 2014
This property was wonderfully updated and maintained, single level, quaint and quiet. Right on the beautiful and uncrowded beach, yet close to grocery store, restaurants and local...
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$105
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1 / 7
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Studio, 1 Bathroom, Sleeps 2
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5 of 5 stars Reviewed July 24, 2014
So close to the beach, exactly what I was looking for. The studio was cozy and clean, cutely furnished. We loved the outdoor shower and will definitely return again!
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$115
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1 / 6
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Studio, 1 Bathroom, Sleeps 4
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$4,900
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1 / 10
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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$200
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1 / 6
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3 Bedrooms, 4 Bathrooms, Sleeps 8
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$2,550
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1 / 18
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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$75
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1 / 14
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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$157
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1 / 6
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1 Bedroom, 1 Bathroom, Sleeps 4
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$3,800
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1 / 7
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1 Bedroom, 2 Bathrooms, Sleeps 4
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4 of 5 stars Reviewed April 28, 2014
I stayed here with my husband and daughter. The location was great as it is close to the bay and ocean. The neighborhood is quiet with nice neighbors. The peacocks in the...
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$219
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1 / 9
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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5 of 5 stars Reviewed May 2, 2014
We three enjoyed four days in late April. Kitchen has every spatula know to mankind, among other tools. Balcony table nicely shaded in the afternoon with sun lounger out in the...
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$125
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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$150
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1 / 23
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3 Bedrooms, 3 Bathrooms, Sleeps 5
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$1,000
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5 Bedrooms, 5 Bathrooms, Sleeps 10
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$350
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1 / 77
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3 Bedrooms, 3 Bathrooms, Sleeps 6
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Suitability

  • Wheelchair access (11)
  • Elder access (47)
  • Suitable for children (36)
  • Pet friendly (8)
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  • Air Conditioning (90)
  • Other outdoor space (84)
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Book Online(51)

Suitability

  • Wheelchair access (11)
  • Elder access (47)
  • Suitable for children (36)
  • Pet friendly (8)
  • Smoking allowed (0)

Amenities

  • Air Conditioning (90)
  • Other outdoor space (84)
  • Internet (83)
  • Parking (73)
  • Washer/Dryer (64)
  • View all amenities
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.