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Vacation Rentals in Longboat Key, FL

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  • Flexible dates & rates
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Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
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All 97 Rentals in Longboat Key
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$160
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
35 photos Details
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$225
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
12 photos Details
Reviews (11) Make Inquiry
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$135
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1 Bedroom, 1 Bathroom, Sleeps 4
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Also consider
1 bed/1 bath on Longboat Key Beach
1 Bedroom, sleeps 4
$180 / night
Beachfront Longboat Key Studio #1
Sleeps 4
$115 - $182 / night
Las Hermanas/Starfish Beach front Longboat Key #3
1 Bedroom, sleeps 4
$924 - $1,505 / week
Soaring Spirits on Longboat Key updated 4 BR canal front pool home
4 Bedrooms, sleeps 7
$263 - $454 / night
From
$1,500
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
12 photos Details
Reviews (3) Make Inquiry
From
$350
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
32 photos Details
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$179
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 7
14 photos Details
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$195
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 10
13 photos Details
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From
$149
Per Night
Studio, 1 Bathroom, Sleeps 5
16 photos Details
Reviews (13) Make Inquiry
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From
$83
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
44 photos Details
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From
$154
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
14 photos Details
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From
$3,800
Per Month
1 Bedroom, 2 Bathrooms, Sleeps 4
7 photos Details
Reviews (1) Make Inquiry
From
$132
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
7 photos Details
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$171
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
29 photos Details
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From
$110
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 6
8 photos Details
Reviews (11) Make Inquiry
From
$186
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
26 photos Details
Reviews (4) Make Inquiry
From
$219
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
9 photos Details
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From
$1,650
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 8
19 photos Details
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From
$178
Per Night
1 Bedroom, 1 Bathroom, Sleeps 6
23 photos Details
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$143
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
16 photos Details
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From
$2,500
Per Month
3 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details
Reviews (1) Make Inquiry
From
$3,500
Per Month
2 Bedrooms, 2 Bathrooms, Sleeps 4
25 photos Details
Reviews (1) Make Inquiry
From
$126
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 6
21 photos Details
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From
$169
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
21 photos Details
Reviews (1) Make Inquiry
From
$400
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 12
1 photo Details
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From
$145
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
13 photos Details
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From
$105
Per Night
Studio, 1 Bathroom, Sleeps 2
7 photos Details
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From
$200
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
5 photos Details
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From
$2,550
Per Month
2 Bedrooms, 2 Bathrooms, Sleeps 6
18 photos Details
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From
$175
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
40 photos Details
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From
$110
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
29 photos Details
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From
$167
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
41 photos Details
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From
$3,500
Per Month
3 Bedrooms, 2 Bathrooms, Sleeps 6
23 photos Details
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From
$214
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
6 photos Details
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From
$75
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
14 photos Details
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From
$771
Per Night
5 Bedrooms, 5 Bathrooms, Sleeps 10
23 photos Details
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From
$2,500
Per Month
2 Bedrooms, 2 Bathrooms, Sleeps 4
24 photos Details
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From
$2,000
Per Month
2 Bedrooms, 2 Bathrooms, Sleeps 4
26 photos Details
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From
$4,500
Per Month
3 Bedrooms, 2 Bathrooms, Sleeps 8
25 photos Details
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From
$4,000
Per Month
2 Bedrooms, 2 Bathrooms, Sleeps 4
25 photos Details
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From
$3,600
Per Month
3 Bedrooms, 3 Bathrooms, Sleeps 8
24 photos Details
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Book Online(32)
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Suitability

  • Wheelchair access (6)
  • Elder access (40)
  • Suitable for children (47)
  • Pet friendly (5)
  • Smoking allowed (0)

Amenities

  • All pools (68)
  • Public pool (55)
  • Air Conditioning (54)
  • Other outdoor space (53)
  • Internet (51)
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Book Online(32)

Suitability

  • Wheelchair access (6)
  • Elder access (40)
  • Suitable for children (47)
  • Pet friendly (5)
  • Smoking allowed (0)

Amenities

  • All pools (68)
  • Public pool (55)
  • Air Conditioning (54)
  • Other outdoor space (53)
  • Internet (51)
  • 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.