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Vacation Rentals in Longboat Key, FL

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All 131 Rentals in Longboat Key
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From
$193
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
22 photos Details Reviews (1) Make Inquiry
From
$132
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
7 photos Details Reviews (2) Make Inquiry
From
$135
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
18 photos Details Reviews (1) Make Inquiry
Also consider
Private Island House On The Water
2 Bedrooms, sleeps 6
$357 / night
Cedars East 821 On Longboat Key
2 Bedrooms, sleeps 5
$223 / night
32% Discount Sept/Oct - Beautiful Updated Condo at Sand Cay Beach with Great Ocean Views.
2 Bedrooms, sleeps 6
$139 - $299 / night
Birdie of Paradise On Longboat Key
3 Bedrooms, sleeps 6
$218 - $423 / night
From
$132
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
7 photos Details Reviews (3) Make Inquiry
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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From
$105
Per Night
Studio, 1 Bathroom, Sleeps 2
Bookings
7 photos Details Reviews (1) Make Inquiry
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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From
$179
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 7
Bookings
14 photos Details Reviews (4) Make Inquiry
5 of 5 stars Reviewed August 28, 2013
Well kept and well located condo in a small comfortable complex. Right on beach and you can enjoy sunsets from your screened in porch. Many nice updates in kitchen, bedroom and...
5 of 5 stars Reviewed January 11, 2013
My family (Mother, husband, 2 teenage children) stayed in unit 118 of this condo for a week. The unit is fabulous, well stocked and right on the beach - gorgeous views all day...
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From
$157
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
16 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed June 13, 2014
I am reluctant to review the property because it might be more difficult to get the weeks I want! My husband and I first went to this place 35 years ago when friends recommended...
4 of 5 stars Reviewed May 12, 2014
This condo was just right for my husband myself and our young 18 mo. old daughter. The space was clean and bright. The resort pool and beach location on the Gulf was ideal. It...
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From
$190
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
10 photos Details Make Inquiry
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From
$1,000
Per Night
5 Bedrooms, 5 Bathrooms, Sleeps 10
-19 photos Details Make Inquiry
From
$3,000
Per Month
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
16 photos Details Make Inquiry
From
$115
Per Night
Studio, 1 Bathroom, Sleeps 4
Bookings
6 photos Details Make Inquiry
From
$63
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
Booking
23 photos Details Make Inquiry
From
$110
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
29 photos Details Make Inquiry
From
$142
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
6 photos Details Make Inquiry
From
$186
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
18 photos Details Make Inquiry
From
$167
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
41 photos Details Make Inquiry
From
$4,000
Per Month
3 Bedrooms, 2 Bathrooms, Sleeps 6
23 photos Details Make Inquiry
From
$350
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
77 photos Details Make Inquiry
From
$162
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
9 photos Details Reviews (1) Make Inquiry
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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From
$171
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
29 photos Details Reviews (3) Make Inquiry
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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From
$169
Per Night
1 Bedroom, 1 Bathroom, Sleeps 6
17 photos Details Make Inquiry
From
$195
Per Night
1 Bedroom, 1 Bathroom, Sleeps 6
23 photos Details Make Inquiry
From
$193
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
27 photos Details Make Inquiry
From
$1,800
Per Month
1 Bedroom, 1 Bathroom, Sleeps 4
19 photos Details Make Inquiry
From
$175
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
22 photos Details Make Inquiry
From
$119
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
22 photos Details Make Inquiry
From
$175
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
22 photos Details Make Inquiry
From
$2,550
Per Month
2 Bedrooms, 2 Bathrooms, Sleeps 6
18 photos Details Make Inquiry
From
$175
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
22 photos Details Make Inquiry
From
$89
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
20 photos Details Make Inquiry
From
$3,000
Per Month
3 Bedrooms, 2 Bathrooms, Sleeps 6
26 photos Details Make Inquiry
From
$1,800
Per Month
2 Bedrooms, 2 Bathrooms, Sleeps 4
23 photos Details Make Inquiry
From
$100
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
21 photos Details Make Inquiry
From
$127
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
21 photos Details Make Inquiry
From
$95
Per Night
2 Bedrooms, 7 Bathrooms, Sleeps 4
25 photos Details Make Inquiry
From
$3,000
Per Month
2 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details Make Inquiry
From
$3,750
Per Month
2 Bedrooms, 2 Bathrooms, Sleeps 4
24 photos Details Make Inquiry
From
$75
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
14 photos Details Make Inquiry
From
$175
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
25 photos Details Make Inquiry
From
$3,800
Per Month
1 Bedroom, 2 Bathrooms, Sleeps 4
Booking
7 photos Details Reviews (1) Make Inquiry
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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Suitability

  • Wheelchair access (10)
  • Elder access (47)
  • Suitable for children (50)
  • Pet friendly (6)
  • Smoking allowed (0)

Amenities

  • All pools (99)
  • Air Conditioning (92)
  • Internet (87)
  • Other outdoor space (86)
  • Public pool (76)
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Book Online(56)

Suitability

  • Wheelchair access (10)
  • Elder access (47)
  • Suitable for children (50)
  • Pet friendly (6)
  • Smoking allowed (0)

Amenities

  • All pools (99)
  • Air Conditioning (92)
  • Internet (87)
  • Other outdoor space (86)
  • Public pool (76)
  • 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.