We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation Rentals in Longboat Key, FL

Use a credit card to book with our Peace of Mind Protection.
Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
More filters
All 131 Rentals in Longboat Key
loading...
Sort by
From
$105
Per Night
Studio, 1 Bathroom, Sleeps 2
Bookings
7 photos Details
Reviews (1) Make Inquiry
From
$924
Per Week
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
7 photos Details
Reviews (1) Make Inquiry
From
$3,800
Per Month
1 Bedroom, 2 Bathrooms, Sleeps 4
Booking
7 photos Details
Reviews (1) Make Inquiry
Also consider
Birdie of Paradise On Longboat Key
3 Bedrooms, sleeps 6
$218 - $423 / night
Soaring Spirits on Longboat Key updated 4 BR canal front pool home
4 Bedrooms, sleeps 7
$263 - $454 / night
Updated condo in serene setting  beach and bay
2 Bedrooms, sleeps 4
$50 - $167 / night
Gulf Front Condo on Expansive White Sandy Beach
1 Bedroom, sleeps 4
$83 / night
From
$132
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
7 photos Details
Reviews (1) Make Inquiry
From
$143
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
16 photos Details
Reviews (2) Make Inquiry
From
$179
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 7
Bookings
14 photos Details
Reviews (4) Make Inquiry
From
$3,795
Per Week
3 Bedrooms, 2 Bathrooms, Sleeps 6
23 photos Details
Make Inquiry
From
$186
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
18 photos Details
Make Inquiry
Get the List
From
$63
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
16 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
$142
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
6 photos Details
Make Inquiry
From
$75
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
14 photos Details
Make Inquiry
From
$3,000
Per Month
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
16 photos Details
Make Inquiry
From
$89
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
20 photos Details
Make Inquiry
From
$193
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
27 photos Details
Make Inquiry
From
$195
Per Night
1 Bedroom, 1 Bathroom, Sleeps 6
23 photos Details
Make Inquiry
From
$175
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
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
22 photos Details
Make Inquiry
From
$175
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
22 photos Details
Make Inquiry
From
$1,800
Per Month
1 Bedroom, 1 Bathroom, Sleeps 4
19 photos Details
Make Inquiry
From
$127
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
21 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
$3,000
Per Month
3 Bedrooms, 2 Bathrooms, Sleeps 6
26 photos Details
Make Inquiry
From
$100
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
21 photos Details
Make Inquiry
From
$1,800
Per Month
2 Bedrooms, 2 Bathrooms, Sleeps 4
23 photos Details
Make Inquiry
From
$175
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
25 photos Details
Make Inquiry
From
$95
Per Night
2 Bedrooms, 7 Bathrooms, Sleeps 4
25 photos Details
Make Inquiry
From
$115
Per Night
Studio, 1 Bathroom, Sleeps 4
Bookings
6 photos Details
Make Inquiry
From
$167
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
8 photos Details
Reviews (1) Make Inquiry
From
$171
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
29 photos Details
Reviews (3) Make Inquiry
From
$2,550
Per Month
2 Bedrooms, 2 Bathrooms, Sleeps 6
18 photos Details
Make Inquiry
From
$1,214
Per Night
5 Bedrooms, 5 Bathrooms, Sleeps 10
-19 photos Details
Make Inquiry
From
$189
Per Night
1 Bedroom, 1 Bathroom, Sleeps 6
17 photos Details
Make Inquiry
From
$157
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
6 photos Details
Make Inquiry
From
$110
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
29 photos Details
Make Inquiry
From
$200
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 8
6 photos Details
Make Inquiry
From
$464
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
77 photos Details
Make Inquiry
Go to map view
Book Online(55)
Use filters to find the best results!

Suitability

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

Amenities

  • All pools (97)
  • Air Conditioning (92)
  • Internet (87)
  • Other outdoor space (86)
  • Parking (73)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List
Nearby cities
Filter search results by:
Book Online(55)

Suitability

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

Amenities

  • All pools (97)
  • Air Conditioning (92)
  • Internet (87)
  • Other outdoor space (86)
  • Parking (73)
  • 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.