Search Cottages in Longboat Key

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Cottages in Longboat Key

The Inn On Siesta Key

3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (189)
"Great place to stay! "
United States
Carlos
The price is AED 606
AED 889 total
includes taxes & fees
19 Nov - 20 Nov
The Inn On Siesta Key

Florida Charm Minifarm🐓 HotTub-POOL-Chickens! Near I75, I275. Pets, trailers OK

Palmetto
10.0 out of 10, Exceptional, (1)
"The accommodations were very comfortable and clean. Quiet neighborhood. Host was extremely helpful and pleasant. The screened porch off of the kitchen was a great place to relax with the dogs. We didn't get an opportunity to enjoy the pool and hot tub because of our other obligations but definitely will plan on staying again the next time I need to visit the area. It was like a home away from home."
United States
Douglas T.
The price is AED 367
AED 901 total
includes taxes & fees
19 Nov - 20 Nov
Florida Charm Minifarm🐓 HotTub-POOL-Chickens! Near I75, I275. Pets, trailers OK

Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly

2.0 star property
Nokomis
10.0 out of 10, Exceptional, (1)
"Host was very accommodating and kind. The cottage was cozy and well kept. Waking up with the ocean breeze off the river and the quiet neighborhood was so relaxing. I would highly recommend!"
United States
Michael A.
The price is AED 324
AED 606 total
includes taxes & fees
1 Dec - 2 Dec
Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly

The "Grouper"

Sunny Shores
9.2 out of 10, Wonderful, (42)
"Great location."
United States
Harold S.
The price is AED 364
AED 782 total
includes taxes & fees
19 Nov - 20 Nov
The "Grouper"

7mi to Anna Maria Newly Renovated Private Cottage

Bradenton
10.0 out of 10, Exceptional, (2)
"I stayed for 9 days. It was in a great location in Bradenton...just minutes from the beach, shopping and dining. It was clean and quiet. I would stay there again."
United States
MO L.
The price is AED 331
AED 1,008 total
includes taxes & fees
20 Nov - 21 Nov
7mi to Anna Maria Newly Renovated Private Cottage

Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms

Casey Key
9.2 out of 10, Wonderful, (69)
"Quiet beautiful beachfront location! We had a wonderful stay and plan on coming back! Thank you very much!"
United States
Katherine Z.
The price is AED 1,003
AED 2,101 total
includes taxes & fees
22 Nov - 23 Nov
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms

Steps to Beach+bikes VaCay getaway on PaG island

Pass-a-Grille
9.8 out of 10, Exceptional, (19)
"Super cute location and unit! Close parking and within walking distance to restaurants (dinner, lunch, breakfast) and soooo close to the beach! "
United States
Shaunte W.
Steps to Beach+bikes VaCay getaway on PaG island

Adorable Cottage with Covered Balconies and Private Pool

Anna Maria
9.6 out of 10, Exceptional, (41)
"Amazing cottage with plenty of amenities and a fantastic location. Just a few minutes walk to the beach, shopping and restaurants. Check-in and check-out were a breeze. The only hiccup was issues with parking. Often the single reserved space below was taken by restaurant clients."
United States
C. S.
The price is AED 837
AED 1,916 total
includes taxes & fees
19 Nov - 20 Nov
Adorable Cottage with Covered Balconies and Private Pool

Nest Cottage Across street from beach and Heated Pool

Siesta Key
10.0 out of 10, Exceptional, (2)
"Clean, modern and staff is amazing. Room ready before noon received text notification from owners. This is now our new go to after 19 years of staying up the street. All of everything is provided in rooms and for beach life, well maintained and fun atmosphere no pressures except to make memories here."
United States
Marti C.
The price is AED 793
AED 1,691 total
includes taxes & fees
19 Nov - 20 Nov
Nest Cottage Across street from beach and Heated Pool

Sunny PaG Island rental w/bikes-just steps2beach

Pass-a-Grille
9.0 out of 10, Wonderful, (18)
"Short walk to the beach and well-kept property. Very neat area."
United States
Emily M.
The price is AED 485
AED 985 total
includes taxes & fees
19 Nov - 20 Nov
Sunny PaG Island rental w/bikes-just steps2beach

Beautiful Condo on Pine Ave, 2 Blocks to Beach

Anna Maria
8.8 out of 10, Excellent, (23)
"Great location, clean, and spacious. Pool didn’t work fir a couple of days but they got it fixed the day before we left "
United States
Paris K.
The price is AED 709
AED 1,680 total
includes taxes & fees
19 Nov - 20 Nov
Beautiful Condo on Pine Ave, 2 Blocks to Beach

Romantic Island Getaway! Just Steps from the Beach

2.0 star property
Bradenton Beach
8.8 out of 10, Excellent, (3)
"It was great! Check in was super easy and anything you would need is nearby. "
United States
Thomas N.
The price is AED 551
AED 1,307 total
includes taxes & fees
19 Nov - 20 Nov
Romantic Island Getaway! Just Steps from the Beach

Beautiful Guest House Near the Beach with Private Pool!

Anna Maria
8.6 out of 10, Excellent, (29)
"Great place, super clean, convenient location, awesome pool!"
United States
Rafael C.
The price is AED 657
AED 1,546 total
includes taxes & fees
19 Nov - 20 Nov
Beautiful Guest House Near the Beach with Private Pool!

5 star Guest House heated pool on the water!

South Sarasota
The price is AED 918
AED 1,848 total
includes taxes & fees
19 Nov - 20 Nov
5 star Guest House heated pool on the water!

Steps 2 Beach-Island Cottage w/king bd+2bike+parking

Pass-a-Grille
9.8 out of 10, Exceptional, (41)
"Quiet neighborhood away from the tourist areas. 50 steps to a beautiful white sandy beach:) charming little place, very clean and comfortable. sunsets were beautiful and almost no rain all week:)"
United States
James C.
The price is AED 639
AED 1,225 total
includes taxes & fees
4 Dec - 5 Dec
Steps 2 Beach-Island Cottage w/king bd+2bike+parking

Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom

Casey Key
9.4 out of 10, Exceptional, (106)
"Great stay, right on a beautiful private beach. Casey key is a great place, highly recommend this place!"
United States
Kathleen P.
The price is AED 1,095
AED 2,125 total
includes taxes & fees
19 Nov - 20 Nov
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom

Haven cottage Across street from beach and Heated Pool

Siesta Key
9.8 out of 10, Exceptional, (7)
"It was a beautiful place. Great staff. Awesome experience."
United States
Nicholas M.
Haven cottage Across street from beach and Heated Pool
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Longboat Key Hotel Reviews

Frequently asked questions

Why book your cottage in Longboat Key with Expedia?
Booking a cottage in Longboat Key is as easy as deciding on your travel dates and selecting your ideal place for outdoor recreation and relaxation. From high-end retreats to affordable properties and cottages that come with amenities like a kitchenette, Expedia has something for all traveler tastes. As for the best deals around? We've got them too!
How can I find cheap cottages in Longboat Key?
Expedia is here to help you track down cheap cottages in Longboat Key. To find a fantastic stay in a couple of quick clicks, simply use our handy filter tool to tailor your search results by star rating, budget and amenities.