A coastal cityscape with a sunset over the water, featuring several high-rise buildings and palm trees.

Search Cottages in Longboat Key

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
18 Sep - 20 Sep
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Longboat Key cottages

House (2 Bedrooms) | Interior

1. Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach

Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach
3.0 star property
Bradenton
10.0 out of 10, Exceptional, (3 reviews)
"Very nice place to stay. Clean and a lot of amenities. We enjoyed all the little touches that went into decorating the house, giving it a beach house feel. We would definitely stay here again. "
United States
Rob
The price is AED 643
AED 1,234 total
includes taxes & fees
2 Sep - 3 Sep
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach
Balcony view

2. The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (206 reviews)
"The property was perfect. Walk to down town and the beach. Loved the provisions for the beach which made it so convenient. Room was super clean and overall the property was well maintained."
United States
Stephen
The price is AED 716
AED 1,013 total
includes taxes & fees
2 Sep - 3 Sep
The Inn On Siesta Key
Property grounds

3. Coastal Luxury 7mi to Anna Maria Private Cottage

Coastal Luxury 7mi to Anna Maria Private Cottage
Bradenton
10.0 out of 10, Exceptional, (11 reviews)
"Very nice location. "
United States
Daniel o.
The price is AED 248
AED 914 total
includes taxes & fees
2 Sep - 3 Sep
Coastal Luxury 7mi to Anna Maria Private Cottage
Hair dryer, towels, soap, shampoo

4. Sunny Lido Studio - Modern Touches

Sunny Lido Studio - Modern Touches
Lido Key
The price is AED 364
AED 1,277 total
includes taxes & fees
2 Sep - 3 Sep
Sunny Lido Studio - Modern Touches
Outdoor dining

5. Cozy Lido Key Studio Steps to Beach & Kayaking

Cozy Lido Key Studio Steps to Beach & Kayaking
Lido Key
The price is AED 343
AED 1,250 total
includes taxes & fees
2 Sep - 3 Sep
Cozy Lido Key Studio Steps to Beach & Kayaking
Exterior

6. Yellow Palm Cottage steps from the beach

Yellow Palm Cottage steps from the beach
Siesta Key Village
10.0 out of 10, Exceptional, (2 reviews)
"This place was so cute and quaint! It was just a short walk to the village and to the beach. The grounds were beautiful! A little oasis in the backyard. . Would stay here again!!!"
United States
Tami B.
The price is AED 464
AED 2,268 total
includes taxes & fees
4 Sep - 5 Sep
Yellow Palm Cottage steps from the beach
1 bedroom, iron/ironing board, WiFi, bed sheets

7. Cozy Lido Key Bungalow by Pool & Beach

Cozy Lido Key Bungalow by Pool & Beach
Lido Key
The price is AED 323
AED 1,224 total
includes taxes & fees
3 Sep - 4 Sep
Cozy Lido Key Bungalow by Pool & Beach
Property grounds

8. Pink Mango Cottage steps from the beach

Pink Mango Cottage steps from the beach
Siesta Key Village
The price is AED 402
AED 2,183 total
includes taxes & fees
7 Sep - 8 Sep
Pink Mango Cottage steps from the beach
Property grounds

9. Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Anna Maria
9.6 out of 10, Exceptional, (129 reviews)
"Very nice property! Clean and lovely water view!"
United States
Sadie E.
The price is AED 1,098
AED 2,401 total
includes taxes & fees
7 Sep - 8 Sep
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Property grounds

10. Haven cottage Across street from beach and Heated Pool

Haven cottage Across street from beach and Heated Pool
Siesta Key
9.8 out of 10, Exceptional, (7 reviews)
"Enjoyed the property, a very nice little unit, very clean and enjoyable"
United States
Michael M.
The price is AED 834
AED 1,982 total
includes taxes & fees
2 Sep - 3 Sep
Haven cottage Across street from beach and Heated Pool
Exterior

11. Adorable Cottage with Covered Balconies and Private Pool

Adorable Cottage with Covered Balconies and Private Pool
Anna Maria
9.8 out of 10, Exceptional, (51 reviews)
"Pleasantly surprised how great this place was - awesome backyard setup and incredible location "
United States
Cyrus M.
The price is AED 932
AED 3,404 total
includes taxes & fees
17 Sep - 18 Sep
Adorable Cottage with Covered Balconies and Private Pool
Exterior

12. Beautiful Guest House Near the Beach with Private Pool!

Beautiful Guest House Near the Beach with Private Pool!
Anna Maria
8.8 out of 10, Excellent, (37 reviews)
"House was in great condition and very comfortable. Ideal location! "
United States
Scott B.
Beautiful Guest House Near the Beach with Private Pool!
Exterior

13. Blue Dolphin Cottage steps from the beach

Blue Dolphin Cottage steps from the beach
Siesta Key Village
The price is AED 441
AED 2,233 total
includes taxes & fees
4 Sep - 5 Sep
Blue Dolphin Cottage steps from the beach
Exterior

14. Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Sarasota
9.2 out of 10, Wonderful, (190 reviews)
"Right across the beach Less then 5 minutes Good space - rooms nice ad clean "
United States
ASHISH
The price is AED 795
AED 1,566 total
includes taxes & fees
2 Sep - 3 Sep
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Property grounds

15. Beautiful Condo on Pine Ave, 2 Blocks to Beach

Beautiful Condo on Pine Ave, 2 Blocks to Beach
Anna Maria
8.8 out of 10, Excellent, (29 reviews)
"Nice place, a little noisy in the morning but a good convenient location for a girls trip. It was clean and beds were decent. The water pressure was not great but that being said, I would stay here again!"
United States
Amy H.
The price is AED 932
AED 3,124 total
includes taxes & fees
2 Sep - 3 Sep
Beautiful Condo on Pine Ave, 2 Blocks to Beach
Pool

16. Cabana Cottage Across street from Beach and Heated Pool

Cabana Cottage Across street from Beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful property and fantastic location. Everything you need at your fingertips for an enjoyable beach stay without ever having to leave the island!"
United States
Meghan J.
The price is AED 921
AED 3,648 total
includes taxes & fees
2 Sep - 3 Sep
Cabana Cottage Across street from Beach and Heated Pool
1 bedroom, iron/ironing board, WiFi, bed sheets

17. Lido Bungalow Walk to Beach & St. Armand's Circle

Lido Bungalow Walk to Beach & St. Armand's Circle
Lido Key
The price is AED 323
AED 1,224 total
includes taxes & fees
2 Sep - 3 Sep
Lido Bungalow Walk to Beach & St. Armand's Circle
Property grounds

18. 3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
The price is AED 8,668
AED 11,333 total
includes taxes & fees
3 Sep - 4 Sep
3716 7th Ave W
Exterior

19. Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
South Village
9.6 out of 10, Exceptional, (90 reviews)
"Would definitely stay here again. Great location and great house! Owner was quick and helpful with communication."
United States
Clarissa S.
The price is AED 364
AED 1,113 total
includes taxes & fees
2 Sep - 3 Sep
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Dining

20. Lookout Cottage Across street from Beach and Heated Pool

Lookout Cottage Across street from Beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (1 review)
"The place was beautiful, tastefully furnished and decorated, and so clean! Plenty of towels and nice sheets. Loved the amenities like the pool and the beach chairs. The best part is the location - right across the street from a fantastic beach, close enough to walk to the main business district but not so close that you have to deal with all the people of you don’t want to. Perfect place for a couple looking for some R&R!"
United States
Keeley L.
The price is AED 926
AED 2,097 total
includes taxes & fees
3 Sep - 4 Sep
Lookout 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Longboat Key Hotel Reviews

Zota Beach Resort

Zota Beach Resort

8/10 Good
"Everything was great but would rather skip the valet parking. Would rather park and secure my own auto."
Anthony 1-night trip
Posted 14 hours ago
Zota Beach Resort

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.