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

Search Longboat Key Cottage Rentals from CA $352

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Our top choices for Longboat Key cottages

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 CA $243
CA $467 total
includes taxes & fees
Aug 31 - Sep 1
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach

2. The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (205 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 CA $271
CA $383 total
includes taxes & fees
Aug 31 - Sep 1
The Inn On Siesta Key

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 CA $100
CA $352 total
includes taxes & fees
Aug 31 - Sep 1
Coastal Luxury 7mi to Anna Maria Private Cottage

4. Cozy Lido Key Bungalow by Pool & Beach

Cozy Lido Key Bungalow by Pool & Beach
Lido Key
The price is CA $122
CA $465 total
includes taxes & fees
Sep 3 - Sep 4
Cozy Lido Key Bungalow by Pool & Beach

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

Lido Bungalow Walk to Beach & St. Armand's Circle
Lido Key
The price is CA $122
CA $462 total
includes taxes & fees
Sep 1 - Sep 2
Lido Bungalow Walk to Beach & St. Armand's Circle

6. Sunny Lido Studio - Modern Touches

Sunny Lido Studio - Modern Touches
Lido Key
The price is CA $138
CA $481 total
includes taxes & fees
Sep 1 - Sep 2
Sunny Lido Studio - Modern Touches

7. 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 CA $416
CA $909 total
includes taxes & fees
Aug 31 - Sep 1
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

8. 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 CA $353
CA $1,271 total
includes taxes & fees
Sep 17 - Sep 18
Adorable Cottage with Covered Balconies and Private Pool

9. 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.
The price is CA $344
CA $1,181 total
includes taxes & fees
Sep 11 - Sep 12
Beautiful Guest House Near the Beach with Private Pool!

10. 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 CA $353
CA $1,194 total
includes taxes & fees
Sep 7 - Sep 8
Beautiful Condo on Pine Ave, 2 Blocks to Beach

11. 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 CA $322
CA $754 total
includes taxes & fees
Sep 1 - Sep 2
Haven cottage Across street from beach and Heated Pool

12. 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 CA $300
CA $591 total
includes taxes & fees
Sep 2 - Sep 3
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

13. 3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
The price is CA $3,183
CA $4,179 total
includes taxes & fees
Sep 2 - Sep 3
3716 7th Ave W

14. 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 CA $341
CA $1,349 total
includes taxes & fees
Sep 1 - Sep 2
Cabana Cottage Across street from Beach and Heated Pool

15. Cozy Lido Key Studio Steps to Beach & Kayaking

Cozy Lido Key Studio Steps to Beach & Kayaking
Lido Key
The price is CA $130
CA $471 total
includes taxes & fees
Sep 1 - Sep 2
Cozy Lido Key Studio Steps to Beach & Kayaking

16. 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 CA $138
CA $420 total
includes taxes & fees
Aug 31 - Sep 1
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

17. Nook Cottage Across street from beach and Heated Pool

Nook Cottage Across street from beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (4 reviews)
"They have really thought of everything and gone above and beyond to make our stay as comfortable as possible. Everything was very clean! Paige was a wonderful guide and host for the local area!"
United States
Derek N.
The price is CA $315
CA $915 total
includes taxes & fees
Aug 31 - Sep 1
Nook Cottage Across street from beach and Heated Pool

18. Nest Cottage Across street from beach and Heated Pool

Nest Cottage Across street from beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (2 reviews)
"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 CA $315
CA $751 total
includes taxes & fees
Aug 31 - Sep 1
Nest Cottage Across street from beach and Heated Pool

19. 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 CA $315
CA $751 total
includes taxes & fees
Aug 31 - Sep 1
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.
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Top Longboat Key Hotel Reviews

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Longboat Key Cottages information

Number of reviews
764
Accommodation
19 Cottages
Lowest Price
CA $352
Highest Price
CA $4,179

Frequently asked questions

Are there any family-friendly cottages in Longboat Key?
Put your feet up at Queen's Gate Resort, a 2.5-star cottage just a short drive from downtown. Conveniences here include a nearby beach and WiFi. Another family-friendly option where you can swap the concrete jungle for wide open spaces is 105b 12th Street South Front 2 Bedroom Apts By Redawning. A barbecue grill and WiFi help make this 3-star cottage a guest favourite. After checking in and chilling in your comfortable new digs, it's time to head out and start exploring. Coquina Beach and Cortez Beach are among the best family-friendly attractions in Longboat Key.
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.

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