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

Search Longboat Key Cottages

Check prices for these dates

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

Our top choices for Longboat Key cottages

A patio with two blue lounge chairs, a potted plant, and a gravel area.

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
$297 nightly
The price is $336
Sep 2 - Sep 3
Total with taxes and fees
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach
A pool area with a blue deck, lounge chairs, a barbecue, and a view of buildings in the background.

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
$244 nightly
The price is $276
Sep 2 - Sep 3
Total with taxes and fees
The Inn On Siesta Key
A keyless entry system with a red pathway leading to a gated entrance.

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.
$224 nightly
The price is $249
Sep 2 - Sep 3
Total with taxes and fees
Coastal Luxury 7mi to Anna Maria Private Cottage
A bathroom with a toilet, a glass-enclosed shower, and a framed picture on the wall.

4. Sunny Lido Studio - Modern Touches

Sunny Lido Studio - Modern Touches
Lido Key
$306 nightly
The price is $340
Sep 2 - Sep 3
Total with taxes and fees
Sunny Lido Studio - Modern Touches
A patio with a table set for two, a blue umbrella, and a white fence with plants.

5. Cozy Lido Key Studio Steps to Beach & Kayaking

Cozy Lido Key Studio Steps to Beach & Kayaking
Lido Key
$306 nightly
The price is $340
Sep 2 - Sep 3
Total with taxes and fees
Cozy Lido Key Studio Steps to Beach & Kayaking
A yellow house with a white door and number 5306.

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.
$570 nightly
The price is $613
Sep 4 - Sep 5
Total with taxes and fees
Yellow Palm Cottage steps from the beach
A bedroom with a bed, a bedside table, a mirror, a ceiling fan, and a view of a kitchen area.

7. Cozy Lido Key Bungalow by Pool & Beach

Cozy Lido Key Bungalow by Pool & Beach
Lido Key
$299 nightly
The price is $333
Sep 3 - Sep 4
Total with taxes and fees
Cozy Lido Key Bungalow by Pool & Beach
A hammock tied between two palm trees, a pink building with a red roof, and a bush with red flowers.

8. Pink Mango Cottage steps from the beach

Pink Mango Cottage steps from the beach
Siesta Key Village
$551 nightly
The price is $591
Sep 7 - Sep 8
Total with taxes and fees
Pink Mango Cottage steps from the beach
A balcony with wicker furniture, a grill, and a view of a marina with boats and greenery.

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.
$587 nightly
The price is $654
Sep 7 - Sep 8
Total with taxes and fees
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
A balcony with a white railing, a blue chair, and a view of palm trees and a house.

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.
$484 nightly
The price is $540
Sep 2 - Sep 3
Total with taxes and fees
Haven cottage Across street from beach and Heated Pool
A coastal residential area with houses, a river, and palm trees.

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.
$832 nightly
The price is $927
Sep 17 - Sep 18
Total with taxes and fees
Adorable Cottage with Covered Balconies and Private Pool
A two-story building with a balcony, signs indicating no beach parking, and bicycles parked outside.

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.
$769 nightly
The price is $856
Sep 11 - Sep 12
Total with taxes and fees
Beautiful Guest House Near the Beach with Private Pool!
A small, single-story building with a blue roof and yellow walls, surrounded by a white picket fence and palm trees.

13. Blue Dolphin Cottage steps from the beach

Blue Dolphin Cottage steps from the beach
Siesta Key Village
$563 nightly
The price is $605
Sep 4 - Sep 5
Total with taxes and fees
Blue Dolphin Cottage steps from the beach
A two-story building with a blue exterior and white railings.

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
$379 nightly
The price is $423
Sep 2 - Sep 3
Total with taxes and fees
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
A covered outdoor area with wicker furniture, a glass table, and a view of a residential street.

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.
$763 nightly
The price is $851
Sep 2 - Sep 3
Total with taxes and fees
Beautiful Condo on Pine Ave, 2 Blocks to Beach
A pool area with a blue deck, lounge chairs, a barbecue, and a view of buildings in the background.

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.
$921 nightly
The price is $993
Sep 2 - Sep 3
Total with taxes and fees
Cabana Cottage Across street from Beach and Heated Pool
A bedroom with a bed, a desk, a wardrobe, and a ceiling fan.

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

Lido Bungalow Walk to Beach & St. Armand's Circle
Lido Key
$299 nightly
The price is $333
Sep 2 - Sep 3
Total with taxes and fees
Lido Bungalow Walk to Beach & St. Armand's Circle
A white house with a covered porch, surrounded by a gravel driveway and various tropical plants.

18. 3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
$2,691 nightly
The price is $3,040
Sep 10 - Sep 11
Total with taxes and fees
3716 7th Ave W
A residential house with a white fence, a palm tree, and a parked car.

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.
$272 nightly
The price is $303
Sep 2 - Sep 3
Total with taxes and fees
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
A kitchen with white cabinets, a coffee bar, a wooden shelf with decorative items, and a view of the outside.

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.
$506 nightly
The price is $564
Sep 3 - Sep 4
Total with taxes and fees
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

Zota Beach Resort

Zota Beach Resort

10/10 Excellent
"We come to this wonderful resort for our anniversary almost every year. The location is fantastic - quiet beach, the Gulf is terrific to swim in and accomodations are superb! The restaurant and staff are terrific. It really is a paradise! No need to fly to the islands when you have a perfect spot right here in Florida!"
Rose 4-night trip
Posted 3 hours ago
Zota Beach Resort

Find out more about Longboat Key

Longboat Key Cottages information

Number of reviews
761
Accommodation
19 Cottages
Lowest Price
$249
Highest Price
$3,040

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 favorite. 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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