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

Search Longboat Key Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Longboat Key cottages

A two-story house with a green exterior, a blue door, and orange trim.

1. The "Grouper"

The "Grouper"
Sunny Shores
9.6 out of 10, Exceptional, (76 reviews)
"We enjoyed our stay, close to shops and beach!"
United States
Savannah S.
$191 nightly
The price is $213
Oct 18 - Oct 19
Total with taxes and fees
The "Grouper"
A patio with two blue lounge chairs, a potted plant, and a gravel area.

2. 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
Oct 18 - Oct 19
Total with taxes and fees
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach
A small, single-story house with a white exterior, a brick planter with palm trees, and a white picket fence.

3. Cozy Private Cottage, Minutes to Anna Maria Island

Cozy Private Cottage, Minutes to Anna Maria Island
Bradenton
9.8 out of 10, Exceptional, (14 reviews)
"Clean and nice place"
United States
Ismael
$235 nightly
The price is $262
Oct 19 - Oct 20
Total with taxes and fees
Cozy Private Cottage, Minutes to Anna Maria Island
A pool area with a blue deck, lounge chairs, a barbecue, and a view of buildings in the background.

4. The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (211 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
$277 nightly
The price is $313
Oct 18 - Oct 19
Total with taxes and fees
The Inn On Siesta Key
A patio area with a grill, potted plants, and a building with a teal door.

5. Beach Tree Cottage,Walk To Beach& Siesta

Beach Tree Cottage,Walk To Beach& Siesta
2.0 star property
Siesta Key Village
$325 nightly
The price is $367
Oct 18 - Oct 19
Total with taxes and fees
Beach Tree Cottage,Walk To Beach& Siesta
A yellow house with a porch, a mailbox, and a number 5306 on the door.

6. Yellow Palm Cottage, Heart of Siesta Key

Yellow Palm Cottage, Heart of Siesta Key
2.0 star property
Siesta Key Village
$341 nightly
The price is $385
Oct 18 - Oct 19
Total with taxes and fees
Yellow Palm Cottage, Heart of Siesta Key
A room with a dining table, chairs, a television, a sofa, and a lamp.

7. BlueDolphin Cottage Walk To Siesta Beach

BlueDolphin Cottage Walk To Siesta Beach
2.5 star property
Siesta Key Village
$347 nightly
The price is $392
Oct 19 - Oct 20
Total with taxes and fees
BlueDolphin Cottage Walk To Siesta Beach
A bedroom with a bed, a ceiling fan, a window with curtains, a wooden wardrobe, and a framed picture on the wall.

8. Cozy Lido Studio by Beach & St Armand's

Cozy Lido Studio by Beach & St Armand's
Lido Key
$397 nightly
The price is $442
Oct 31 - Nov 1
Total with taxes and fees
Cozy Lido Studio by Beach & St Armand's
A rectangular pool with white lounge chairs and a white fence, surrounded by palm trees and a building with balconies.

9. Lido Key Casita w Pool Steps to the Beach

Lido Key Casita w Pool Steps to the Beach
Lido Key
$370 nightly
The price is $412
Nov 4 - Nov 5
Total with taxes and fees
Lido Key Casita w Pool Steps to the Beach
A single-story house with a blue exterior, a front door, and a small porch area.

10. Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.

Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
Desoto Lakes
$221 nightly
The price is $247
Oct 19 - Oct 20
Total with taxes and fees
Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
A two-story building with a blue exterior and white railings.

11. 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, (192 reviews)
"Loved the location of this property! The property manager was easy to contact and the property was exactly as shown in the pictures. Would stay here again!"
United States
Tracie B.
$356 nightly
The price is $397
Oct 18 - Oct 19
Total with taxes and fees
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
A residential house with a white fence, a palm tree, and a parked car.

12. 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
Oct 24 - Oct 25
Total with taxes and fees
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
A balcony with wicker furniture, a grill, and a view of a marina with boats and greenery.

13. 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)
"Place is great and clean. Love how smooth everything was. Jenny is easy to communicate as well"
United States
Natalia D.
$523 nightly
The price is $583
Oct 18 - Oct 19
Total with taxes and fees
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
A balcony with two wooden chairs and a small round table, surrounded by white railings and palm trees.

14. Sunny PaG Island rental w/bikes-just steps2beach

Sunny PaG Island rental w/bikes-just steps2beach
Pass-a-Grille
9.4 out of 10, Exceptional, (28 reviews)
"Wonderful place to stay. Great location to the beach, restaurants and shopping. If you want a peaceful getaway highly recommend."
United States
Janise W.
$289 nightly
The price is $321
Nov 1 - Nov 2
Total with taxes and fees
Sunny PaG Island rental w/bikes-just steps2beach
A modern house with a driveway, a tree with purple lighting, and a white car parked in front.

15. Escape near Siesta Key with Hot Tub, BBQ, and Fire pit

Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
Sarasota
8.4 out of 10, Very good, (10 reviews)
"The house was truly lovely, and the hosts were exceptionally caring, kind, and attentive in their communication. It was wonderful to be so close to the beach, with stores conveniently nearby, making the stay feel comfortable and welcoming."
United States
Kandra R.
$334 nightly
The price is $372
Oct 25 - Oct 26
Total with taxes and fees
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
A white house with a covered porch, surrounded by a gravel driveway and various tropical plants.

16. 3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
$2,636 nightly
The price is $2,979
Oct 25 - Oct 26
Total with taxes and fees
3716 7th Ave W
Shared sunbathing deck by the pool, at the resort.

17. Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key
9.6 out of 10, Exceptional, (8 reviews)
"The most well maintained property I've ever stayed."
United States
Russ H.
$313 nightly
The price is $349
Oct 20 - Oct 21
Total with taxes and fees
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
A beachfront property with a single-story house, a paved driveway, and a palm tree in the foreground.

18. Direct Beachfront 2BR Cottage on Casey Key!

Direct Beachfront 2BR Cottage on Casey Key!
Casey Key
9.4 out of 10, Exceptional, (84 reviews)
"Great vacation!!"
United States
Dominic C.
$449 nightly
The price is $501
Oct 18 - Oct 19
Total with taxes and fees
Direct Beachfront 2BR Cottage on Casey Key!
A yellow house with a blue door and the number 2202.

19. Steps 2 Beach- Cottage w/king bd +2bikes +parking

Steps 2 Beach- Cottage w/king bd +2bikes +parking
Pass-a-Grille
9.6 out of 10, Exceptional, (52 reviews)
"Clean, quiet and an easy walk to the beach."
United States
Marion W.
$427 nightly
The price is $476
Oct 18 - Oct 19
Total with taxes and fees
Steps 2 Beach- Cottage w/king bd +2bikes +parking
A riverfront restaurant with outdoor seating and a view of the water.

20. NOKOMIS BEACH BUNGALOW 229 15 mins walk to the beach

NOKOMIS BEACH BUNGALOW 229 15 mins walk to the beach
Nokomis
9.2 out of 10, Wonderful, (33 reviews)
"Great location"
United States
Susan C.
$278 nightly
The price is $310
Oct 18 - Oct 19
Total with taxes and fees
NOKOMIS BEACH BUNGALOW 229 15 mins walk to the beach
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

Charming 1-bedroom, beachfront condo in marvelous Longboat Key

Charming 1-bedroom, beachfront condo in marvelous Longboat Key

10/10 Excellent
"Nice place, very clean, and grounds are well kept. Loved that the beach was out our back door!"
Tim C. 6-night trip
Posted 4 days ago
Charming 1-bedroom, beachfront condo in marvelous Longboat Key

Find out more about Longboat Key

Longboat Key Cottages information

Number of reviews
832
Accommodation
19 Cottages
Lowest Price
$213
Highest Price
$2,979

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.

Explore a world of travel with Expedia