Longboat Key Cottages

Q: 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.

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

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Our top choices for Longboat Key cottages

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

1. The "Grouper"

Sunny Shores

Canyon L.

HK$1,599 total

includes taxes & fees

10 Nov - 11 Nov

An outdoor patio with green metal chairs and tables, a red umbrella, and a building with balconies in the background.

2. Beach Tree Cottage,Walk To Beach& Siesta

Siesta Key Village

HK$2,768 total

includes taxes & fees

10 Nov - 11 Nov

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

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

Bradenton

Rob

HK$2,634 total

includes taxes & fees

16 Nov - 17 Nov

A two-story house with a balcony, a small porch, and a driveway.

4. Anna Maria Island Beach Front Cottage

Bradenton Beach, FL, 34217

HK$5,221 total

includes taxes & fees

10 Nov - 11 Nov

A small, single-story house with a white exterior, a brick planter with palm trees, and a white picket fence.

5. Cozy Private Cottage, Minutes to Anna Maria Island

Bradenton

Ismael

HK$1,914 total

includes taxes & fees

10 Nov - 11 Nov

A yellow house with a porch, a mailbox, and a number 5306 on the door.

6. Yellow Palm Cottage, Heart of Siesta Key

Siesta Key Village

HK$3,668 total

includes taxes & fees

10 Nov - 11 Nov

A patio with a sun lounger, a table with chairs, and an umbrella.

7. Beach View 100ft To Beach and SPA

Siesta Key Village

HK$3,175 total

includes taxes & fees

11 Nov - 12 Nov

A pool area with a blue deck, lounge chairs, a barbecue, and a view of buildings in the background.

8. The Inn On Siesta Key

Siesta Key

"Thank you Paige & Gabe! My husband & I had a wonderful stay last week in The Nook at your beautiful Inn. Absolutely loved the old Florida charm and perfect location. Your Inn is immaculately kept as well as comfortable. We especially loved our private patio with the fire pit at The Nook. The location of The Inn could not be more perfect being less than a 5 minute walk across the street to Siesta Key beach as well as a short 10 minute walk to town with all the restaurants & shops. Thanks again...

Karen Jean

HK$2,551 total

includes taxes & fees

10 Nov - 11 Nov

A small, single-story building with a porch, surrounded by tropical vegetation.

9. BlueDolphin Cottage Walk To Siesta Beach

Siesta Key Village

HK$3,556 total

includes taxes & fees

10 Nov - 11 Nov

A covered porch with a sign reading "BEACH HOUSE," outdoor seating, a grill, and a view of the water.

10. Bridge Street Pier Beach House + Dog-friendly

Bridge Street

Michelle R.

HK$3,679 total

includes taxes & fees

23 Nov - 24 Nov

A rectangular pool with white lounge chairs and a white fence, surrounded by palm trees and a building with balconies.

11. Lido Key Casita w Pool Steps to the Beach

Lido Key

Felecia P.

HK$3,087 total

includes taxes & fees

18 Nov - 19 Nov

A patio with a table set for two, a blue umbrella, and a white fence.

12. Lido Beach Studio with Heated Pool

Lido Key

Lorraine B.

HK$3,071 total

includes taxes & fees

12 Nov - 13 Nov

A white house with a covered porch, surrounded by a gravel driveway and various tropical plants.

13. 3716 7th Ave W

Bradenton

HK$24,191 total

includes taxes & fees

11 Nov - 12 Nov

A two-story building with a blue exterior and white railings.

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

Sarasota

Tracie B.

HK$3,082 total

includes taxes & fees

13 Nov - 14 Nov

A backyard with a tree, a wooden fence, a blue shed, and a house with a door.

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

Desoto Lakes

HK$1,898 total

includes taxes & fees

24 Nov - 25 Nov

Shared sunbathing deck by the pool, at the resort.

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

Siesta Key

Russ H.

HK$2,624 total

includes taxes & fees

10 Nov - 11 Nov

A balcony with wicker furniture, a grill, and a view of a marina with boats and greenery.

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

Anna Maria

Terrence H.

HK$4,686 total

includes taxes & fees

10 Nov - 11 Nov

A residential house with a white fence, a palm tree, and a parked car.

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

South Village

Clarissa S.

HK$2,384 total

includes taxes & fees

10 Nov - 11 Nov

A yellow building with a blue door and a white staircase.

19. Beach Getaway Near Rays, Bikes & Gear

Pass-a-Grille

Cathy P.

HK$2,585 total

includes taxes & fees

1 Dec - 2 Dec

A bathroom with a toilet, a glass-enclosed shower, and a framed picture on the wall.

20. Coastal Studio, Walk to St Armand's or Lido Beach

Lido Key

Kevin C.

HK$4,508 total

includes taxes & fees

25 Nov - 26 Nov

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Top Longboat Key Hotel Reviews

Charming 1-bedroom, beachfront condo in marvelous Longboat Key

8/10 Good

"Perfect location! You can walk right out to the beach from the property. The view was stunning, we had the most breathtaking views from our lanai every night. Close to Publix for ease of grocery shopping.Would stay again!"

Fall sale ready for a luxury 5-floor penthouse 60 ft from water,

10/10 Excellent

"My Husband and I stayed here at this beautiful oceanfront condo at Longboat Key the last week of October 2026. It was perfect in every way. The space was just right for us. We Loved waking up to the Oceanfront views and being right on the water made it extra special. It was comfortable, inviting and the perfect place to unwind and enjoy the beauty of Longboat Key. We couldn't have asked for a better stay and would happily return. Highly recommend!"

Take a peek at awesome reviews 50 feet from the sand

10/10 Excellent

"The condo was clean and tastefully furnished. The bedroom was luxurious with a comfortable mattress and high-end bedding. The view was stunning and we were steps from the beach and the pool as well. We loved how peaceful Longboat Key is. Our host was helpful and communicative. We would definitely stay at this property again!"

Direct Oceanview: Open October 26th - 29th!

10/10 Excellent

"Heidi was the best VRBO host we’ve ever had. She has thought of every comfort on property and her communication is superb, always friendly, caring and helpful. We loved the second floor balcony for viewing the gulf and the ease of being on the beach and near the pool. We hope to stay at one of her properties on Longboat Key again."

Now Open! 7-Night Deal – Oceanfront w/ Private Balcony & Stunning Views

8/10 Good

"The ocean front balcony and the property location was excellent, as well as the regularly maintained grounds left everything very clean and neat. The inside of the rental was much smaller than anticipated and proved very difficult to place our luggage and unpack anything. The bed was extremely hard and bery cramped. On a plus side, the private balcony views and the water pressure in the shower were amazing! Communication, the parking lot and check-in were also great."

Find out more about Longboat Key

Longboat Key Cottages information

Number of reviews	792
Accommodation	19 Cottages
Lowest Price	HK$1,599
Highest Price	HK$24,191

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 traveller 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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Anna Maria Island Holiday Rentals

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Search Cottages in Longboat Key

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Longboat Key cottages

1. The "Grouper"

2. Beach Tree Cottage,Walk To Beach& Siesta

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

4. Anna Maria Island Beach Front Cottage

5. Cozy Private Cottage, Minutes to Anna Maria Island

6. Yellow Palm Cottage, Heart of Siesta Key

7. Beach View 100ft To Beach and SPA

8. The Inn On Siesta Key

9. BlueDolphin Cottage Walk To Siesta Beach

10. Bridge Street Pier Beach House + Dog-friendly

11. Lido Key Casita w Pool Steps to the Beach

12. Lido Beach Studio with Heated Pool

13. 3716 7th Ave W

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

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

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

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

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

19. Beach Getaway Near Rays, Bikes & Gear

20. Coastal Studio, Walk to St Armand's or Lido Beach

Find holiday rentals that suit your style

Top Longboat Key Hotel Reviews

Charming 1-bedroom, beachfront condo in marvelous Longboat Key

Find out more about Longboat Key

Longboat Key Cottages information

Frequently asked questions

Explore a world of travel with Expedia