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

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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, (75 reviews)
"We enjoyed our stay, close to shops and beach!"
United States
Savannah S.
The price is €195
includes taxes & fees
8 Oct - 9 Oct
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
The price is €297
includes taxes & fees
3 Oct - 4 Oct
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
10.0 out of 10, Exceptional, (13 reviews)
"Clean and nice place"
United States
Ismael
The price is €214
includes taxes & fees
8 Oct - 9 Oct
Cozy Private Cottage, Minutes to Anna Maria Island
A small, single-story mobile home with a front porch, a small attached garage, and a clock tower.

4. Bridge Street Beach House | Wi-Fi | Center of All

Bridge Street Beach House | Wi-Fi | Center of All
Bridge Street
10.0 out of 10, Exceptional, (5 reviews)
"Great location, clean accommodations, good communication with host. ..."
United States
leslie m.
The price is €372
includes taxes & fees
26 Oct - 27 Oct
Bridge Street Beach House | Wi-Fi | Center of All
A balcony with wicker furniture, a grill, and a view of a marina with boats and greenery.

5. 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.
The price is €530
includes taxes & fees
3 Oct - 4 Oct
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
A hammock tied between two palm trees, a pink building with a red roof, and a bush with red flowers.

6. Pink Mango Cottage steps from the beach

Pink Mango Cottage steps from the beach
Siesta Key Village
10.0 out of 10, Exceptional, (1 review)
Pink Mango Cottage steps from the beach
A patio with a table set for two, a blue umbrella, and a white fence.

7. Studio by Lido Beach w heated pool

Studio by Lido Beach w heated pool
Lido Key
The price is €333
includes taxes & fees
31 Oct - 1 Nov
Studio by Lido Beach w heated pool
A bathroom with a toilet, a glass-enclosed shower, and a framed picture on the wall.

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

Coastal Studio, Walk to St Armand's or Lido Beach
Lido Key
10.0 out of 10, Exceptional, (1 review)
"5 Stars: This cozy studio was exactly what we were looking for. Alexander was pleasant and friendly, the check in/check out process was easy. The location was fabulous- perhaps slightly too far to walk to St.Armand’s , but a quick ride on the rentable VEO bikes/scooters. The accommodations were clean, and beachy. We did not have an opportunity to use the pool, so I do have any objective comments for the pool. If we are in the area again, we would definitely stay here again!"
United States
lisa o.
The price is €310
includes taxes & fees
4 Oct - 5 Oct
Coastal Studio, Walk to St Armand's or Lido Beach
A single-story house with a blue exterior, a front door, and a small porch area.

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

Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
Desoto Lakes
The price is €240
includes taxes & fees
12 Oct - 13 Oct
Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
A yellow house with a porch, a mailbox, and a number 5306 on the door.

10. Yellow Palm Cottage, Heart of Siesta Key

Yellow Palm Cottage, Heart of Siesta Key
2.0 star property
Siesta Key Village
The price is €324
includes taxes & fees
4 Oct - 5 Oct
Yellow Palm Cottage, Heart of Siesta Key
A coastal residential area with houses, a river, and a beach.

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, (53 reviews)
"Pleasantly surprised how great this place was - awesome backyard setup and incredible location "
United States
Cyrus M.
The price is €810
includes taxes & fees
3 Oct - 4 Oct
Adorable Cottage with Covered Balconies and Private Pool
A covered outdoor area with wicker furniture, a glass table, and a view of a residential street.

12. 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 €814
includes taxes & fees
24 Oct - 25 Oct
Beautiful Condo on Pine Ave, 2 Blocks to Beach
A two-story building with a blue exterior and white railings.

13. 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.
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
A modern house with a driveway, a tree with purple lighting, and a white car parked in front.

14. 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.
The price is €410
includes taxes & fees
8 Oct - 9 Oct
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.

15. 3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
The price is €2,723
includes taxes & fees
8 Oct - 9 Oct
3716 7th Ave W
A rectangular pool with white lounge chairs and a white fence, surrounded by palm trees and a building with balconies.

16. Lido Key Casita w Pool Steps to the Beach

Lido Key Casita w Pool Steps to the Beach
Lido Key
The price is €304
includes taxes & fees
5 Oct - 6 Oct
Lido Key Casita w Pool Steps to the Beach
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.
The price is €318
includes taxes & fees
4 Oct - 5 Oct
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
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.

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 €274
includes taxes & fees
4 Oct - 5 Oct
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
A balcony with two wooden chairs and a small round table, surrounded by white railings and palm trees.

19. 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.
The price is €319
includes taxes & fees
7 Oct - 8 Oct
Sunny PaG Island rental w/bikes-just steps2beach
A small house with a porch, surrounded by a grassy yard and dense foliage.

20. Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches

Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches
Nokomis
The price is €230
includes taxes & fees
8 Oct - 9 Oct
Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches
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

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

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

10/10 Excellent
"View fantastic of the gulf! Watched dolphins daily along with exotic wildlife Very clean room. Very comfortable and enjoyable. Once you check in, won’t need anything to go out for if you stock food! Had a wonderful stay. Communication with the host was smooth and effortless! Will not hesitate to go back!!!!!! Laundry facilities on site! Overall had a delightful stay!"
Anna S. 5-night trip
Posted 16 hours ago
Now Open! 7-Night Deal – Oceanfront w/ Private Balcony & Stunning Views

Find out more about Longboat Key

Longboat Key Cottages information

Number of reviews
583
Accommodation
19 Cottages
Lowest Price
€195
Highest Price
€2,723

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.