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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

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, (77 reviews)
"We enjoyed our stay, close to shops and beach!"
United States
Savannah S.
The price is AED 364
AED 782 total
includes taxes & fees
24 Oct - 25 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 AED 643
AED 1,234 total
includes taxes & fees
22 Oct - 23 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
9.8 out of 10, Exceptional, (14 reviews)
"Clean and nice place"
United States
Ismael
The price is AED 261
AED 922 total
includes taxes & fees
21 Oct - 22 Oct
Cozy Private Cottage, Minutes to Anna Maria Island
A pair of stacked front-loading washing machines in a commercial setting.

4. Beach View 100ft To Beach and SPA

Beach View 100ft To Beach and SPA
2.0 star property
Siesta Key Village
The price is AED 704
AED 1,530 total
includes taxes & fees
24 Oct - 25 Oct
Beach View 100ft To Beach and SPA
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
The price is AED 489
AED 1,287 total
includes taxes & fees
21 Oct - 22 Oct
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
The price is AED 542
AED 1,347 total
includes taxes & fees
21 Oct - 22 Oct
Yellow Palm Cottage, Heart of Siesta Key
A kitchen with a sink, stove, microwave, and refrigerator.

7. BlueDolphin Cottage Walk To Siesta Beach

BlueDolphin Cottage Walk To Siesta Beach
2.5 star property
Siesta Key Village
The price is AED 552
AED 1,358 total
includes taxes & fees
21 Oct - 22 Oct
BlueDolphin Cottage Walk To Siesta Beach
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, (2 reviews)
"This studio was perfect for a quick weekend getaway. The just was very responsive, and the property was very clean.We arrived after dark, and had to look around a bit to find the right unit (front of the office bldg.), but the host was available to assist. Good amenities and proximity to Lido Beach/ St. Armand Circle."
United States
Kevin C.
Coastal Studio, Walk to St Armand's or Lido Beach
A bedroom with a bed, a ceiling fan, a window with curtains, a wooden wardrobe, and a framed picture on the wall.

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

Cozy Lido Studio by Beach & St Armand's
Lido Key
Cozy Lido Studio by Beach & St Armand's
A two-story building with a blue exterior and white railings.

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

11. 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 AED 364
AED 1,106 total
includes taxes & fees
25 Oct - 26 Oct
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
A single-story house with a blue exterior, a front door, and a small porch area.

12. 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 AED 383
AED 963 total
includes taxes & fees
20 Nov - 21 Nov
Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
A covered outdoor area with wicker furniture, a glass table, and a view of a residential street.

13. 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 AED 992
AED 3,198 total
includes taxes & fees
24 Oct - 25 Oct
Beautiful Condo on Pine Ave, 2 Blocks to Beach
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 AED 624
AED 1,379 total
includes taxes & fees
25 Oct - 26 Oct
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
Shared sunbathing deck by the pool, at the resort.

15. 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 AED 404
AED 1,215 total
includes taxes & fees
21 Oct - 22 Oct
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
A balcony with wicker furniture, a grill, and a view of a marina with boats and greenery.

16. 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 AED 915
AED 2,143 total
includes taxes & fees
21 Oct - 22 Oct
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
A rectangular pool with white lounge chairs and a white fence, surrounded by palm trees and a building with balconies.

17. Lido Key Casita w Pool Steps to the Beach

Lido Key Casita w Pool Steps to the Beach
Lido Key
10.0 out of 10, Exceptional, (1 review)
The price is AED 545
AED 1,512 total
includes taxes & fees
4 Nov - 5 Nov
Lido Key Casita w Pool Steps to the Beach
A balcony with two wooden chairs and a small round table, surrounded by white railings and palm trees.

18. 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 AED 454
AED 1,181 total
includes taxes & fees
21 Oct - 22 Oct
Sunny PaG Island rental w/bikes-just steps2beach
A white house with a covered porch, surrounded by a gravel driveway and various tropical plants.

19. 3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
The price is AED 8,148
AED 10,746 total
includes taxes & fees
22 Oct - 23 Oct
3716 7th Ave W
A yellow building with a blue door and a white staircase.

20. Rays Baseball close! Beach Getaway| Bikes +Gear

Rays Baseball close! Beach Getaway| Bikes +Gear
Pass-a-Grille
9.8 out of 10, Exceptional, (34 reviews)
"We love staying at this nice cozy beach house! It's so close to the beach.And such a nice quiet location!"
United States
Cathy P.
The price is AED 664
AED 1,447 total
includes taxes & fees
26 Oct - 27 Oct
Rays Baseball close! Beach Getaway| Bikes +Gear
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

The Resort at Longboat Key Club

The Resort at Longboat Key Club

10/10 Excellent
"5"
EMILIO 2-night trip
Posted 2 days ago
The Resort at Longboat Key Club

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