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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Longboat Key holiday homes

A beachside restaurant with a thatched roof, wooden tables, and chairs, overlooking a sandy beach and the ocean.

1. LAST MINUTE DEAL, Charming Elevated Duplex – Relaxing Beach Getaway Near Anna Maria Island- Bay access

LAST MINUTE DEAL, Charming Elevated Duplex – Relaxing Beach Getaway Near Anna Maria Island- Bay access
Sunny Shores
9.6 out of 10, Exceptional, (44 reviews)
"Superb value, quiet area, responsive owner, very nicely appointed; will definitely book again for next visit to Anna Maria Island!"
United States
Bryce W.
The price is £360
includes taxes & fees
10 Nov - 11 Nov
LAST MINUTE DEAL, Charming Elevated Duplex – Relaxing Beach Getaway Near Anna Maria Island- Bay access
An aerial view of a coastal island with a white sandy beach, dense vegetation, and a clear blue sea.

2. Heated Pool, Fire Pit & Outdoor Kitchen

Heated Pool, Fire Pit & Outdoor Kitchen
Bradenton
10.0 out of 10, Exceptional, (92 reviews)
"The house was perfect for our family and super easy access to the beach / sound. The rooms were specious and clean and the pool was great!"
United States
Kristen P.
The price is £446
includes taxes & fees
11 Nov - 12 Nov
Heated Pool, Fire Pit & Outdoor Kitchen
A sandy pathway leading to a beach, flanked by green foliage and rope barriers.

3. Modern Coastal Charm • Near AMI Beach-IMG Academy

Modern Coastal Charm • Near AMI Beach-IMG Academy
Bradenton
10.0 out of 10, Exceptional, (41 reviews)
"Everything was Perfect! Highly recommend, will Defiantly stay again "
United States
Melanie L.
The price is £224
includes taxes & fees
15 Nov - 16 Nov
Modern Coastal Charm • Near AMI Beach-IMG Academy
A dining area with a dark wooden table, four chairs, and a hanging lamp.

4. Lakeview Bradenton Rental Near Beaches & IMG

Lakeview Bradenton Rental Near Beaches & IMG
South Bradenton
9.8 out of 10, Exceptional, (6 reviews)
"Very clean and comfortable. "
United States
Dee F.
The price is £180
includes taxes & fees
1 Dec - 2 Dec
Lakeview Bradenton Rental Near Beaches & IMG
A beach with a hotel in the background.

5. Beach House Kids & Pets OK Oct, Nov, Dec DISCOUNTED! AMIsland White Sand Beaches

Beach House Kids & Pets OK Oct, Nov, Dec DISCOUNTED! AMIsland White Sand Beaches
Bradenton
9.8 out of 10, Exceptional, (46 reviews)
"Close to the beach and restaurants.Had everything we needed."
United States
thomas F.
The price is £450
includes taxes & fees
29 Nov - 30 Nov
Beach House Kids & Pets OK Oct, Nov, Dec DISCOUNTED! AMIsland White Sand Beaches
A wooden beach pavilion with a checkered roof and open sides, overlooking the beach.

6. Anna Maria Beach Condo 1/1

Anna Maria Beach Condo 1/1
Bradenton Beach
9.8 out of 10, Exceptional, (239 reviews)
"Great place to stay!"
United States
Donna B.
The price is £267
includes taxes & fees
10 Nov - 11 Nov
Anna Maria Beach Condo 1/1
A covered swimming pool with lounge chairs and umbrellas, surrounded by a fence and trees.

7. "Stingray" 3 miles to Anna Marie

"Stingray" 3 miles to Anna Marie
Bradenton
9.8 out of 10, Exceptional, (39 reviews)
"Property was great and location was ideal for our weekend getaway"
United States
Agnieszka
The price is £262
includes taxes & fees
14 Nov - 15 Nov
"Stingray" 3 miles to Anna Marie
A modern outdoor seating area with two blue chairs and a large potted plant.

8. Pet-Friendly Bradenton Home 1.5 Mi to Cortez Beach

Pet-Friendly Bradenton Home 1.5 Mi to Cortez Beach
Bradenton
10.0 out of 10, Exceptional, (36 reviews)
"Very comfortable, clean, convenient location. Great place to stay."
United States
Karen B.
The price is £245
includes taxes & fees
16 Nov - 17 Nov
Pet-Friendly Bradenton Home 1.5 Mi to Cortez Beach
A backyard with a swimming pool, palm trees, and a patio area.

9. "Barracuda"

"Barracuda"
Sunny Shores
9.8 out of 10, Exceptional, (33 reviews)
"Beautiful property! Loved the pool and area was close to the beach and restaurants. Loved it , would stay here again!"
United States
James H.
The price is £310
includes taxes & fees
11 Nov - 12 Nov
"Barracuda"
A beach with clear turquoise water, people swimming and walking on the shore, and several beach umbrellas and sun loungers.

10. "Manatee" 3 miles to Anna Marie<br>

"Manatee" 3 miles to Anna Marie<br>
Bradenton
9.8 out of 10, Exceptional, (18 reviews)
"Great location and really nice pool. Had a great week here, easy to get to the island and also close to shopping and dining."
United States
Matthew H.
The price is £283
includes taxes & fees
22 Nov - 23 Nov
"Manatee" 3 miles to Anna Marie<br>
A beach with clear turquoise water, white sand, and a row of trees and buildings along the shore.

11. IMG Lake & Beach Home Pool White Sand Beaches SEPTEMBER, Oct, Nov, Dec SPECIALS!

IMG Lake & Beach Home Pool White Sand Beaches SEPTEMBER, Oct, Nov, Dec SPECIALS!
South Bradenton
9.8 out of 10, Exceptional, (140 reviews)
"Beautiful pool, nice kitchen, and close to Anna Marie Island."
United States
Gary B.
The price is £422
includes taxes & fees
29 Nov - 30 Nov
IMG Lake & Beach Home Pool White Sand Beaches SEPTEMBER, Oct, Nov, Dec SPECIALS!
An outdoor patio with a pool, lounge chairs, a fire pit, and string lights.

12. 🏝 4BR Tropical Oasis w/ Heated Pool + Game Room + 10 Min to Anna Maria and IMG

🏝 4BR Tropical Oasis w/ Heated Pool + Game Room + 10 Min to Anna Maria and IMG
Bradenton
10.0 out of 10, Exceptional, (18 reviews)
"Spacious and neat, we definitely enjoyed enjoyed our stay."
United States
Aracely T.
The price is £429
includes taxes & fees
10 Nov - 11 Nov
🏝 4BR Tropical Oasis w/ Heated Pool + Game Room + 10 Min to Anna Maria and IMG
A bedroom with a bed, a ceiling fan, a nightstand, a lamp, a potted plant, and a sliding glass door leading to a bathroom.

13. Charming home near Anna Maria Island with Jacuzzi

Charming home near Anna Maria Island with Jacuzzi
Bradenton
9.8 out of 10, Exceptional, (21 reviews)
"Loved our stay! "
United States
Brittany C.
The price is £249
includes taxes & fees
22 Nov - 23 Nov
Charming home near Anna Maria Island with Jacuzzi
A beach with clear turquoise water and a sandy shore.

14. Paradise Retreat with HEATED POOL-- Need We Say More

Paradise Retreat with HEATED POOL-- Need We Say More
South Bradenton
10.0 out of 10, Exceptional, (196 reviews)
"great place to stay host should get over a 5 star"
United States
Stacie
The price is £286
includes taxes & fees
10 Nov - 11 Nov
Paradise Retreat with HEATED POOL-- Need We Say More
A wooden deck with two Adirondack chairs, a thatched umbrella, and a view of a marina with boats.

15. Cottage on the canal

Cottage on the canal
Bradenton
10.0 out of 10, Exceptional, (170 reviews)
"Great location for boating and ready beach access."
United States
J J.
The price is £387
includes taxes & fees
11 Nov - 12 Nov
Cottage on the canal
An aerial view of a coastal area with a long stretch of beach, clear turquoise waters, and a densely populated residential area with buildings lining the shore.

16. Funky Flamingo! Beach Gear and Heated Pool

Funky Flamingo! Beach Gear and Heated Pool
Bradenton
9.2 out of 10, Wonderful, (16 reviews)
"Great amenities and location. Very clean and had everything we needed. Would definitely stay again!"
United States
Sarah D.
Funky Flamingo! Beach Gear and Heated Pool
A two-story house with a covered porch, a small front yard, and a clear blue sky.

17. The Hideaways at Point Pleasant (Palm Side)

The Hideaways at Point Pleasant (Palm Side)
Bradenton
10.0 out of 10, Exceptional, (177 reviews)
"Great downtown location! We enjoyed our stay!"
United States
Diane M.
The price is £217
includes taxes & fees
10 Nov - 11 Nov
The Hideaways at Point Pleasant (Palm Side)
A compact, stainless steel LG ThinQ washer and dryer unit in a small, enclosed laundry room with a white door and light-colored walls.

18. Cozy Studio in Quiet Neighborhood

Cozy Studio in Quiet Neighborhood
Bradenton
9.0 out of 10, Wonderful, (14 reviews)
"Very clean and wonderful area"
United States
Jared B.
The price is £119
includes taxes & fees
22 Nov - 23 Nov
Cozy Studio in Quiet Neighborhood
A covered outdoor seating area with a view of a lake and a house in the background.

19. Stylish Lake View House: Minutes to Beaches & IMG, Pet-friendly

Stylish Lake View House: Minutes to Beaches & IMG, Pet-friendly
Bradenton
10.0 out of 10, Exceptional, (26 reviews)
"We had a wonderful weekend stay! The place was clean, comfortable, and exactly as described. It had everything we needed for a weekend vacation. Thank you again"
United States
Jennifer P.
The price is £310
includes taxes & fees
10 Nov - 11 Nov
Stylish Lake View House: Minutes to Beaches & IMG, Pet-friendly
A modern living room with a blue sofa, a dining table with chairs, a woven rug, and a kitchen area in the background.

20. Lobster Louie's Inn - Cozy 2/1 Mins from Beaches. Fenced yard. Pet Friendly.

Lobster Louie's Inn - Cozy 2/1 Mins from Beaches. Fenced yard. Pet Friendly.
Whitfield Estates
9.0 out of 10, Wonderful, (26 reviews)
"Great clean adorable place"
United States
Joann G.
The price is £218
includes taxes & fees
10 Nov - 11 Nov
Lobster Louie's Inn - Cozy 2/1 Mins from Beaches. Fenced yard. Pet Friendly.
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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Learn more about Longboat Key

Pristine white-sand beaches stretch for miles where dolphins play just offshore during sunset walks. Kayak through mangrove tunnels in the morning, then enjoy fresh grouper at waterfront restaurants where no one minds your flip-flops.

See all hotels in Longboat Key
A coastal town with a beach, residential areas, and a marina.