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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Longboat Key holiday homes

A wooden pathway leading to a beach with lush greenery and a clear sky.

1. Ground Floor, Steps to Sand – Silver Sands #243A by RVA

Ground Floor, Steps to Sand – Silver Sands #243A by RVA
Longboat Key
8.6 out of 10, Excellent, (64 reviews)
"Would def stay here again!"
United States
Tammie and David
Ground Floor, Steps to Sand – Silver Sands #243A by RVA
A sandy pathway leading to a beach, flanked by green foliage and rope barriers.

2. 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)
"Very cute 2 bedroom place with parking, Wi-fi, private fenced outdoor space. Safe location convenient drive to the beach. Would stay there again."
United States
Dawn Z.
The price is £227
includes taxes & fees
25 Sept - 26 Sept
Modern Coastal Charm • Near AMI Beach-IMG Academy
A beachside restaurant with a thatched roof, wooden tables, and chairs, overlooking a sandy beach and the ocean.

3. 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 £354
includes taxes & fees
25 Sept - 26 Sept
LAST MINUTE DEAL, Charming Elevated Duplex – Relaxing Beach Getaway Near Anna Maria Island- Bay access
A covered swimming pool with lounge chairs and umbrellas, surrounded by a fence and trees.

4. "Stingray" 3 miles to Anna Marie

"Stingray" 3 miles to Anna Marie
Bradenton
9.8 out of 10, Exceptional, (36 reviews)
"Property was great and location was ideal for our weekend getaway"
United States
Agnieszka
The price is £228
includes taxes & fees
27 Sept - 28 Sept
"Stingray" 3 miles to Anna Marie
A beach with clear turquoise water, people swimming and walking on the shore, and several beach umbrellas and sun loungers.

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

"Manatee" 3 miles to Anna Marie<br>
Bradenton
9.8 out of 10, Exceptional, (18 reviews)
"Everything was great!!"
United States
Jean S.
The price is £245
includes taxes & fees
25 Sept - 26 Sept
"Manatee" 3 miles to Anna Marie<br>
A modern outdoor seating area with two blue chairs and a large potted plant.

6. 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 £252
includes taxes & fees
25 Sept - 26 Sept
Pet-Friendly Bradenton Home 1.5 Mi to Cortez Beach
A modern kitchen with a stainless steel refrigerator, a microwave, and a coffee bar.

7. Free Heated Pool•5 min drive to AMI•Hot Tub•Near IMG•Fire Pit•Full Kitchen

Free Heated Pool•5 min drive to AMI•Hot Tub•Near IMG•Fire Pit•Full Kitchen
Bradenton
9.8 out of 10, Exceptional, (34 reviews)
"Thank you for the stay. Our family had a great time together."
United States
Tonya H.
Free Heated Pool•5 min drive to AMI•Hot Tub•Near IMG•Fire Pit•Full Kitchen
A dining area with a dark wooden table, four chairs, and a hanging lamp.

8. Lakeview Bradenton Rental Near Beaches & IMG

Lakeview Bradenton Rental Near Beaches & IMG
South Bradenton
9.6 out of 10, Exceptional, (4 reviews)
"Very clean and comfortable. "
United States
Dee F.
The price is £185
includes taxes & fees
7 Oct - 8 Oct
Lakeview Bradenton Rental Near Beaches & 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.

9. 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 £241
includes taxes & fees
26 Sept - 27 Sept
Charming home near Anna Maria Island with Jacuzzi
A beach with clear turquoise water and a sandy shore.

10. 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, (194 reviews)
"great place to stay host should get over a 5 star"
United States
Stacie
The price is £287
includes taxes & fees
30 Sept - 1 Oct
Paradise Retreat with HEATED POOL-- Need We Say More
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 £409
includes taxes & fees
30 Sept - 1 Oct
IMG Lake & Beach Home Pool White Sand Beaches SEPTEMBER, Oct, Nov, Dec SPECIALS!
A backyard with a wooden fence, outdoor furniture, and string lights.

12. Vacation Home With POOL and BBQ Near Anna Maria Island

Vacation Home With POOL and BBQ Near Anna Maria Island
Bradenton
10.0 out of 10, Exceptional, (6 reviews)
"We throughly enjoyed our stay. It was very clean, comfortable and it had everything we needed."
United States
Kim F.
The price is £457
includes taxes & fees
25 Sept - 26 Sept
Vacation Home With POOL and BBQ Near Anna Maria Island
An aerial view of a coastal island with a white sandy beach, dense vegetation, and a clear blue sea.

13. Tropical Oasis Near AMI | Pool + Dogs Welcome

Tropical Oasis Near AMI | Pool + Dogs Welcome
Bradenton
10.0 out of 10, Exceptional, (90 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 £441
includes taxes & fees
27 Sept - 28 Sept
Tropical Oasis Near AMI | Pool + Dogs Welcome
A beach with a hotel in the background.

14. 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 £414
includes taxes & fees
5 Oct - 6 Oct
Beach House Kids & Pets OK Oct, Nov, Dec DISCOUNTED! AMIsland White Sand Beaches
A covered outdoor seating area with a view of a lake and a house in the background.

15. 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 appreciated and enjoyed our stay at the house. The beds were comfortable and the kitchen very well stocked. It was convenient to the beaches and IMG Academy. "
United States
Alison W.
The price is £308
includes taxes & fees
15 Oct - 16 Oct
Stylish Lake View House: Minutes to Beaches & IMG, Pet-friendly
A swimming pool with a tiled edge, surrounded by a white fence, and four lounge chairs.

16. Heated Pool Florida Home 10 miles beach 3 miles IMG

Heated Pool Florida Home 10 miles beach 3 miles IMG
Bradenton
9.6 out of 10, Exceptional, (28 reviews)
"Great, family-friendly home. It was clean, comfortable and the host was very responsive to any questions we had. It is close to shopping plazas and easy to find. We would definitely stay here again and highly recommend! "
United States
Elizabeth R.
The price is £345
includes taxes & fees
25 Sept - 26 Sept
Heated Pool Florida Home 10 miles beach 3 miles IMG
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 £222
includes taxes & fees
5 Oct - 6 Oct
The Hideaways at Point Pleasant (Palm Side)
Two kayaks, one blue and one yellow, parked on a gravel surface.

18. Cottage on the canal

Cottage on the canal
Bradenton
10.0 out of 10, Exceptional, (165 reviews)
"Great location for boating and ready beach access."
United States
J J.
The price is £402
includes taxes & fees
27 Sept - 28 Sept
Cottage on the canal
A beach with clear turquoise water and a sandy shore.

19. Paradise Cove -- A perfect Beach Getaway

Paradise Cove -- A perfect Beach Getaway
Bradenton
10.0 out of 10, Exceptional, (160 reviews)
"Great place to stay! Host was easy to communicate with and was very hospitable. House was super clean and very nice. "
United States
Carol E.
The price is £294
includes taxes & fees
28 Sept - 29 Sept
Paradise Cove -- A perfect Beach Getaway
A house with a porch, number 203, and a ceiling fan.

20. The Hideaways at Point Pleasant (Pine Side)

The Hideaways at Point Pleasant (Pine Side)
Bradenton
9.8 out of 10, Exceptional, (182 reviews)
"Great location. Super quiet! "
United States
John R.
The price is £222
includes taxes & fees
5 Oct - 6 Oct
The Hideaways at Point Pleasant (Pine Side)
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
"After an anniversary trip last year and then again in May with our family, my husband and I returned again for our Anniversary! Everything was superb, especially the water pressure from the shower head!! That felt so good after our 14 hour drive!! Right on the beach and not too crowded! Our kids were jealous they couldn’t come back this time. We can’t wait to come back again with the family!"
Bonnie L. 3-night trip
Posted 2 days ago
Now Open! 7-Night Deal – Oceanfront w/ Private Balcony & Stunning Views

Find out more about Longboat Key

Longboat Key Holiday Homes information

Number of reviews
918
Accommodation
147 Holiday Homes
Lowest Price
£185
Highest Price
£457