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
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Longboat Key vacation 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)
"We had the most wonderful stay despite the cold temps for most it! The staff at our location are above and beyond to make sure you have everything you need! Highly recommend!"
United States
Sahra S.
The price is ￥24,974
￥54,210 total
includes taxes & fees
Sep 1 - Sep 2
Ground Floor, Steps to Sand – Silver Sands #243A by RVA
A beachside restaurant with a thatched roof, wooden tables, and chairs, overlooking a sandy beach and the ocean.

2. 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 ￥14,248
￥78,332 total
includes taxes & fees
Sep 1 - Sep 2
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.

3. "Stingray" 3 miles to Anna Marie

"Stingray" 3 miles to Anna Marie
Bradenton
9.6 out of 10, Exceptional, (35 reviews)
"Property was great and location was ideal for our weekend getaway"
United States
Agnieszka
The price is ￥21,612
￥47,774 total
includes taxes & fees
Sep 1 - Sep 2
"Stingray" 3 miles to Anna Marie
An aerial view of a coastal island with a white sandy beach, dense vegetation, and a clear blue sea.

4. Tropical Oasis Near AMI | Pool + Dogs Welcome

Tropical Oasis Near AMI | Pool + Dogs Welcome
Bradenton
10.0 out of 10, Exceptional, (89 reviews)
"Everything was above and beyond excellent! Very well equipped and cozy home feels."
United States
Carly S.
The price is ￥31,824
￥96,353 total
includes taxes & fees
Sep 1 - Sep 2
Tropical Oasis Near AMI | Pool + Dogs Welcome
A modern outdoor seating area with two blue chairs and a large potted plant.

5. 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, (35 reviews)
"Very comfortable, clean, convenient location. Great place to stay."
United States
Karen B.
The price is ￥21,132
￥54,384 total
includes taxes & fees
Sep 1 - Sep 2
Pet-Friendly Bradenton Home 1.5 Mi to Cortez Beach
A modern kitchen with a stainless steel refrigerator, a microwave, and a coffee bar.

6. 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, (33 reviews)
"Clean house in a great area! Good communication with host. "
United States
Tyler B.
The price is ￥25,294
￥89,745 total
includes taxes & fees
Sep 1 - Sep 2
Free Heated Pool•5 min drive to AMI•Hot Tub•Near IMG•Fire Pit•Full Kitchen
A sandy pathway leading to a beach, flanked by green foliage and rope barriers.

7. 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 ￥18,250
￥47,614 total
includes taxes & fees
Sep 1 - Sep 2
Modern Coastal Charm • Near AMI Beach-IMG Academy
A beach with clear turquoise water, white sand, and a row of trees and buildings along the shore.

8. IMG Lake & Beach Home Pool White Sand Beaches Aug, Sept, Oct, Nov, Dec SPECIALS!

IMG Lake & Beach Home Pool White Sand Beaches Aug, Sept, 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 ￥18,410
￥84,423 total
includes taxes & fees
Sep 1 - Sep 2
IMG Lake & Beach Home Pool White Sand Beaches Aug, Sept, Oct, Nov, Dec SPECIALS!
A beach with clear turquoise water and a sandy shore.

9. 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, (191 reviews)
"Enjoyed my stay. "
United States
Stephanie R.
The price is ￥22,765
￥58,142 total
includes taxes & fees
Sep 2 - Sep 3
Paradise Retreat with HEATED POOL-- Need We Say More
Two kayaks, one blue and one yellow, parked on a gravel surface.

10. Cottage on the canal

Cottage on the canal
Bradenton
10.0 out of 10, Exceptional, (163 reviews)
"Great location for boating and ready beach access."
United States
J J.
The price is ￥40,023
￥87,714 total
includes taxes & fees
Sep 1 - Sep 2
Cottage on the canal
A beach with clear turquoise water, people swimming and walking on the shore, and several beach umbrellas and sun loungers.

11. "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 ￥22,253
￥52,777 total
includes taxes & fees
Sep 7 - Sep 8
"Manatee" 3 miles to Anna Marie<br>
A bedroom with a bed, a ceiling fan, a nightstand, a lamp, a potted plant, and a sliding glass door leading to a bathroom.

12. 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 ￥26,367
￥51,999 total
includes taxes & fees
Sep 1 - Sep 2
Charming home near Anna Maria Island with Jacuzzi
An outdoor patio with a pool, lounge chairs, a fire pit, and string lights.

13. 🏝 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, (15 reviews)
"Spacious and neat, we definitely enjoyed enjoyed our stay."
United States
Aracely T.
The price is ￥21,353
￥85,290 total
includes taxes & fees
Sep 1 - Sep 2
🏝 4BR Tropical Oasis w/ Heated Pool + Game Room + 10 Min to Anna Maria and IMG
A waterfront promenade with a bridge in the background, a metal sculpture, and palm trees.

14. Private Resort:Pool, Game Room, Near IMG & Beaches

Private Resort:Pool, Game Room, Near IMG & Beaches
Bradenton
10.0 out of 10, Exceptional, (17 reviews)
"Great clean place with a very nice pool in a perfectly located area!"
United States
Lance R.
The price is ￥24,638
￥109,297 total
includes taxes & fees
Sep 1 - Sep 2
Private Resort:Pool, Game Room, Near IMG & Beaches
A backyard with a wooden fence, outdoor furniture, and string lights.

15. 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 ￥28,816
￥97,719 total
includes taxes & fees
Sep 4 - Sep 5
Vacation Home With POOL and BBQ Near Anna Maria Island
A beach with waves and a cloudy sky.

16. Ila's Beach House: Near IMG-Heated Salt Pool- Pets OK-Modern Organic Smart Home

Ila's Beach House: Near IMG-Heated Salt Pool- Pets OK-Modern Organic Smart Home
South Bradenton
9.8 out of 10, Exceptional, (63 reviews)
"Wonderful place! "
United States
Janelle K.
The price is ￥29,777
￥80,282 total
includes taxes & fees
Sep 1 - Sep 2
Ila's Beach House: Near IMG-Heated Salt Pool- Pets OK-Modern Organic Smart Home
A beach with clear turquoise water and a sandy shore.

17. Paradise Cove -- A perfect Beach Getaway

Paradise Cove -- A perfect Beach Getaway
Bradenton
10.0 out of 10, Exceptional, (158 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 ￥26,799
￥67,598 total
includes taxes & fees
Sep 1 - Sep 2
Paradise Cove -- A perfect Beach Getaway
A covered outdoor seating area with a view of a lake and a house in the background.

18. 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 ￥27,567
￥68,683 total
includes taxes & fees
Sep 2 - Sep 3
Stylish Lake View House: Minutes to Beaches & IMG, Pet-friendly
A backyard with a swimming pool, palm trees, and a patio area.

19. "Barracuda"

"Barracuda"
Sunny Shores
9.6 out of 10, Exceptional, (29 reviews)
"Amazing place clean close to the beach awesome"
United States
James W.
The price is ￥31,218
￥68,287 total
includes taxes & fees
Sep 7 - Sep 8
"Barracuda"
A swimming pool with a tiled edge, surrounded by a white fence, and four lounge chairs.

20. 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 ￥25,454
￥75,237 total
includes taxes & fees
Sep 1 - Sep 2
Heated Pool Florida Home 10 miles beach 3 miles IMG
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

Zota Beach Resort

Zota Beach Resort

10/10 Excellent
"Great location and accommodation. Great customer Service."
Stefan 2-night trip
Posted 1 hour ago
Zota Beach Resort

Find out more about Longboat Key

Longboat Key Vacation Homes information

Number of reviews
316
Accommodation
147 Vacation Homes
Lowest Price
￥17,019
Highest Price
￥89,140