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

Holiday Homes in Longboat Key

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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 NZ$516
includes taxes & fees
24 Sept - 25 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 NZ$826
includes taxes & fees
24 Sept - 25 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 NZ$529
includes taxes & fees
28 Sept - 29 Sept
"Stingray" 3 miles to Anna Marie
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, (36 reviews)
"Very comfortable, clean, convenient location. Great place to stay."
United States
Karen B.
The price is NZ$577
includes taxes & fees
24 Sept - 25 Sept
Pet-Friendly Bradenton Home 1.5 Mi to Cortez Beach
A beach with clear turquoise water, white sand, and a row of trees and buildings along the shore.

6. 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 NZ$952
includes taxes & fees
29 Sept - 30 Sept
IMG Lake & Beach Home Pool White Sand Beaches SEPTEMBER, Oct, Nov, Dec SPECIALS!
A beach with clear turquoise water, people swimming and walking on the shore, and several beach umbrellas and sun loungers.

7. "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 NZ$566
includes taxes & fees
29 Sept - 30 Sept
"Manatee" 3 miles to Anna Marie<br>
An outdoor patio with a pool, lounge chairs, a fire pit, and string lights.

8. 🏝 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, (16 reviews)
"Spacious and neat, we definitely enjoyed enjoyed our stay."
United States
Aracely T.
The price is NZ$934
includes taxes & fees
28 Sept - 29 Sept
🏝 4BR Tropical Oasis w/ Heated Pool + Game Room + 10 Min to Anna Maria and IMG
A modern kitchen with a stainless steel refrigerator, a microwave, and a coffee bar.

9. 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.
The price is NZ$1,097
includes taxes & fees
24 Sept - 25 Sept
Free Heated Pool•5 min drive to AMI•Hot Tub•Near IMG•Fire Pit•Full Kitchen
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, (165 reviews)
"Great location for boating and ready beach access."
United States
J J.
The price is NZ$955
includes taxes & fees
29 Sept - 30 Sept
Cottage on the canal
A dining area with a dark wooden table, four chairs, and a hanging lamp.

11. 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 NZ$412
includes taxes & fees
7 Oct - 8 Oct
Lakeview Bradenton Rental Near Beaches & IMG
A beach with clear turquoise water and a sandy shore.

12. 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, (193 reviews)
"great place to stay host should get over a 5 star"
United States
Stacie
The price is NZ$668
includes taxes & fees
28 Sept - 29 Sept
Paradise Retreat with HEATED POOL-- Need We Say More
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 NZ$556
includes taxes & fees
29 Sept - 30 Sept
Charming home near Anna Maria Island with Jacuzzi
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 NZ$955
includes taxes & fees
23 Oct - 24 Oct
Beach House Kids & Pets OK Oct, Nov, Dec DISCOUNTED! AMIsland White Sand Beaches
A beach with clear turquoise water and a sandy shore.

15. Paradise Cove -- A perfect Beach Getaway

Paradise Cove -- A perfect Beach Getaway
Bradenton
10.0 out of 10, Exceptional, (159 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 NZ$687
includes taxes & fees
27 Sept - 28 Sept
Paradise Cove -- A perfect Beach Getaway
A covered outdoor seating area with a view of a lake and a house in the background.

16. 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 NZ$732
includes taxes & fees
24 Sept - 25 Sept
Stylish Lake View House: Minutes to Beaches & IMG, Pet-friendly
An aerial view of a coastal island with a white sandy beach, dense vegetation, and a clear blue sea.

17. 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 NZ$1,040
includes taxes & fees
27 Sept - 28 Sept
Tropical Oasis Near AMI | Pool + Dogs Welcome
A backyard with a swimming pool, palm trees, and a patio area.

18. "Barracuda"

"Barracuda"
Sunny Shores
9.6 out of 10, Exceptional, (30 reviews)
"Amazing place clean close to the beach awesome"
United States
James W.
The price is NZ$738
includes taxes & fees
24 Sept - 25 Sept
"Barracuda"
A swimming pool with a surrounding garden and a covered area with a metal roof.

19. Backyard Oasis & Resort Style Pool

Backyard Oasis & Resort Style Pool
Bradenton
10.0 out of 10, Exceptional, (67 reviews)
"Great house! Super clean and amazing pool area. Would stay again!"
United States
Katina M.
The price is NZ$765
includes taxes & fees
27 Sept - 28 Sept
Backyard Oasis & Resort Style Pool
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 NZ$812
includes taxes & fees
24 Sept - 25 Sept
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

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 1 day 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
847
Accommodation
147 Holiday Homes
Lowest Price
NZ$412
Highest Price
NZ$1,097

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