Longboat Key Holiday Houses

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Our top choices for Longboat Key holiday homes

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

Bradenton

thomas F.

includes taxes & fees

1 Dec - 2 Dec

A sandy pathway leading to a beach, flanked by green foliage and rope barriers.

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

Bradenton

Melanie L.

includes taxes & fees

12 Nov - 13 Nov

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

Sunny Shores

Bryce W.

includes taxes & fees

9 Nov - 10 Nov

An aerial view of a coastal island with a white sandy beach, dense vegetation, and a clear blue sea.

4. Heated Pool & Fire Pit | 200 Palms

Bradenton

Kristen P.

includes taxes & fees

9 Nov - 10 Nov

A covered swimming pool with lounge chairs and umbrellas, surrounded by a fence and trees.

5. "Stingray" 3 miles to Anna Marie

Bradenton

Agnieszka

includes taxes & fees

8 Nov - 9 Nov

A dining area with a dark wooden table, four chairs, and a hanging lamp.

6. Lakeview Bradenton Rental Near Beaches & IMG

South Bradenton

Dee F.

includes taxes & fees

1 Dec - 2 Dec

A modern outdoor seating area with two blue chairs and a large potted plant.

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

Bradenton

Karen B.

includes taxes & fees

8 Dec - 9 Dec

A wooden beach pavilion with a checkered roof and open sides, overlooking the beach.

8. Anna Maria Beach Condo 1/1

Bradenton Beach

Donna B.

includes taxes & fees

8 Nov - 9 Nov

A hot tub under a wooden pergola with a pool in the background.

9. CANAL FRONT! Bring or rent a boat, near AMI/IMG + HEATED POOL

Bayshore Gardens

Josh

A coastal view with a sandy beach and clear turquoise waters.

10. Bella by the Sea Unit B

Bradenton Beach

Lindsey T.

A backyard with a swimming pool, palm trees, and a patio area.

11. "Barracuda"

Sunny Shores

James H.

includes taxes & fees

8 Nov - 9 Nov

A beach with clear turquoise water, people swimming and walking on the shore, and several beach umbrellas and sun loungers.

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

Bradenton

Matthew H.

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

Bradenton

Brittany C.

A beach with clear turquoise water, white sand, and a row of trees and buildings along the shore.

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

South Bradenton

Gary B.

includes taxes & fees

29 Nov - 30 Nov

A beach with clear turquoise water and a sandy shore.

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

South Bradenton

Stacie

includes taxes & fees

10 Nov - 11 Nov

An outdoor patio with a pool, lounge chairs, a fire pit, and string lights.

16. 🏝 4BR Tropical Oasis w/ Heated Pool + Game Room + 10 Min to Anna Maria and IMG

Bradenton

Aracely T.

includes taxes & fees

9 Nov - 10 Nov

A wooden deck with two Adirondack chairs, a thatched umbrella, and a view of a marina with boats.

17. Cottage on the canal

Bradenton

J J.

A beach with clear shallow waters, a sandy shore, and a few buildings in the background.

18. Cortez Beach Retreat "Poolside" - $150,000 Pool + Hot Tub, Dog-friendly

Bradenton Beach

esther e.

A waterfront promenade with a bridge in the background, a metal sculpture, and palm trees.

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

Bradenton

Dennis B.

A two-story house with a covered porch, a small front yard, and a clear blue sky.

20. The Hideaways at Point Pleasant (Palm Side)

Bradenton

Diane M.

includes taxes & fees

8 Nov - 9 Nov

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Top Longboat Key Hotel Reviews

Charming 1-bedroom, beachfront condo in marvelous Longboat Key

8/10 Good

"Location: Excellent, right on the beach with necessary and convenient shopping nearby. Amenities: Fair. Simple low-cost improvements would include a smart tv, including eliminating the power-ugly connections in the living room and bedroom. Bedside light switches work with difficulty; these could economically be replaced. The couch is fine but worn. The frig is good, but it has no ice-maker, no ice-cube trays; no water pitcher is provided."

The St. Regis Longboat Key Resort

10/10 Excellent

"This is the absolute best vacation we’ve ever taken in our lives and barely left the resort at all for our entire stay! For the level of luxury this resort offers it blew our minds how family friendly it was as well. Our son is 6 and autistic and every single staff member we came into contact with made sure he enjoyed the stay just as much as any other kiddo. The restaurants are amazing, the pool atmosphere is out of this world, beach access is wonderful, rooms and complimentary self care products were top tier. Our butler Tori was stellar and made the entire stay even more magical for our son. The offerings here from the spa to the food to the service and atmosphere were just exquisite. We will be coming back to St, Regis longboat key again and again. I am getting absolutely nothing from writing this review I just want to express our deepest gratitude for making our getaway beyond relaxing, fun, and unforgettable!"

Fall sale ready for a luxury 5-floor penthouse 60 ft from water,

10/10 Excellent

"My Husband and I stayed here at this beautiful oceanfront condo at Longboat Key the last week of October 2026. It was perfect in every way. The space was just right for us. We Loved waking up to the Oceanfront views and being right on the water made it extra special. It was comfortable, inviting and the perfect place to unwind and enjoy the beauty of Longboat Key. We couldn't have asked for a better stay and would happily return. Highly recommend!"

Take a peek at awesome reviews 50 feet from the sand

10/10 Excellent

"The condo was clean and tastefully furnished. The bedroom was luxurious with a comfortable mattress and high-end bedding. The view was stunning and we were steps from the beach and the pool as well. We loved how peaceful Longboat Key is. Our host was helpful and communicative. We would definitely stay at this property again!"

Direct Oceanview: Open October 26th - 29th!

10/10 Excellent

"Heidi was the best VRBO host we’ve ever had. She has thought of every comfort on property and her communication is superb, always friendly, caring and helpful. We loved the second floor balcony for viewing the gulf and the ease of being on the beach and near the pool. We hope to stay at one of her properties on Longboat Key again."

Now Open! 7-Night Deal – Oceanfront w/ Private Balcony & Stunning Views

8/10 Good

"The ocean front balcony and the property location was excellent, as well as the regularly maintained grounds left everything very clean and neat. The inside of the rental was much smaller than anticipated and proved very difficult to place our luggage and unpack anything. The bed was extremely hard and bery cramped. On a plus side, the private balcony views and the water pressure in the shower were amazing! Communication, the parking lot and check-in were also great."

Find out more about Longboat Key

Longboat Key Holiday Homes information

Number of reviews	1,232
Accommodation	128 Holiday Homes
Lowest Price	NZ$393
Highest Price	NZ$1,055

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Check prices for these dates

Our top choices for Longboat Key holiday homes

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

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