Longboat Key Vacation Home Rentals from CA $344: Search Top Private Vacation Homes for Rent

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

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Our top choices for Longboat Key vacation 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

Sunny Shores

Bryce W.

CA $673 total

includes taxes & fees

Oct 3 - Oct 4

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

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

Bradenton

Dawn Z.

CA $422 total

includes taxes & fees

Oct 3 - Oct 4

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

3. "Stingray" 3 miles to Anna Marie

Bradenton

Agnieszka

CA $519 total

includes taxes & fees

Oct 5 - Oct 6

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

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

South Bradenton

Gary B.

CA $786 total

includes taxes & fees

Oct 11 - Oct 12

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>

Bradenton

Matthew H.

CA $562 total

includes taxes & fees

Oct 6 - Oct 7

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

Bradenton

Karen B.

CA $479 total

includes taxes & fees

Oct 3 - Oct 4

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

7. Anna Maria Beach Condo 1/1

Bradenton Beach

Donna B.

CA $545 total

includes taxes & fees

Oct 5 - Oct 6

Two kayaks, one blue and one yellow, parked on a gravel surface.

8. Cottage on the canal

Bradenton

J J.

CA $779 total

includes taxes & fees

Oct 8 - Oct 9

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Top Longboat Key Hotel Reviews

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

10/10 Excellent

"View fantastic of the gulf! Watched dolphins daily along with exotic wildlife Very clean room. Very comfortable and enjoyable. Once you check in, won’t need anything to go out for if you stock food! Had a wonderful stay. Communication with the host was smooth and effortless! Will not hesitate to go back!!!!!! Laundry facilities on site! Overall had a delightful stay!"

Step from the Beach.Renovated ground Floor unit 63

10/10 Excellent

"Loved the location. So nice to have the beach amenities like an umbrella, beach towels and chairs available. Love the closeness to the beach even though you can’t see the water from the room. So nice to be able to walk back and forth. Screened in porch was nice. Room was a little small but the amenities were worth the small room. Liked that it was ground level. Loved that the shower had a handheld sprayer, so nice when at the beach. Pool was nice."

Direct Oceanview: Open Tomorrow Early Check-In!

10/10 Excellent

"If you are looking for a great experience at Longboat Key. This is it. Heidi, the host was great. She was easy and quick to respond to any and all questions. She even sent cake for my birthday (Thanks again). The condo location is outstanding, right on the beach and our view was phenomenal. We had the best sunsets each night. The condo was well maintained and equipped with all your basic needs. Would highly recommend and hope to stay again."

Charming 1-bedroom, beachfront condo in marvelous Longboat Key

10/10 Excellent

"This beachfront condo is wonderful! The kitchen was well equipped, the unit very clean and very comfortable. The host was very responsive and easy to work with. Longboat Key is a beautiful area and we loved the location of this unit-quiet beach with an amazing view! I will book again, and highly recommend!"

Charming Cabana Beach Club #8 - Your Coastal retreat Awaits!#9 also available.

10/10 Excellent

"Michaela‘s place was a dream to stay at! Everything was easy from the travel, to the amenities provided (extra towels were a plus) and it was only a few steps from the beach! The area was so quiet and serene which made it easy to unwind."

End of summer sale Take a peek awesome reviews 50 feet from sand

10/10 Excellent

"What a view! It was just breathtaking! Jim is wonderful to work with and communicates very efficiently and promptly. We arrived a little early, and I checked to see if the condo would possibly be cleaned and ready. Since it was we were we were able to check right in. Big thank you for that! We would definitely stay here again!"

Find out more about Longboat Key

Longboat Key Vacation Homes information

Number of reviews	953
Accommodation	147 Vacation Homes
Lowest Price	CA $344
Highest Price	CA $900

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Our top choices for Longboat Key vacation homes

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