Longboat Key Villas

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 villas

A house with a turquoise door, a welcome sign, and a window with blinds.

1. Peaceful Villa, 3.3 mi to the Beach & Big Parking

Bradenton

Shanna Lee

HK$3,382 total

includes taxes & fees

10 Nov - 11 Nov

A single-story house with a white exterior, a dark roof, and a front door.

2. Lakefront 2BR Bradenton Rental Near IMG & Beaches

South Bradenton

Laura

HK$3,118 total

includes taxes & fees

8 Dec - 9 Dec

A modern single-story house with a paved driveway, a basketball hoop, and a well-maintained lawn.

3. HeatedPool • HotTub • OutdoorKitchen/Theater/Games

South Bradenton

Alisha M.

HK$4,510 total

includes taxes & fees

10 Nov - 11 Nov

A bicycle parked outside a building with a 'Hello' mat at the entrance.

4. [Beach Elements] pool view withprivate beach access

Siesta Key

Natalie M.

HK$2,104 total

includes taxes & fees

18 Nov - 19 Nov

A dining area with a table and chairs, a green wall with a sign, and a view of palm trees and greenery.

5. Salty Lime Villa 2-Riverview w/pool on riverwalk, near AMI beaches, pet friendly

Bradenton

Kara H.

HK$2,307 total

includes taxes & fees

10 Nov - 11 Nov

A resort with a swimming pool, a covered patio, and a view of the ocean.

6. Sunswept Villa 4-riverwalk/park front w/ pool, near AMI beaches - pet friendly!

Bradenton

Terri B.

HK$2,372 total

includes taxes & fees

8 Dec - 9 Dec

An aerial view of a house with a swimming pool, surrounded by lush greenery and palm trees.

7. Tranquil Tide Villa -Riverview w/pool on riverwalk, near AMI beach, pet friendly

Bradenton

Kay S.

HK$2,307 total

includes taxes & fees

16 Nov - 17 Nov

A covered patio with a table and chairs, a stone floor, and a view of a residential street and greenery.

8. AUTUMN SPECIAL!!! 2/2 BEAUTIFUL VILLA! 2 BR, 2 BA, Heated pool and Jacuzzi! WiFi

Sarasota

Sharon M.

HK$3,388 total

includes taxes & fees

10 Nov - 11 Nov

A sunlit balcony with a round glass table and wicker chairs, overlooking a well-maintained lawn and a house in the background.

9. Bright Spacious Villa with a Pool – 15 min from Siesta Beach #1 Beach in the USA

Sarasota

Jennie A.

HK$2,885 total

includes taxes & fees

17 Nov - 18 Nov

An outdoor kitchen with a grill, cooking utensils, and a view of lush greenery.

10. Heated Pool • Sleeps 25 • Pickle/Bball • Theater

Bradenton

Adam D.

HK$6,117 total

includes taxes & fees

10 Nov - 11 Nov

11. BEAUTIFUL 2/2 VILLAS, KING BED, High speed Wi-Fi, Heated Pool and Jacuzzi!

Sarasota

Misty S.

HK$3,388 total

includes taxes & fees

10 Nov - 11 Nov

Beachfront retreat with pool, palm-lined grounds, and direct beach access

12. Beachfront · Heated Pool · King Bed

Holmes Beach

HK$4,972 total

includes taxes & fees

7 Dec - 8 Dec

A patio with a round table and chairs, a blue umbrella, and a view of a building with a balcony.

Casey Key

HK$2,906 total

includes taxes & fees

30 Nov - 1 Dec

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Top Longboat Key Hotel Reviews

Charming 1-bedroom, beachfront condo in marvelous Longboat Key

8/10 Good

"Perfect location! You can walk right out to the beach from the property. The view was stunning, we had the most breathtaking views from our lanai every night. Close to Publix for ease of grocery shopping.Would stay again!"

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