
Villa vacation rentals in Longboat Key
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Top-rated villa rentals in Longboat Key
Guests agree: these villas are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Longboat Key villa rentals
Private villa rentals

NEW Family Haven: Near Honeymoon Island
This place was idyllic for the five kiddos 6 and under and 4 adults we had for a fun kick off to summer vacation. They thought of everything at this house to make it very family friendly: step stools, kid sized toilet seats, playroom, changing tables, noise machines, child locks on cupboards, pool toys, etc. We were blown away! And the location was perfection. 10 min and you’re at the serene Honey Moon Island; not much further to downtown Dunedin and then Clearwater beach. Truly the best stay for our summer beach vacation.

Villa Luxe~Heated Saltwater Pool~Near Beaches
My family and I had an amazing stay at Biljana’s home! The house is exactly as shown in the photos. The entire house was spotless on our arrival. Everything inside is totally upgraded and has beautiful finishes. The floors are gorgeous and the kitchen has everything you could possibly need. We loved the fact the house was stocked with toiletries (shampoo, body wash, dish soap, paper towels) etc. and the fact they have beach chairs, umbrellas, beach towels, and even a cooler for you to use. They truly let you into their home with open arms and allow you to access all their things. The heated saltwater pool was warm at 80 degrees and clean. The pool vacuum is awesome and clears all the debris in just an hour or so. Biljana and her husband respond to all your needs very quickly and are so friendly! Only thing I may recommend is updating some outdoor pool furniture such as the patio table and chairs. Would 100% stay here in the future!

Tiki Bella Villa (Entire home with Pool)
The home was as described. We really enjoyed the pool, and everything we needed was there. Our dog loved the fenced backyard too. The mattresses were very comfortable. While we were a little hesitant about plane noise after our arrival, the air traffic didn’t interrupt our sleep or fun at all. Highly recommend Gina’s listing, and we would definitely stay there again.

Cheerful 2 bd 2 bt Villa close to Siesta Key Beach
Beautiful home, wife and I really like it a lot!

Robinhood Beach Villa near Siesta Key Beach!
The stay was great. It was super clean and had all the needed items. The location was very convenient as well.

7891 Timberwood, Sarasota, Florida
We enjoyed the villa. It was close to Siesta Keys. There were a lot of restaurants close by

Mi Pequeña Casa - 2/2 on a lake
We had a great stay. My wife and I had a great time in the area and this listing was centrally located to everything we wanted to do. House was updated and very clean! Will definitely be staying here again!

NEW-Cheerful 2-bedroom villa-13 min. to Siesta Key
Agata's villa was perfect and she was very responsive when we had a question. We appreciated the well equipped kitchen, modern appliances, lanai dining table, the reading lights and comfortable furniture in the living room, the bathtub as well as shower in both bathrooms, the Smart TV (there are three TVs), and the beach and children's equipment in the garage. The complex is lovely, peaceful and private -- a good place to take a walk, swim in the pool, play pickleball with an active group, use the billiards table in the clubhouse, join in on occasional activities such as bingo or trivia. The area is close to grocery shopping, The Legacy Trail for biking, Tamiami Trail and convenient for traveling to area beaches. We plan to go back here again and again. Thank you, Agata!
Luxury villa rentals

Luxurious 4-Bedroom Retreat with Pool
This property was fantastic! Located in a great spot near shopping and restaurants, it made exploring Siesta Keys so convenient. The host was incredibly responsive and attentive, which made our stay even more enjoyable. The home was well-equipped with everything we needed, including beach chairs, beach towels, a large cooler with wheels, and a cart with wheels—perfect for days at the beach! We absolutely loved the patio and pool area; it was the perfect place to relax after a day of exploring. I would highly recommend this property to anyone visiting Siesta Keys and would definitely stay here again on our next trip. Truly a wonderful experience!

Lakeside Villa
Amazing lake house, loved it

Modern Luxury Retreat - Heated Pool Spa, Game Room
The house was exactly as shown in the pictures—clean and well-maintained. The location is great, with easy access to several beautiful beaches nearby. The pool area was definitely a highlight and made for a relaxing stay. Martin and Anna were really proactive in communication, which made the whole experience smooth.

Luxury home in the heart of South Tampa & POOL!
The house was beautiful and well equipped! The pool was huge and clean, our kids loved playing with the provided floaties and toys. Isabella even put the lights and waterfall on for us and heated the pool for us on our second day. Plenty of towels for the pool and bathrooms. We have stayed in a few Airbnb’s now and I would say this was the best! Isabella was paid a lot of attention to detailing with the decor in the house and providing kitchen, bathroom and other items. Very prompt to respond and checking in on us. We would love to stay here when we visit Tampa again.

Siesta Key Palm Paradise w/ Heated Salt Water Pool
First time in Florida and what a wonderful house we got to stay at. The house is so beautiful we all loved the pool. Very quiet neighborhood. It’s just a couple miles away from Siesta Beach. Lots of local restaurants near by. We will definitely be back.

5 BR Luxury Beach Villa: Heated Pool & Games Room
We had a great stay, close to the beaches and just as described!

Paradise with a pool, pier and private beach area
Beautiful house! Lots of room for everyone, sparkling clean! Fantastic location. Perfect for our family gathering.

Coastal Villa w/ Amazing Courtyard - Splash Pad!
Easy check in and easy to find. Close to Sarasota beaches!
Villa rentals with a pool

Peaceful bright home minutes from the beach
5 stars! We had a fantastic stay at this home! The house was spotless and very well-equipped with everything we needed—from kitchen supplies to extra towels. The pool and jacuzzi were definitely highlights; perfect for relaxing at the end of the day. It was also great to find a place that’s truly pet-friendly—our dog felt right at home. Everything was just as described, if not better. Highly recommend and would absolutely stay here again!

2 Homes! 4 MN/Beach! SLT Pool, Hotub, Kayaks GM RM
Our stay was great for a bachelorette weekend ! The host was so responsive and got back to us right away. Enough towels for 14 + people. The amenities of the house were great. We enjoyed the use of the pool and hot tub! Definitely recommend staying here :)

Charming 2/2 Village des Pins close to Siesta Key
This villa was very quiet and private. The view of the surrounding area from the lanai was especially enjoyable. It is just a short walk to the pool and to the outdoor grills. The circle is a great place to get a walk in anytime, day or night. The neighborhood is quiet and has a very safe and friendly feel. Clara went out of her way to help when called upon.

4 min Walk to Beach, Pool, Roof Deck
Fantastic stay! The 3BR/3BA home was beautifully decorated and fully equipped with everything we needed. Perfect location—just a short walk to the beach and all the restaurants and shops in downtown Clearwater Beach. We especially loved the rooftop seating area and firepit. The host was excellent and very responsive. Highly recommend!

Waterfront Heated Pool, Sleeps 20 - 4plex
This place was perfect, I wouldnt judge a book by its cover, its super clean, neat and modern inside, all of the separate apartments have the perfect sense of privacy and the penthouse was great to gather in. The patio was perfect to relax and look at the lake, and the pool was always warm. I’d highly recommend this place for a big family!

Luxury waterfront in the heart of treasure island
Great location and space

Your own tropical paradise in Sarasota
We absolutely loved our stay here. Anna was friendly and helpful. The house was spotless, comfortable, and had everything that was needed. The location was unbeatable. Will definitely return! Thank you Anna!

Brand New house with pool and much more
My family and I enjoyed our stay. The house is large and laid out nicely with a big updated kitchen, large primary suite with an awesome bathroom, and of course the pool was an added bonus. Only suggestion is to have extra blankets and more glasses and coffee mugs. It's a great place and I recommend staying!
Quick stats about villa rentals in Longboat Key
Total rentals
10 properties
Nightly prices starting at
G$20,915 GYD before taxes and fees
Total number of reviews
300 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with a pool
10 properties have a pool
Wifi availability
10 properties include access to wifi
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- Anna Maria Island
- Siesta Beach
- Dunedin Beach
- Anna Maria Public Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Busch Gardens Tampa Bay
- Raymond James Stadium
- Cortez Beach
- Lido Key Beach
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- Vinoy Park
- North Beach
- Fort De Soto Park
- Manasota Key Beach
- Streamsong Resort
- Tampa Theatre
- Jannus Live
- Curtis Hixon Waterfront Park