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Villa vacation rentals in Longboat Key

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Popular amenities for Longboat Key villa rentals

Private villa rentals

Guest favorite
A spacious heated saltwater pool is surrounded by a screened enclosure, featuring colorful inflatable floats. A playroom is visible with cheerful decor, while a cozy media room offers comfortable seating. The exterior showcases a welcoming home, with a yard perfect for children’s play.
Villa in Dunedin
5 out of 5 average rating, 16 reviews

NEW Family Haven: Near Honeymoon Island

AmandaRating, 5 stars2 weeks ago
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.
Guest favorite
The dining area features a modern table with gold accents, surrounded by plush gray chairs. A stylish chandelier hangs above, illuminating the space. The open-concept layout offers a clear view of the adjacent kitchen and a spacious living area with a large television.
Villa in Palm Harbor
4.91 out of 5 average rating, 35 reviews

Villa Luxe~Heated Saltwater Pool~Near Beaches

CourtneyRating, 5 stars2 months ago
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!
Superhost
The front entrance of a light blue house is framed by a manicured lawn and lush greenery. A clear pathway leads to the door, bordered by decorative stones and various potted plants. Tall trees provide shade and an inviting atmosphere.
Villa in Sarasota
4.74 out of 5 average rating, 19 reviews

Tiki Bella Villa (Entire home with Pool)

JanaeRating, 5 stars11 months ago
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.
Guest favorite
A modern living space is shown, featuring a comfortable black sofa and a cozy area rug. A large television is mounted on a stylish media unit, with light streaming in from nearby windows. A dining area with a small table and chairs is also visible.
Villa in Sarasota
5 out of 5 average rating, 38 reviews

Cheerful 2 bd 2 bt Villa close to Siesta Key Beach

StevenRating, 5 stars2 weeks ago
Beautiful home, wife and I really like it a lot!
Superhost
A comfortable living and dining area is showcased, featuring a glass dining table with white wooden chairs. A cozy sectional sofa is arranged around a coffee table, with a rug underfoot. Natural light filters through two windows, complemented by decorative artwork on the walls.
Villa in Sarasota
4.93 out of 5 average rating, 14 reviews

Robinhood Beach Villa near Siesta Key Beach!

BrandonRating, 5 stars1 week ago
The stay was great. It was super clean and had all the needed items. The location was very convenient as well.
Guest favorite
A single-story villa is framed by landscaped greenery, featuring shrubs and palms. The exterior showcases a tile roof and light-colored walls, with windows allowing for natural light. A paved driveway is visible, leading to the entrance.
Villa in Sarasota
4.98 out of 5 average rating, 46 reviews

7891 Timberwood, Sarasota, Florida

RobRating, 5 stars2 months ago
We enjoyed the villa. It was close to Siesta Keys. There were a lot of restaurants close by
Superhost
A serene outdoor space is showcased, featuring lush green palm and banana trees gently swaying near a calm body of water. Sunlight reflects off the water's surface, surrounded by a natural landscape of tall grasses and distant trees under a clear blue sky.
Villa in Bradenton
4.75 out of 5 average rating, 102 reviews

My Little House - 2/2 on a lake

MichaelRating, 5 stars4 weeks ago
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!
Top guest favorite
The image showcases a large swimming pool surrounded by a paved patio, featuring multiple lounge chairs positioned along its perimeter. Umbrellas provide shade while trees and green foliage create a natural backdrop under a clear blue sky.
Villa in Sarasota
5 out of 5 average rating, 29 reviews

NEW-Cheerful 2-bedroom villa-13 min. to Siesta Key

CarolRating, 5 stars3 months ago
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

Guest favorite
An inviting outdoor space features a sparkling pool surrounded by patio furniture, ideal for relaxation. The property includes well-maintained gardens and a charming exterior of the villa, showcasing its spacious layout and resort-like atmosphere. Multiple living areas add to the comfort of the home.
Villa in Sarasota
4.97 out of 5 average rating, 36 reviews

Luxurious 4-Bedroom Retreat with Pool

LisaRating, 5 stars4 days ago
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!
Guest favorite
A serene outdoor space features a circular fire pit surrounded by several adirondack chairs. Lush greenery and trees frame the area, while a vibrant sunset paints the sky in soft pastel hues. The lake is visible in the distance, enhancing the peaceful ambiance.
Villa in Thonotosassa
4.95 out of 5 average rating, 43 reviews

Lakeside Villa

JohnRating, 5 stars3 weeks ago
Amazing lake house, loved it
Guest favorite
An outdoor space features a circular fire pit surrounded by several black Adirondack chairs, all set on gravel. The background showcases a heated pool and spa, with a vibrant sunset sky illuminating the scene. The villa and dining area are visible, enhancing the inviting atmosphere.
Villa in Seminole
4.95 out of 5 average rating, 42 reviews

Modern Luxury Retreat - Heated Pool Spa, Game Room

BhawnaRating, 5 stars1 month ago
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.
Top guest favorite
A serene outdoor pool area is enclosed by a screened structure, allowing for a private retreat. Sun loungers are positioned beside the clear, inviting water, and lush greenery surrounds the pool, enhancing the tranquil setting.
Villa in Tampa
5 out of 5 average rating, 74 reviews

Luxury home in the heart of South Tampa & POOL!

LauraRating, 5 stars2 weeks ago
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.
Guest favorite
The outdoor area features a clear saltwater pool surrounded by a spacious patio made of light stone tiles. Lounge chairs are positioned near the water, with tropical palm trees providing a green backdrop and adding to the serene atmosphere.
Villa in Sarasota
4.92 out of 5 average rating, 53 reviews

Siesta Key Palm Paradise w/ Heated Salt Water Pool

JenniferRating, 5 stars1 week ago
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.
Guest favorite
A heated pool is surrounded by comfortable loungers and shaded by a stylish cabana. A spacious patio area features outdoor seating, while lush greenery and tall trees create a serene backdrop under the clear blue sky.
Villa in Seminole
4.97 out of 5 average rating, 58 reviews

5 BR Luxury Beach Villa: Heated Pool & Games Room

JenniferRating, 5 stars6 months ago
We had a great stay, close to the beaches and just as described!
Superhost
A spacious waterfront home is surrounded by green landscaping, palm trees, and open blue skies. A large heated pool is visible in the backyard, adjacent to a well-maintained deck. Comfortable seating is positioned on the sandy area by the water, providing a relaxing atmosphere.
Villa in Osprey
5 out of 5 average rating, 11 reviews

Paradise with a pool, pier and private beach area

LauraRating, 5 stars19 months ago
Beautiful house! Lots of room for everyone, sparkling clean! Fantastic location. Perfect for our family gathering.
Guest favorite
An outdoor area features a lighted splashpad at the center, surrounded by pavers and tropical landscaping. Lounge chairs are positioned nearby, offering a relaxing spot to enjoy the serene atmosphere as soft lights illuminate the garden under a sunset sky.
Villa in Sarasota
4.95 out of 5 average rating, 41 reviews

Coastal Villa w/ Amazing Courtyard - Splash Pad!

Kathleen & AnthonyRating, 5 stars6 days ago
Easy check in and easy to find. Close to Sarasota beaches!

Villa rentals with a pool

Superhost
A private saltwater pool is surrounded by a stone patio and bordered by lush greenery. A large blue umbrella provides shade over a seating area. Potted plants add a pop of color to the serene outdoor setting, ideal for relaxation.
Villa in Venice
4.84 out of 5 average rating, 31 reviews

Peaceful bright home minutes from the beach

DanielleRating, 5 stars1 month ago
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!
Guest favorite
A spacious outdoor pool area features a sparkling pool and a playful inflatable car float. Surrounding lounge chairs provide seating, while a tiki hut offers shaded relaxation. Lush greenery and a wooden fence create a private atmosphere, enhancing the inviting feel of this family-friendly space.
Villa in St. Petersburg
4.87 out of 5 average rating, 30 reviews

2 Homes! 4 MN/Beach! SLT Pool, Hotub, Kayaks GM RM

MichelleRating, 5 stars1 month ago
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 :)
Superhost
The outdoor pool area features a spacious swimming pool alongside a hot tub. Surrounded by tall trees, the space offers a relaxing atmosphere with lounge chairs and umbrellas positioned around the pool deck. Clear blue skies enhance the inviting setting.
Villa in Sarasota
4.7 out of 5 average rating, 10 reviews

Charming 2/2 Village des Pins close to Siesta Key

TomRating, 5 stars15 months ago
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.
Guest favorite
A rooftop terrace is shown with two lounge chairs and a small table. A large umbrella provides shade, while a view of the waterfront and city skyline is visible in the background. The sky displays soft hues of purple and pink, enhancing the serene setting.
Villa in Clearwater Beach
4.97 out of 5 average rating, 30 reviews

4 min Walk to Beach, Pool, Roof Deck

BrysonRating, 5 stars3 weeks ago
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!
Guest favorite
Villa in Largo
4.97 out of 5 average rating, 92 reviews

Waterfront Heated Pool, Sleeps 20 - 4plex

Caitlin Rating, 5 stars6 days ago
absolutely the best place you would want to stay with a group of friends. these units are amazing. love the idea of having 3 downstairs little units/apartments, and the big penthouse unit upstairs to be able to hang out, cook and play games. would definitely stay again in the future!
Guest favorite
Villa in Treasure Island
4.88 out of 5 average rating, 17 reviews

Luxury waterfront in the heart of treasure island

Donal FrancisRating, 5 stars2 weeks ago
Great location and space
Guest favorite
A modern kitchen features sleek cabinetry, stainless steel appliances, and a central island with seating. Light-colored countertops and wood grain flooring create a bright and inviting space. Natural light is provided by a window, while an open layout connects the kitchen to the living area.
Villa in Sarasota
4.83 out of 5 average rating, 53 reviews

Your own tropical paradise in Sarasota

MayaRating, 5 stars2 months ago
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!
Superhost
Villa in Riverview
4.8 out of 5 average rating, 46 reviews

Brand New house with pool and much more

KatelynRating, 5 stars2 months ago
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

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Manatee County
  5. Longboat Key
  6. Villa rentals