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Villa holiday rentals in Longboat Key

Find and book unique villas on Airbnb

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Popular amenities for villa rentals in Longboat Key

Private villa rentals

Superhost
Villa in Gulf Cove
4.79 out of 5 average rating, 34 reviews

Canal Front 3-Bedroom Grand Villa with Pool

JenniferRating, 5 stars1 week ago
Absolutely LOVED our stay! Host and owners were VERY responsive, even during a minor issue at check in, they responded and had it resolved extremely fast. Very clean, comfortable, neighbors were so friendly, we felt very safe, this place made our girls’ weekend PERFECT! And the salt water pool?! Chef’s kiss!!!! We loved it!! Thank you so much for having us and allowing us to enjoy this little slice of heaven in Florida!
Guest favourite
Villa in Palmetto
5 out of 5 average rating, 20 reviews

The Sea House

MichelleRating, 5 stars1 month ago
Couldn’t have found a better place to stay for our trip. After full days at the beaches, sightseeing, and exploring it was so nice to get back to our little house to enjoy the quiet and relaxing oasis. Truly a wonderful place to stay.
Superhost
Villa in Bradenton
5 out of 5 average rating, 3 reviews

Florida Villa Sunrise - 4 Bedroom Home with Pool

SashakaylaRating, 5 stars1 month ago
This home was everything that was promised. It was huge. My family were able to check in a few hours early which really sweetened the deal. The home really suited my family needs. There were toys and strollers, beach toys, and bikes. It was awesome! Will definitely come back next year!
Guest favourite
Villa in Sarasota
5 out of 5 average rating, 6 reviews

Newly Remodeled Luxury Beach Villa on Siesta Key!

KaylaRating, 5 stars1 month ago
We had a lovely stay at Villa 7! It was clean, comfortable, and had everything we needed (and more!). The kitchen was well stocked, the beach toys were a fabulous treat for the kids, and we loved the fun garage space! Kat was quick to respond to any questions and very friendly. We appreciated the clear instructions, recommendations, and information she shared with us. We walked to the beach and the pool and could easily rinse off using the outdoor shower. We also enjoyed walking to the Daquiri Deck & Captain Curts, and taking the free Breeze Trolley into the village. This location is great and the villa itself is very nice!! Definitely recommend :)
Superhost
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 favourite
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 favourite
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
Guest favourite
Villa in Largo
4.91 out of 5 average rating, 44 reviews

Here Love Blooms: 1B Secluded Villa for Romance.

SimonaRating, 5 stars1 week ago
My husband and I had an amazing stay here! Everything was just as described. It was very a peaceful and enjoyable experience. The space is very clean, organized, and comfy! Although we were on vacation, it truly felt like home. We definitely recommend staying here, as we would love to come again one day!

Luxury villa rentals

Guest favourite
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 favourite
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 favourite
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 favourite
Villa in Indian Rocks Beach
4.9 out of 5 average rating, 42 reviews

Villa Blanca - Waterfront Midcentury Modern Home

CarrieRating, 5 stars2 weeks ago
Villa Blanca was everything we could ask for and then some! We were greeted with a bottle of wine, chocolates and a note from Debbie on the counter. Not many Airbnb's offer that type of personal touch and we appreciated it. The home and grounds are well maintained, the house was clean, everything you could need in the kitchen was available. This is the perfect getaway home! Thank you Debbie for your hospitality!
Guest favourite
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 favourite
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
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 favourite
Villa in Sarasota
4.95 out of 5 average rating, 41 reviews

Coastal Villa w/ Amazing Courtyard - Splash Pad!

Kathleen & AnthonyRating, 5 stars5 days ago
Easy check in and easy to find. Close to Sarasota beaches!

Villa rentals with a pool

Guest favourite
Villa in Palm Harbor
4.91 out of 5 average rating, 35 reviews

Villa Luxe~Heated Saltwater Pool~Near Beaches

CourtneyRating, 5 stars1 month 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
Villa in Bayou Oaks
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.
Superhost
Villa in Largo
4.86 out of 5 average rating, 63 reviews

Best deal in town!

BarbaraRating, 5 stars2 months ago
The residence was clean and met our needs for the 9 family members that stayed (3 nights). The kitchen has plenty of counter space. The home was roomy enough for all, but some of the seating (blue chairs in photos) was not in the home. If you are traveling with elders, just note that 2 of the 3 bathrooms have smaller than standard doors. My mom’s walker would not fit through them. The beds are very comfortable. We would stay here again if coming to town.
Guest favourite
Villa in Bay Crest Park
5 out of 5 average rating, 28 reviews

(BAYC) Heated Pool Villa. Boat rental available

GiftyRating, 5 stars2 months ago
Thank you for the stay. It made our weekend wonderful. Our kids loved the pool and game room.
Superhost
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 favourite
Villa in Largo
4.97 out of 5 average rating, 92 reviews

Waterfront Heated Pool, Sleeps 20 - 4plex

Caitlin Rating, 5 stars5 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 favourite
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!
Top guest favourite
Villa in Bradenton
5 out of 5 average rating, 38 reviews

River Pointe 3/2 Lakefront Home with Heated Pool

MichelleRating, 5 stars2 months ago
Immediately upon arrival, I thought that the pictures did not do this place justice. It was clean, spotless, and very well stocked this house had everything we could possibly need and even things we didn’t even think we needed it, but had available. We enjoyed the location being fairly close to the beach yet private and away from The madness of the tourists. We really enjoyed sitting in the pool or on the back patio and watch all the wildlife, especially the birds coming and going. It was peaceful, relaxing, and everything we needed to get away from the Midwest for spring break. Thank you so much to the host For staying in communication and being so great.

Quick stats about villa rentals in Longboat Key

  • Total rentals

    10 properties

  • Nightly prices starting at

    ₹8,608 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