
Villa holiday 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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Longboat Key villa rentals
Private villa rentals

Villa Luxe~Heated Saltwater Pool~Near Beaches
My group of 9 was well accommodated and had an amazing stay! Highly recommend to any and all.

The Sea House
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.

Casa Del Sol
Laura’s place was beautiful and we had a lovely stay. We unfortunately did not have any pans, but Laura was very responsive and helpful and had brought over something for us to use and then ordered some off Amazon for us as well. The mattress in the master bedroom was a little too firm for us, but it didn’t hinder us or our sleep. Overall, everything was clean and amazing, Laura was very friendly and extremely responsive and we had a great time!

Florida Villa Sunrise - 4 Bedroom Home with Pool
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!

Robinhood Beach Villa near Siesta Key Beach!
Th host Chad was super nice person and very understanding he responded in a timely matter. The place was nice and looked like the pictures did. I would definitely book with Chad again !

Newly Remodeled Luxury Beach Villa on Siesta Key!
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 :)

Siesta Villa
We enjoyed staying at this privet quate property. It is as described and showns on the puctures. The property is located in quiet neighborhood, the landscape is well maintained. I didnt know at first it is a condo and there is other rental conected but we never heard any noice. It was very peaceful. Beautiful grounds. Full kitchen, has everything you need to cook a full meals, spacious rooms. The property has everything you need for vocation. It is close to alot of stores. About 15-20 min to popular beaches. Also there is a swiming pool at the property, very clean and well maintained, though we didnt use it alot. Showers were very clean, and good water pressure. I highly recomend this place ! The owner is friendly and responsive. Few things i would improve: the kitchen pans are stainless steel and it was hard to cook in them. Food would stick and burnt at the bottom. There are plenty of beach chairs but not umbrella unfortunately. Overall wonderful place!

My Little House - 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!
Luxury villa rentals

Solar Heated Pool Paradise/5mins 2 beach/Games/BBQ
I rented Vans place to be close to my Aunt. The home is beautiful and fully equipt. I've never rented an airbnb that felt so much like home, and Vans olace exceeded my expectations. My girls and I were able to relax and spend quality time with my aunt poolside, have some great meals, and conversation, while also having a ton of fun. I will definitively look to rent this home on my next trip to visit.

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!
We had a wonderful stay at Isabella’s home! It was the perfect place for a family getaway. The house is beautiful, clean, and very well maintained. The beds were extremely comfortable, which made for a great night's sleep. The pool area was awesome — a great spot to relax and enjoy the Florida weather. Isabella was a fantastic host, very responsive and welcoming. We would definitely stay here again and highly recommend it to anyone visiting the area!

4 min Walk to Beach, Pool, Hot Tub, 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!

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

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

Calico AMI – Steps to Sand, Family Paradise!
My husband and I, along with our two daughters, son in laws and 17-month-old granddaughter had a wonderful stay at Calico. The house was stocked with everything you could possibly need and was in a great location. We enjoyed the pool, the fun games and were so grateful for the supply and use of all the beach equipment. Celine was a great host, very responsive and quick to answer any questions we had. Thank you Celine for all the helpful tips, the amazing guidebook and sharing your beautiful home with us. It was our first time visiting Anna Maria Island and we can’t wait to come back!
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!

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.

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.

Dolphin Cove Waterfront St. Pete Beach w/ Pool
Great place to stay, will say it was missing the most random stuff like a broom to sweep floors/cleaning supplies. Trash bags and things like that. I left my box of trash bags and a broom there hoping the next guest can catch a break but the home was great neighbors were nice. No problems at all

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
$165 NZD 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
Wi-Fi availability
10 properties include access to Wi-Fi
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- Anna Maria Island
- Siesta Beach
- Anna Maria Public Beach
- Dunedin Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Cortez Beach
- Lido Key Beach
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- North Beach
- Fort De Soto Park
- Manasota Key Beach
- Vinoy Park
- Jannus Live
- Streamsong Resort
- Tampa Theatre
- ZooTampa at Lowry Park