
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 villa rentals in Longboat Key
Private villa rentals

IRB Harbor House Semiprivate Waterfront Pool Villa
Will 100% be back! The home was beautiful and felt like we were at our own private resort. Thoughtful touches throughout. To be on the water but walkable to the beach - all around an incredible week. It was private. The host was awesome, great at anticipating our needs and super responsive when needed. Takes great pride in a well maintained and updated home. Home was stocked with all that we needed. Didn’t want to leave! Hard to believe it was better in person than the photos show!

Canal Front 3-Bedroom Grand Villa with Pool
Perfect place for a short vacation or long stay. Host was quick to respond on questions. The pool is a big plus for this property. Will book again if available for future vacations.

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!

SEALAND 3/2 Modern Villa w/ Pool near Siesta
This was one of the BEST air b&b’s I have stayed at in Sarasota so far!! Aside from the beautiful weather Inas home was very clean, and had all the amenities needed!! The pictures look exactly like what her home has to offer. She was very responsive and kind. We asked for the pool heated for the extra daily charge and she did it immediately! Very close and convenient to all grocery stores, gas stations and restaurants. About a 10 minute ride to beautiful siesta key beach. I give 10 Stars !!! Highly recommend!! Thank you Ina for hosting us and we hope to be back soon !!!! For the next guests enjoy!!

V3- 1 BR, waterfront villa, 2 min walk 2 beach
We had a great stay! We would definitely stay again!

Siesta Key Palm Paradise w/ Heated Salt Water Pool
This house was great for our family! Close to multiple beaches. The house was well stocked, the host was very responsive. The pool was great, there is a fire pit as well. The pictures describe this place well! If we stay in Sarasota again we would definitely book here.

Florida Living
Had a great stay at this clean and relaxing property! The pool was great and everything met or exceeded expectations.
Luxury villa rentals

Lakeside Villa
This was not only an incredible house, but Kyle was also an amazing host. He was extremely responsive and genuinely cared about our stay. We can’t stop raving about how lovely this place was—gorgeous views, cozy cabin vibes, peaceful, and private. We’d definitely come back.

6BR Heated Pool Triplex Perfect for Gatherings
Great place with plenty space a loaded kitchen and lots of beds. They do have a $200 hold on a different site than Airbnb you have to send but overall a great place.

Best deal in town!
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.

5BR LUX Pool Villa | w/ Sauna | Near The Beach
this place was so beautiful. we definitely recommend if you were in the area this is where you want to be. thanks again for being a great host.

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

Glamorous 3 Bedroom Villa w/Pool in Sarasota Area
Pavel is an amazing host! House was spotless, extremely clean. The pool is heated and the whole pool area is beautifully lit up at night. Highly recommend!

The Emerald Villa, Eco-Luxury by the Sea
Enjoyed our stay. The house worked well for our family of six adults and one child. Nix was very responsive. The public beach access was an easy walk across the street from the house.

Perfect Location w/ pool -close to beach or DT!
We lucked out when we found Kimberley’s pet friendly home for a quick holiday weekend getaway. The location to Siesta Key was incredible but just far enough away that we could get a peaceful night. The home was well stocked and spacious for our group of 2 adults, 2 kids and 2 dogs and we had a great time going for walks and even doing an Easter egg hunt in the yard. Such a memorable trip with plenty of beach time, private pool time and an incredible nights sleep with the softest sheets ever! The house was really clean and although I was a little nervous with a 1bed/1 bath attached, we rarely saw the guests and when they were home they were respectful and quiet. Don’t think twice about booking this little gem!
Villa rentals with a pool

Newly updated 3-bed, 2-bath w/pool. Beaches close
Kelly's place was beautiful, clean and well maintained. The kitchen was well stocked, there were plenty of towels, blankets, and linens. The pool was clean and well maintained. We enjoyed our stay in this nice and quite neighborhood.

Solar Heated Pool Paradise/5mins 2 beach/Games/BBQ
The place was really cute and comfortable. The only thing , and this is not criticism just a suggestion , a clothes line outside to hang dry your clothes would be super helpful so you don’t have to use the dryer all the time . Apart from that all was great 🥰🥰🥰

Villa Perdomo Family
We loved our stay at Antonio’s! Place was very clean, had lots of space and had everything we needed. We used the fire pit and the pool each day. We were in town for the women’s basketball final four. Took a little longer to get downtown than we hoped but that was due to traffic. I would highly recommend!Antonio was very responsive, let us get in the house early and was quick to respond. If ever traveling to Tampa I would book again.

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!
Even better than the pictures! This place was absolutely fantastic. All of my guests loved the property and the backyard was incredible! We had a great time grilling and swimming in the pool! The pool bath is a super nice feature and it’s beautiful! The house was super clean and had plenty of parking. The street was quiet and the neighborhood felt safe. You could even take a morning walk to Wawa for coffee if you wanted to. It’s also a 3 minute car ride to Target and Publix so it’s super easy to get anything you need. Isabella was very sweet and responsive. 10/10 I would absolutely rebook again.

Waterfront-6 BR-Heated Pool-Game Room-Fire Pit
Bee & Peter’s place is amazing! Such a personal and charming house which guarantees you to have fun. Also communication is fantastic with responses being close to instant. Very pleasant experience

Busch Gardens Deluxe Edition w/heatedpool
House was perfect for me and my family, easily able to locate restaurants, bush gardens 3 minutes away, door dash and uber easily found home with no difficulties. Will stay again

Southern Charm Villa with Pool
Our stay at Adina’s was great! Very clean and spacious bedroom. Walkable to Bayshore and quick drive to Hyde Park. Adina was very responsive and flexible with a late check out to accommodate our later flight. The baked goodies she made were an added bonus!
Quick stats about villa rentals in Longboat Key
Total rentals
10 properties
Nightly prices starting at
£75 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
- Cortez Beach
- Lido Key Beach
- Busch Gardens Tampa Bay
- Amalie Arena
- Raymond James Stadium
- Gulfport Beach Recreation Area
- North Beach
- Clearwater Beach
- Coquina Beach
- Vinoy Park
- Manasota Key Beach
- Fort De Soto Park
- Tampa Theatre
- Curtis Hixon Waterfront Park
- ZooTampa at Lowry Park