
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
Get the amount of space that is right for you.
Popular amenities for Longboat Key villa rentals
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.

Paradise Villa- Sarasota
We loved the pool and the house was great!

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!!

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

Boho -Minimalist villa
We had such a fantastic experience all around. From the close proximity to the stadium, to the great communication from our host, it was everything we needed for a great stay.

Endless Summer Villa 3BR/2BA Heated Pool & Canal
My family, daughter’s family and I stayed @ Paulina’s beautiful home during spring break and couldn’t have asked for a better place to vacation. Everything described about the home was spot on. We had our baby grandchild stay with us and the home had everything to accommodate. Thanks for hosting our family Paulina!
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!

Calico AMI – Steps to Sand, Family Paradise!
Our family of 8 stayed very comfortably at Calico! It was stocked with everything we needed. The location was awesome…close walk to beach, across the street from grocery, easy to catch the trolly and biking distance to anything! We absolutely loved every minute of our family beach vacation! Thanks Celine for letting us stay at your beautiful Calico home. Hope we can come back sometime!

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.

Island Paradise
Zoie was an amazing host and the place is beautiful and just as shown in the pictures! Great views and everything inside and outside the house is very well maintained. It’s a beautiful place to relax and enjoy with family and friends. We had a great time and will definitely come back again if we are in the area.
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.

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!

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
We stayed at this Airbnb for two nights with a group of 16. The home looked exactly like the photos, and the host had a very fast response time. We really enjoyed our stay. The hot tub was a favorite, and the game room added so much fun to our trip!

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
Quick stats about villa rentals in Longboat Key
Total rentals
10 properties
Nightly prices starting at
$138 CAD 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