
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
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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!

SEALAND 3/2 Modern Villa w/ Pool near Siesta
The home was very clean and cute! The beds were very comfy! Bathrooms were cleaned and stocked! We enjoyed making a home made breakfast and enjoyed the warm pool! We appreciated the cooler and umbrella available for the beach. The basketball was a plus for our 10 year old! The kids even had fun with Alexa! Host was very very responsive! We would definitely book to stay here again! It felt like we were staying at a family members house!

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
We had an amazing stay at this house Very comfortable house. Very clean pool. Everything perfect. I highly recommend it

Mermaid Villa Ocean Front!
The mermaid villa was beyond our expectations. It was roomy enough for four adults, two bathrooms lots of stuff in the kitchen and the patio was gorgeous. It’s directly across the street from beach access and very walkable to the downtown area.

Southern Charm Villa with Pool
We loved our stay at the villa! It’s in a quiet, beautiful neighborhood off Bayshore in a great location. Adina was the kindest host and delivered freshly baked treats every morning. Will be back for another refreshing weekend!

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!
Luxury villa rentals

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!

Clearwater Villa Heated Pool, Golf, 4K Projector
This place left me and my 20 family members in awe. ITS BEAUTIFUL AND HUGE! We had 10 adults and 10 kids and the house was packed with activities for all of us. The pool was a big hit with both adults and kids, the garage air hockey and backyard mini golf were always occupied, and the coffee machine ran all day! The house was very easy to keep cold as there are multiple fans and thermostats everywhere. The fans on the porch and balcony were life savers too. The pool came jam packed with toys from the chest outside. The fire pit was definitely a must for the kids smores! Im not going to lie, we were deff loud some nights both indoors and outdoors and it didn’t cause any issues. There was enough bathrooms to keep us all clean throughout our stay and a bonus washer and dryer! Overall the trip was BANGING! We will most definitely one back again for sure! We did do one beach day and wish we did more since we were so close to the beach! Thanks again for the amazing stay!!

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.

Close to Beaches|Pool|Fire Pit|Game Room|King Beds
We really enjoyed our stay and the amenities. The pool was nice and so was the screened in room and game room. The hosts were wonderful and we look forward to staying again some time. Thank you!

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

Cheerful 3-bed villa with heated pool+beach staff
We really enjoyed our stay! The house was very clean, comfortable and had everything we needed. We really appreciated having the beach gear, including a wagon the transport everything. Very convenient! Beautiful beaches within 30 minutes. Wellen Park and Warm Mineral Springs worth checking out! Irina was very responsive. Pool temp was a little cooler than our comfort level and some of the outdoor things are a bit warn (basketball hoop broken, pool floats, etc.). Other than that the place was just perfect! Highly recommend!

NEW Family Haven: Near Honeymoon Island
No details overlooked - a family paradise! Our hosts were very helpful and the entire stay was wonderful - HIGHLY RECOMMENDED!

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!

Luxurious Poolside Retreat in Sarasota
Alex was very professional and promptly addressed any issues we had. By issues I mean, getting us more towels and fixing the pool where it was losing water. Would definitely recommend this place!

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!

Dolphin Cove Waterfront St. Pete Beach w/ Pool
We loved our short but sweet stay at this house! Beautiful property, stunning pool, awesome views. Perfect for a family to relax and unwind and have fun.
Quick stats about villa rentals in Longboat Key
Total rentals
10 properties
Nightly prices starting at
$155 AUD 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
- Cortez Beach
- Lido Key Beach
- Busch Gardens Tampa Bay
- Amalie Arena
- Raymond James Stadium
- Gulfport Beach Recreation Area
- Clearwater Beach
- North Beach
- Coquina Beach
- Vinoy Park
- Manasota Key Beach
- Fort De Soto Park
- Tampa Theatre
- Curtis Hixon Waterfront Park
- Streamsong Resort