
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 villa rentals in Longboat Key
Private villa rentals

Villa Luxe~Heated Saltwater Pool~Near Beaches
My family and I had a wonderful stay. It was just as pictured and just perfect for our family. The pool was a bonus after a full day of sightseeing. The upgraded appliances were also a joy to use. I would highly recommend, and would love to visit again. Thank you again for making us feel welcome 😃

Booking for Summer! Short walk to the beach-Unit A
Great place just seconds from the beach! We arrived late (2 a.m.) from canceled fights and had trouble with the lock code. (User error) Someone answered my call immediately and got us right in. There’s beach supplies such as a wagon, chairs, umbrella and even towels, which were so convenient. I highly reccomend this place! Great stay!

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
We absolutely loved this home! I really appreciated how clean the home was kept. We felt safe in the quiet neighborhood. We went to Tampa a lot during our stay for Busch Gardens and we loved how it was outside of all the craziness of Tampa. We would definitely recommend this home. Our kids loved taking a bath in the master bathroom tub and hanging out in the hammock on the porch! :)

Luxurious Family Villa with pool 29 min the beach
My family and I had a great time . The pool was great and the house was clean and had everything we needed and listed on the description. The AC thermostat was locked but I texted host and he responded almost immediately and adjusted temp to my liking. We felt like at home . We had no issues and I would recommend this place to other people. It is a great place to stay for families specially with kids like ours.

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!
Kat’s place was AMAZING, this was our 3rd year staying at Crescent Arms however our first year with Kat at Villa 7 and in our opinion it has been the nicest by far!! Kat was very helpful from start to finish. The place was spectacular we literally didn’t need or want for anything!! Can’t wait to go back!!!

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!
Luxury villa rentals

Luxurious 4-Bedroom Retreat near Siesta Key
This property was fantastic! Located in a great spot near shopping and restaurants, it made exploring Siesta Keys so convenient. The host was incredibly responsive and attentive, which made our stay even more enjoyable. The home was well-equipped with everything we needed, including beach chairs, beach towels, a large cooler with wheels, and a cart with wheels—perfect for days at the beach! We absolutely loved the patio and pool area; it was the perfect place to relax after a day of exploring. I would highly recommend this property to anyone visiting Siesta Keys and would definitely stay here again on our next trip. Truly a wonderful experience!

Lakeside Villa
Amazing lake house, loved it

(HGR) Heated pool villa. Boat rental available
Vildana is a fabulous host. She allowed us to check in an hour early, and responds quickly to any questions or concerns. We had a great time at her place.

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
Great location! So many restaurants and shops that are walkable. Beach access so easy. Place was very clean and had everything we needed.

5 BR Luxury Beach Villa: Heated Pool & Games Room
Our family of 11 had a great stay. Plenty of space for a large group and nice backyard. location was perfect - close to everything we wanted - the beautiful beaches, shopping, restaurants, Tampa, Clearwater and St. Petersburg.

Paradise with a pool, pier and private beach area
Beautiful house! Lots of room for everyone, sparkling clean! Fantastic location. Perfect for our family gathering.

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

Bean Point Residence Unit B by SeaBreeze Vacation
This place was wonderful. Best part..the pool and the location to the beach. You could easily walk back to the house from the beach if you forgot something. Easy to run out to see the beautiful sunsets. The pool was awesome. We used it a lot. So nice to have all of the provided amenities including beach towels, beach wagon, beach chairs, umbrellas, shampoo, soap, etc. paper towels, laundry pods, dishwasher pods. Could have used a few things like salt and pepper in the kitchen but they were very generous with the amenities. The area is quiet with just a little traffic going by. The place was VERY clean. Only thing to know which didn't bother us is the laundry room is off one of the bedrooms so if doing laundry at night it's pretty loud, and you have to go through that bedroom to get to the pool. Again didn't really bother us but might depending on your situation. could also go ti pool from front. Close to Rod & Reel Pier for great lunch. about 15 min walk to shuttle and Pine Ave.

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.

Sunny Gulf Coast Villa: Direct Beach & Pool Access
Lovely place. Room was clean and spacious. Check-in and check-out were easy as could be. Everyone was friendly and helpful. Beautiful beach. Highly recommend.

Dolphin Cove Waterfront St. Pete Beach w/ Pool
My parents and I and our 3 dogs absolutely loved our stay here. We enjoyed the back yard and pool more than we enjoyed going to the beach! The house was extremely clean, and we loved the huuuuge TV in the living room. The kitchen is pretty bare bones as far as cooking and cleaning items, but that was a minor issue for us. My dad said he wanted to come back to this house at least 20 times haha. We'll be back!

Luxury waterfront in the heart of treasure island
Great location and space

NEW-Cheerful 2-bedroom villa-13 min. to Siesta Key
Agata's villa was perfect and she was very responsive when we had a question. We appreciated the well equipped kitchen, modern appliances, lanai dining table, the reading lights and comfortable furniture in the living room, the bathtub as well as shower in both bathrooms, the Smart TV (there are three TVs), and the beach and children's equipment in the garage. The complex is lovely, peaceful and private -- a good place to take a walk, swim in the pool, play pickleball with an active group, use the billiards table in the clubhouse, join in on occasional activities such as bingo or trivia. The area is close to grocery shopping, The Legacy Trail for biking, Tamiami Trail and convenient for traveling to area beaches. We plan to go back here again and again. Thank you, Agata!

The Palm Island Villa Luxury 4 BDR Waterfront Home
Very responsive to any questions i had
Quick stats about villa rentals in Longboat Key
Total rentals
10 properties
Nightly prices starting at
$129 SGD 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
- 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