
Vacation rentals with a pool in Longboat Key
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Top-rated rentals with a pool in Longboat Key
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Popular amenities for Longboat Key rentals with a pool
House rentals with a pool

Sea AMI
I came down with 2 friends for a moms getaway and we had a wonderful time. This sweet little house is perfect and we will definitely be back. Amy is so nice and accommodating. The house was very clean and convenient to everything we wanted to do. Can’t wait to visit again.

Breezy Harbor AMI pool retreat near the Beach
The house was a good size for what we needed! The pool was perfect for the kids. Lots of amenities and space for the kids to play. The outdoor shower was perfect for beach days! The only issue noted was that the cleaning team was there until at 3p, but when she seen we had arrived, she promptly gathered her things and hurried off. We told her to take her time, but she insisted she was done. This is a great place for families and keeps you away from the hustle and bustle of bean point, which I like!

The Shell House
Very beautiful house within easy walking distance to the beach. It was very clean and the check in and out process was easy. My family and I had a great time. The beaches were beautiful and just a short walk from the house. The pool in the back yard was private and perfect for my family. The decor and landscaping was great! I highly recommend staying here. It was perfect!

“Enfuego!”
When I saw this new listing, I hesitated—no reviews and almost too-perfect photos. But the owners quickly answered my questions, were responsive, and I’m so glad we booked. The home is exactly as pictured: spotless, spacious, beautifully designed. The pool area is a dream—plenty of space for our group of 11 (with 4 kids), with waterfall features, a sauna, and even a sandy play area. The movie room and golf simulator were a hit too! Beds are comfy, rooms are big and inviting, Wi-Fi is great. Peaceful, safe neighborhood with tons of privacy. Carter and Naomi were responsive and kind to any concerns we had, and took care of everything. Amazing hosts. This home is a gem.

Pickleball | Heated Pool | Game Room | 4 Min to Be
10 toes down best Air B&B I’ve stayed at. My best friend’s wife is built like a Baluga whale and even she fit in the bed.

Cozy Boho Bungalow Pool/Spa QR Code Walkthrough
Lisa house was and is beautiful you feel right at home. The spa was everything you could ask for it was my 40th birthday and she even had a small cake and balloons for me the was a really nice touch I would recommend anyone looking for a lovely bungalow style home too check Ms.Lisa home out you won’t be disappointed I promise

Sea Shack - 2bd/2ba POOL Home
Words can't describe what this place looks and feels like! It is beautiful, comfortable and accessible. If you are looking for a nice place to stay and enjoy the beach and pool all day, this is the spot. It has all the necessary amenities for the trip. They do have beach chairs, cart, umbrella and beach toys. The arrival and check in was no hassle at all, had no need to contact the host, as everything was well taken care of and it had written detailed instructions for further assistance. The BEACH is extremely beautiful.

Sunset View
We had a blast! The house was everything we expected and Renee was very responsive! Zero complaints! 10/10
Condo rentals with a pool

ON THE BEACH Condo, SPA -1 bd/1 ba. Trolley!
The place was exactly as advertised and I loved how close we were to the beach. It also was pretty private and the beach wasn’t crowded at all. Even though it was great, we probably wouldn’t stay here again because of the shower. My bf has had knee surgery and it was extremely difficult to get into the shower. The side of the tub was very very high, I had to lift my knee to my chest to get into the tub and my bf struggled a lot with his bad knee to do that to get into the shower. I still give the place 5 stars because it was as advertised I just didn’t realize from photos that the bathroom would be difficult for us to manage, and that’s our personal problem not a problem with the Airbnb. Everything else was perfect!

"Jewel At The Shores" Gulf Front, sleeps 5
Excellent location! Everything you need is in the condo. Hope to come back soon!

Chambre 303-Great Beachfront Condo!
Amazing place right on the beach and walking distance to John’s Pass. Everything was just as advertised. Plenty of space and awesome view of the ocean from the balcony (the high Adirondack chairs on the balcony added a good touch and made for easy viewing). Easy beach access. Clean, Furnished nicely, and bed was comfortable. Has everything you’ll need for a fun relaxing vacation. We’ll be back!

Spectacular beach to bay views from this resort.
Our stay was great! The place and location were perfect! We had absolutely everything we needed. Communication was awesome! Thanks so much!! Lara and Thomas Boulder Co

Sea Side Sunsets Unit C
Great place on the beach, walking distance to restaurants. Great vibes and awesome sunsets!!

King Oceanfront Suite! Kitchenette + Balcony!
We enjoyed our stay at the Island Inn. The staff was very friendly and the host was quick to respond to our questions. We liked the view from the room and that we were right on the beach. It was helpful having beach chairs and umbrellas to use so we didn't have to pay for them everyday. I think it was great for 2 adult guests, any more than that and the space might start feeling a little cramped. We used the grills outside to cook as well as the hot plates so we were able to make whatever we wanted. Great view of the sunset from the building, we watched the sun go down from the balcony and beach, very peaceful at night. Overall a great stay!

Beachfront 2/2 Condo on Treasure Island, 305W Ocea
This condo was absolutely beautiful!! So clean and very accommodating!! It had an amazing closet full of beach accessories!! We love places like this because we usually fly down and it’s so helpful to have things to take to the beach without having to buy it. We would hands down recommend this place over and over and we hope to return in the future!

Beach, dolphin/manatee sightings, fishing, sunset
Love, love, love this place! Becky and Tyler were super sweet and very responsive! Check-in was smooth, the place was beautiful and comfortable! This is definitely one of our most favorite vacations that we have been on!
Home rentals with a private pool

New! Beautiful Pool Home Near Siesta Key Beach
It was a short stay for us, but it was exactly what we needed! The house was fully stocked with necessities. Instructions were very clear, not overwhelming. The neighborhood is nice, very close to supermarkets, shopping, restaurants, coffe shops, beach, and local areas whether you want a casual night out or a party night out! Great location😉

Great 6br for All Ages/heated Pool 5 Min to Beach
Place was amazing! I would give 6 stars if I could! Check in and check out were easy and host always responded very quickly to any messages! Will definitely stay here again and recommend it to anyone else! The house is also a lot bigger in person! Thanks again guys, I loved your place!

Sunny Palmetto Oasis: 4br Home with Private Pool
Thank you RedAwning Rental for the stay in Palmetto!

Comfy Home W/ Heated Pool Near Siesta Key Beach
Quick stats about vacation rentals with a pool in Longboat Key
Total rentals
740 properties
Nightly prices starting at
ﺩ.ﺇ147 before taxes and fees
Total number of reviews
6.9K reviews
Family-friendly rentals
600 properties are a good fit for families
Pet-friendly rentals
90 properties allow pets
Rentals with dedicated workspaces
220 properties have a dedicated workspace
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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