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Vacation rentals with a pool in Longboat Key

Find and book unique homes with a pool on Airbnb

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Popular amenities for Longboat Key rentals with a pool

House rentals with a pool

Guest favorite
A spacious bedroom features a large bed with striped bedding, complemented by two nightstands with lamps. Sliding glass doors open to a private backyard with a plunge pool. Natural light floods the room, highlighting the warm wooden ceiling and inviting decor.
Home in Holmes Beach
4.96 out of 5 average rating, 181 reviews

Sea AMI

DanielleRating, 5 stars3 weeks ago
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.
Guest favorite
A private heated pool is surrounded by tropical landscaping and palm trees, creating a serene outdoor space. Two lounge chairs are positioned beside the pool, and a small table is visible on the lawn. Bright sunlight casts a warm glow over the vibrant plants.
Home in Holmes Beach
4.95 out of 5 average rating, 103 reviews

Breezy Harbor AMI pool retreat near the Beach

KimberlyRating, 5 stars2 weeks ago
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!
Superhost
A private heated pool is surrounded by tropical palms, featuring a gently curved shape with clear blue water. Two white adirondack chairs are positioned nearby on a paved patio, inviting relaxation in a tranquil outdoor setting.
Home in Anna Maria
5 out of 5 average rating, 6 reviews

The Shell House

CindyRating, 5 stars3 weeks ago
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!
Superhost
Home in Bradenton
4.83 out of 5 average rating, 6 reviews

“Enfuego!”

AlisonRating, 5 stars5 days ago
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.
Guest favorite
A vibrant outdoor space features a heated saltwater pool surrounded by comfortable lounge chairs. Colorful shade sails provide protection from the sun, while an umbrella-shaded dining area accommodates eight. Lush palm trees complete the tropical ambiance, creating a perfect relaxation spot.
Home in Cove
4.99 out of 5 average rating, 99 reviews

Pickleball | Heated Pool | Game Room | 4 Min to Be

DylanRating, 5 stars1 month ago
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.
Top guest favorite
A bright living room features a large, light-colored couch adorned with patterned cushions. A swing chair hangs in the corner, and a coffee table sits in front of the couch. Soft lighting and large windows enhance the cozy atmosphere.
Home in Sarasota
5 out of 5 average rating, 75 reviews

Cozy Boho Bungalow Pool/Spa QR Code Walkthrough

CalvinRating, 5 stars5 days ago
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
Guest favorite
An outdoor area features a crystal-clear pool surrounded by paver stones. A set of six wooden chairs and a table are positioned nearby, complemented by two lounge chairs. The exterior of the vacation home displays a vibrant blue-green facade with large windows reflecting the sunlight.
Home in Anna Maria
5 out of 5 average rating, 7 reviews

Sea Shack - 2bd/2ba POOL Home

KarlaRating, 5 stars3 weeks ago
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.
Top guest favorite
A private pool area is surrounded by lush greenery and palm trees. The curved pool features clear blue water, complemented by lounge chairs and a shaded seating area. A second-story balcony offers scenic views, while a barbecue grill is positioned nearby for outdoor dining.
Home in Bradenton Beach
5 out of 5 average rating, 19 reviews

Sunset View

AngelaRating, 5 stars1 week ago
We had a blast! The house was everything we expected and Renee was very responsive! Zero complaints! 10/10

Condo rentals with a pool

Superhost
A beachside area is shown with several white chaise lounges arranged on the sandy surface, facing the ocean. Gentle waves can be seen lapping at the shore under a clear blue sky, accentuated by wispy clouds and coastal grasses in the foreground.
Condo in Bradenton Beach
4.69 out of 5 average rating, 13 reviews

ON THE BEACH Condo, SPA -1 bd/1 ba. Trolley!

ElizabethRating, 5 stars1 month ago
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!
Guest favorite
A heated swimming pool is bordered by a spacious deck featuring multiple lounge chairs. The vibrant colored building complements the blue sky, while the Gulf is visible in the background, suggesting a scenic setting for relaxation.
Condo in Indian Shores
4.93 out of 5 average rating, 136 reviews

"Jewel At The Shores" Gulf Front, sleeps 5

DerekRating, 5 stars2 weeks ago
Excellent location! Everything you need is in the condo. Hope to come back soon!
Guest favorite
A spacious living area is furnished with a comfortable sofa and two armchairs, all in calming blue hues. Natural light floods the room through sliding glass doors that lead to a private balcony offering views of the beach. A flat-screen TV is positioned across from the seating area.
Condo in Madeira Beach
4.92 out of 5 average rating, 13 reviews

Chambre 303-Great Beachfront Condo!

JosephRating, 5 stars3 weeks ago
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!
Top guest favorite
Condo in Treasure Island
4.99 out of 5 average rating, 188 reviews

Spectacular beach to bay views from this resort.

LaraRating, 5 stars1 week ago
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
Guest favorite
An open living area showcases large sliding glass doors with stunning ocean views. A comfortable seating arrangement features a dark leather couch and coordinating throw pillows. A modern ceiling fan hangs above, while a dining table is set with a centerpiece and blue accents.
Condo in Independence Square
5 out of 5 average rating, 9 reviews

Sea Side Sunsets Unit C

AngelaRating, 5 stars1 month ago
Great place on the beach, walking distance to restaurants. Great vibes and awesome sunsets!!
Superhost
The heated swimming pool features clear blue water surrounded by lounge chairs and palm trees, with beach access visible in the background. The vibrant red walls of the property create a contrasting backdrop against the coastal scenery.
Condo in Treasure Island
4.85 out of 5 average rating, 150 reviews

King Oceanfront Suite! Kitchenette + Balcony!

ChrisRating, 5 stars1 day ago
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!
Guest favorite
Condo in Treasure Island
4.92 out of 5 average rating, 131 reviews

Beachfront 2/2 Condo on Treasure Island, 305W Ocea

AprilRating, 5 stars5 days ago
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!
Top guest favorite
Condo in Treasure Island
4.98 out of 5 average rating, 125 reviews

Beach, dolphin/manatee sightings, fishing, sunset

KaitlynRating, 5 stars2 weeks ago
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!

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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