
Holiday rentals with a pool in Longboat Key
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Longboat Key
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Longboat Key rentals with a pool
House rentals with a pool

Pool Oasis | Karaoke | 5G | Theater 135" | Grill
Everything was just like the listing stated. Easy access to everything and plenty to do in the house itself. Its funny but they have notes posted around the house with different instructions or just to let you what light switches you are using. Only problem I had, I couldnt beat PAC MAN!!!!!! WOULD definitely recommend!!

Oasis in Largo. Beautiful pool house, hot tub.
We loved staying at Nga’s place. Sophia who we had to contact with any issues was amazing. We ran into a few problems in the beginning but she was quick to respond and take care of it. The pool was very nice. The canal really behind the house was my husband’s favorite place to relax. A lot of wildlife which he really enjoyed. The neighborhood was quiet and neighbors were very friendly. I loved the screen in porch with a tv. We definitely would stay again if we came back in this area. I can’t say enough about how great Sophia was. You can’t go wrong renting this place.

Lovely pool house 5 minutes from the beach
Had a lovely stay here. Communication with Carmen was fantastic. Decorating in home was tasteful and lovely and we felt right at home.

Dream Villa
Lovely accommodations. Pool was fantastic. Quiet surroundings. Screened in patio and very spacious. We lucked out with beautiful weather.

Tranquil Home. 2 minutes to Indian Rock Beach...
Gisele's place was clean and just like the pictures showed. The pool area was nice with a large Weber grill and lots of chairs . There were plenty of pool rafts in the garage for our use. Grocery stores, liquor stores, and restaurants all within a short drive and some within walking distance. The neighborhood was friendly and quiet and had a Catholic church within a 2 minute walk. We would definitely consider staying again!

Poolside Bliss in Clearwater! Heated-pool/Spa
This was a great place for me and my family. She was very kind ! Definitely would stay here again …..

Spacious House w/ Pool & Hot Tub near Tampa
Enjoyed our stay, we used the pool and hot tub. It worked out great. Plenty of space to hang out and enjoy yourself when you’re not out doing. All the dishes and pans were easily found to cook at the house, that was excellent for us

Beautiful, Spacious Heated Pool Home
We booked with Alice last minute after our previous rental didn’t work out and we are so glad because this home was perfect! Immaculate, great kitchen, pool was great, master shower was amazing! Lots of fluffy beach towels, nice assortment of beach toys and floats for the pool, fold up bag chairs, cooler, large washer and dryer… it had everything our small family needed and more. We will be back!
Condo rentals with a pool

Lovely Condo, Heated Pools, AMI, IMG, Top beaches
Perfect service, very friendly, comfortable and well-located area

POOL SIDE right on the BEACH 2 bdrm condo
This condo was perfect for our family vacation! We had everything we could have needed and our host made everything so easy.

*Waterfront *2 Bedroom Condo *Amazing Sunsets*Pool
Our family had a wonderful time at this condo! We enjoyed waking to see the ocean every day and also had enough space to relax on our vacation. Helena provides a beach bag with towels and sand toys that were a very nice touch for our beach day. The staff at the bar/restaurant were great and we also felt safe with the 24 hour security guards on duty. This place really made our trip extra special!

Tiki Themed Waterfront Condo on Tampa Bay
Chris was very helpful and proactive through messages and short videos. Made everything easy. Would definitely stay again.

Lovely 2 bedrooms condo with pool in Boca Ciega
Matt was the best at explaining everything and. Was so quick. To respond and answer and questions I had as well as give me great info around the area. Would rent from him again for sure and recommend him to anyone looking for a great place and helpful with any questions you might have.

SUNNY DELIGHT! HEATED POOL 2 miles to the beach🐶
Sandra's Place was EVERYTHING thats in the posting. She has everything there for you in case u missed something while packing. The place feels like its urs, furnished well, felt like home. Thanks Sandra

Peaceful retreat, pool, hot tub, near Siesta Key!
Suzanne was very responsive, the residence was clean, spacious and well equipped. Will definitely stay again.

POOL VIEW IN A MODERN CONDO - Feel at Home
The condo was great. Impeccably clean and provided everything you might need during your stay. It was excellent value for the rate. It was also a very short and simple drive to get to Clearwater beach. I would definitely go back.
Quick stats about holiday rentals with a pool in Longboat Key
Total rentals
740 properties
Nightly prices starting at
$63 AUD 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
Destinations to explore
- St Petersburg Holiday rentals
- Tampa Bay Holiday rentals
- Seminole Holiday rentals
- Tampa Holiday rentals
- Central Florida Holiday rentals
- Four Corners Holiday rentals
- Kissimmee Holiday rentals
- Orlando Holiday rentals
- Saint Johns River Holiday rentals
- Fort Lauderdale Holiday rentals
- Gold Coast Holiday rentals
- Miami Holiday rentals
- House rentals Longboat Key
- Rentals with a kayak Longboat Key
- Villa rentals Longboat Key
- Rentals with a hot tub Longboat Key
- Fitness-friendly rentals Longboat Key
- Beach condo rentals Longboat Key
- Rentals with outdoor seating Longboat Key
- Cottage rentals Longboat Key
- Rentals with a fire pit Longboat Key
- Family-friendly rentals Longboat Key
- Beachfront rentals Longboat Key
- Beach house rentals Longboat Key
- Rentals with a patio Longboat Key
- Condo rentals Longboat Key
- Waterfront rentals Longboat Key
- Pet-friendly rentals Longboat Key
- Kid-friendly rentals Longboat Key
- Rentals with a fireplace Longboat Key
- Rentals with a washing machine and dryer Longboat Key
- Apartment rentals Longboat Key
- Rentals with beach access Longboat Key
- Townhouse rentals Longboat Key
- Rentals with lake access Longboat Key
- Rentals with an EV charger Longboat Key
- Rentals with pools Manatee County
- Rentals with pools Florida
- Rentals with pools United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Crescent Beach
- John's Pass
- Cortez Beach
- Bean Point Beach
- Lido Key Beach
- Busch Gardens Tampa Bay
- Amalie Arena
- Raymond James Stadium
- North Beach
- Clearwater Beach
- Vinoy Park
- Coquina Beach
- Tampa Theatre
- Curtis Hixon Waterfront Park
- Fort De Soto Park
- Manasota Key Beach
- Streamsong Resort
- ZooTampa at Lowry Park
- Myakka River State Park
- Tropicana Field
- Van Wezel Performing Arts Hall
- Clearwater Marine Aquarium
- Lakewood National Golf Club
- Splash Harbour Water Park