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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.
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Popular amenities for Longboat Key rentals with a pool
House rentals with a pool
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Pool Oasis | Karaoke | 5G | Theater 135" | Grill
Very cool place to stay. We loved the theater room and pool table. The host was the nicest and very responsive. Would definitely stay again.
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Coastal Pool Home + Golf + Beaches
Very nice house and pool in a great location for our yearly group golf trip.
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Tranquil Home. 2 minutes to Indian Rock Beach...
This was a great home for our stay! We had a great time and will definitely reach out on our next trip!
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Poolside Bliss in Clearwater! Heated-pool/Spa
The place was beautiful and well-located, making it perfect for our stay. The host was incredibly responsive and kind, addressing our questions and concerns quickly. Highly recommend.
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Beautiful House with Heated pool
Our girls trip weekend was a huge success!! We all had a wonderful stay here and we didn’t have a single complaint. Check in was super easy and went off without a hitch. The house is exactly as pictured, very open and comfortable. We did not have a single issue while staying! Highly recommend staying here, I promise we will be back!
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Beautiful, Spacious Heated Pool Home
Very comfortable stay would definitely stay again.
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Spacious Heated Pool Home Near Siesta Key
The house is a beautiful place, part clean, cozy. And it's centrally located. I just love it
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Villa Endless Summer
Since the house was perfect, there really weren’t any concerns to share with Tu. We just had a few questions prior to our visit and Tu always answered on a timely basis. Everything was nice and clean, right down to the pool and the house was supplied properly. The view was beautiful and peaceful, the sunrise and sundown were exquisite.
Condo rentals with a pool
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Lovely Condo, Heated Pools, AMI, IMG, Top beaches
We enjoyed this place very much. Very clean. Excellent location. The host was very responsive.
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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.
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*Waterfront *2 Bedroom Condo *Amazing Sunsets*Pool
We enjoyed our stay! The property was very clean and comfortable. Helena welcome us and wished us well and safe travels when we departed. We would definitely stay there again.
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Tiki Themed Waterfront Condo on Tampa Bay
We were beyond impressed with this place. it was exactly as described and Chris's videos before check in were amazing production, but so helpful. We almost backed out on a warning of "hurricane damage" dont let it stop you. it's minimal, and while the sundeck would be beautiful, there's so many other places to sit and enjoy the sunset/ views. its private enough you don't feel like you are staying next to a group of hotels, but inclusive enough that you get to enjoy live music and really good on site food. we had the best time. if anyone ever tells us they are heading to Tampa we will recommend this place every single time
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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.
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SUNNY DELIGHT! HEATED POOL 2 miles to the beach🐶
Sandra’s place is lovely! Extremely clean, comfortable, and well stocked kitchen and toiletries. She really has thought of everything. It was helpful having ziploc bags and containers for packing food on the go, spices and pantry essentials, first aid kit for a bandaid that was needed, fans for the bedrooms, etc. I stayed here for a girls weekend and the three of us would all highly recommend it!
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Peaceful retreat, pool, hot tub, near Siesta Key!
Great place to stay! It was a very safe community with nice extras and was pretty close to the beaches. So nice to have the extra beach supplies to go shark tooth hunting at Caspersen Beach. The condo was clean and spacious.
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5 *Waterfront Condo,3 Beds,2 Baths, Pool, HOT-TUB.
David's place was absolutely amazing! We have never stayed in an AirBNB before, but the next one will definitely have big shoes to fill. David has everything you could want and more. The pictures matched exactly what we got. He had beach toys, beach towels, coolers. wagon, beach chairs. umbrella, and many other things. Kitchen had everything you would have at home. The only thing you will need to bring is clothes. Every time I contacted David before our vacation, he responded usually within a few hours. While we were there he answered almost immediately. I can't say enough good things about David's condo and him as an owner. Highly recommend! Watching the dolphins during breakfast was a plus! Thank you for everything David!
Quick stats about holiday rentals with a pool in Longboat Key
Total rentals
720 properties
Nightly prices starting at
$63 AUD before taxes and fees
Total number of reviews
6.5K reviews
Family-friendly rentals
580 properties are a good fit for families
Pet-friendly rentals
80 properties allow pets
Rentals with dedicated workspaces
220 properties have a dedicated workspace
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