
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

Pool Oasis | Karaoke | 5G | Theater 135" | Grill
We had a wonderful time. It was a quiet neighborhood. The house had everything we needed. The hosts were great on communication and always responsive. The beds were comfortable. The theater was great! They were great with reminders to put out the trash and responded quickly with any questions we had. I would highly recommend staying with them.

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
Anthony was so helpful, proactive for all the needs of the house, extremely responsive, helpful, and his place is absolutely amazing! 10/10 recommend!!!!!

16 Sandals
We had 13 girls stay at Beverly’s and there was plenty of space. The pool was clean and had lots of chairs around. There’s plenty to walk to but also a quick uber to downtown St. Pete and Tampa. She answered any and all questions, and so quickly! Highly recommend saying here with your girlfriends☺️

Beautiful House with Heated pool
If you are looking for the absolute BEST place in Siesta Key to stay…THIS IS IT! Before the trip even began Gabriel was so responsive and helpful to all of my questions. When we arrived at the sweetest bungalow on the street, I knew we were in for such a treat. We had 9 women that stayed at the home and everyone had plenty of room and was very comfortable. The home was deceivingly big! We also rented the cottage and it is absolutely precious! All of the women absolutely adored this place. We walked to coffee in the mornings and the beach was right at the end of the street! It’s in a perfect location! We LOVED the outdoor pool…the home came with beach chairs and the best beach wagon I’ve ever used. When I say the house has everything…I couldn’t think of anything she didn’t think of. And last and most important thing to me is the cleanliness of the home… this house was pristine! Stop scrolling…this is your place!

Beautiful, Spacious Heated Pool Home
Our family had a great stay. Quiet neighborhood, private, warm pool with flotations. Kitchen was adequately stocked with utensils, pans etc. House was clean. Plenty of bath and beach towels. Washer/dryer. Beach coolers, chairs and umbrellas available. Hope to return.

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
Condo rentals with a pool

Lovely Condo, Heated Pools, AMI, IMG, Top beaches
Host was fast to reply. Place was lovely. Convenient to all the activities we planned (baseball spring training, golf, beach and restaurants). Only issue was bedroom drawer was off track and host was notified and appreciated we let her know and will address. The jacuzzi jets were not working, but I wouldn’t hold that against the host. I would stay her again.

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
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.

Tiki Themed Waterfront Condo on Tampa Bay
Words and pictures cannot explain how awesome the tiki theme is at this place. Floor to ceiling every inch is well thought out and fits the fun theme for a stay in Tampa. Chris was very responsive and informative of the entire experience from check in to check out. I would definitely seek to stay here again if ever in the area!

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!
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.

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
730 properties
Nightly prices starting at
$64 AUD before taxes and fees
Total number of reviews
6.6K 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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- Crescent Beach
- John's Pass
- Cortez Beach
- Bean Point Beach
- Lido Key Beach
- Busch Gardens Tampa Bay
- Amalie Arena
- North Beach
- Raymond James Stadium
- Clearwater Beach
- Vinoy Park
- Coquina Beach
- Curtis Hixon Waterfront Park
- Tampa Theatre
- Fort De Soto Park
- Tropicana Field
- Manasota Key Beach
- ZooTampa at Lowry Park
- Splash Harbour Water Park
- Lakewood National Golf Club
- Streamsong Resort
- River Strand Golf and Country Club
- Sand Key Beach
- Honeymoon Island State Park