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Vacation rentals with a pool in Holiday
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Holiday
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Holiday rentals with a pool
House rentals with a pool
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Home in Tampa
4.91 out of 5 average rating, 139 reviewsPool Oasis | Karaoke | 5G | Theater 135" | Grill
Such a fun house! We loved the movie room, and pool the most. Very comfy beds, house was free of clutter. Definitely recommend!
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Home in Tampa
4.95 out of 5 average rating, 41 reviewsUpscale Tampa Dream Home Pool, Golf, Pool Table
Great place to stay, we had a wonderful time!
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Home in Spring Hill
4.65 out of 5 average rating, 71 reviewsModern Pool Home Wi Fi Cable, Optional Pool Heat
wow ! beautiful, well maintained home ! the home was clean with lots of natural light. kitchen was well equipped with cooking Utensils. the pool was AMAZING 👏 back yard was full fenced making for lots of Privacy. strongly recommend. the rental agreement was basically the Exact same thing as the airbnb website so no need to be worried. affordable & well wroth it . Melinda was such a pleasure to work with . my family will be returning in sep for another week . plenty of family activities , groceries store and restaurants. located in a quiet and safe neighborhood. lots of towels and cleaning supplies. comfortable beds with lauge master. overall 5 stars.
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Home in Hudson
4.87 out of 5 average rating, 15 reviewsHudson retreat, 3 Bedroom Pool Home!
Did great communications regarding the hurricanes! The house was great
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Home in Seminole
4.92 out of 5 average rating, 108 reviews4 bedroom and private pool, near to Clearwater
Maria was super responsive and answered any questions we had. The house was great and accommodating. The pool was cold as it’s not heated but was perfect to float in on the hot sunny days! Definitely would stay here again!
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Home in Largo
4.81 out of 5 average rating, 78 reviewsTranquil 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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Home in Palm Harbor
5 out of 5 average rating, 32 reviewsBeautiful house with pool, fire pit, billiard room
This home is beautiful, in a quiet neighborhood! The thoughtful owners have really gone the extra mile to include everything to make your stay fun for all ages, with lots of games for younger and older kids. The property inside and out is spotless and super organized to make everything easy for you! The best part is you can walk to local town centers with great restaurants, cafes, parks, bike and walking trails!
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Home in Seminole
5 out of 5 average rating, 23 reviewsAffordable luxe pool home near beaches
Sue and Joe are amazing host. The pictures of the home are beautiful but its even better in person. Both Joe and Sue were very quick to respond to any questions that I had. The home had everything you could need for your vacation. My Family and I will definitely be back to their Airbnb in the future.
Condo rentals with a pool
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Condo in Indian Shores
4.9 out of 5 average rating, 20 reviewsPOOL 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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Condo in Tampa
4.93 out of 5 average rating, 76 reviews*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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Condo in Tampa
4.96 out of 5 average rating, 130 reviewsTiki Themed Waterfront Condo on Tampa Bay
We stayed 1 night before boarding a cruise. Was exactly as described. Very cozy and very convenient to restaurants. Would highly recommend, close to port as well. Thanks for a very easy 1 night stay!
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Condo in St. Petersburg
4.91 out of 5 average rating, 22 reviewsLovely 2 bedrooms condo with pool in Boca Ciega
We had a great stay! The views were gorgeous from our balcony each evening and our host Matt was extremely responsive. He had great recommendations on pet-friendly beaches. Location was perfect to get between beaches and downtown St. Pete. We highly recommend this place, host and stay!
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Condo in Seminole
4.97 out of 5 average rating, 143 reviewsSUNNY 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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Condo in Madeira Beach
4.81 out of 5 average rating, 129 reviewsLovely Water View Condo, Top Floor, Steps to Beach
From start to finish the experience with Kristin’s place was excellent. The location is fantastic, the unit was adorable with everything we needed, and Kristin was a great host. I highly recommend this property and host. Right now.
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Condo in Clearwater
4.93 out of 5 average rating, 143 reviews5 *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!
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Condo in Indian Shores
4.89 out of 5 average rating, 44 reviewsIntracoastal | Indian Shores | Beach across street
My husband and I loved staying here for our honeymoon. Very close to lots of local attractions like Jon’s pass and Indian rocks beach. For the fishing lovers, the location of being right on the intercostal was great for night fishing and there’s some nearby parks that having fishing piers as well. Really enjoyed the pool on site as well
Quick stats about vacation rentals with a pool in Holiday
Total rentals
30 properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
1.1K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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