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
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Popular amenities for Holiday rentals with a pool
House rentals with a pool
Home in Tampa
4.91 out of 5 average rating, 130 reviewsPool Oasis | Karaoke | 5G | Theater 135" | Grill
This air bnb has provided more than enough. There were a couple of things that were broken but it is to be expected as this seems to be an air bnb meant to entertain. There was plenty of room for the amount of people we had. plenty of entertainment and the customer service was very responsive and they are quick to help in anyway they can. The only critic I had was the cleaner arriving 40mins before check out. The person I spoke with said the cleaner had a confusion of our time being 12pm but arrived 9:20am? I did ask for an extension but was clearly told 10am was the time due to the next booking. So it was confusing that she arrived at 9:20am. We felt rushed for the time we paid for. Overall it we enjoyed the stay.
Home in Tampa
5 out of 5 average rating, 34 reviewsUpscale Tampa Dream Home Pool, Golf, Pool Table
Angels place was just like described, spotless clean, easy to get to, close to main attractions. The only couple things missing in the house were bedside table lamps to make the house a bit more homey and perhaps a few blankets on couches. But these are minor things. Angel was incredibly quick in communicating and responding to our questions. He connected us with local tennis pros who we were able to take several classes with and absolutely loved the experience. Overall this place made for a fantastic stay!!
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
Home in Seminole
4.92 out of 5 average rating, 107 reviews4 bedroom and private pool, near to Clearwater
due to Helene there was no wifi. Maria and her husband purchased a separate wifi device just so we had wifi. very responsive and helpful.
Home in Largo
4.82 out of 5 average rating, 77 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!
Home in Spring Hill
4.91 out of 5 average rating, 32 reviewsUnique Relaxing Pool Home
Wonderful house, nicely decorated,great mattresses and bedding as well as towels. The location was really good many other cities around easy to get to. Nice neighborhood I did not give 5 starts on some because it said they were clothes hangers, they were only five. I truly believe the former guest may have taking them. I have a second home that I let people use and they do that, they take them; crazy. The refrigerator needed a little more cleaning but nothing bad I’m just very picky. The other thing I would have love to find dishes detergent not only for dishwasher, a bottle of some cleaning product like Clorox, I like to clean my toilette daily and last, a toaster. We come to to the area once a year to visit the grandchildren No doubt that we will stay there every year. Felt at home 🩷🩷🩷
Home in Palm Harbor
5 out of 5 average rating, 31 reviewsBeautiful house with pool, fire pit, billiard room
The house is super clean & cute ! Neighborhood was quiet and felt safe. The house is very well equipped, u have everything you need and more. Especially if you have kids ! Lots of games, puzzles, coloring etc. The yard was great and the heated pool perfect to relax in! Tomasz was great with communication and accommodating. Overall great stay! Would rent again. Thank you !!!
Home in Seminole
5 out of 5 average rating, 22 reviewsAffordable luxe pool home near beaches
Sue and Joe were very easy to communicate with and they were very helpful. The house was exactly what we needed.
Condo rentals with a pool
Condo in Tampa
4.93 out of 5 average rating, 75 reviews*Waterfront *2 Bedroom Condo *Amazing Sunsets*Pool
Loved It❣️ VERY Clean, had everything we needed to keep my 4yo happy and Helena provided great recommendations around the area🎉 Whisky Joe's and the pool bar food were both delicious, the staff was very friendly and, THE AMAZING SUNSET....WOW🥰🥰🥰🥰
Condo in Tampa
4.97 out of 5 average rating, 118 reviewsTiki Themed Waterfront Condo on Tampa Bay
I booked this tiki-themed Airbnb an hour before arriving for a spontaneous birthday trip, and it was everything I hoped for and more! The pictures truly don’t do the place justice—it’s even better in person! The attention to detail in the decor created the perfect tropical vibe. The host was incredibly helpful, providing step-by-step videos for everything from checking in to turning off the talking parrot (a fun and unique touch!). Their communication made the entire process seamless and stress-free. This was such a memorable stay, and I’m already looking forward to coming back soon! Highly recommend!
Condo in Clearwater Beach
4.92 out of 5 average rating, 128 reviewsBeachfront Condo with Centerline Sunsets
Great location. Beautiful views. Easy walk to shops and restaurants. Very responsive host - Peter kept us informed throughout hurricane clean-up, which we very much appreciated. The unit is comfortable, but there are a few signs of wear and tear. It's also not as well stocked as some of the other units we've stayed in - be sure to pack shower gel or soap! All in all, though, we really enjoyed our stay!
Condo in Clearwater
4.95 out of 5 average rating, 112 reviewsPOOL VIEW IN A MODERN CONDO - Feel at Home
We were displaced due to hurricane Milton and found this place to stay close to our old place. The owner was very helpful and was able to respond immediately and got us in. The only challenge was needing to complete another paperwork to submit for the condo and printing out the parking number. Other than that, the place was perfect. Clean with several towels, appliances and utensils complete. Just no frying pan but we brought 1. We will definitely recommend the place if we have friends looking to visit the area.
Condo in Madeira Beach
4.81 out of 5 average rating, 124 reviewsLovely Water View Condo, Top Floor, Steps to Beach
Stayed for a few days in December, really great location that’s less than a five minute walk to the beach and to lots of restaurants and shopping at John’s Pass! Great suite with a nice balcony and awesome view as well, would definitely stay here again!
Condo in Clearwater
4.86 out of 5 average rating, 139 reviews2 Bedroom Vacation Condo
We enjoyed our stay very much. The place was beautiful and spacious with the high ceilings being a plus. The location was ideal for a private area experience while being only 10 min away from the amazing clearwater beach. Aphroditi was a great host and the place had everything we needed. We loved being right by a Publix and a couple of restaurants and stores. We are already planing our next stay.
Condo in Clearwater
4.93 out of 5 average rating, 142 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!
Condo in Saint Petersburg
4.86 out of 5 average rating, 441 reviewsWaterfront condo on top floor @ Boca Ciega Resort
Nice place. Good view. Easy check in.
Quick stats about vacation rentals with a pool in Holiday
Total rentals
30 properties
Nightly prices starting at
$30 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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