Vacation rentals with a pool in Haines City
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Top-rated rentals with a pool in Haines City
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Popular amenities for Haines City rentals with a pool
House rentals with a pool
Home in Winter Haven
4.99 out of 5 average rating, 113 reviewsCheerful 4 Bed, 3 Bath Home with Screened Pool
Great place to stay.
Home in Davenport
4.91 out of 5 average rating, 124 reviewsThe Shire -Private Pool & Hot Tub, Close to parks!
This home has such a great layout. Monica was a wonderful and attentive host. This location is close to everything Orlando has to offer. The pool and hot tub were lovely. This home looked even better in person. The beds and pillows were so comfortable. We cannot wait to come back.
Home in Davenport
4.83 out of 5 average rating, 12 reviewsSplash & Play ~ Poolside Bliss ~ 15 Mins to Disney
My family and I really enjoyed the place and will definitely book again. The pool was great to help us relax after Disney and Sea world. The kitchen was well equipped and helped save a ton.
Home in Davenport
5 out of 5 average rating, 10 reviewsCasa El Paraiso pool house w| 5 bedrooms.
I have no complaints about my stay in the house, excellent people and friendly hosts, very quiet neighborhood I recommend it 100% . Everything is as seen in the photos and better the house is excellent, everything very clean, without a doubt I would rent it again.
Home in Clermont
4.92 out of 5 average rating, 144 reviewsStylish Villa Private Pool-SPA Near Parks Disney!
Guillermo was an amazing host with a beautiful location. 10/10 would visit again.
Home in Davenport
4.81 out of 5 average rating, 177 reviews4BR-2KingMasters-Private Pool-Spa*-Fully Remodeled
We were very satisfied with our stay. We were here for 1 month in January. Tatyana was always very responsive and considerate. One night the smoke alarms went off for some reason. The fire department was called and they suspected that the system was too old. Tatyana immediately had a handyman come in the next day and replace them all. Anyone’s house may need some minor maintenance from time to time. Tatyana has a regular routine of maintenance that she adheres to strictly. We felt very much at home. The property was clean. The provisions were more than adequate. Thank you Tatyana!
Home in Davenport
4.8 out of 5 average rating, 10 reviewsBeautiful Lake View Pool House *Brand new Hot Tub*
Excellent home, nice neighbourhood easy communication with host. questions quickly answered, great holiday would definitely go back, thank you.
Home in Kissimmee
4.87 out of 5 average rating, 15 reviews2024 New Pet-Friendly Heated Pool Mini Golf Disney
Really nice place. Good safe neighborhood. Close to Disney, restaurants, Walmart. Hosts were very accommodating and helpful. Would definitely stay here again and recommend!
Condo rentals with a pool
Condo in Four Corners
4.87 out of 5 average rating, 139 reviewsLUXURY RESORT & GOLF CONDO MIN CLOSE TO DISNEY
It is what it is, basically perfect to host a family who wants to be in the vicinity of the main theme parks.
Condo in Kissimmee
4.76 out of 5 average rating, 217 reviewsPool View Family Condo Disney Universal Orlando
Host gave us a teapot when we requested for which we were so grateful. And didn’t even hurry up to leave the house when we were late for check out.
Condo in Kissimmee
4.78 out of 5 average rating, 94 reviewsCondo Minutes from Disney - No Hidden Fees
The apartment is very comfortable, it has everything you need for a good stay with the family and is located in a quiet area with easy access to everything. It is close to Disney parks and close to all kinds of shops, supermarkets and restaurants. Gary is very diligent, offers clear instructions, and was on the lookout for us to have no issues on arrival.
Condo in Kissimmee
4.79 out of 5 average rating, 202 reviewsCondo near Disney Orlando 3 Bdr
Great place, super close to Disney and other amenities! Highly recommend!
Condo in Kissimmee
4.92 out of 5 average rating, 122 reviewsDisney Lux Resort - 2BR w/ Pool, Hot Tub & Lanai
Great place! Apt was so cute and felt just like home. Parking was great and very convenient location. Will definitely stay here again.
Condo in Kissimmee
4.85 out of 5 average rating, 126 reviewsLovely 3-BR Condo With Pool 5.7mi from Disney!
Wonderful and comfortable apartment! Plenty of extra blankets and towels during Florida’s winter week! I love the small touches like coffee, salt & pepper, and water bottles already available. 10 minute drive to WDW! Would stay again!
Condo in Kissimmee
4.82 out of 5 average rating, 121 reviewsLovely 3BR 2BA condo, great amenities and location
Jose’s place was extremely comfortable. We spent a couple of days at Disney World and came back exhausted. Everyone rested up so well in the accommodation. Would highly recommend the condo!! Felt totally 5 star. You do need to go through an id process to enter each time. But this was seamless. I respected and appreciated the security it offered. Thank you Jose, when we come back we would definitely stay here again!
Condo in Kissimmee
4.81 out of 5 average rating, 227 reviewsStunning condo close to everything!
Excellent stay. The apartment is just like the photos and description. Best by far, the location, and the service of the host. We felt so comfortable, 15 minutes from all the parks. Doris is very friendly and responds immediately. I would definitely wash it again.
Home rentals with a private pool
Home in Haines City
4.8 out of 5 average rating, 5 reviewsNew Listing! Minniehaha Castle Retreat
Owners were very responsive , flexible and accommodating. The place was clean, easy to get in and out of and the kids loved it. The kids loved the bedrooms and the pool. It was extremely close to our Ironman Florida start as well. Bathrooms clean and bedrooms phenomenal. So much space. Can’t say enough about how great our stay was and the owner was a pleasure.
Home in Davenport
4.96 out of 5 average rating, 108 reviewsAiry, Stylish Home with Pool Heat Included in Davenport
Our family had a fantastic stay at Phil's place. The communication was great from both Sue and Phil. The house has a very warm, lived in feel and we loved that. The rooms were really spacious and comfortable. The beds were really good. Great that TV's are available in all rooms with access to Netflix, Prime etc.. The location was lovely, very quiet and felt extremely safe. Good grocery options nearby and close enough to main feature parks without being too near!! We had the pool heated and it was perfect. The Kids absolutely loved it. It stayed warm even the unusual cold snap.... We felt right at home and loved our stay. Would definitely recommend.
Villa in Kissimmee
4.79 out of 5 average rating, 242 reviewsVisit Disney World from a Sunny Home with a Pool
Home was as described. We visited the week of Christmas and the weather was a bit cool. The home did not heat very well even when the heat was turned on. The beds are a little uncomfortable but nothing major. The home is on a corner lot next to the road in and out the neighborhood, at night it was noisy because of the cars jumping the speed bump on the end of the house where the master bedroom is located. The pool table sticks tips are broken so we could not play pool but that was ok. We provided our own wash clothes but towels were provided. Other than the things listed the home is beautiful and clean. We had plenty of room. I would consider staying again.
Villa in Kissimmee
4.89 out of 5 average rating, 38 reviewsFamily Retreat Near Disney with Pool & Hot Tub!
Perfect place to stay for a family going to the parks. Quick drive to parks, easy to come back to for a mid day break, good pool and hot tub and cool themed rooms. Would absolutely stay again if we come back to Orlando.
Home in Haines City
5 out of 5 average rating, 5 reviewsBeautiful Lakeview Retreat Drivable to Theme Parks
Great view of the lake and plenty of games and toys to keep the whole family entertained.
Townhouse in Kissimmee
4.83 out of 5 average rating, 222 reviewsBeach House with Private Pool and Clubhouse near Disney
Jader’s team was super helpful at every turn! Perfect location for family or friends traveling for Disney
Home in Davenport
4.45 out of 5 average rating, 11 reviewsCharming Davenport Retreat with Private Pool
This was the perfect place to stay for a week at the theme parks with families from out of town. The host is super responsive and friendly. Private fenced back yard and pool with nice lighting were extra special.
Quick stats about vacation rentals with a pool in Haines City
Total rentals
630 properties
Nightly prices starting at
$20 before taxes and fees
Total number of reviews
9.5K reviews
Family-friendly rentals
570 properties are a good fit for families
Pet-friendly rentals
70 properties allow pets
Rentals with dedicated workspaces
350 properties have a dedicated workspace
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