
Vacation rentals with a pool in Winter Haven
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Winter Haven
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Popular amenities for Winter Haven rentals with a pool
House rentals with a pool

Cozy, Relaxing & Fun Gateway!
I want to express my gratitude to Jovanni. The house was lovely and cozy. It was spotless, and we had a great time enjoying the pool. Overall, we had a wonderful experience and truly appreciated our stay.

15% Off Florida Summer Vacation Rentals
There is so much to be said about this property! Beautiful home! Beautiful view of the lake! Accommodations better than pictured! Full kitchen with every appliance and great quality. The master bedroom bed was as comfortable as our home bed! The bedding was great quality! We will be back to this property!

Lakefront House w/ Private Pool, Beach & Dock
We had a wonderful stay and would love to return! Very clean and comfortable. Lots of amenities and activities, making for a perfect stay! ✨

A beautiful cozy home with heating pool
We had a wonderful stay. The host was very accommodating to anything we needed. He is a great host and we will definitely be returning.

Cozy Lakefront Home w/ Pool -7 mins from Legoland
The house in general is fantastic, the beds are very comfortable everything is good but the front yard and the back yard need a little more love to make the house perfect other than that we really enjoyed our stay and recommend the house to anyone who visits Winter Haven

Stunning 4BR home w/Pool
I was very well pleased with the stay. The pool was nice and warm. The surrounding was peaceful and quiet. I really would love to come back again. Also, the cleanness of the house was excellent.

4/2 New Spacious Pool Home
Everything was great. Home was fully stocked with everything you and your family may need. My babies enjoyed the pool and Lego room. If we’re ever in this area again, I would definitely book with Rachel!

Heated Pool | Luxury Design | Disney | Golf Course
Our family (2 adults and 2 kids under 10 yrs) enjoyed our week long stay. There were a few things that needed attention with this property. I communicated those with Lukasz and he was responsive. I am sure those will be taken care of quickly. Some thing to note is that this property does back up to the golfing fairway. They grounds keepers will be out before dawn mowing and fertilizing before those early tee times. The machines are muffled and you can tell that they try their best to not distribute but you can hear them. It never disturbed our kids but it did wake the adults. If you are a light sleeper or like to sleep in, that may not be great for you. This being said, we LOVED the house, pool, hot tub, outdoor patio and everything that it had with it. The kids enjoyed the themed bedrooms as well. The short drive to Legoland was perfect. We went to a few parks in Haines as well. We would stay here again without question.
Condo rentals with a pool

tranquil resort, near Disney, no extra fee.208
I had a great stay at Jennifer’s place. The home was good and the location was perfect for our Disney trip - it was about a 20 - 30 minute drive depending on traffic and which park we were going to. Jennifer was also very responsive to our needs and provided clear instructions that helped us navigate the entire process. I would absolutely stay at this place again as it was worth the price.

Luxury 3 Bedroom Home at ChampionsGate Golf Resort
Excellent service and quality, the host is very concerned about his guests. 100% recommended

15 min from Disney On- site Bar, Restaurant & Gym
The accommodation is exactly as described and even better. With easy access to the direct highway to Universal and Disney. The check-in instructions were also very clear, making the check-in process easy. It was sparkling when we entered and had everything you need to cook and feel at home. It is spacious and ideal for 5 people Ellis was very responsive to our questions and always answered immediately. We would definitely choose it again to return! Thank you!!

Spacious Apartment Near Disney
They place was cute and close to get restaurant and entertainment host is responsive

3BR/2BA Mediterranean Style Condo Near Disney
Our family had a great stay! Close to Disney and suited our family well. Many restaurants and a Publix super close by. Would definitely stay again when in the area.

Orlando Spacious 2-Suites & Resort-Style Pool
I enjoyed my stay here so much. The apartment was so cute and cozy, super clean and spacious. It is in a gated property so itself safe and overall a great location. If and when I am back in town, I will definitely stay here again.

No BNB fees -Oasis Condo 5 min to Disney
Very beautiful location, calm surroundings and very close to all attractions

Full-Service Gated Resort, Disney, Universal, MCO!
Thank you AJ and Nicole had a wonderful time this weekend definitely recommend
Home rentals with a private pool

Disney's Championsgate: Private Pool & Arcade Fun!
This property was very nice and matched the photos to a T. The house was spotless & very spacious. The renovated design was modern and the themed rooms were perfectly executed. The only downside was the check-in process at the gate, but after a quick phone call, the issue was resolved. I absolutely loved the space. 10/10.

Minniehaha Castle Retreat
This house was ideal for our weekend. Everything we needed was provided, and the extras pillows, towels, and toiletries were a nice touch. The pool water heater was a great addition, making the water perfect for the time of year ($10 a day was worth it) . We enjoyed our stay and would recommend it to others.

Airy, Stylish Home with Pool Heat Included in Davenport
Had a great stay at Phil's place. The home was perfect for mother's day weekend. My daughter loved the pool. The home was clean! 10/10 recommend.

Visit Disney World from a Sunny Home with a Pool
I can’t say enough good things about this Airbnb – it was absolutely incredible from start to finish. The space was spotless, nicely decorated and had every amenity we could have possibly needed (and then some!). It truly felt like a home away from home, with thoughtful touches throughout that made our stay extra special. The host was communicative welcoming and very helpful!

Family Retreat Near Disney with Pool & Hot Tub!
This home is just at pictured. Has everything you’ll need. Grill and propane being available on site were a very nice bonus. Hot tub and heated pool were fantastic after walking all day. Host was amazing and communication was very quick. Highly recommend this place and location

Beautiful Lakeview Retreat Drivable to Theme Parks
This place was perfect for our two families (10 people in total) while we visited Legoland. Kitchen and hangout space was great.

Sleeps 16! Pool + Arcade | Orlando Resort Retreat
Pictures shown is exactly how the place looks. Felt secure in the neighborhood. Plenty of amenities. Pool and hot tub was a plus. Game room was also a plus for the little ones.

Amazing Dream Solterra Villa -Disney/club/pool/spa
They house is exactly like described and had a lot of room. The cleaning could be a bit better, but they apparently had a very short turn-around. Be prepared to have parties going on around you. They do not enforce the noise ordinance at midnight like they should. We were not their to party, so this did have an affect on some of our guests. Overall, it was a pleasant stay. Edward is a super host for a reason. He always returned my emails and texts. When we needed something he was sure to get it to us. He made us feel comfortable about this purchase from the very beginning.
Quick stats about vacation rentals with a pool in Winter Haven
Total rentals
150 properties
Total number of reviews
4.5K reviews
Family-friendly rentals
100 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
90 properties have a dedicated workspace
Wifi availability
150 properties include access to wifi
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- Universal Studios Florida
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