
Holiday 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!

Breathtaking Home
We thought our holiday weekend in FL was ruined due to another AirBnb not being what we were expecting and had to abruptly leave but still had two days in FL. Host responded very fast and friendly, answered all my questions. The house was absolutely what we were looking for, stuff for kids and adults and right across from clubhouse and water park.

Luxury Tropical Themed Villa With Lake View!
We had a wonderful stay!

Central Florida Pool Home
We had a wonderful time with adventures such as LegoLand, Disneys Blizzard Beach and Polk County nature center. We also really enjoyed the swimming pool and pool table. My family also all thought the bedding and linen set up was very comfortable. The oversized tub is not something we have at home and that was lovely too. The house is also a couple blocks from a gas station and grocery store. This was the perfect Airbnb choice for this kid friendly vacation. 🌻🌻

Legoland Poolside Paradise
Loved loved loved this Airbnb property! Very kid friendly which sold us. And the pool was a plus. I would definitely stay here again. FYI this property is right around the corner from the theme park which made our trip even better! The host is real time responsive and very helpful. And the place was extremely clean. Thank you Jeff & Marcie!

Cozy Golf-Pool Home in Davenport
We had a great stay host was great very responsive close to everything

Luxury Home 4/3 near Disney, 2 Masters
The home was beautiful, walking up the the home the directions to enter the home was very easy. Opening the door the house was very clean and smelled refreshed. Bedrooms were good size and the private pool was a big hit. My kids enjoyed it and there was alot of pool toys and life jackets for the little ones. The kitchen had alot of cookware. In the playroom were beach toys, strollers and even highchair which helped my babies. Game room had plenty of activities for all ages of kids. Laundry room was very helpful as well. Doug was responding quickly was amazing! They had a book with all information regarding home, rules and people to contact for major needs. My family and I had the best family vacation and we couldn't of done it without Douglas and Kathy. HIGHLY recommend staying in their property. Can't wait to come back and visit.
Apartment rentals with a pool

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

Spacious Apartment Near Disney
Ana was always super responsive, and incredibly flexible and helpful with the apartment's vehicle registration when my flight was delayed past the front office being closed.

15 min from Disney On- site Bar, Restaurant & Gym
The accommodation is as described and even better. With easy access to the highway directly 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 needed 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!!

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

Disney Orlando Bahama Bay Resort Theme Parks &More
We really liked staying here during our Disney vacation. It’s about 20-25 minutes from the parks. Condo was clean, well stocked, and very quiet in the area. Bed was very comfortable. We would definitely stay here again. 2 pools/hot tubs close to unit as well as splash pad.

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 holiday 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
- Orange County Convention Center
- Universal's Volcano Bay
- Old Town Kissimmee
- Discovery Cove
- Disney's Animal Kingdom Theme Park
- Universal Orlando Resort
- SeaWorld Orlando
- Disney Springs
- Raymond James Stadium
- ESPN Wide World of Sports
- Busch Gardens Tampa Bay
- Amalie Arena
- Amway Center
- Epcot
- Magic Kingdom Park
- Reunion West
- Aquatica
- ChampionsGate Golf Club
- Disney's Hollywood Studios
- Kissimmee Lakefront Park
- Walt Disney World Resort Golf
- Island H2O Water Park
- ICON Park