Winter Garden rentals with pool

We found 31,096 rentals with pool — enter your dates for availability

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

Are there any holiday rentals with a pool in Winter Garden?
Pick from 31,096 holiday rentals with a pool in Winter Garden that offer all the privacy, amenities and space you need for a splashing good time. Consider houses in well-known areas such as Paradise Heights, Reavills Corner and Metro West.
How much does it cost to stay in a holiday rental with a pool in Winter Garden?
Prices vary depending on length of stay, season and property location, so enter your travel details to find a stay where splashing good times await. Whatever your budget or style, Stayz has holiday rentals with a pool in Winter Garden for all kinds of guests.
When is the best time to book a holiday rental with a pool in Winter Garden?
If you'd love to experience Winter Garden at one of its busiest times, plan your trip for February. That's when temperatures range from around 14ºC to 23ºC, and when the majority of Stayz guests book a holiday rental with a pool here. Of course, there are other excellent times to visit this corner of Orange County, so do some homework into which month or season best suits your plans.
What holiday rentals with a pool in Winter Garden have nice views?
Houses with views of historic areas are among the types of holiday rentals with a pool you can book in Winter Garden. If you're looking for stays that promise a splashing great time as well as outlooks worth writing home about, Stayz can help you find them.
Are there holiday rentals with a private pool in Winter Garden?
In Winter Garden, you won't find any holiday rentals with a private pool, but we do have some fantastic getaways that'll tempt you. From basic amenities like living rooms to desirable perks like hot tubs, our accommodation come with an array of features to cater to every budget and preference. And the best thing? You and whoever you're holidaying with will get the entire place all to yourselves.
What are the top things to do in Winter Garden?
Universal Studios Florida, Magic Kingdom® Park and Orange County Convention Centre are top attractions that'll keep the whole family occupied in Winter Garden. There's nothing like travel to get everyone together, so check out our holiday home rentals in this exciting destination.
Why should I book my holiday rental with a pool with Stayz?
When you book a holiday rental with a pool with us, you'll get more than the basic hotel experience — think a private space with a place to kick back by the water. You're also covered by our Book with Confidence Guarantee. This means we're here to help your stay go right throughout your entire getaway. Have an unexpected change to the itinerary? Check out our cancellation policies to find out if you are eligible for a full refund.