Winter Park rentals with pool

We found 753 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 Park?
Pick one of our 753 holiday rentals with a pool in Winter Park and get ready for a splashing great time. Aloma, Orwin Manor and Rose Isle are among the city's most popular areas.
How much does it cost to stay in a holiday rental with a pool in Winter Park?
If you're hoping to save on your holiday rental with a pool, our filters will help. Once you've done your initial search, fine-tune your results based on your preferences, including property type, price and features and amenities. We've got holiday homes in Winter Park for all types of budgets and needs, so take advantage of our filters to find the ideal stay.
When is the best time to book a holiday rental with a pool in Winter Park?
Our holiday rentals with a pool in Winter Park are in peak demand in July. Expect average temperatures of between 25ºC and 33ºC if you're visiting this part of North Orlando then. If there's limited availability in July, consider your options in the month before or after.
What holiday rentals with a pool in Winter Park have nice views?
To make your Winter Park escape even more unforgettable, book one of Bookabach's holiday rentals with a pool — and a gorgeous view to boot. Once you've completed your initial search, use our filters to refine your results by location and the vistas you'd like to gaze at.
Are there holiday rentals with a private pool in Winter Park?
Morning, noon or night, you can go swimming whenever you please when you book a holiday rental with a private pool in Winter Park. To find Bookabach properties that'll bring an extra dose of fun to your getaway, use our "Private pool" filter.
What are the top things to do in Winter Park?
You'll always have something cool to do with the crew when you stay at a holiday home rental with a pool in Winter Park. Venture out and visit major sights like Universal Studios Florida, Florida Mall and Universal's Islands of Adventure, then come back to kick back and relax poolside.
Why should I book my holiday rental with a pool with Bookabach?
Booking a holiday rental with a pool with Bookabach means you get the whole place for your exclusive use — your own private retreat to have a splashing good time without any distractions or interruptions from other people. Also, our flexible payment and cancellation policies allow you to amend your plans if necessary.