Winter Park rentals with pool

Pick one of our 791 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.

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.

Our holiday rentals with a pool in Winter Park are in peak demand in July. Expect average temperatures of between 25ºC (77ºF) and 33ºC (91ºF) 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.

To make your Winter Park escape even more unforgettable, book one of Vrbo’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.

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 Vrbo properties that’ll bring an extra dose of fun to your getaway, use our “Private pool” filter.

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.

When you book a holiday rental with a pool with Vrbo, you’ll get more than the standard hotel experience — think a private space with a place to relax by the water. You’re also covered by our Book with Confidence Guarantee. This means we’re here to guarantee a hassle-free stay throughout your entire trip. Plus, when you join our free One Key™ rewards programme, you can earn OneKeyCash™* and spend it on all eligible bookings on Vrbo. Have an unexpected change of plans? Check out our cancellation policies to find out if you are eligible for a full refund. *OneKeyCash disclaimer - OneKeyCash is not redeemable for cash and can only be used on Vrbo.