Winter Haven villa rentals

Our filters make it a cinch to find a villa rental in Winter Haven that matches your budget. Narrow your search by entering your maximum total or nightly price. Also consider your timing. Prices can vary based on peak seasons or special events or festivals. Off-peak times may offer lower rates.

Consider taking a trip to Winter Haven in February, when the average temperature is between 55ºF (13ºC) and 73ºF (23ºC). This is the most popular time of year for guests to stay in a villa rental in this destination, which is located in Polk County.

If you prefer your trip to come with scenic views of historic areas, we’ve got some villa rentals in Winter Haven that are right up your street. Search for a villa with vistas by using our handy “Highly rated for location” filter under “Property reviews” and see what pops up.

Equipped with an array of amenities like swimming pools, beautiful courtyards and high-tech home entertainment systems, our upmarket villa rentals in Winter Haven offer a high-end travel experience. You can look forward to the very best in plush furnishings, ample space and a setting that guarantees a private and relaxing vacation for you and your guests.

It’s easy to see why many families love Winter Haven, with popular attractions like LEGOLAND® Florida, Chain of Lakes Park and Bok Tower Gardens to explore. Uncover this destination’s wonders together and then return to the comforts of your villa rental.

Whether you’re looking for a spacious villa rental in the mountains, by the sea or elsewhere, we’ve got accommodations in incredible settings. Whatever you pick, one thing remains the same — you’ll always have the entire villa to yourself. And with our loyalty program, One Key™, you can earn OneKeyCash™* on eligible bookings on Vrbo, Expedia and Hotels.com. Toss in our Book with Confidence Guarantee and flexible cancellation policies and you’ve got a trip that’s worry-free from start to finish. *OneKeyCash disclaimer - OneKeyCash is not redeemable for cash and can only be used on Vrbo, Expedia and Hotels.com.