Winter Haven rentals with pool

Select from 886 vacation rentals with a pool in Winter Haven that have all the privacy, space and amenities you need for a splashing great time. Browse houses in popular neighborhoods such as Inwood, Cypress Gardens and Jan Phyl Village.

A number of factors will influence the price of a vacation rental with a pool in Winter Haven, such as property size and when and how long you’re traveling. All you need to do is key in your travel dates and any preferences to find a house where you can have some poolside fun.

The weather conditions will help you decide when it’s the ideal time to plan a poolside adventure. Many people visiting Polk County book a Winter Haven vacation rental with a pool in February, when average temperatures range from 55ºF (13ºC) to 73ºF (23ºC).

Stay at a vacation rental with a pool in Winter Haven and you can spend your break switching between taking dips and staring out at terrific vistas. Some of our more popular rental houses in this destination boast views of historic areas.

From making whirlpools with the kids to midnight dips beneath the stars, a vacation rental with a private pool offers plenty of possibilities for fun and relaxation. If you’re traveling to Winter Haven, use our “Private pool” filter to find accommodations that come with this premium perk.

Get your Winter Haven escape off to a terrific start by heading to top attractions like LEGOLAND® Florida, Chain of Lakes Park and Bok Tower Gardens. Stay in a Vrbo vacation home rental with the family and then discover this destination’s wonders together.

Booking your vacation rental with a pool with Vrbo means you get the whole place for your exclusive use — your own private space for poolside fun with no interruptions or distractions from others. Plus, our flexible payment and cancellation policies give you the freedom to amend your plans if you need to. And if you join our One Key™ rewards program, you can earn OneKeyCash™* on eligible bookings on Vrbo, Expedia and Hotels.com. *OneKeyCash disclaimer - OneKeyCash is not redeemable for cash and can only be used on Hotels.com, Expedia and Vrbo.