Winter Park rentals with pool

We found 734 rentals with pool — enter your dates for availability

Find spaces that suit your style

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  • 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?
Book one of our 734 holiday rentals with a pool in Winter Park and get ready for a splashing great time. Elk Court Cabins, Hideaway Village South and Bear Crossing are among the city's most sought-after neighbourhoods.
How much does it cost to stay in a holiday rental with a pool in Winter Park?
A number of factors will determine the price of a holiday rental with a pool in Winter Park, such as property size and when and how long you plan to stay. All you need to do is enter your holiday dates and preferences to find a house where you can have a splashing good time.
When is the best time to book a holiday rental with a pool in Winter Park?
If you want to enjoy Winter Park at one of its busiest times, plan your escape for January. That's when average temperatures range from -14ºC to -3ºC, and when most guests unwind in a holiday rental with a pool here. Of course, there are other great times to visit this corner of Grand County, so do some homework into which month or season is the best fit for your plans.
What holiday rentals with a pool in Winter Park have nice views?
If your idea of the ideal escape involves poolside activities and picturesque vistas, you'll find Winter Park holiday rentals with a pool that provide just that. Stay in one with snowy views and dive into a blissful holiday experience.
Are there holiday rentals with a private pool in Winter Park?
From poolside get-togethers to solo soaks, a holiday rental with a private pool offers ample possibilities for fun and relaxation. If you're travelling to Winter Park, use our "Private pool" filter to find properties that come with this luxurious extra.
What are the top things to do in Winter Park?
You'll always have something fun to do with the crew when you check into a holiday home rental with a pool in Winter Park. Head out and explore leading attractions like Winter Park Ski Resort, Ski Granby Ranch and Trestle Bike Park, then return to recharge and relax poolside.
Why should I book my holiday rental with a pool with Stayz?
No sharing your space, no awkward small talk with strangers. When you book a Stayz holiday rental with a pool, you'll have the entire place to yourself to splish splash around. Need to change or cancel your travel itinerary? Our flexible cancellation policies let you book your rental house with total peace of mind.