Winter Park houses

We found 1,017 houses — 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 home rentals in Winter Park?
Choose one of our 1,017 holiday home rentals in Winter Park and you'll have the ideal base for your next big adventure. Elk Court Cabins, Hideaway Village South and Bear Crossing are some of the city's most popular areas.
How much does it cost to stay in a holiday rental house in Winter Park?
Discover a range of holiday home rentals in Winter Park, where prices vary to match every preference. From wallet-friendly picks to high-end properties, Bookabach makes it a breeze to compare options and narrow your search to find the perfect stay for your getaway.
When is the best time to rent a holiday house in Winter Park?
Consider taking a trip to Winter Park in January, when average temperatures are between -14ºC and -3ºC. This is the most popular time for guests to stay in a holiday home rental in this destination, which is located in Grand County.
Where can I rent a Winter Park holiday house with great views?
Jump in and book one of our Winter Park houses with snowy views. The only thing better than spending your trip in a Bookabach holiday home rental? Kicking back in a property with incredible scenery right outside your window.
Does Winter Park have any weekend house rentals?
Bookabach has a range of terrific houses that are available for weekend rental. Simply key in your dates of travel and look forward to a whirlwind few days of fun. If you don't find the perfect holiday home rental in Winter Park straight away, just change your dates and search again.
Are there any pet-friendly house rentals in Winter Park?
With 10 pet-friendly holiday home rentals in Winter Park, you can spend your next getaway with your furry companion right by your side. Along with a comfortable bed for everyone, lots of houses also include features like fenced-in yards and free dog treats. See what's available by selecting the "Pets allowed" filter.
What are the top things to do in Winter Park?
Get your Winter Park getaway off to an amazing start by heading to popular attractions like Winter Park Ski Resort, Ski Granby Ranch and Trestle Bike Park. Stay in a Bookabach holiday home rental with the family and then uncover the best of this destination together.
Why should I book my holiday rental house with Bookabach?
When you choose a Bookabach holiday home rental, the only people you have to share your living space with are those you bring with you. It'll just be you, your nearest and dearest and the entire property to yourselves. Our flexible cancellation policies also mean you can book your rental house with confidence if you have to change your plans.