Book Holiday Homes in Winter Park
More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)
We keep it easy with the option to pay now or later on select accommodation
Book up 'til the last second - millions of rooms to crash tonight^
Featured Holiday Homes in Winter Park

Luxe Downtown Winter Park Private Hot Tub 4 BR

Large 7 Bedroom Home, Mountain Setting, 3 family rooms, Hot Tub.

Large Beautiful Townhome, Private Hot Tub, Near Shuttle Route, In Town, WIFI

Base Camp 490 Private Hot Tub

Ranch Creek Lodge | Pet Welcome! | Private Hot Tub | Near Ski Trails

Beautiful 3 Bedroom Townhome In Downtown Winter Park With Private Hot Tub

Welcoming Modern Ski & Adventure Retreat: Free Ski Resort Shuttle right outside!

Luxury Villa 558 I Great Views I Hot Tub I Best Price I FREE Adventures Daily

Mountain Views | Walk to Downtown & Activities
Winter Park Holiday Houses
Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Winter Park vacation homes are the perfect way for you to wing it.
Holiday houses in Winter Park let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Winter Park in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Winter Park adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Winter Park with your name on it.
No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Winter Park vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.
Winter Park Holiday Homes essential information
Accommodation | 798 Holiday Homes |
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Lowest Price | AU$244 |
Highest Price | AU$335 |
Popular accommodation | Luxe Downtown Winter Park Private Hot Tub 4 BR, Large 7 Bedroom Home, Mountain Setting, 3 family rooms, Hot Tub., Large Beautiful Townhome, Private Hot Tub, Near Shuttle Route, In Town, WIFI, Base Camp 490 Private Hot Tub, Ranch Creek Lodge | Pet Welcome! | Private Hot Tub | Near Ski Trails, Beautiful 3 Bedroom Townhome In Downtown Winter Park With Private Hot Tub, Welcoming Modern Ski & Adventure Retreat: Free Ski Resort Shuttle right outside!, Luxury Villa 558 I Great Views I Hot Tub I Best Price I FREE Adventures Daily, Mountain Views | Walk to Downtown & Activities |
Holiday Homes in Winter Park
Top Locations for Holiday Homes in Winter Park
More accommodations in Winter Park
Top trending hotels in Winter Park

Winter Park Mountain Lodge

Gravity Haus Winter Park

The Vintage Hotel

Best Western Alpenglo Lodge
More ways to explore Winter Park
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.