Winter Park mountain rentals

We found 423 mountain rentals — enter your dates for availability

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November 2025

December 2025

Find the best place to stay - Winter Park

Showing deals for: 29 Jan - 1 Feb

Premier Host

Golden Bear Pines by Destination Big Bear: Walk to Snow Summit! Fenced Yard! Pet Friendly! HOT TUB!

Sleeps 9 · 4 bedrooms · 2 bathrooms

for 3 nights, 1 cabin

AU$1,402 per night

includes taxes & fees

Premier Host

Tehama Cottage by Destination Big Bear : Close to Bear Mountain Resort & Zoo! Ping Pong Table!

Sleeps 9 · 3 bedrooms · 2 bathrooms

for 3 nights, 1 cabin

AU$882 per night

includes taxes & fees

BEAUTIFUL Spacious patio - BEAUTIFUL Spacious patio with string lights, a gas fire pit and Natural Gas BBQ!

Premier Host

5-STAR 2500 sqft home! NEW AC, HOT TUB, GAME ROOM, & EV! Close to LAKE/SLOPES

Sleeps 12 · 3 bedrooms · 2 bathrooms

for 3 nights, 1 home

AU$1,616 per night

includes taxes & fees

Premier Host

Bear mountain resort 5bd 3 bath sleeps 2600 sq

Sleeps 12 · 5 bedrooms · 3 bathrooms

for 3 nights, 1 cabin

AU$1,233 per night

includes taxes & fees

Top rated rentals - Winter Park

Premier Host

Cozy Stay

Absolutely lovely home, perfect for the two people. Warm fireplace and comfortable soft bed. Was the perfect get away and would definitely stay again given the chance. I would say the highlight of the stay was watching the vibrant birds and squirrels that came to visit!

Jessica M.

Stayed Jan 2023

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