Find Vacation Rentals in Winter Park, Grand County

We have 3,942 properties to choose from
Winter Park
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Winter Park
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Popular Winter Park Vacation Rentals

Find the perfect Winter Park vacation rental

House Winter Park
$562 per night
House ∙ 12 guests ∙ 4 bedrooms
5.0
Outstanding
Winter Park, Grand County, Colorado, United States
Details
Vacasa
Details
Details
House Winter Park
$142 per night
House ∙ 9 guests ∙ 3 bedrooms
4.5
Excellent (28 ratings)
Winter Park, Grand County, Colorado, United States
Details
Vacasa
Details
Details
House Winter Park
$127 per night
House ∙ 8 guests ∙ 2 bedrooms
5.0
Outstanding (41 ratings)
Winter Park, Grand County, Colorado, United States
Details
Vrbo
Details
Details
Condo Winter Park
$174 per night
Condo ∙ 7 guests ∙ 2 bedrooms
5.0
Outstanding (79 ratings)
Winter Park, Grand County, Colorado, United States
Details
Vrbo
Details
Details
House Winter Park
-7%
$155
$145 per night
House ∙ 10 guests ∙ 3 bedrooms
4.7
Excellent (31 ratings)
Winter Park, Grand County, Colorado, United States
Details
Vacasa
Details
Details
House Winter Park
$287 per night
House ∙ 12 guests ∙ 5 bedrooms
4.9
Outstanding (76 ratings)
Winter Park, Grand County, Colorado, United States
Details
Vrbo
Details
Details
Condo Winter Park
$118 per night
Condo ∙ 6 guests ∙ 2 bedrooms
5.0
Outstanding (69 ratings)
Winter Park, Grand County, Colorado, United States
Details
Vrbo
Details
Details
Condo Winter Park
$119 per night
Condo ∙ 6 guests ∙ 2 bedrooms
5.0
Outstanding (8 ratings)
Winter Park, Grand County, Colorado, United States
Details
Vrbo
Details
Details
Condo Winter Park
$144 per night
Condo ∙ 10 guests ∙ 3 bedrooms
4.7
Excellent (171 ratings)
Winter Park, Grand County, Colorado, United States
Details
Vrbo
Details
Details
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Vacation rentals and apartments with air conditioning

House  Winter Park
$174 per night
House ∙ 6 guests ∙ 2 bedrooms
5.0
Outstanding (10 ratings)
Winter Park, Grand County, Colorado, United States
Air conditioning
Details
HomeToGo
Details
Details
House  Winter Park
$203 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
Outstanding (2 ratings)
Winter Park, Grand County, Colorado, United States
Air conditioning
Details
HomeToGo
Details
Details
House  Winter Park
$174 per night
House ∙ 8 guests ∙ 2 bedrooms
5.0
Outstanding (15 ratings)
Winter Park, Grand County, Colorado, United States
Air conditioning
Details
HomeToGo
Details
Details
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Apartments and vacation rentals with a kitchen

House  Winter Park
$441 per night
House ∙ 10 guests ∙ 4 bedrooms
Winter Park, Grand County, Colorado, United States
Kitchen
Details
HomeToGo
Details
Details
House  Winter Park
$155 per night
House ∙ 9 guests ∙ 3 bedrooms
4.5
Excellent (28 ratings)
Winter Park, Grand County, Colorado, United States
Kitchen
Details
Vrbo
Details
Details
House  Winter Park
$155 per night
House ∙ 10 guests ∙ 3 bedrooms
4.7
Excellent (31 ratings)
Winter Park, Grand County, Colorado, United States
Kitchen
Details
Vrbo
Details
Details
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Vacation Homes With Terraces

House  Winter Park
$306 per night
House ∙ 12 guests ∙ 4 bedrooms
5.0
Outstanding (6 ratings)
Winter Park, Grand County, Colorado, United States
Balcony/Patio
Details
HomeToGo
Details
Details
House  Winter Park
$184 per night
House ∙ 8 guests ∙ 2 bedrooms
5.0
Outstanding (2 ratings)
Winter Park, Grand County, Colorado, United States
Balcony/Patio
Details
HomeToGo
Details
Details
House  Winter Park
$184 per night
House ∙ 6 guests ∙ 2 bedrooms
5.0
Outstanding (2 ratings)
Winter Park, Grand County, Colorado, United States
Balcony/Patio
Details
HomeToGo
Details
Details
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Frequently Asked Questions

How much does it cost to book a vacation rental in Winter Park?

Accommodation in Winter Park cost from $120 per night.

Is it possible to find vacation rentals in Winter Park?

Tripping.com offers great selection on vacation rentals with 3,942 offers currently available in Winter Park.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Vacation Rentals in Winter Park

Looking for the perfect vacation rental for your Winter Park getaway? Tripping.com’s got you covered. Whether you’re seeking a vacation home, cabin rental or cottage, Winter Park offers 3827 affordable vacation home rentals to choose from, with far more amenities, space and comforts than the average hotel room. Select from 3426 properties with high-speed WiFi Internet, 1254 full with jacuzzi and pool, and homes complete with outdoor patio, great for entertaining with guests. Whatever your needs, find the perfect home rental that best matches your accommodation style and budget. For travelers planning for an extended stay, long-term lodging and corporate rentals only cost an average of $11119 a month. Save hundreds with affordable vacation rentals on Tripping.com and, in many cases, book directly online so you’re all set to go. Winter Park has 3827 gorgeous homes with 299 pet-friendly rentals to choose from, perfect for your dog or cat. Check out our vacation rental listings now to get the latest deals, and book the right vacation home rental for you and the whole family. Feel at home wherever you are and experience an unforgettable vacation with Tripping.com. Search properties from 11 vacation rental sites in Winter Park where the top providers in that area are HomeAway, Expedia, and RedAwning. There are 1710 HomeAway rentals, 564 Expedia short term rentals and 516 RedAwning vacation rentals.

Popular Day Trips Near Winter Park

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What are the trendiest neighborhoods in Winter Park?

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