Find Vacation Rentals in Winter Park, Grand County

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Popular Winter Park Vacation Rentals

Find the perfect Winter Park vacation rental

House Winter Park
from $208 per night
8 guests ∙ 5 bedrooms

House

4.7
Excellent(49 ratings)
Winter Park, Grand County, Colorado, United States
Vrbo
Details
House Winter Park
from $338 per night
House ∙ 10 guests ∙ 4 bedrooms

203 m² House

4.6
Excellent(34 ratings)
Winter Park, Grand County, Colorado, United States
Vrbo
Details
House Winter Park
from $630 per night
House ∙ 16 guests ∙ 7 bedrooms

288 m² House

4.9
Outstanding(135 ratings)
Winter Park, Grand County, Colorado, United States
Vrbo
Details
House Winter Park
from $1,035 per night
19 guests ∙ 10 bedrooms

House

4.7
Excellent(54 ratings)
Winter Park, Grand County, Colorado, United States
Vrbo
Details
House Winter Park
from $508 per night
16 guests ∙ 8 bedrooms

House

4.8
Outstanding(94 ratings)
Winter Park, Grand County, Colorado, United States
Vrbo
Details
Condo Winter Park
from $122 per night
Condo ∙ 6 guests ∙ 2 bedrooms

79 m² Condo

5.0
Outstanding(76 ratings)
Winter Park, Grand County, Colorado, United States
Vrbo
Details
House Winter Park
from $270 per night
House ∙ 10 guests ∙ 4 bedrooms

195 m² House

5.0
Outstanding
Winter Park, Grand County, Colorado, United States
Vacasa
Details
House Winter Park
from $343 per night
House ∙ 12 guests ∙ 5 bedrooms

219 m² House

4.9
Outstanding(89 ratings)
Winter Park, Grand County, Colorado, United States
Vrbo
Details
House Winter Park
from $352 per night
12 guests ∙ 4 bedrooms

House

4.9
Outstanding(111 ratings)
Winter Park, Grand County, Colorado, United States
Vrbo
Details
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Vacation rentals with Wi-Fi

House  Winter Park
from $659 per night
House ∙ 12 guests ∙ 5 bedrooms

164 m² House

4.9
Outstanding(59 ratings)
Winter Park, Grand County, Colorado, United States
Internet
Vrbo
Details
House  Winter Park
from $195 per night
8 guests ∙ 3 bedrooms

House

4.8
Outstanding(37 ratings)
Winter Park, Grand County, Colorado, United States
Internet
Vacasa
Details
House  Winter Park
from $446 per night
House ∙ 16 guests ∙ 7 bedrooms

372 m² House

5.0
Outstanding(87 ratings)
Winter Park, Grand County, Colorado, United States
Internet
Vrbo
Details
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Cabins and Homes With Fireplaces

House  Winter Park
from $581 per night
House ∙ 12 guests ∙ 5 bedrooms

325 m² House

Winter Park, Grand County, Colorado, United States
Fireplace
HomeToGo
Details
House  Winter Park
-9%
$246
from $323 per night
House ∙ 8 guests ∙ 3 bedrooms

169 m² House

4.8
Outstanding(19 ratings)
Winter Park, Grand County, Colorado, United States
Fireplace
Vacasa
Details
House  Winter Park
from $429 per night
14 guests ∙ 4 bedrooms

House

4.7
Excellent(50 ratings)
Winter Park, Grand County, Colorado, United States
Fireplace
Vacasa
Details
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Apartments and vacation rentals with a kitchen

House  Winter Park
from $473 per night
House ∙ 12 guests ∙ 5 bedrooms

232 m² House

4.9
Outstanding(29 ratings)
Winter Park, Grand County, Colorado, United States
Kitchen
Vrbo
Details
Apartment  Winter Park
from $234 per night
Apartment ∙ 12 guests ∙ 3 bedrooms

195 m² Apartment

5.0
Outstanding(107 ratings)
Winter Park, Grand County, Colorado, United States
Kitchen
HomeToGo
Details
Apartment  Winter Park
from $428 per night
Apartment ∙ 8 guests ∙ 3 bedrooms

201 m² Apartment

4.9
Outstanding(53 ratings)
Winter Park, Grand County, Colorado, United States
Kitchen
HomeToGo
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 $126 per night.

Is it possible to find vacation rentals in Winter Park?

Tripping.com offers great selection on vacation rentals with 5,246 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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