Find Vacation Rentals in Winter Park, Grand County

Winter Park
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Popular Winter Park Vacation Rentals

Find the perfect Winter Park vacation rental

Apartment Winter Park
e.g. 10/12 - 10/19 (Wed - Wed)
-63%
$804
$297 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
4.9
"Excellent" (7 ratings)
Winter Park, Grand County, Colorado, United States
Details
Vacasa
Details
Apartment Winter Park
e.g. 5/8 - 5/15 (Sun - Sun)
-65%
$263
$92 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Winter Park, Grand County, Colorado, United States
Details
Vacasa
Details
Apartment Winter Park
e.g. 5/21 - 5/28 (Sat - Sat)
-58%
$252
$107 per night
Apartment ∙ 3 guests ∙ 1 bedroom
Winter Park, Grand County, Colorado, United States
Details
Vacasa
Details
Apartment Winter Park
e.g. 5/29 - 6/5 (Sun - Sun)
-41%
$458
$271 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
3.9
"Good" (5 ratings)
Winter Park, Grand County, Colorado, United States
Details
Vacasa
Details
Apartment Winter Park
e.g. 5/14 - 5/21 (Sat - Sat)
-76%
$440
$108 per night
Apartment ∙ 4 guests ∙ 1 bedroom
4.4
"Very good" (3 ratings)
Winter Park, Grand County, Colorado, United States
Details
Vacasa
Details
Apartment Winter Park
e.g. 5/7 - 5/14 (Sat - Sat)
-76%
$349
$84 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Winter Park, Grand County, Colorado, United States
Details
Vacasa
Details
Apartment Winter Park
e.g. 4/16 - 4/23 (Sat - Sat)
-20%
$205
$165 per night
Apartment ∙ 4 guests ∙ 1 bedroom
5.0
"Excellent" (1 rating)
Winter Park, Grand County, Colorado, United States
Details
Vacasa
Details
Apartment Winter Park
e.g. 5/14 - 5/21 (Sat - Sat)
-70%
$380
$115 per night
Apartment ∙ 4 guests ∙ 1 bedroom
4.8
"Excellent" (4 ratings)
Winter Park, Grand County, Colorado, United States
Details
Vacasa
Details
Apartment Winter Park
e.g. 5/14 - 5/21 (Sat - Sat)
-77%
$397
$92 per night
Apartment ∙ 4 guests ∙ 1 bedroom
4.5
"Outstanding" (6 ratings)
Winter Park, Grand County, Colorado, United States
Details
Vacasa
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Cabins and Homes With Fireplaces

Apartment Fireplace Winter Park
e.g. 4/16 - 4/23 (Sat - Sat)
-76%
$307
$74 per night
Apartment ∙ 2 guests ∙ 1 bedroom
4.6
"Outstanding" (10 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
Fireplace
Details
skyrun
Details
Apartment Fireplace Winter Park
e.g. 9/24 - 10/1 (Sat - Sat)
-83%
$653
$108 per night
Apartment ∙ 2 guests ∙ 1 bedroom
4.6
"Outstanding" (10 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
Fireplace
Details
skyrun
Details
Apartment Fireplace Winter Park
e.g. 4/16 - 4/23 (Sat - Sat)
-78%
$498
$109 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (1 rating)
Winter Park, Grand County, Colorado, United States
Free cancellation
Fireplace
Details
skyrun
Details
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Vacation rentals with Wi-Fi

Apartment Internet Winter Park
e.g. 4/16 - 4/23 (Sat - Sat)
-76%
$307
$74 per night
Apartment ∙ 4 guests ∙ 1 bedroom
3.9
"Good" (12 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
Internet
Details
skyrun
Details
Apartment Internet Winter Park
e.g. 9/10 - 9/17 (Sat - Sat)
-75%
$636
$159 per night
Apartment ∙ 4 guests ∙ 1 bedroom
4.3
"Very good" (8 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
Internet
Details
skyrun
Details
Condo Internet Winter Park
e.g. 10/8 - 10/15 (Sat - Sat)
-48%
$419
$220 per night
Condo ∙ 4 guests ∙ 1 bedroom
Winter Park, Grand County, Colorado, United States
Free cancellation
Internet
Details
HomeToGo
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Apartments and vacation rentals with a kitchen

Condo Kitchen Winter Park
e.g. 10/15 - 10/22 (Sat - Sat)
-39%
$221
$134 per night
Condo ∙ 2 guests ∙ 1 bedroom
4.3
"Very good" (2164 ratings)
Winter Park, Grand County, Colorado, United States
Kitchen
Details
Expedia
Details
Apartment Kitchen Winter Park
e.g. 5/6 - 5/13 (Fri - Fri)
-73%
$492
$132 per night
Apartment ∙ 4 guests ∙ 1 bedroom
4.9
"Excellent" (5 ratings)
Winter Park, Grand County, Colorado, United States
Kitchen
Details
Vacasa
Details
Apartment Kitchen Winter Park
e.g. 5/13 - 5/20 (Fri - Fri)
-72%
$304
$85 per night
Apartment ∙ 4 guests ∙ 1 bedroom
5.0
"Excellent" (2 ratings)
Winter Park, Grand County, Colorado, United States
Kitchen
Details
Vacasa
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 $74 per night.

Is it possible to find vacation rentals in Winter Park?

Tripping.com offers great selection on vacation rentals with 2,539 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

What are the trendiest neighborhoods in Winter Park?

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