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Winter Park Vacation Rentals

Find 3,349 available offers from 8 partners
Winter Park
Anytime
Guests

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
Cabin
Lodge
House
Distance to center
1 km
2 km
5 km
Rating
4.5+
4+
3.5+

Best Vacation Home Deals in Winter Park

Save up to 77%

Condo Winter Park
Aug 5 - Aug 12
-77%
$900
$203 per night
Condo ∙ 6 guests ∙ 1 bedroom
Elegant Condo in Winter Park with Private Balcony + Woodland Views
Winter Park, Grand County, Colorado, United States
Details
skyrun
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3,349 unique vacation homes from 8 providers can be booked in Winter Park, with prices starting at $111 a night. By directly analyzing these accommodations, HomeToGo highlights the best deals and the most popular vacation homes in Winter Park.

Top-Rated Offers and Accommodations in Winter Park

Book Vacation Rentals with the Highest User Rating

House Winter Park
Apr 6 - Apr 13
$1,179 per night
House ∙ 15 guests ∙ 4 bedrooms
Family Friendly Lovely House in Fraser with Private Patio + Great Views
5.0
"Excellent" (7 ratings)
Winter Park, Grand County, Colorado, United States
Details
Vrbo
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House Winter Park
Aug 19 - Aug 26
-81%
$2,114
$405 per night
House ∙ 10 guests ∙ 3 bedrooms
Family Friendly Vacation Home in Fraser with Private Patio + Mountain Views
5.0
"Excellent" (7 ratings)
Winter Park, Grand County, Colorado, United States
Details
Winter Park Escapes
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House Winter Park
Oct 14 - Oct 21
-31%
$1,263
$875 per night
House ∙ 12 guests ∙ 4 bedrooms
Family Friendly House in Winter Park with Exterior Patio + Epic Views
5.0
"Excellent" (6 ratings)
Winter Park, Grand County, Colorado, United States
Details
Vrbo
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Recommended Vacation Rentals in Winter Park

Find your perfect vacation rental in Winter Park: from $145 per night

Condo Winter Park
Aug 5 - Aug 12
-77%
$896
$202 per night
Condo ∙ 6 guests ∙ 1 bedroom
Elegant Condo in Winter Park with Private Balcony + Woodland Views
Winter Park, Grand County, Colorado, United States
Details
skyrun
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House Winter Park
$267 per night
House ∙ 5 guests ∙ 2 bedrooms
House in Winter Park with Electric Fireplace + Vast Views
5.0
"Excellent" (8 ratings)
Winter Park, Grand County, Colorado, United States
Details
Vrbo
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Condo Winter Park
$194 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Condo in Winter Park with Private Balcony + Picturesque View
5.0
"Excellent" (2 ratings)
Winter Park, Grand County, Colorado, United States
Details
Vrbo
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House Winter Park
$493 per night
House ∙ 14 guests ∙ 4 bedrooms
Family Friendly House in Fraser with Grill, Sauna & Pool + Incredible Views
5.0
"Excellent" (1 rating)
Winter Park, Grand County, Colorado, United States
Details
Vrbo
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Condo Winter Park
$111 per night
Condo ∙ 2 guests ∙ 1 bedroom
Condo in Winter Park with Indoor-Outdoor Pool
4.6
"Outstanding" (132 ratings)
Winter Park, Grand County, Colorado, United States
Details
Vrbo
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House Winter Park
$244 per night
House ∙ 8 guests ∙ 3 bedrooms
House in Winter Park with Grill
4.8
"Excellent" (72 ratings)
Winter Park, Grand County, Colorado, United States
Details
Vrbo
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Condo Winter Park
$171 per night
Condo ∙ 6 guests ∙ 1 bedroom
Condo in Winter Park with Yard
4.9
"Excellent" (135 ratings)
Winter Park, Grand County, Colorado, United States
Details
Vrbo
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Condo Winter Park
$248 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Condo in Winter Park + Location Views
5.0
"Excellent" (37 ratings)
Winter Park, Grand County, Colorado, United States
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Condo Winter Park
$251 per night
Condo ∙ 4 guests ∙ 1 bedroom
Condo in Winter Park with Grill & Pool
4.9
"Excellent" (17 ratings)
Winter Park, Grand County, Colorado, United States
Details
Vrbo
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Budget-friendly Rentals in Winter Park

Find Fantastic yet Inexpensive Rentals

House Winter Park
$438 per night
House ∙ 10 guests ∙ 4 bedrooms
Vacation Home in Fraser with Free Parking + Mountain View
5.0
"Excellent" (15 ratings)
Winter Park, Grand County, Colorado, United States
Details
Vrbo
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Condo Winter Park
$251 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Condo in Winter Park with Large Balcony + Wonderful Views
5.0
"Excellent" (105 ratings)
Winter Park, Grand County, Colorado, United States
Details
Vrbo
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House Winter Park
$236 per night
House ∙ 7 guests ∙ 2 bedrooms
House in Fraser with Sauna, Pool & Grill
4.7
"Outstanding" (68 ratings)
Winter Park, Grand County, Colorado, United States
Details
Vrbo
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Apartments and vacation rentals with a kitchen

Cook up a feast on your next vacation and book a Winter Park rental with full kitchen.

Condo Kitchen Winter Park
$242 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Condo in Fraser + Great Views
5.0
"Excellent" (120 ratings)
Winter Park, Grand County, Colorado, United States
Details
Vrbo
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Condo Kitchen Winter Park
$333 per night
Condo ∙ 8 guests ∙ 2 bedrooms
Wonderful Condo in Winter Park with Indoor Pool + Amazing Views
5.0
"Excellent" (190 ratings)
Winter Park, Grand County, Colorado, United States
Details
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Condo Kitchen Winter Park
$164 per night
Condo ∙ 7 guests ∙ 2 bedrooms
Lovely Condo in Winter Park with Indoor Pool + Excellent Views
4.9
"Excellent" (139 ratings)
Winter Park, Grand County, Colorado, United States
Details
Vrbo
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Vacation rentals with a fireplace

Get warm and cozy on cold winter nights in Winter Park by booking a vacation home with a fireplace.

House Fireplace Winter Park
$480 per night
House ∙ 12 guests ∙ 5 bedrooms
House in Winter Park with Pool, Sauna & Grill + Mountain Views
5.0
"Excellent" (280 ratings)
Winter Park, Grand County, Colorado, United States
Details
Vrbo
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House Fireplace Winter Park
$274 per night
House ∙ 10 guests ∙ 3 bedrooms
Beautiful Vacation Home in Fraser with Grill + Beautiful Views
4.9
"Excellent" (121 ratings)
Winter Park, Grand County, Colorado, United States
Details
Vrbo
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House Fireplace Winter Park
$423 per night
House ∙ 10 guests ∙ 4 bedrooms
Vacation Home in Winter Park with Pool & Grill
5.0
"Excellent" (52 ratings)
Winter Park, Grand County, Colorado, United States
Details
Vrbo
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Apartments with a balcony or patio

Looking for a home with a balcony? Check out these vacation homes in Winter Park with their own private patios and balconies.

House Balcony/Patio Winter Park
$251 per night
House ∙ 7 guests ∙ 2 bedrooms
House in Fraser with Grill
4.9
"Excellent" (67 ratings)
Winter Park, Grand County, Colorado, United States
Details
Vrbo
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Condo Balcony/Patio Winter Park
$392 per night
Condo ∙ 8 guests ∙ 3 bedrooms
Condo in Winter Park with Pool & Grill
5.0
"Excellent" (98 ratings)
Winter Park, Grand County, Colorado, United States
Details
Vrbo
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Condo Balcony/Patio Winter Park
$164 per night
Condo ∙ 7 guests ∙ 2 bedrooms
Rental Condo in Fraser with Pool & Grill + Postcard Views
5.0
"Excellent" (4 ratings)
Winter Park, Grand County, Colorado, United States
Details
Vrbo
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Popular Rental Amenities in Winter Park

  • Pool (1,559)
  • Pet-friendly (324)
  • WiFi (3,580)
  • Jacuzzi (1,096)
  • Kitchen (3,483)
  • Air conditioning (264)
  • Washing machine (2,165)
  • TV (3,355)
  • Fireplace (3,318)
  • Parking (906)
  • Balcony/patio (314)
  • Grill (1,921)

Many users spend more time comparing the vacation rentals providing a pool. Nearly half of the accommodations have one there. Interestingly, our data shows that more condo include a pool than apartment rental. Also, they can host 6 people, on average, while apartment rental with pools can host an average of 6 people. If you would ideally like to be close to the water, many of the accommodations providing a pool are located within 2 kilometres of the waterfront.

Price and Availability Index in Winter Park

Click on any bar to see price and availability information

Vacation Rental Price Information in Winter Park

In the above graph, you will find information on average prices of the vacation homes & apartments in Winter Park. The most expensive prices are in December (12/23 - 12/30). Prices reach an average of $1,288 per night. The week with the lowest average prices is in April (4/27 - 5/4).

Rental availability information in Winter Park

The availability graph shows the percentage of available rentals in Winter Park. Be careful if you plan to go to Winter Park in August, as it comprises the busiest week of the next 12 months (8/31 - 9/7). On the other hand, the week with the most available offers is in December (12/9 - 12/16).

The Weather in Winter Park

max.
Min.
-9°
-14°
18 days 18
max.
Min.
-7°
-14°
20 days 20
max.
Min.
-3°
-10°
11 days 11
max.
Min.
-2°
-9°
20 days 20
max.
Min.

-5°
22 days 22
max.
Min.
11°
13 days 13
max.
Min.
12°
20 days 20
max.
Min.
10°
20 days 20
max.
Min.

14 days 14
max.
Min.

-5°
13 days 13
max.
Min.
-5°
-11°
15 days 15
max.
Min.
-9°
-15°
19 days 19
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Check out the climate diagram for Winter Park. July is the warmest month of the year in Winter Park with temperatures reaching a maximum average of 12°. No heat wave is expected in December, where minimum average temperatures usally hit a -15° low. It may rain 22 days in May while it typically rains only 11 days in March.

7-Day Weather Forecast in Winter Park

Sat., 23 Sep.
12°

15%

11 h

24 km/h

Sun., 24 Sep.
14°
-1°

10%

12 h

17 km/h

Mon., 25 Sep.
18°

10%

12 h

10 km/h

Tue., 26 Sep.
21°

0%

11 h

7 km/h

Wed., 27 Sep.
19°

0%

8 h

14 km/h

Thu., 28 Sep.
21°

10%

11 h

7 km/h

Fri., 29 Sep.
21°

0%

8 h

8 km/h

Information about vacation rentals in Winter Park

🏡 Vacation rentals available 3,349 homes
💳 Possible discounts up to 77%
🌙 Nightly prices starting at $111
⭐ Popular amenities Pool, Pets allowed and Internet
🐾 Pet friendly homes 264 homes
🏊 Vacation rentals with pools 1,374 homes

Frequently Asked Questions

What is the typical price of a vacation home in Winter Park?

The starting price for House rental or Apartment rental in Winter Park is $111 per night.

What is the typical availability of House rental in Winter Park?

We found 3,349 vacation homes in Winter Park available for your next trip.

What are the most popular vacation home amenities in Winter Park?

Many travellers are searching for Pool, Pets allowed, and Internet when booking a vacation home in Winter Park.

How many House rental and Apartment rental can I find in Winter Park?

Winter Park has 3,349 House rental and Apartment rental available to book.

Are there pet-friendly vacation rentals in Winter Park?

Finding a vacation rental in Winter Park that allows dogs is definitely possible, with 264 pet-friendly homes on offfer.

What's the best month to visit Winter Park?

The warmest time of year in Winter Park is July and June, with the nightly price of a vacation home starting at $111.

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