Winter Park Vacation Rentals - HomeToGo base64Hash Winter Park Vacation Rentals - HomeToGo

Winter Park Vacation Rentals

Find 3,615 available offers from 13 partners
Winter Park
Anytime
Guests
Winter Park
Anytime
Guests

Popular Filters to find the Perfect Rental in Winter Park

2 Adults
1 Bedroom
4 Adults
Pets allowed
Pool
House
Internet

Vacation rentals and apartments with air conditioning

Keep cool during your trip to Winter Park and book a vacation rental with air conditioning.

House  Winter Park
Sept 7 - Sept 14
-7%
$355
$330 per night
House ∙ 8 guests ∙ 2 bedrooms

Family Friendly House in Winter Park with Private Patio + Mountain Views

5.0
Outstanding (15 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
Air conditioning
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House  Winter Park
Sept 7 - Sept 14
-7%
$355
$330 per night
House ∙ 6 guests ∙ 2 bedrooms

Family Friendly Nice Vacation Home in Winter Park with Private Patio + Great Views

5.0
Outstanding (10 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
Air conditioning
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House  Winter Park
Sept 7 - Sept 14
-7%
$355
$330 per night
House ∙ 11 guests ∙ 2 bedrooms

Family Friendly House in Winter Park with Sauna, Pool & Grill + Great Views

5.0
Outstanding (48 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
Air conditioning
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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.

House  Winter Park
Sept 8 - Sept 15
$235 per night
House ∙ 8 guests ∙ 2 bedrooms

House in Fraser with Wood-Burning Fireplace + Mountain Views

5.0
Outstanding (41 ratings)
Winter Park, Grand County, Colorado, United States
Kitchen
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House  Winter Park
Sept 14 - Sept 21
-7%
$370
$345 per night
House ∙ 6 guests ∙ 2 bedrooms

Family Friendly Vacation Home in Fraser with Awesome Patio

5.0
Outstanding (12 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
Kitchen
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House  Winter Park
Sept 7 - Sept 14
-7%
$355
$330 per night
House ∙ 8 guests ∙ 2 bedrooms

Family Friendly Vacation Home in Winter Park with Private Balcony + Great Views

4.9
Outstanding (66 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
Kitchen
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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  Winter Park
Sept 3 - Sept 10
-7%
$609
$568 per night
House ∙ 12 guests ∙ 4 bedrooms

Family Friendly House in Winter Park with Grill, Jacuzzi & Sauna

5.0
Outstanding (6 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
Balcony/Patio
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House  Winter Park
Sept 6 - Sept 13
-7%
$369
$345 per night
House ∙ 6 guests ∙ 2 bedrooms

Vacation Home in Winter Park with Grill, Pool & Sauna

5.0
Outstanding (2 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
Balcony/Patio
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House  Winter Park
Sept 7 - Sept 14
-7%
$495
$462 per night
House ∙ 11 guests ∙ 3 bedrooms

House in Winter Park with Sauna, Pool, Hot Tub

5.0
Outstanding (2 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
Balcony/Patio
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Best Vacation Home Deals in Winter Park

Save up to 8%

House Winter Park
Sept 3 - Sept 10
-8%
$1,037
$955 per night
House ∙ 14 guests ∙ 5 bedrooms

Family Friendly Vacation Home in Granby with Jacuzzi, Pool & Patio + Great Views

4.9
Outstanding (29 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
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House Winter Park
Sept 7 - Sept 14
-7%
$880
$814 per night
House ∙ 10 guests ∙ 3 bedrooms

Family Friendly Vacation Home in Winter Park with Pool, Patio & Grill + Enjoy Views

5.0
Outstanding (5 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
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House Winter Park
Sept 3 - Sept 10
-7%
$1,103
$1,021 per night
House ∙ 16 guests ∙ 5 bedrooms

Family Friendly House in Winter Park with Patio, Grill, Hot Tub + Great Views

5.0
Outstanding (51 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
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Find a vacation home that meets your preferences among the 3,615 welcoming vacation rentals from more than 12 vacation rental websites in Winter Park. HomeToGo directly highlights the best offers by comparing all of the available vacation rentals in Winter Park from its various partners.

Recommended Vacation Rentals in Winter Park

Find your perfect vacation rental in Winter Park: from $199 per night

House Winter Park
Sept 21 - Sept 28
-7%
$576
$535 per night
House ∙ 10 guests ∙ 3 bedrooms

Family Friendly House in Winter Park with Sauna, Jacuzzi & Grill + Mountain Views

5.0
Outstanding (36 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
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Condo Winter Park
Sept 14 - Sept 21
-51%
$660
$323 per night
Condo ∙ 8 guests ∙ 3 bedrooms

Lovely Condo in Granby with Private Garage + Amazing Views

5.0
Outstanding (59 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
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House Winter Park
Sept 3 - Sept 10
-7%
$481
$448 per night
House ∙ 10 guests ∙ 3 bedrooms

Family Friendly Vacation Home in Fraser with Private Patio + Mountain Views

5.0
Outstanding (13 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
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House Winter Park
Jun 20 - Jun 27
-7%
$734
$685 per night
House ∙ 12 guests ∙ 4 bedrooms

Family Friendly Vacation Home in Winter Park with Grill, Sauna, Hot Tub + Great Views

4.9
Outstanding (38 ratings)
Winter Park, Grand County, Colorado, United States
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House Winter Park
Sept 3 - Sept 10
-7%
$363
$338 per night
House ∙ 8 guests ∙ 2 bedrooms

House in Fraser with Grill, Sauna & Pool

5.0
Outstanding (2 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
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House Winter Park
Sept 3 - Sept 10
-7%
$1,103
$1,021 per night
House ∙ 12 guests ∙ 4 bedrooms

Family Friendly House in Winter Park with Grill, Sauna & Pool + Breath-Taking Views

5.0
Outstanding (6 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
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Condo Winter Park
Oct 19 - Oct 26
-6%
$212
$198 per night
Condo ∙ 4 guests ∙ 1 bedroom

Lovely Condo in Winter Park with Uncovered Parking + Great Views

4.8
Outstanding (31 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
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House Winter Park
Sept 3 - Sept 10
-7%
$754
$698 per night
House ∙ 10 guests ∙ 4 bedrooms

Family Friendly Vacation Home in Granby with Private Patio + Great Views

4.9
Outstanding (45 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
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Accommodation Winter Park
Apr 26 - May 3
-8%
$1,925
$1,770 per night
Accommodation ∙ 14 guests ∙ 5 bedrooms

Rental in Fraser with Grill & Jacuzzi

5.0
Outstanding (17 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
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Budget-friendly Rentals in Winter Park

Find Fantastic yet Inexpensive Rentals

House Winter Park
Sept 3 - Sept 10
-7%
$678
$631 per night
House ∙ 14 guests ∙ 4 bedrooms

Pleasant House in Winter Park with Pool, Patio & Jacuzzi + Great Views

4.8
Outstanding (52 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
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House Winter Park
Sept 21 - Sept 28
-7%
$499
$466 per night
House ∙ 7 guests ∙ 3 bedrooms

Family Friendly Vacation Home in Winter Park with Jacuzzi, Pool & Grill + Unobstructed Views

5.0
Outstanding (2 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
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House Winter Park
Sept 21 - Sept 28
-7%
$631
$587 per night
House ∙ 12 guests ∙ 4 bedrooms

Vacation Home in Fraser with Sauna, Pool & Patio + Natural Views

5.0
Outstanding (5 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
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Top-Rated Offers and Accommodations in Winter Park

Book Vacation Rentals with the Highest User Rating

House Winter Park
Jun 22 - Jun 29
-7%
$885
$820 per night
House ∙ 10 guests ∙ 4 bedrooms

Family Friendly House in Winter Park with Outdoor Fireplace + Great Views

4.9
Outstanding (26 ratings)
Winter Park, Grand County, Colorado, United States
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House Winter Park
Sept 3 - Sept 10
-7%
$901
$837 per night
House ∙ 12 guests ∙ 5 bedrooms

Nice House in Winter Park with Sauna, Patio & Grill + Amazing Views

5.0
Outstanding (9 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
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House Winter Park
Jun 20 - Jun 27
-7%
$477
$445 per night
House ∙ 10 guests ∙ 3 bedrooms

Family Friendly House in Winter Park with Outdoor Pool

5.0
Outstanding (5 ratings)
Winter Park, Grand County, Colorado, United States
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Popular Rental Amenities in Winter Park

  • Pool (1,499)
  • Pet-friendly (375)
  • WiFi (3,711)
  • Jacuzzi (1,319)
  • Kitchen (3,620)
  • Air conditioning (326)
  • Washing machine (2,692)
  • TV (3,630)
  • Fireplace (3,361)
  • Parking (1,070)
  • Balcony/patio (1,434)
  • Grill (1,907)

Winter Park is a good vacation destination if you want an accommodation with a pool, as 37% of the vacation rentals there have one. Additionally, more Condo have pools than any other accommodation type. They are a great choice if you go in a group of 6, as that is the number of people they can welcome on average. If you would ideally like to be close to the water, more than half of the vacation homes including a pool are situated 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

The graph shows the average rental prices for the next twelve months in Winter Park. $1,498 is the highest price average in the next twelve months. Prices decrease in a week of May (5/3 – 5/10), where average prices are $366.

Rental availability information in Winter Park

Find out the percentage of available rentals in Winter Park with the graph above. In May (5/3 – 5/10), only 13 are available. People tend to travel less to Winter Park during a week in June (6/15 – 6/22) when only 28% of the rentals are booked.

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°. On the other hand, you could have temperatures dropping under -15° in December. The rainiest month is May while the driest month is March.

7-Day Weather Forecast in Winter Park

Wed., 19 Jun.
15°
14°

55%

4 h

24 km/h

Thu., 20 Jun.
22°
13°

50%

2 h

12 km/h

Fri., 21 Jun.
19°
17°

15%

1 h

20 km/h

Sat., 22 Jun.
19°
17°

15%

5 h

13 km/h

Sun., 23 Jun.
21°
18°

10%

3 h

19 km/h

Mon., 24 Jun.
24°
19°

5%

2 h

12 km/h

Tue., 25 Jun.
24°
21°

0%

1 h

15 km/h

Information about vacation rentals in Winter Park

🏡 Vacation rentals available 3,615 rentals
🌙 Nightly prices starting at $199
⭐ Popular amenities Pool, Pets allowed and Internet
🐾 Pet friendly homes 371 homes
🏊 Vacation rentals with pools 1,344 homes
4 reviews
Winter Park vacation rentals have an average rating of 4.5/5 on 4 reviews left by travelers.

Frequently Asked Questions

What is the typical availability of vacation rentals in Winter Park?

At the moment, there are 3,615 vacation homes from 12 different providers in Winter Park.

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

When looking to book a vacation home in Winter Park, the most requested amenities include Pool, Pets allowed, and Internet.

Are there pet-friendly vacation rentals in Winter Park?

Yes, there are 371 pet-friendly vacation rentals in Winter Park, with an average nightly price of $699.

What's the best month to book a vacation rental in Winter Park?

The warmest time of year in Winter Park is July and June, with the nightly price of a vacation home starting at $199.

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