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

Winter Park Vacation Rentals

Find 5,203 available offers from 14 partners
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Recommended Vacation Rentals in Winter Park

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

House Winter Park
-7%
May 10 - May 17
House ∙ 12 guests ∙ 5 bedrooms

219 m² House

Winter Park, Grand County, Colorado, United States
$593$552
per night
Outstanding(87 ratings)
$593$552
per night
View deal
Apartment Winter Park
-55%
Nov 16 - Nov 23
Apartment ∙ 6 guests ∙ 2 bedrooms

85 m² Apartment

Winter Park, Grand County, Colorado, United States
$569$258
per night
$569$258
per night
View deal
Apartment Winter Park
-71%
Nov 16 - Nov 23
Apartment ∙ 6 guests ∙ 2 bedrooms

88 m² Apartment

Winter Park, Grand County, Colorado, United States
$716$208
per night
Outstanding(3 ratings)
$716$208
per night
View deal
Condo Winter Park
-78%
Nov 16 - Nov 23
Condo ∙ 5 guests ∙ 2 bedrooms

123 m² Condo

Winter Park, Grand County, Colorado, United States
$1,372$305
per night
$1,372$305
per night
View deal
Maisonette Winter Park
-53%
Nov 9 - Nov 16
Maisonette ∙ 12 guests ∙ 4 bedrooms

186 m² Maisonette

Winter Park, Grand County, Colorado, United States
$1,002$470
per night
$1,002$470
per night
View deal
House Winter Park
-8%
May 10 - May 17
House ∙ 16 guests ∙ 6 bedrooms

297 m² House

Winter Park, Grand County, Colorado, United States
$1,081$995
per night
Outstanding(163 ratings)
$1,081$995
per night
View deal
House Winter Park
-33%
Nov 30 - Dec 7
Free cancellation
House ∙ 12 guests ∙ 4 bedrooms

327 m² House

Winter Park, Grand County, Colorado, United States
$1,438$970
per night
Outstanding(19 ratings)
$1,438$970
per night
View deal
Apartment Winter Park
-60%
Nov 16 - Nov 23
Apartment ∙ 8 guests ∙ 3 bedrooms

130 m² Apartment

Winter Park, Grand County, Colorado, United States
$896$362
per night
Outstanding(4 ratings)
$896$362
per night
View deal
Condo Winter Park
-69%
Nov 9 - Nov 16
Condo ∙ 6 guests ∙ 2 bedrooms

Condo

Winter Park, Grand County, Colorado, United States
$932$288
per night
$932$288
per night
View deal
Condo Winter Park
-67%
Apr 12 - Apr 19
Condo ∙ 8 guests ∙ 3 bedrooms

112 m² Condo

Winter Park, Grand County, Colorado, United States
$817$269
per night
$817$269
per night
View deal
House Winter Park
-33%
Apr 28 - May 5
Free cancellation
House ∙ 14 guests ∙ 3 bedrooms

229 m² House

Winter Park, Grand County, Colorado, United States
$1,056$703
per night
Outstanding(3 ratings)
$1,056$703
per night
View deal
Apartment Winter Park
-63%
Nov 16 - Nov 23
Apartment ∙ 8 guests ∙ 2 bedrooms

111 m² Apartment

Winter Park, Grand County, Colorado, United States
$789$289
per night
Outstanding(34 ratings)
$789$289
per night
View deal
Apartment Winter Park
-62%
Nov 30 - Dec 7
Apartment ∙ 8 guests ∙ 2 bedrooms

92 m² Apartment

Winter Park, Grand County, Colorado, United States
$558$211
per night
Outstanding(36 ratings)
$558$211
per night
View deal
House Winter Park
-70%
Nov 9 - Nov 16
House ∙ 10 guests ∙ 4 bedrooms

178 m² House

Winter Park, Grand County, Colorado, United States
$2,373$719
per night
Outstanding(32 ratings)
$2,373$719
per night
View deal
Apartment Winter Park
-71%
Nov 10 - Nov 17
Apartment ∙ 6 guests ∙ 3 bedrooms

139 m² Apartment

Winter Park, Grand County, Colorado, United States
$789$229
per night
Outstanding(5 ratings)
$789$229
per night
View deal

Vacation rentals and apartments with air conditioning

Condo  Winter Park
May 3 - May 10
-67%
$815
$271 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Winter Park, Grand County, Colorado, United States
Air conditioning
View deal
House  Winter Park
Nov 9 - Nov 16
-52%
$817
$392 per night
House ∙ 11 guests ∙ 2 bedrooms
5.0
Outstanding(74 ratings)
Winter Park, Grand County, Colorado, United States
Air conditioning
View deal
Apartment  Winter Park
Nov 16 - Nov 23
-49%
$602
$307 per night
Apartment ∙ 2 guests ∙ 1 bedroom
4.7
Excellent(38 ratings)
Winter Park, Grand County, Colorado, United States
Air conditioning
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Vacation rentals with a fireplace

Apartment  Winter Park
Nov 16 - Nov 23
-51%
$594
$292 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
5.0
Outstanding(3 ratings)
Winter Park, Grand County, Colorado, United States
Fireplace
View deal
Apartment  Winter Park
Nov 1 - Nov 8
-68%
$848
$273 per night
Apartment ∙ 7 guests ∙ 2 bedrooms
5.0
Outstanding(140 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
Fireplace
View deal
House  Winter Park
Nov 9 - Nov 16
-63%
$1,082
$398 per night
House ∙ 6 guests ∙ 2 bedrooms
4.9
Outstanding(50 ratings)
Winter Park, Grand County, Colorado, United States
Fireplace
View deal
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Apartments with a balcony or patio

House  Winter Park
Nov 9 - Nov 16
-42%
$826
$482 per night
House ∙ 8 guests ∙ 2 bedrooms
5.0
Outstanding(5 ratings)
Winter Park, Grand County, Colorado, United States
Balcony/Patio
View deal
House  Winter Park
Nov 16 - Nov 23
-57%
$1,641
$714 per night
House ∙ 12 guests ∙ 4 bedrooms
5.0
Outstanding(10 ratings)
Winter Park, Grand County, Colorado, United States
Balcony/Patio
View deal
Accommodation  Winter Park
Apr 12 - Apr 19
-23%
$2,573
$1,973 per night
Accommodation ∙ 14 guests ∙ 5 bedrooms
5.0
Outstanding(19 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
Balcony/Patio
View deal
See all offers

Best Vacation Home Deals in Winter Park

Save up to 60%

House Winter Park
Nov 9 - Nov 16
-49%
$2,088
$1,070 per night
House ∙ 12 guests ∙ 5 bedrooms
5.0
Outstanding(15 ratings)
Winter Park, Grand County, Colorado, United States
View deal
House Winter Park
May 10 - May 17
-12%
$1,064
$935 per night
House ∙ 16 guests ∙ 5 bedrooms
5.0
Outstanding(123 ratings)
Winter Park, Grand County, Colorado, United States
View deal
Condo Winter Park
Nov 9 - Nov 16
-60%
$794
$315 per night
Condo ∙ 8 guests ∙ 3 bedrooms
Winter Park, Grand County, Colorado, United States
View deal

Find a vacation home that meets your preferences among the 5,203 welcoming vacation rentals from more than 14 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.

Budget-friendly Rentals in Winter Park

Find Fantastic yet Inexpensive Rentals

House Winter Park
Nov 9 - Nov 16
-30%
$1,165
$815 per night
House ∙ 12 guests ∙ 5 bedrooms
4.9
Outstanding(80 ratings)
Winter Park, Grand County, Colorado, United States
View deal
House Winter Park
Nov 16 - Nov 23
-57%
$1,087
$465 per night
House ∙ 10 guests ∙ 3 bedrooms
5.0
Outstanding(40 ratings)
Winter Park, Grand County, Colorado, United States
View deal
House Winter Park
May 3 - May 10
-65%
$1,145
$400 per night
House ∙ 6 guests ∙ 2 bedrooms
4.9
Outstanding(40 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
View deal

Top-Rated Offers and Accommodations in Winter Park

Book Vacation Rentals with the Highest User Rating

House Winter Park
May 3 - May 10
-39%
$1,298
$793 per night
House ∙ 12 guests ∙ 3 bedrooms
5.0
Outstanding(76 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
View deal
House Winter Park
May 3 - May 10
-56%
$870
$386 per night
House ∙ 7 guests ∙ 2 bedrooms
5.0
Outstanding(15 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
View deal
House Winter Park
Nov 30 - Dec 7
-62%
$994
$373 per night
House ∙ 8 guests ∙ 2 bedrooms
4.7
Excellent(8 ratings)
Winter Park, Grand County, Colorado, United States
View deal

Customer ratings and reviews

How are reviews collected?
Guest
Verified Guest by HomeToGo

Absolutely wonderful. New, convenient, and beautifully appointed with new, clean appliances, and plenty of sunshine. Hot tub and fire pit make for a nice social gathering spot. Very quiet. Loved the Nordic ski and hiking available right outside our door!

Reviewed on 3/7/2024 | Group
House Winter Park
from $421 per night
HomeToGo
House ∙ 10 guests ∙ 3 bedrooms
5.0
Outstanding(5 ratings)
Winter Park, Grand County, Colorado, United States
View deal
from $421 per night
House ∙ 10 guests ∙ 3 bedrooms
5.0
Outstanding(5 ratings)
Winter Park, Grand County, Colorado, United States
HomeToGo
View deal
Guest
Verified Guest by HomeToGo

Difficulties with parking (QR code did not work, after 4 days our bill was close to 400,00 instead 76 dollars). No towels for hot tub. In the shower, no shower gel.

Reviewed on 1/31/2024 | Couple
Condo Winter Park
from $203 per night
HomeToGo
Condo ∙ 4 guests ∙ 1 bedroom
4.5
Excellent(47 ratings)
Winter Park, Grand County, Colorado, United States
View deal
from $203 per night
Condo ∙ 4 guests ∙ 1 bedroom
4.5
Excellent(47 ratings)
Winter Park, Grand County, Colorado, United States
HomeToGo
View deal

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Explore 15 million+ rentals, the world’s biggest selection of vacation homes.

Popular Rental Amenities in Winter Park

  • Pool (1,816)
  • Pet-friendly (789)
  • WiFi (4,882)
  • Jacuzzi (1,989)
  • Kitchen (4,835)
  • Air conditioning (388)
  • Washing machine (2,761)
  • TV (4,695)
  • Fireplace (4,428)
  • Parking (1,379)
  • Balcony/patio (1,335)
  • Grill (1,922)

Winter Park is a good vacation destination if you want an accommodation with a pool, as 35% 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, nearly 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. $1,228 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 $435.

Rental availability information in Winter Park

Find out the percentage of available rentals in Winter Park with the graph above. In October (10/18 – 10/25), only 14 are available. People tend to travel less to Winter Park during a week in December (12/14 – 12/21) when only 44% of the rentals are booked.

Information about vacation rentals in Winter Park

🏡 Vacation rentals available 5,287 rentals
💳 Possible discounts up to 69%
🌙 Nightly prices starting at $195
⭐ Popular amenities Pool, Pets allowed and Internet
🐾 Pet friendly homes 802 homes
🏊 Vacation rentals with pools 1,840 homes
5 reviews
Winter Park vacation rentals have an average rating of 4.4/5 on 5 reviews left by travelers.

Frequently Asked Questions

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

At the moment, there are 5,287 vacation homes from 14 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 802 pet-friendly vacation rentals in Winter Park, with an average nightly price of $814.

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 $195.

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