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

Winter Park Vacation Rentals

Find 4,939 available home rentals from 13 partners
Anytime
1 guest
Anytime
1 guest

Top 15 Recommended vacation rentals in Winter Park

Find your perfect vacation rental in Winter Park from just $182 per night!

Apartment Winter Park
-59%
Oct 30 - Nov 6
Free cancellation
Apartment ∙ 6 guests ∙ 2 bedrooms

85 m² Apartment

Winter Park, Grand County, Colorado, United States
$1,152$244
per night
$1,152$244
per night
View deal
Apartment Winter Park
-65%
May 3 - May 10
Free cancellation
Apartment ∙ 4 guests ∙ 1 bedroom

41 m² Apartment

Winter Park, Grand County, Colorado, United States
$845$181
per night
$845$181
per night
View deal
House Winter Park
-60%
Apr 26 - May 3
House ∙ 8 guests ∙ 3 bedrooms

141 m² House

Winter Park, Grand County, Colorado, United States
$1,509$408
per night
$1,509$408
per night
View deal
Condo Winter Park
-69%
Apr 26 - May 3
Condo ∙ 6 guests ∙ 2 bedrooms

Condo

Winter Park, Grand County, Colorado, United States
$1,509$349
per night
$1,509$349
per night
View deal
Apartment Winter Park
-51%
Nov 30 - Dec 7
Apartment ∙ 6 guests ∙ 2 bedrooms

88 m² Apartment

Winter Park, Grand County, Colorado, United States
$1,196$335
per night
Outstanding(3 ratings)
$1,196$335
per night
View deal
Apartment Winter Park
-68%
Nov 1 - Nov 8
Free cancellation
Apartment ∙ 6 guests ∙ 2 bedrooms

88 m² Apartment

Winter Park, Grand County, Colorado, United States
$988$210
per night
Outstanding(3 ratings)
$988$210
per night
View deal
Apartment Winter Park
-63%
Apr 26 - May 3
Free cancellation
Apartment ∙ 8 guests ∙ 3 bedrooms

130 m² Apartment

Winter Park, Grand County, Colorado, United States
$1,627$380
per night
Outstanding(4 ratings)
$1,627$380
per night
View deal
Condo Winter Park
-70%
Apr 26 - May 3
Condo ∙ 6 guests ∙ 2 bedrooms

97 m² Condo

Winter Park, Grand County, Colorado, United States
$1,262$305
per night
$1,262$305
per night
View deal
House Winter Park
-62%
Apr 5 - Apr 12
House ∙ 8 guests ∙ 3 bedrooms

185 m² House

Winter Park, Grand County, Colorado, United States
$1,682$413
per night
$1,682$413
per night
View deal
Apartment Winter Park
-57%
Dec 15 - Dec 22
Apartment ∙ 6 guests ∙ 3 bedrooms

232 m² Apartment

Winter Park, Grand County, Colorado, United States
$2,038$424
per night
$2,038$424
per night
View deal
Chalet Winter Park
-68%
Apr 12 - Apr 19
Chalet ∙ 12 guests ∙ 4 bedrooms

246 m² Chalet

Winter Park, Grand County, Colorado, United States
$3,386$857
per night
$3,386$857
per night
View deal
Apartment Winter Park
-70%
Nov 30 - Dec 7
Apartment ∙ 8 guests ∙ 2 bedrooms

111 m² Apartment

Winter Park, Grand County, Colorado, United States
$1,422$322
per night
Outstanding(34 ratings)
$1,422$322
per night
View deal
Condo Winter Park
-72%
Dec 7 - Dec 14
Condo ∙ 5 guests ∙ 2 bedrooms

123 m² Condo

Winter Park, Grand County, Colorado, United States
$2,741$525
per night
$2,741$525
per night
View deal
Condo Winter Park
-47%
Nov 30 - Dec 7
Condo ∙ 6 guests ∙ 2 bedrooms

113 m² Condo

Winter Park, Grand County, Colorado, United States
$1,379$322
per night
$1,379$322
per night
View deal
Apartment Winter Park
-65%
Nov 1 - Nov 8
Free cancellation
Apartment ∙ 6 guests ∙ 3 bedrooms

139 m² Apartment

Winter Park, Grand County, Colorado, United States
$1,344$283
per night
Outstanding(5 ratings)
$1,344$283
per night
View deal

Vacation rentals with a fireplace

House  Winter Park
Apr 5 - Apr 12
-62%
$1,958
$603 per night
House ∙ 12 guests ∙ 5 bedrooms
Winter Park, Grand County, Colorado, United States
Fireplace
View deal
Maisonette  Winter Park
Apr 5 - Apr 12
-51%
$2,491
$583 per night
Maisonette ∙ 12 guests ∙ 4 bedrooms
Winter Park, Grand County, Colorado, United States
Fireplace
View deal
Apartment  Winter Park
Oct 30 - Nov 6
-70%
$1,394
$300 per night
Apartment ∙ 7 guests ∙ 2 bedrooms
5.0
Outstanding(142 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
Fireplace
View deal
See all offers

Vacation rentals and apartments with air conditioning

Apartment  Winter Park
Jan 18 - Jan 25
$545 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
Winter Park, Grand County, Colorado, United States
Free cancellation
Air conditioning
View deal
Apartment  Winter Park
Nov 30 - Dec 7
$592 per night
Apartment ∙ 11 guests ∙ 3 bedrooms
Winter Park, Grand County, Colorado, United States
Air conditioning
View deal
Apartment  Winter Park
Apr 5 - Apr 12
-55%
$1,267
$317 per night
Apartment ∙ 4 guests ∙ 1 bedroom
5.0
Outstanding(3 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
Air conditioning
View deal
See all offers

Best Vacation Home Deals in Winter Park

Save up to 80%

Apartment Winter Park
Nov 8 - Nov 15
-80%
$1,510
$312 per night
Apartment ∙ 7 guests ∙ 3 bedrooms
4.8
Outstanding(33 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
View deal
Apartment Winter Park
Nov 8 - Nov 15
-80%
$1,081
$215 per night
Apartment ∙ 7 guests ∙ 2 bedrooms
4.5
Excellent(33 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
View deal
House Winter Park
May 3 - May 10
-46%
$4,519
$1,054 per night
House ∙ 16 guests ∙ 5 bedrooms
5.0
Outstanding(71 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
View deal

Find a vacation home that meets your preferences among the 4,939 welcoming vacation rentals from more than 13 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

Apartment Winter Park
Oct 30 - Nov 6
-67%
$1,618
$356 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
Winter Park, Grand County, Colorado, United States
Free cancellation
View deal
Maisonette Winter Park
Apr 12 - Apr 19
-67%
$2,491
$583 per night
Maisonette ∙ 12 guests ∙ 4 bedrooms
Winter Park, Grand County, Colorado, United States
View deal
Apartment Winter Park
Dec 10 - Dec 17
-71%
$1,255
$277 per night
Apartment ∙ 7 guests ∙ 2 bedrooms
5.0
Outstanding(1 rating)
Winter Park, Grand County, Colorado, United States
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
-56%
$1,569
$332 per night
House ∙ 6 guests ∙ 2 bedrooms
4.9
Outstanding(40 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
View deal
Apartment Winter Park
Apr 26 - May 3
-54%
$1,330
$319 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
5.0
Outstanding(39 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
View deal
Accommodation Winter Park
Apr 12 - Apr 19
-42%
$4,981
$1,836 per night
Accommodation ∙ 14 guests ∙ 5 bedrooms
5.0
Outstanding(19 ratings)
Winter Park, Grand County, Colorado, United States
Free cancellation
View deal

Customer ratings and reviews

How are reviews collected?
Randall V.
Guest verified by HomeToGo

Enjoyed the stay. Will rebook when we return. Just a few suggestions. Need more coasters. Need a regular kitchen broom. Refrigerator was too cold and froze a lot of our food. Had to turn it down. Need hand soap and air freshener for bathrooms. One of the knobs on the grill wouldn’t turn off and we smelled gas. Turned off at the tank. Tried to take trash to the designated location on Reunion but couldn’t find receptacle possibly because snow had built up. Need better info on kitchen items provided (crock pot waffle maker).

Reviewed on 12/30/2024 | Family
House Winter Park
from $718 per night
HomeToGo
House ∙ 10 guests ∙ 3 bedrooms
5.0
Outstanding(9 ratings)
Winter Park, Grand County, Colorado, United States
View deal
from $718 per night
House ∙ 10 guests ∙ 3 bedrooms
5.0
Outstanding(9 ratings)
Winter Park, Grand County, Colorado, United States
HomeToGo
View deal
Jane K.
Guest verified 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 $494 per night
HomeToGo
House ∙ 10 guests ∙ 3 bedrooms
5.0
Outstanding(5 ratings)
Winter Park, Grand County, Colorado, United States
View deal
from $494 per night
House ∙ 10 guests ∙ 3 bedrooms
5.0
Outstanding(5 ratings)
Winter Park, Grand County, Colorado, United States
HomeToGo
View deal
Izabela P.
Guest verified 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 $206 per night
HomeToGo
Condo ∙ 4 guests ∙ 1 bedroom
4.5
Excellent(49 ratings)
Winter Park, Grand County, Colorado, United States
View deal
from $206 per night
Condo ∙ 4 guests ∙ 1 bedroom
4.5
Excellent(49 ratings)
Winter Park, Grand County, Colorado, United States
HomeToGo
View deal

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Popular Rental Amenities in Winter Park

  • Pool (1,884)
  • Pet-friendly (779)
  • WiFi (4,774)
  • Jacuzzi (2,234)
  • Kitchen (4,676)
  • Air conditioning (425)
  • Washing machine (2,720)
  • TV (4,488)
  • Fireplace (4,220)
  • Parking (1,233)
  • Balcony/patio (1,399)
  • Grill (2,008)

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 House rental 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. $1,569 is the highest price average in the next twelve months. Prices decrease in a week of April (4/26 – 5/3), where average prices are $471.

Rental availability information in Winter Park

Find out the percentage of available rentals in Winter Park with the graph above. In January (1/17 – 1/24), only 10 are available. People tend to travel less to Winter Park during a week in April (4/26 – 5/3) when only 34% of the rentals are booked.

Information about vacation rentals in Winter Park

🏡 Vacation rentals available 4,939 rentals
💳 Possible discounts up to 81%
🌙 Nightly prices starting at $182
⭐ Popular amenities Pool, Pets allowed and Internet
🐾 Pet friendly homes 752 homes
🏊 Vacation rentals with pools 1,816 homes
66,534 reviews
Winter Park vacation rentals have an average rating of 4.6/5 on 66,534 reviews left by travelers.

Frequently Asked Questions

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

At the moment, there are 4,939 vacation homes from 13 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 752 pet-friendly vacation rentals in Winter Park, with an average nightly price of $763.

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 $182.

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