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

Winter Park Vacation Rentals

Find 3,709 available home rentals from 13 partners
Anytime
Guests
Anytime
Guests

  • Price per night

    • Up to $100
    • $100 - $199
    • From $200

  • Accommodation types

    • Cabin
    • Lodge
    • House

  • Distance to center

    • 2 km
    • 5 km
    • Any

  • Rating

    • 4.5+
    • 4+

  • Booking Options

    • Instant Booking

  • Services

    • Pool
    • WiFi
    • Jacuzzi
    • Kitchen
    • Air conditioning
    • Washing machine
    • TV
    • Fireplace
    • Parking
    • Balcony/patio
    • Dishwasher
    • Microwave
    • Yard
    • Sauna
    • Crib
    Show more

  • Accommodation type

    • Pet-friendly
    • No smoking
    • No pets
    • Wheelchair access

  • Activities

    • Grill
    • Fishing

Top 15 Recommended vacation rentals in Winter Park

Find your perfect vacation rental in Winter Park from just $146 per night!

House Winter Park
House ∙ 18 guests ∙ 4 bedrooms

277 m² House

Winter Park, Grand County, Colorado, United States
from $721
per night
Outstanding(23 ratings)
from $721
per night
View deal
Condo Winter Park
Condo ∙ 8 guests ∙ 3 bedrooms

150 m² Condo

Winter Park, Grand County, Colorado, United States
from $336
per night
Outstanding(9 ratings)
from $336
per night
View deal
Condo Winter Park
Condo ∙ 8 guests ∙ 3 bedrooms

121 m² Condo

Winter Park, Grand County, Colorado, United States
from $314
per night
Outstanding(42 ratings)
from $314
per night
View deal
House Winter Park
House ∙ 12 guests ∙ 4 bedrooms

223 m² House

Winter Park, Grand County, Colorado, United States
from $323
per night
Outstanding(86 ratings)
from $323
per night
View deal
House Winter Park
House ∙ 14 guests ∙ 5 bedrooms

296 m² House

Winter Park, Grand County, Colorado, United States
from $735
per night
Outstanding(32 ratings)
from $735
per night
View deal
Cabin Winter Park
Cabin ∙ 14 guests ∙ 5 bedrooms

418 m² Cabin

Winter Park, Grand County, Colorado, United States
from $899
per night
Excellent(30 ratings)
from $899
per night
View deal
House Winter Park
House ∙ 14 guests ∙ 5 bedrooms

304 m² House

Winter Park, Grand County, Colorado, United States
from $439
per night
Outstanding(110 ratings)
from $439
per night
View deal
House Winter Park
House ∙ 12 guests ∙ 4 bedrooms

House

Winter Park, Grand County, Colorado, United States
from $462
per night
Outstanding(119 ratings)
from $462
per night
View deal
House Winter Park
House ∙ 6 guests ∙ 2 bedrooms

116 m² House

Winter Park, Grand County, Colorado, United States
from $342
per night
Outstanding(24 ratings)
from $342
per night
View deal
House Winter Park
House ∙ 12 guests ∙ 5 bedrooms

House

Winter Park, Grand County, Colorado, United States
from $404
per night
Outstanding(48 ratings)
from $404
per night
View deal
House Winter Park
House ∙ 16 guests ∙ 4 bedrooms

House

Winter Park, Grand County, Colorado, United States
from $515
per night
Outstanding(94 ratings)
from $515
per night
View deal
House Winter Park
House ∙ 9 guests ∙ 4 bedrooms

House

Winter Park, Grand County, Colorado, United States
from $512
per night
Outstanding(37 ratings)
from $512
per night
View deal
House Winter Park
House ∙ 11 guests ∙ 4 bedrooms

186 m² House

Winter Park, Grand County, Colorado, United States
from $853
per night
Outstanding(16 ratings)
from $853
per night
View deal
Condo Winter Park
Condo ∙ 5 guests ∙ 2 bedrooms

Condo

Winter Park, Grand County, Colorado, United States
from $264
per night
from $264
per night
View deal
House Winter Park
House ∙ 8 guests ∙ 3 bedrooms

105 m² House

Winter Park, Grand County, Colorado, United States
from $308
per night
Outstanding(84 ratings)
from $308
per night
View deal

Vacation rentals with a fireplace

House Winter Park
from $1,563 per night
House ∙ 14 guests ∙ 5 bedrooms

400 m² House

5.0
Outstanding(27 ratings)
Winter Park, Grand County, Colorado, United States
Fireplace
View deal
House Winter Park
from $918 per night
House ∙ 16 guests ∙ 6 bedrooms

255 m² House

4.6
Excellent(151 ratings)
Winter Park, Grand County, Colorado, United States
Fireplace
View deal
House Winter Park
from $588 per night
House ∙ 14 guests ∙ 5 bedrooms

139 m² House

4.9
Outstanding(68 ratings)
Winter Park, Grand County, Colorado, United States
Fireplace
View deal
See all offers

Apartments with a balcony or patio

House Winter Park
from $641 per night
House ∙ 14 guests ∙ 4 bedrooms

232 m² House

5.0
Outstanding(33 ratings)
Winter Park, Grand County, Colorado, United States
Balcony/Patio
View deal
House Winter Park
from $704 per night
House ∙ 12 guests ∙ 3 bedrooms

167 m² House

5.0
Outstanding(36 ratings)
Winter Park, Grand County, Colorado, United States
Balcony/Patio
View deal
House Winter Park
from $583 per night
House ∙ 12 guests ∙ 4 bedrooms

279 m² House

5.0
Outstanding(17 ratings)
Winter Park, Grand County, Colorado, United States
Balcony/Patio
View deal
See all offers

Cabins with a sauna

House Winter Park
from $421 per night
House ∙ 7 guests ∙ 3 bedrooms

204 m² House

Winter Park, Grand County, Colorado, United States
Sauna
View deal
House Winter Park
from $457 per night
House ∙ 10 guests ∙ 3 bedrooms

214 m² House

5.0
Outstanding(1 rating)
Winter Park, Grand County, Colorado, United States
Sauna
View deal
Apartment Winter Park
from $220 per night
Apartment ∙ 7 guests ∙ 2 bedrooms

88 m² Apartment

4.8
Outstanding(14 ratings)
Winter Park, Grand County, Colorado, United States
Sauna
View deal
See all offers

Budget-friendly Rentals in Winter Park

Find Fantastic yet Inexpensive Rentals

House Winter Park
from $905 per night
House ∙ 16 guests ∙ 7 bedrooms

House

4.8
Outstanding(143 ratings)
Winter Park, Grand County, Colorado, United States
View deal
House Winter Park
from $651 per night
House ∙ 10 guests ∙ 4 bedrooms

House

4.8
Outstanding(82 ratings)
Winter Park, Grand County, Colorado, United States
View deal
House Winter Park
from $426 per night
House ∙ 12 guests ∙ 4 bedrooms

178 m² House

4.9
Outstanding(70 ratings)
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
from $448 per night
House ∙ 9 guests ∙ 3 bedrooms

162 m² House

5.0
Outstanding(124 ratings)
Winter Park, Grand County, Colorado, United States
View deal
Condo Winter Park
from $146 per night
Condo ∙ 4 guests ∙ 1 bedroom

42 m² Condo

4.7
Excellent(118 ratings)
Winter Park, Grand County, Colorado, United States
View deal
Condo Winter Park
from $665 per night
Condo ∙ 10 guests ∙ 4 bedrooms

146 m² Condo

5.0
Outstanding(72 ratings)
Winter Park, Grand County, Colorado, United States
View deal

Discover real guest reviews to help you choose the perfect stay in Winter Park

How are reviews collected?
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 $437 per night
House ∙ 10 guests ∙ 3 bedrooms
5.0
Outstanding(6 ratings)
Winter Park, Grand County, Colorado, United States
View deal

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Popular Rental Amenities in Winter Park

  • Pool (1,276)
  • Pet-friendly (603)
  • WiFi (3,623)
  • Jacuzzi (2,378)
  • Kitchen (3,566)
  • Air conditioning (364)
  • Washing machine (2,604)
  • TV (3,607)
  • Fireplace (3,314)
  • Parking (1,143)
  • Balcony/patio (1,434)
  • Grill (1,789)

Winter Park is a good vacation destination if you want an accommodation with a pool, as 34% 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. $838 is the highest price average in the next twelve months. Prices decrease in a week of May (5/16 – 5/23), where average prices are $770.

Rental availability information in Winter Park

Find out the percentage of available rentals in Winter Park with the graph above. In November (11/7 – 11/14), only 6 are available. People tend to travel less to Winter Park during a week in December (12/13 – 12/20) when only 34% of the rentals are booked.

Information about vacation rentals in Winter Park

🏡 Vacation rentals available 3,709 rentals
💳 Possible discounts up to 14%
🌙 Nightly prices starting at $146
⭐ Popular amenities Pool, Pets allowed and Internet
🐾 Pet friendly homes 599 homes
🏊 Vacation rentals with pools 1,261 homes
6 reviews
Winter Park vacation rentals have an average rating of 4.7/5 on 6 reviews left by travelers.

Frequently Asked Questions

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

At the moment, there are 3,709 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 599 pet-friendly vacation rentals in Winter Park, with an average nightly price of $823.

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 $146.

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