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Check prices for these dates

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Jan 31 - Feb 2
In two weeks
Feb 7 - Feb 9
In one month
Feb 21 - Feb 23
In two months
Mar 21 - Mar 23

Compare 59 Vacation Homes in Winter Park with updated reviews, rates, and availability.

New Downtown Luxury Hideaway Skiing
Townhome, Multiple Beds, Balcony, Mountain View (Downtown Luxury Hideaway) | Balcony view

New Downtown Luxury Hideaway Skiing

4.0 star property
New Downtown Luxury Hideaway Skiing
Whisk Away to Winter Park! 2 BDR 5 Min From Skiing
Condo, Multiple Beds, Pool Access, Mountain View (Cozy Winter Park Mountain Cabin) | Private kitchen | Fridge, microwave, oven, stovetop

Whisk Away to Winter Park! 2 BDR 5 Min From Skiing

3.5 star property
10.0 out of 10, Exceptional, (2)
"The condominium was very sufficient to my needs along with my guests. The provided all the necessity in kitchen area. As well as the entire living area. Overall, I would stay there again if I am ever in Winter Park for the Jazz Festival."
Whisk Away to Winter Park! 2 BDR 5 Min From Skiing
Luxury in Downtown Winter Park
Luxury Townhome | Private kitchen | Full-size fridge, microwave, oven, stovetop

Luxury in Downtown Winter Park

4.5 star property
10.0 out of 10, Exceptional, (3)
"We took our family to Winter Park and this was an excellent location. The owner/property manager was great and responded very quickly to my messages. The location was right in the middle of town and within walking distance of shops and restaurants. I highly recommend this property! "
Luxury in Downtown Winter Park
Arrow Luxury Rooftop Shopping and More!
Townhome, Multiple Beds, Hot Tub, Mountain View (Arrow Luxury Rooftop) | Private kitchen | Fridge, microwave, oven, stovetop

Arrow Luxury Rooftop Shopping and More!

4.5 star property
Arrow Luxury Rooftop Shopping and More!
Willows Way 106 3 Bedroom Townhouse by RedAwning
Townhome, 3 Bedrooms | Exterior

Willows Way 106 3 Bedroom Townhouse by RedAwning

3.5 star property
Willows Way 106 3 Bedroom Townhouse by RedAwning
Antler Way At Lakota.... 3 Bedroom Townhouse by RedAwning
Townhome, 3 Bedrooms | Outdoor spa tub

Antler Way At Lakota.... 3 Bedroom Townhouse by RedAwning

3.0 star property
Antler Way At Lakota.... 3 Bedroom Townhouse by RedAwning
Fraser Crossing/Founders Pointe, Condo , 2 Bedroom (Premium Unit 4185)
Condo, 2 Bedrooms | Living area | TV, fireplace

Fraser Crossing/Founders Pointe, Condo , 2 Bedroom (Premium Unit 4185)

3.5 star property
Fraser Crossing/Founders Pointe, Condo , 2 Bedroom (Premium Unit 4185)
Lower Bear Trail 3 Bedroom Townhouse by RedAwning
Townhome, 3 Bedrooms | Outdoor spa tub

Lower Bear Trail 3 Bedroom Townhouse by RedAwning

3.0 star property
Lower Bear Trail 3 Bedroom Townhouse by RedAwning
Rendezvous Discovery 3 Br 3 Bedroom Home by RedAwning
House, 3 Bedrooms | Exterior

Rendezvous Discovery 3 Br 3 Bedroom Home by RedAwning

3.5 star property
Rendezvous Discovery 3 Br 3 Bedroom Home by RedAwning
Silversnow 476 3 Bedroom Townhouse by RedAwning
Townhome, 3 Bedrooms | Marina

Silversnow 476 3 Bedroom Townhouse by RedAwning

3.0 star property
Silversnow 476 3 Bedroom Townhouse by RedAwning
Summit Place At Lakota 4 Bedroom Townhouse by RedAwning
Townhome, 4 Bedrooms | Outdoor spa tub

Summit Place At Lakota 4 Bedroom Townhouse by RedAwning

3.0 star property
Summit Place At Lakota 4 Bedroom Townhouse by RedAwning
Village View, Townhouse | Fireplace at Parry Peak Lofts (Premium-Rated Condo 106)
Townhome, 3 Bedrooms | Private kitchen | Fridge, coffee/tea maker, toaster

Village View, Townhouse | Fireplace at Parry Peak Lofts (Premium-Rated Condo 106)

3.0 star property
Village View, Townhouse | Fireplace at Parry Peak Lofts (Premium-Rated Condo 106)
Base Camp At Iron Horse... 4 Bedroom Townhouse by RedAwning
Townhome, 4 Bedrooms | Dining

Base Camp At Iron Horse... 4 Bedroom Townhouse by RedAwning

3.0 star property
Base Camp At Iron Horse... 4 Bedroom Townhouse by RedAwning
Crestview Place
Apartment, 3 Bedrooms | 2 bedrooms, individually decorated, individually furnished

Crestview Place

2.0 star property
9.0 out of 10, Wonderful, (6)
"Great location with easy access to free bus to Winter Park Resort. Walking distance to restaurants, bars, and ski shops."
Crestview Place
Spacious Balsh Blvd Home with Private Hot Tub by RedAwning
House, 5 Bedrooms | Outdoor spa tub

Spacious Balsh Blvd Home with Private Hot Tub by RedAwning

3.5 star property
4.0 out of 10, (1)
Spacious Balsh Blvd Home with Private Hot Tub by RedAwning
12 Yukon Lane Townhome by Stay Winter Park
Townhome, 4 Bedrooms | Private kitchen | Fridge, microwave, oven, coffee/tea maker

12 Yukon Lane Townhome by Stay Winter Park

3.5 star property
12 Yukon Lane Townhome by Stay Winter Park
Willows At Grand Park 4 Bedroom Home by RedAwning
House, 4 Bedrooms | Private kitchen | Fridge, oven, coffee/tea maker, toaster

Willows At Grand Park 4 Bedroom Home by RedAwning

3.5 star property
Willows At Grand Park 4 Bedroom Home by RedAwning
Mountain Willow At Grand Park 4 Bedroom Home by RedAwning
House, 4 Bedrooms | Private kitchen | Fridge, oven, coffee/tea maker, electric kettle

Mountain Willow At Grand Park 4 Bedroom Home by RedAwning

3.5 star property
Mountain Willow At Grand Park 4 Bedroom Home by RedAwning
Dreamcatcher At Lakota 5 Bedroom Home by RedAwning
Townhome, 5 Bedrooms | Living area

Dreamcatcher At Lakota 5 Bedroom Home by RedAwning

2.5 star property
Dreamcatcher At Lakota 5 Bedroom Home by RedAwning
Winterstar Townhome 3 Bedroom Townhouse by RedAwning
Condo, 3 Bedrooms | Exterior

Winterstar Townhome 3 Bedroom Townhouse by RedAwning

3.5 star property
Winterstar Townhome 3 Bedroom Townhouse by RedAwning
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Winter Park

Zephyr Mountain Lodge
Front of property - evening/night

Zephyr Mountain Lodge

3.5 star property
8.2 out of 10, Very Good, (645)
"We loved our stay there. The location could not be more convenient for skiing. "
The price is NT$15,361
NT$18,327 total
includes taxes & fees
Feb 3 - Feb 4
Zephyr Mountain Lodge
A Frame Club
Outdoor spa tub

A Frame Club

3.5 star property
9.0 out of 10, Wonderful, (83)
"Had a great time with my girl for her birthday although we are from Florida and not use to mountains and below zero temperatures the stay was nice and cozy"
A Frame Club
Indian Peaks Resort
Family Loft, 2 Bedrooms, Hot Tub, Mountain View | 2 bedrooms, premium bedding, laptop workspace, blackout drapes

Indian Peaks Resort

3.5 star property
9.2 out of 10, Wonderful, (120)
"Sin duda regresaré nos encanto Ami y a mi familia "
Indian Peaks Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.