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Check prices for these dates

Next weekend
Feb 28 - Mar 2
In two weeks
Mar 7 - Mar 9
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Mar 21 - Mar 23
In two months
Apr 18 - Apr 20

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
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
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
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
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)
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!
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
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
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
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
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
Bear Trail 3 Bedroom Townhouse by RedAwning
Townhome, 3 Bedrooms | Property grounds

Bear Trail 3 Bedroom Townhouse by RedAwning

3.5 star property
Bear Trail 3 Bedroom Townhouse by RedAwning
102 Willows Way 3 Bedroom Townhouse by RedAwning
Townhome, 3 Bedrooms | Marina

102 Willows Way 3 Bedroom Townhouse by RedAwning

3.5 star property
8.0 out of 10, Very Good, (1)
"Great walkable location. Hidden nearby lots of activities. "
102 Willows Way 3 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)
Wapiti 4 Bedroom Duplex by RedAwning
Duplex, 4 Bedrooms | View from property

Wapiti 4 Bedroom Duplex by RedAwning

3.0 star property
Wapiti 4 Bedroom Duplex by RedAwning
Fraser Crossing/Founders Pointe, Condo , 2 bedroom (Premium-Rated Condo 3506)
Condo, 2 Bedrooms | 2 bedrooms, iron/ironing board, free WiFi

Fraser Crossing/Founders Pointe, Condo , 2 bedroom (Premium-Rated Condo 3506)

3.5 star property
Fraser Crossing/Founders Pointe, Condo , 2 bedroom (Premium-Rated Condo 3506)
Iron Horse Manor 4 Bedroom Home
House, 4 Bedrooms | Living area | Smart TV

Iron Horse Manor 4 Bedroom Home

3.0 star property
Iron Horse Manor 4 Bedroom Home
Silversnow 476 3 Bedroom Townhouse by RedAwning
Aerial view

Silversnow 476 3 Bedroom Townhouse by RedAwning

3.0 star property
Silversnow 476 3 Bedroom Townhouse 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
Antler At Lakota 407 3 Bedroom Home
House, 3 Bedrooms | Private kitchen | Fridge, oven, coffee/tea maker, toaster

Antler At Lakota 407 3 Bedroom Home

3.0 star property
Antler At Lakota 407 3 Bedroom Home
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

A Frame Club
Outdoor spa tub

A Frame Club

3.5 star property
9.0 out of 10, Wonderful, (88)
"During our stay I don't think we had any visits from the cleaning crew. They had an envelope to give tips to them and I thought it was a joke. Overall the cabin was very nice and comfortable."
A Frame Club
Zephyr Mountain Lodge
Front of property - evening/night

Zephyr Mountain Lodge

3.5 star property
8.2 out of 10, Very Good, (650)
"Very easy vacation for my family!"
The price is NT$16,346
NT$19,503 total
includes taxes & fees
Feb 26 - Feb 27
Zephyr Mountain Lodge
Silverado II Resort & Event Center
Unit 511 | 2 bedrooms, bed sheets

Silverado II Resort & Event Center

3.5 star property
8.2 out of 10, Very Good, (150)
"Property was spacious and comfortable. Great location right near a shuttle to the mountain and other locations in town. "
Silverado II Resort & Event Center
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.