2327+ Private Villas and Holiday Rentals in Winter Park |
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Winter Park Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Winter Park

Discover more than 2327 vacation rentals available in Winter Park. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Winter Park.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Winter Park, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Winter Park. On average, places to stay near Winter Park offer 1059.28 ft², with nightly prices averaging US $413.

With Casai, finding and comparing holiday rentals in Winter Park is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Winter Park

Type Count
Vacation Homes 831
Holiday Apartments 363
Villas 3

Use these Quick Filters to Find a Holiday Rental in Winter Park

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Winter Park.

Weather in Winter Park, CO

View the weather forecast for Winter Park before booking your Winter Park Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Winter Park, CO

Casai offers a large selection of top attractions around Winter Park . Research things to do on your vacation before you visit Winter Park.


Winter Park Ski Resort
Village Cabriolet Ski Lift
Zephyr Express Ski Lift
Amaze'n Maze Winter Park
Winter Park Visitor Center
Trestle Bike Park
Olympia Express Ski Lift
Arrow Ski Lift
Blue Sky Massage
Discovery Ski LIft
Challenger Ski Lift
Iron Horse Ski Lift
Moffat Tunnel West Portal
Bella Vita
Pioneer Express Ski Lift
Eskimo Express Ski Lift
Super Gauge Express Ski Lift
Black Tie Ski Rentals of Winter Park
Body Kneads Massage and Pilates
Looking Glass Ski Lift

Other Places to Stay in Winter Park, CO


Bella Vita 4,044 Properties
Blue Sky Massage 4,044 Properties
Winter Park Visitor Center 4,037 Properties
Hideaway Village South 3,995 Properties
Elk Court Cabins 3,960 Properties
Body Kneads Massage and Pilates 3,844 Properties
Grand Park Community Recreation Center 3,136 Properties
Pioneer Express Ski Lift 2,986 Properties
Black Tie Ski Rentals of Winter Park 2,963 Properties
Eskimo Express Ski Lift 2,961 Properties
Old Town 85 Properties
Bear Crossing 30 Properties

Frequently Asked Questions About Winter Park?

What are the top holiday rentals in Winter Park?

With numerous options available in Winter Park, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Winter Park:

How many holiday rentals have private pools in Winter Park?

Discover a selection of holiday rentals with private pools near Winter Park with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Winter Park are best for families?

If you're searching for a family-friendly holiday home in Winter Park, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Winter Park:

How many Casai.com holiday rentals are available in Winter Park?

As of 2025, Casai boasts over 2327 properties listed in the Winter Park area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Winter Park.

Nearby Neighborhood (5) 
Neighborhood Property Count
Rendezvous Vacation Rentals in Winter Park, Colorado 167
Old Town Vacation Rentals in Winter Park, Colorado 85
Bear Crossing Vacation Rentals in Winter Park, Colorado 30
Elk Court Cabins Vacation Rentals in Winter Park, Colorado 3960
Hideaway Village South Vacation Rentals in Winter Park, Colorado 3995

People Also Ask

There are 2327 Winter Park, CO Holiday Rentals

Recently Booked Holiday Rentals in Winter Park