2475+ Vacation Rentals & Holiday Homes in Winter Park |
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Winter Park Accommodations - Hotels & Rentals

About Winter Park Vacation Rentals

Discover More than 2475 Incredible Getaway Rentals Available in Winter Park. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in Winter Park.

Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in Winter Park, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in Winter Park. The Average Size of Places to Stay Near Winter Park is 1088.65 ft², with Prices Averaging US $508 per Night.

Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in Winter Park. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.

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Top Hotels & Vacation Rentals in Winter Park

Type Count
Vacation Homes 859
Holiday Apartments 371
Villas 4

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

★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in Winter Park with Online Reservations.

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

Activities Winter ParkGuest Reviews Local Attractions

A Large Selection of Hotels and Vacation Rentals from Around the World Winter ParkGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey


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

Find Hotels & Vacation Rentals in these Cities and Neighborhoods


Bella Vita 3,526 Properties
Blue Sky Massage 3,525 Properties
Winter Park Visitor Center 3,517 Properties
Hideaway Village South 3,477 Properties
Elk Court Cabins 3,455 Properties
Body Kneads Massage and Pilates 3,353 Properties
Grand Park Community Recreation Center 2,760 Properties
Pioneer Express Ski Lift 2,571 Properties
Black Tie Ski Rentals of Winter Park 2,550 Properties
Eskimo Express Ski Lift 2,548 Properties
Old Town 74 Properties
Bear Crossing 27 Properties

Frequently Asked Questions About Winter Park?

What are the top hotels, lake houses & vacation rentals in Winter Park?

We provide an array of great vacation destinations in Winter Park. If you are looking to stay in or around the Winter Park area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Winter Park:

How many Hotels & Vacation Rentals have private pools in Winter Park?

We have 94 Hotels & Vacation Rentals featuring a private pool in and near Winter Park. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which hotel, lake house, or vacation rental in Winter Park is best for families?

Searching for a family-friendly getaway in Winter Park? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.

How many hotels, resorts, or rentals are available in Winter Park?

Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2026 is over 2475 in the Winter Park area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in Winter Park.

Nearby Neighborhood (5) 
Neighborhood Property Count
Rendezvous Vacation Rentals in Winter Park, Colorado 153
Old Town Vacation Rentals in Winter Park, Colorado 74
Bear Crossing Vacation Rentals in Winter Park, Colorado 27
Elk Court Cabins Vacation Rentals in Winter Park, Colorado 3455
Hideaway Village South Vacation Rentals in Winter Park, Colorado 3477

People Also Ask

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