Winter Park Vacation Homes

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Vacation Homes in Winter Park

Don't see what you're looking for?
See all available properties in Winter Park
View all properties
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.

Hotel Options in Winter Park

    The Vintage Hotel

    The Vintage Hotel

    100 Winter Park Dr Winter Park CO
    $144 nightly
    The price is $163 total per night from Aug 16 to Aug 17
    $163 total
    Aug 16 - Aug 17
    Total with taxes and fees
    Gravity Haus Winter Park

    Gravity Haus Winter Park

    78869 US-40 Winter Park CO
    $149 nightly
    The price is $169 total per night from Aug 23 to Aug 24
    $169 total
    Aug 23 - Aug 24
    Total with taxes and fees
    9/10 Wonderful! (860 reviews)
    Zephyr Mountain Lodge

    Zephyr Mountain Lodge

    201 Zephyr Way Winter Park CO
    $220 nightly
    The price is $249 total per night from Jul 26 to Jul 27
    $249 total
    Jul 26 - Jul 27
    Total with taxes and fees
    8.2/10 Very Good! (702 reviews)

Winter Park Vacation Homes

Book vacation homes in Winter Park
Next time you take a group getaway top Winter Park, don’t confine your friends and family to one or two hotel rooms. Instead, snag a deal on a full-sized house and get the best of both worlds. Vacation home rentals are perfect for families and large groups that want to live like locals on vacation. Whether you are searching for a villa that pulls out all the stops or a four-bedroom house to host the best summer vacation ever, Orbitz has a variety of Winter Park vacation homes for rent that are ideal for you. Your perfect pad is only a few clicks away.

Homes for every Winter Park vacation
If you’re planning a vacation with a lot of people, you’ll want room to stretch out, and a rental home has plenty of space. Many vacation homes also come with everything you’ll need for a proper getaway, like kitchens with every gadget you can think of, along with updated furnishings, fancy spa tubs and balconies. You may even wind up in a rental home that has a sprawling backyard for barbecues, games and general relaxation. These rentals offer the added bonus of putting you right in the thick of things in Winter Park; instead of going to a small hotel room at the end of a busy day, you’re going home.

Vacations are all about creating lasting memories, and a Winter Park rental home makes it easy to create good ones. Whether you’re getting the college crowd back together or bringing along your folks and your kids, a trip to Winter Park is sure to be a winner.

Winter Park Vacation Homes essential information

Accommodation
647 Vacation Homes
Lowest Price
$163
Highest Price
$596
Popular accommodation
Fresh Tracks @ Peak View Ridge, Downtown WP Penthouse 219 I Private Hot Tub I Great Views I Bunk Room I Discounted Attractions, Willows at Grand Park 160 | Trails out Your Door | Bubbling Private Hot Tub, 💎 Deluxe Hot Tub W/ Stunning Views | Custom Decor | Across From Ski Resort, Ski In Out Village Condo 4375 I Huge Hot Tub I Views I Heated Garage I Discounted Attractions, Large Beautiful Townhome, Private Hot Tub, Near Shuttle Route, In Town, WIFI, ☺ Timber Ridge Lodge | 4 Miles To Resort | Private Hot Tub | Large Home, Slopeside Luxury Chalet I Hot Tubs I Firepit I Views I Game Room I Theatre I Discounted Attractions, Ranch Creek Lodge | Pet Welcome! | Private Hot Tub | Near Ski Trails