Winter Park Vacation Homes

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Featured Vacation Homes in Winter Park

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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
    $106 nightly
    The price is $120 total per night from Oct 6 to Oct 7
    $120 total
    Oct 6 - Oct 7
    Total with taxes and fees
    Gravity Haus Winter Park

    Gravity Haus Winter Park

    78869 US-40 Winter Park CO
    $126 nightly
    The price is $143 total per night from Sep 14 to Sep 15
    $143 total
    Sep 14 - Sep 15
    Total with taxes and fees
    Winter Park Chateau

    Winter Park Chateau

    405 Lions Gate Drive Winter Park CO
    $127 nightly
    The price is $144 total per night from Sep 21 to Sep 22
    $144 total
    Sep 21 - Sep 22
    Total with taxes and fees
    9.8/10 Exceptional! (163 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
670 Vacation Homes
Lowest Price
$120
Highest Price
$144
Popular accommodation
Luxury Downtown Condo - Private Hot Tub! Walk to Dining and Ski Bus..., Creekside Luxury Retreat • 8BR • Walk to Shops, Dining & Shuttle • Sleeps 22, Downtown WP Villa 558 I Great Views I Private Hot Tub I Discounted Attractions, Ski In Out Luxury Penthouse 4675 I Huge Hot Tub I Great Views I Discounted Attractions, Large Beautiful Townhome, Private Hot Tub, Near Shuttle Route, In Town, WIFI, Slopeside Luxury Chalet I Hot Tubs I Firepit I Views I Game Room I Theatre I Discounted Attractions, Mountain getaway with fireplace, fast WiFi, & high-country views, Downtown WP Loft 14 I Hot Tub I Great Views I Bunk Beds I Discounted Attractions, Lakota Antlers 201 | Private Hot Tub w/ Mountain Views | Deluxe Decor | Across From Ski Resort