Explore and discover new travel adventures

Handpick vacation homes, features, and amenities for a trip that’s tailor-made.
park city winter
View from the balcony at a Daytona Beach vacation rental.

The pool area with modern design at a vacation rental in Palm Springs, CA.

Vacation your way

Travel how you want, where you want this winter

When your winter getaway could take place anywhere, start with your cold-weather must-haves. Browse vacation homes by search filters like property types, features, and cozy amenities. Discover slope-side chalets in snowy Vermont, steaming hot tubs in Swiss mountain lodges, or Montana cabins with crackling fireplaces perfect for warming up after a day of winter adventures.

Winter wonderland escapes

Adventures come in all shapes and sizes — so should your home base. Get inspired by viewing vacation rentals for travelers seeking snowy landscapes, cozy cabin experiences, and winter activities like skiing.

The pool area of a luxury vacation rental in Orlando.
FEATURED LUXURY WINTER ESCAPE

Luxury resort communities in Orlando

Jeeves Florida Rentals by Vacasa

Explore the extraordinary world of Jeeves’ high-end vacation rentals and adventurous amenities. Embark on a journey where magic comes to life: discover magnificent custom vacation homes, stunning pools, and a range of luxurious amenities such as private lazy rivers, state-of-the-art movie theaters, immersive bedroom designs, and so much more.

two dogs lay on a Pendleton dog bed in a vacation home
Tail wagging winter vacation rentals

Pet-friendly vacation rentals and cabins

No one should miss out on vacation, particularly your best friend. So skip the dog sitter and make your next getaway worry-free by exploring our pet-friendly vacation rentals in the Outer Banks and beyond. Choose between lake houses situated on inspiring bodies of water, cabins surrounded by boundless adventure, and everything in between.

Here's where to stay next for a worry-free, pet-friendly escape.

Warm weather getaways

Take your getaway to the next level and browse our vacation rentals by your most desired amenity. Cozy up by the fire, relax poolside, or never leave the hot tub — it’s your vacation.

How to plan a snowbird vacation
View from the balcony at a Daytona Beach vacation rental.
The pool area of a vacation rental in Scottsdale, Arizona.

Explore by snowbird destination

Here, snowbirds have options

Relax along the pristine beaches of Florida, spend the winter experiencing world-class golf in Arizona, snowbird Texas-style, or escape the cold elsewhere altogether.

Family and group-friendly winter getaways

cabin surrounded by snow in durango

Mountain cabins and ski lodges

Winter wonderland escapes are timeless, and 2025 is no exception.

Rustic or luxury cabins, ski-in/ski-out lodges, and cozy chalets near top ski resorts (like Aspen, Vail, or Lake Tahoe) are popular among those seeking snow activities like skiing, snowboarding, and snowshoeing, but we also offer:

Specialty retreats and unique getaways

Choose from homes that keep you in the heart of the action or along the outskirts, with plenty of space and privacy. Whether spread out in the sand or trekking under the trees, your next escape is waiting.

Fully-furnished long-term vacation rentals

Go beyond the weekend by extending your stay at one of the best destinations offering fully-furnished monthly vacation rentals.

Seasonal getaways and more travel inspiration

You’ve got plans, we’ve got getaways. Find the perfect backdrop for every retreat, reunion, or old-fashioned R&R.

aerial view of cabin in vermont in the fall
Fall vacation rentals
View of homes on a beach.
Spring vacation rentals
View from a balcony overlooking the ocean.
Summer vacation rentals
Newlyweds on a balcony at a vacation rental in Alabama.
Mom and daughter sizing wedding dress.
family dines at an outdoor table set up for a party

Explore by festival

Festival season runs all year long. In any given month, each state comes alive with thrilling food, music, and art festivals. Check out what’s happening from coast to coast and start planning a festival getaway.