Winter Vacation Rentals

Winter travelers have a tough decision to make: warm weather getaway or skiing adventure? One thing that both types of trips will have in common is winter vacation rentals. Whether you want to lounge on the beach or soar down the slopes, returning to a vacation rental will be a lovely way to end the day. All the comfort and convenience of a rental - including a private kitchen, laundry facilities, and outdoor space - will take your winter getaway to the next level.

florida keys winter vacation rentals1. The Florida Keys

Some travelers are looking for the tropical waters of the Caribbean without the need to pack a passport. If this sounds like you, plan a trip to the Florida Keys. These islands, located off the southern tip of Florida, offer a long list of fun activities under the sun. Plan a day fishing in the tropical waters, thrill the kids with a day of tubing, or simply lounge on the deck of your vacation rental. Winter temperatures will seem far, far away.

2. Catskills

Ready to brave the cold temperatures instead of running to a beach? If so, check out winter vacation rentals in the Catskills Mountains. Here you can make the most of the season with roaring fires, roasting marshmallows, and sipping on hot chocolate after a day on the slopes. With your own vacation rental, the best of the season will be right on your doorstep. Step outside to build snowmen and make your best snow angel.

3. Galveston, Texas

A warm-weather getaway can be a great strategy for surviving the long winter. One great place to soak up some sunshine is Galveston, Texas. On this long and skinny barrier island you will find many winter vacation rentals to choose between, from the large and luxurious to the quaint and cozy. Many different groups of people choose Galveston including families, young people looking for nightlife, and even couples searching for romance.

winter ski vacation rental aspen4. Aspen, Colorado

For decades, one of the best skiing destinations in the country has been Aspen, Colorado. Choose a vacation rental here and the best ski conditions, the most thrilling ski runs, and the best scenery will be all around you. When it comes to a skiing trip, you are going to want the extra space that comes with a rental. When the craving for a quiet night at home strikes, you can plan a family dinner and game night.

5. Southern California

The weather in southern California can hardly be beat. Here warm temperatures and a lack of humidity all add up to the perfect warm-weather destination for winter getaways. Vacation rentals are all available all along this stretch of coastline from La Jolla to Mission Beach to Newport Beach. Treat your kids to surfing lessons while you dig your toes deep in the sand.

6. Vermont

One of the best places for a ski vacation in the northeast is Vermont. Choose a cabin rental for a quintessential winter getaway. Vermont is a great place to give your kids their first ski lesson and spend some quality family time together at night. Vermont is also ideal for a romantic getaway. Choose a cozy cabin with romantic amenities like a soaking tub and a fireplace.

7. New Orleans

The fun never stops in New Orleans - not even during the winter. Escape the cold winter temperatures for a vacation full of sunshine and spicy food in New Orleans. Choosing a vacation rental will put you right at the center of the action for enjoying a trip full of music, culture and cuisine.

Florida Keys Rentals with Cable and Internet

Oceanfront Luxurious Home with Deep Water Canal and Heated Pool

Breathtaking Ocean Views - 180 degrees of Sunrises and Sunsets! Turquoise waters and gentle sea breezes - enjoy the tropical paradise in the heart of the Keys. Home is located where the street ends and the ocean begins! World famous sport fishin...

Paradise Found*Luxury Oceanfront Key West 3/2 Oceanside Marina

*****PARADISE AT ITS BEST***** A fabulous place to....ENJOY.... INDULGE....RELAX.....and just kick back! Keys style!! Vacation memories are made here! This property is an end unit showcasing additional windows with a h...

4 Bedroom Gulf Front Home, Pool, 100' Dock, Sandy beach Shoreline, Kayaks, View

This property rents from Saturday to Saturday. The home is directly on the Gulf of Mexico's crystal clear waters. It is great for snorkeling, swimming, fishing, kayaking and boating. We include kayaks for your enjoyment. You can fish right from...

Budget Friendly in Upscale Mariners Club Resort! 50' Plasma TV`S!

3-nt minimum ~ Premium dates, 7-nt minimum. 1 King Bed 1 Queen Bed 1 Sleeper Sofa, daybed that makes 2 singles in 3rd bedroom. Tri-level townhouse on the marina and just steps from the clubhouse pool and grotto spa! Free high-speed internet! 50'...

'PORTSIDE MANSION @ THE SEAPORT': Magnificent 3-Building Compound + Large Pool..

In the heart of Old Town, just a half block from the Historic Seaport Harbor, is a very exclusive and unique residence: Two homes and a guest house set on an over-sized corner lot surrounding a spacious courtyard and pool; ideal for a large group ...

Vacation Home Search

Find the perfect rental for your vacation

Join Our Newsletter

Get the latest updates in your email