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

Truman Annex Best Location in Town

Greetings from Paradise, where the temperature is 82 degrees, water temperature 80, and the wind SE at 10, just enough breeze to blow sand in my margarita. 'Margarita Villas' are located in historic Old Town in a beautiful, very private gated com...

::LA PROVENCE @ THE SANCTUARY:: 2 Master Suites / Spa Pool & Private Courtyard..

'La Provence' is a bright and airy private home located in The Sanctuary, a quiet gated enclave set within the already gated grounds of the Key West Golf Club. The setting is idyllic, with lanes free of parked cars and no traffic on this peaceful ...

Fall Specials, Inquire now SUN and FUN in the KEYS!

Spacious home on the West Side of the island, over 2,000 s/f of living space plus balconies! Newer constructed half duplex offers a perfect location and deep water dockage with access to the ocean and gulf through Vaca Cut. Immaculate 3 bedroom, 2...

Dreaming on Duval

There's a fantastic vacation home on Duval Street in historic Key West and it is unique! Dreaming On Duval may be the most luxurious single family vacation rental actually on Duval Street. Steps to everything Key West has to offer, this private ho...

."CASA GRANDE" Over 3400 Sq Ft of Luxury Home in Old Town's 'Heart'

Upon entrance you are greeted by an elegant living room with vaulted ceilings, comfortable furnishings, 50” flat screen TV, and a view straight through to your private heated pool, a must for Key West. The Kitchen is well equipped for cooking all ...

Vacation Home Search

Find the perfect rental for your vacation

Join Our Newsletter

Get the latest updates in your email