When you think of winter destinations, you probably think of places that have activities like skiing, snow tubing, ice skating, snowshoeing, dog sledding, and more. However, when you think of the best destinations for winter trips, don’t forget about the chance to escape the cold to somewhere tropical. Whether you’re into winter sports or relaxing at the beach, winter trips are a great way to enjoy quality time with your family. Plus, timeshare rentals are a great way to save at the top resorts in these fantastic destinations. Keep reading to discover our picks for the best winter getaways for families, with where to go, where to stay, and what to do while you’re there.
- Winter Adventures on Family Vacations to Palm Springs, CA
- Cross Country Skiing and More in Breckenridge, CO
- Family Fun in Key West, FL
- Family Friendly Explorations in Yellowstone National Park
- Warm Outdoor Fun at Lifestyle Holidays Vacation Club at Puerto Plata, DR
- Rent a Timeshare with Timeshares Only
- Buy a Timeshare with Timeshares Only
Winter Adventures on Family Vacations to Palm Springs, CA



A winter vacation to Palm Springs is a fun way to escape the winter chill without missing out on winter fun. With the sunny, comfortable temperatures, it is the perfect time of year to take a day trip to Joshua Tree National Park. Here, you can take fun journeys through the park and see various unique landscapes. Make sure to bring a picnic blanket to lie on while you stargaze from the park at night. While you are in Palm Springs, you can’t miss the chance to take a ride on the Palm Springs Aerial Tramway for awesome views of the snowy mountains. Families also love exploring the downtown area either by bike or on foot. Other family-friendly activities in Palm Springs include visiting outdoor markets, exploring the Living Desert Zoo, and wandering through the Moorten Botanical Garden.
Winter Getaways for Families at Palm Canyon Resort and Spa, A Diamond Resort



To make your Palm Springs trip the perfect winter getaway, we recommend staying somewhere that feels comfortable, convenient, and fun! Palm Canyon Resort and Spa, a Diamond Resort, is just that. During a stay at this resort, you can spend your days enjoying the desert atmosphere while participating in outdoor activities. Some of the best activities are soaking in the heated pool or in the in-cave hot tub, or taking a ride down the water slide. Families with kids will also love the indoor sports court that is attached to the on-site fitness center. This means the little ones can have some fun playing while you sneak in a workout. Adults will love a trip to the property’s Canyon Spa. Here, you can enjoy treatments like massages, facials, scrubs and wraps, making a full spa day a possibility.
Cross Country Skiing and More in Breckenridge, CO



Family ski trips create unforgettable memories for all ages. For families with little ones, it is important to pick family-friendly ski resorts that offer gentle slopes for beginners and cozy lodge retreats. Breckenridge, Colorado, is recognized for its family-friendly skiing and mountain fun, so start packing! If you don’t have your own ski gear, don’t worry, many ski packages include rental equipment and lessons for families. If some family members aren’t into winter sports, many ski resorts also have indoor activities to warm up or keep children entertained while parents ski.
Whether you prefer downhill skiing, cross-country skiing, or hitting the bunny slopes, Breckenridge has something for you. For a ski vacation full of cross-country skiing, a great option is the Breckenridge Nordic Center. This ski resort also offers cross-country skiing lessons, guided snowshoeing adventures, and self-guided excursions. At Breckenridge Ski Resort, you’ll find dedicated learning areas, family zones on the mountains, and a ski school. Plus, kids under four ski free! Since this resort has the ideal terrain for skiers of any level, it is fun for anyone from first-timers to experts.
Winter Getaways for Families at Beaver Run Resort



Accommodations at Beaver Run Resort go far beyond just your typical hotel room. Suites here have everything you need to make a winter family vacation convenient. Each of the studio suite options is great for small families looking for an elevated resort experience. For large winter family vacations, there are larger suite options going all the way up to four bedrooms that accommodate up to 12. Family ski trips often include cozy evenings by the fire with hot cocoa and games. This resort makes that easy, as many of the rooms even have fire pits, kitchens, and living areas. In addition to the villas being great, this resort is packed with amenities like on-site dining, a spa, an arcade, easy slope access, and a free town shuttle. During your stay here, you are sure to have a wonderful winter escape full of unforgettable family moments.
Family Fun in Key West, FL



Vacations to Key West in the wintertime are a chance to enjoy family-friendly fun, island style. During the winter months, Key West has average temperatures in the high 70s to low 80s. This means that not much changes here in the winter; the weather is like summer year-round. This makes it the perfect escape for families looking to take a break from the cold. During your time on the island, families can enjoy a fun mix of sightseeing, relaxing, and learning about the rich history. Plus, there are many attractions that kids will love. From exploring the Key West Aquarium to spotting cats at the Hemingway House, your whole group will have a blast.
A fun way to experience as much of the island as possible during your winter vacation is to ride the hop-on, hop-off trolley. This makes it easy to visit places like the Southernmost Point and Mallory Square all in one day. Spending time exploring all that Key West has to offer is certainly one of the best winter getaways for families.
Winter Getaways for Families at Hyatt Windward Pointe



Located on the Atlantic side of Key West, Hyatt Windward Pointe is ideally placed for all things relaxation. The east side is definitely the quieter side of the island, since it is opposite from the lively attractions like Mallory Square and Duval Street. However, since the island is only 4.2 square miles, you will never be too far from the fun. Therefore, this resort is the perfect mix of just far enough to not be inside the action, but close enough to walk there if you would like. You will also be only one mile from Smathers Beach, one of the most beautiful beaches. The rooms and amenities here also contribute to the laid-back island lifestyle that everyone loves. The two-bedroom villas are designed with all the comforts of home, but in paradise. They feature conveniences like full kitchens, private balconies, and partial ocean views.
Family Friendly Explorations in Yellowstone National Park



National Parks are always a great pick for families, but they offer especially unique experiences in winter, with fewer crowds. From December to February, Yellowstone National Park transforms into a winter wonderland, offering snowmobiling, cross-country skiing, and more. For those who prefer more leisurely activities but want to see the park, a guided snowcoach tour may be perfect. Snowcoaches are heated vehicles with tires that make it easy to get through snowy terrain. This makes them perfect for taking in all of the park’s best sights, without being overly exposed to the cold. Plus, on these tours, guides are experts and will share awesome information about the park. Don’t skip out on this fun chance to see wildlife, iconic geysers, and stunning scenery from the comfort of a warm snowcoach.
For a little added outdoor adventure, snowmobiles are a great way to get around the park. Snowmobile tours in Yellowstone offer exploration of snow-covered landscapes, including Old Faithful. It is important to note that the only way to get to Old Faithful during the winter months is via snowcoach or snowmobile.
Winter Getaways for Families at Worldmark West Yellowstone



West Yellowstone is known to be the best gateway into Yellowstone National Park, and Worldmark West Yellowstone is the perfect place to stay. Just one block away from Yellowstone’s West entrance, it is easy to spot wildlife like bears, elk, bison and more. Plus, this entrance is ideal for visiting geysers like the famous Old Faithful. While spending some time at the resort, be sure to check out the indoor pool, which lets you swim without the cold. This resort also has an owner’s lounge, fitness center, barbecue area, and kid-friendly activities center. For any of your off-property planning needs, take advantage of the concierge staff’s friendly help.
The rooms at this resort will live up to or exceed your expectations with their cozy atmospheres. The suites with private bedrooms offer guests ample space and amenities, including fireplaces, in-unit laundry, full kitchens, and living and dining areas. Or, if you are looking for a smaller space for your family, the studio villas are like an elevated version of a standard hotel room.
Warm Outdoor Fun at Lifestyle Holidays Vacation Club at Puerto Plata, DR



If your goal this winter is to escape the winter blues, then Puerto Plata is the place to be. Lifestyle Holidays Vacation Club at Puerto Plata is an all-inclusive resort that offers guests the opportunity to fully unwind without worrying about transportation, meals, or activities. Everything you need is at the resort! Plus, since the resort is so big, there is a shuttle that runs continuously throughout the day. The shuttle can take you between all of the different hotels on the property, beaches, bars, restaurants, and pools.
When we say you won’t run out of fun things to do at this resort, we really mean it. This resort is packed with activities and opportunities for relaxation. For relaxation, take advantage of the two full-service spas, yoga, 14 pools, and eight beaches. For the kids, check out the two children’s pools, a supervised kids’ club, a playground area, watersports activities, and bike rentals. Adults will love the 20 options for restaurants and 31 bars on the property. While the adults enjoy a night out at the resort, they can be assured that the kids are taken care of at the kids’ club or the teens’ club. Families also can’t miss the unique opportunities for scuba lessons, beach volleyball, dance lessons, and shopping areas.
Rent a Timeshare with Timeshares Only
Still deciding on where to take this year’s winter family getaway? The perfect trip can be closer than you think with Timeshares Only. Our online marketplace is home to timeshares for rent at unbeatable prices, all over the world. So whether you want to participate in the winter activities of Breckenridge, Key West, Puerto Plata, or beyond, its worth checking out! Browse our full selection of winter timeshare rentals at gorgeous resorts and start planning. The search filter features make it easy to find a vacation that fits with your travel dreams, within your budget.
Buy a Timeshare with Timeshares Only
Want to turn your winter trip into a yearly tradition? If one of these timeshare resorts is calling your name, browse Timeshares Only’s resale marketplace. Here, you can find unbeatable deals on some of the best resorts in the most sought-after destinations worldwide. Additionally, on the resale market, you can often find prices that are a fraction of buying directly from the resort developer.