Winter is a pretty amazing time for family travel. School is on break, work slows down, and more holiday weekends are around the corner. Why not make the most of it?

From Boston to Miami Beach, these winter family vacations are packed with adventure and easygoing activities everyone will love – plus family-friendly hotels and resorts with extra-spacious rooms, arcade games, and delicious on-site dining even the picky eaters will enjoy. 

Explore our top picks for the best winter family vacations this year, complete with special pricing and package deals to help you save and plan ahead.

Table of Contents 1. Orlando 2. Miami Beach 3. Boston 4. Washington, D.C. 5. Florida Keys 6. Santa Monica

Get your thrills at Orlando theme parks

Whether you’re five years old or nearing fifty, you can’t help but get swept away in Orlando’s magic. This central Florida city is known as the theme park capital of the world with over a dozen parks to choose from, including Walt Disney World® Resort and Universal Orlando Resort, home to The Wizarding World of Harry Potter. 

Orlando has much to explore beyond the parks, too, like scenic boat rides in Winter Park, luxury outlet malls, and outdoor activities to soak up the winter sun. Visit Wekiwa Springs State Park for paddling and horseback rides, or free-flow through a lazy river at Kelly Park, a popular family attraction inside the Rock Springs Run State Reserve – all just 35 minutes from downtown Orlando. 

Winter also brings the EPCOT International Festival of the Arts, and plenty of holiday happenings, too: a dazzling light show at Leu Gardens, the Grinchmas™ Who-liday Spectacular, and Mickey’s famous Christmas parade at Magic Kingdom® Park. 

Set out to see it all, then kick up your feet at Hotel Landy, a brand-new resort that’s family-friendly, and big on fun. Hotel Landy is an official Universal Partner Hotel and a complimentary shuttle ride away from all three Universal theme parks. Fuel your adventures with Starbucks coffee and snacks at the hotel’s grab-and-go market, then get into mischief with Dr. Gru and Homer Simpson.

Hotel Landy guestrooms are bright and spacious, and stocked with must-have essentials like hydration stations, Keurig coffee makers, and pillowtop beds. We especially love the Skyline View King with floor-to-ceiling windows to watch the nightly fireworks show. 

Outside by the resort-style pool, Liquid Sunshine has craft cocktails for the grown-ups and snacks for kiddos, while Émilie Bar + Lounge, the hotel’s on-site restaurant, offers elevated American cuisine and plain-jane favorites for finicky eaters. There’s also a hot tub, outdoor lawn games, and live entertainment on weekends. If that weren’t enough, Hotel Landy has its own Kinetic Game Room with arcade pinball, sudoku walls, and a seating area for parents. 

Special Offers: Book the Park & Play Package to enjoy a daily $50 dining credit, complimentary parking, late check-out, and complimentary shuttle rides to Universal Orlando Resort.

Make memories in Miami Beach

Further down the Florida coast, Miami Beach has family fun in forms of lazy beach days, art museums, world-class restaurants, and more – perfect for multigenerational families and hard-to-please teens. 
Winter season is extra fun in Miami, too. Catch the South Beach Wine & Food Festival in February, jam with famous musicians at January’s South Beach Jazz Festival, or visit on President’s Day weekend for the annual Coconut Grove Arts Festival.

The oceanfront Cadillac Hotel & Beach Club is an excellent choice for family-friendly hotels in Miami Beach. This European-inspired resort has an entire city block of beach to itself, and a dedicated beach play area for children, plus complimentary towels, umbrellas, and lounge chairs. Steps away you’ll also find not one but two hotel pools: one for families, and one adult-only Cabana Pool with pampering spa treatments for parents in need.  

Even more to love, families have five on-site dining options at the Cadillac Hotel including a beachside raw bar, a pastry cafe, and a classic Italian trattoria with premium cuts of meat, housemade pastas, and sommelier wine lists spotlighting the best Italian winemakers from Tuscany and Barbaresco.

Special Offers:  Book a long weekend with the Cadillac Family Cabana Escape package to receive special pricing on a three-night stay, a $150 dining credit, and a private oceanfront cabana with complimentary snacks.

Switch up the classroom in Boston Seaport

Just because school is on break doesn’t mean learning is, too. Why not take the kids to one of academia’s landmarks? 

Walking through Boston is practically a history lesson on its own. Stroll past revolutionary sites in Beacon Hill, or walk the Freedom Trail to check out Paul Revere’s house and the Old Corner Bookstore that published original scripts by Charles Dickens, Harriet Beecher Stowe, and other literary icons. Re-enact the Boston Tea Party on the harbor a la Samuel Adams, or dip into the Charles River with a family-friendly Duck Tour. Traveling with high schoolers? Walk through campuses like MIT for a glimpse at college life, or visit the Isabella Stewart Gardner Museum for a true crime story with fascinating art.

More art and intrigue await at The Envoy Hotel, a boutique guesthouse in Boston’s Seaport District, minutes from the city’s best museums and winter festivals. The Envoy is big on art and creativity. Above its local art gallery, the hotel’s waterfront suites have funky furnishings and pops of color that make for an exciting stay. Hotel restaurant Para Maria continues the trend with edible works of art inspired by Latin American cuisine and family recipes from Chef Tatiana Rosa. 

The crown jewel of The Envoy Hotel is the rooftop, an ultra-cool outdoor lounge with tons of space for family hangouts. In winter months, Rooftop at The Envoy has glass fireplaces and cozy igloos to keep your little ones warm, plus jaw-dropping views of the Boston harbor and the Seaport skyline – a perfect backdrop for a family photo! 

Special Offers:  The hotel’s Kids Just Want to Have Fun Package ups the ante with four tickets to Boston Children’s Museum, daily breakfast for the whole family, and a welcome amenity for kiddos.

Discover history together in Washington, D.C. 

For even more educational fun, consider a winter family vacation in Washington, D.C. American history plays out every day in The District, from the glorious Capitol Building to the White House, to the Lincoln Memorial where Martin Luther King, Jr. gave his famous speech, “I Have A Dream.” Visit the sites for an immersive civics lesson, then treat your kiddos to one of D.C.’s famous bakeries nearby. (Pro tip: plan ahead to book a Capitol Building tour free of charge!)

Families also have their pick of world-class museums in D.C. Get up close to dinosaur fossils at the National Museum of Natural History, or learn about indigenous cultures at the National Museum of the American Indian.

With so much to see and do, a central location is key for family vacations in D.C. Make yourself at home in the Capitol Hill Hotel, a kid-friendly (and pet-friendly!) hotel in the historic Capitol Hill District. 

Guestrooms and suites at Capitol Hill Hotel are among the largest in D.C., outfitted with residential comforts like kitchenettes, separate living spaces, and work desks with ergonomic chairs. Families also have access to children’s amenities such as highchairs, pack ‘n play cribs, and rollaway beds, plus daily continental breakfast, self-service laundry, and a 24-hour fitness center.

Special Offers:  Reserve three nights or more and enjoy up to 20% off your D.C. vacation with the hotel’s Monumental Getaway Package.

Go island hopping in the Florida Keys

Is your family big on adventure? Consider winter vacation in the Florida Keys, a chain of tropical islands with breathtaking scenery and loads of outdoor activities. We’re talking scuba diving and kayak tours, sunrise paddles, sports fishing, parasailing, and so much more. 

Key West, the southernmost island, offers all of the excitement and even more family-friendly activities: a shipwreck treasure museum, butterfly garden, and evening ghost tours, too. 

You’d be hard-pressed to find a more beautiful and relaxing Key West hotel than Parrot Key Hotel & Villas. Located just beyond the hustle and bustle, Parrot Key feels like a private hideaway with tropical gardens and waterfront bungalows overlooking the Gulf of Mexico. This hidden gem is one of Key West’s quieter resorts because of its location, though fear not, the best of Old Town and Duval Street are just a 10-minute shuttle ride away! 

The hotel’s “beachfront” is a peaceful slice of paradise for reading, napping, and playing in the sand – and a fabulous vantage point for Key West’s famous sunsets. Pick your favorite hammock and get ready for the show, best enjoyed with a Cuban sandwich and frozen drink in hand.

More delicious eats await at The Grove, the hotel’s tropical restaurant with all-day menus for poolside feasting. Speaking of pools, Parrot Key has four of them and convenient on-site water sports that take off directly from the dock. Thrill-seeking teens (and parents!) should check out the jet ski tour, an action-packed ride through Key West’s turquoise blue water. 

Special Offers:  With the resort’s Stay and Play Package, families enjoy a three-night stay in their choice of villa or two-bedroom suite, plus a $100 dining credit, family dolphin tour, family beach games, and an in-room welcome amenity.

Soak up the sun in Santa Monica

Santa Monica is one of the most iconic neighborhoods in Los Angeles, famous for its beaches and buzzy restaurant scene that even the locals love. 

Of course there are kid-friendly museums and galleries to browse, but the beach is the main draw here. Roll out a towel and laze the day away with beach volleyball and a good book as Cali surfers take on the swell. Later, rent a bicycle to cruise past Muscle Beach and down the 3rd Street Promenade for a bit of live entertainment by LA’s street performers. Families can’t miss Pacific Park, a famous beachfront amusement park on the Santa Monica Pier with pay-as-you-go rides, carnival games, bumper cars, and more. 

There are many hotels on the boardwalk, but we’re partial to The Ambrose Hotel, an award-winning, eco-friendly hotel in a residential neighborhood, close to the pier but far enough away for peace and quiet.

This Santa Monica hotel has an exclusive suite designed for families, aptly named the Family Room, an ultra-spacious retreat with two connecting king rooms and a private entrance, L’Occitane bath products, a writing desk for winter homework, and complimentary bicycle rentals.

Beyond its specialty suite, The Ambrose has all the on-site amenities you need for a convenient, stress-free family vacation like Peloton bikes and a spacious fitness center, 24-hour coffee and tea service, and nightly wine and beer tastings for grown-ups. There’s also in-room dining for breakfast and lunch, and sandwiches galore across the street at Tartine Bakery, a cult-favorite cafe and bakery from San Francisco slinging tartines, health-conscious salads, and all-day breakfast deliciousness. 

Special Offers:  Book the Family Getaway Package to enjoy a VIP welcome amenity with popcorn and chocolate for kids, a daily $20 dining credit, and complimentary late check-out.

Where will winter break take you this year? Discover our hotels and resorts for a bit of inspiration, and start planning your best family vacation yet with Independent Collection’s exclusive Special Offers.