10 Best Vacations for Families With Toddlers

Choose one of the best vacations for toddlers and plan your trip on FlipKey.

Best Vacations for Toddlers

The key to planning a worry-free vacation with toddlers is choosing the right destination. Whether it’s an exciting city brimming with hands-on activities, a peaceful beach, or a rural setting where kids can explore, it has to be a place where both the young and getting older can have fun (after all, it’s your vacation, too!).

To help you choose, we’ve hand-picked 10 of the best vacations for toddlers from coast to coast. From the action-packed streets of Washington, DC to the picturesque shores of San Diego, the places on our list make every curious toddler’s favorite question—”Why?”—easy to answer. We’ve even included our top pick for a kid-friendly attraction your little ones will love.

With more than 300,000 rentals to choose from on FlipKey, opt for a vacation home during your family getaway and benefit from extra space, free laundry, and a full kitchen to prepare meals for even the pickiest of eaters.

Captiva Island, Florida

Find the perfect rental for your family on FlipKey.

Captiva Island rests just off the coast of southwest Florida in the emerald waters of the Gulf of Mexico. It’s known for its shallow waters and gentle waves, which make it an ideal beach vacation spot for families with toddlers. With your little ones at your side, chase waves retreating into the ocean, build an enormous sandcastle, or comb the beach for colorful seashells—the possibilities are endless! Choose a beachfront condo with kid-friendly activities (think kite-making and coconut-painting) or book a vacation home with tons of space for a stress-free getaway in Captiva Island.

Top kid-friendly attraction: Sanibel Sea School

See all Captiva Island vacation rentals from FlipKey!

Pigeon Forge, Tennessee

Book a spacious cabin in Pigeon Forge.

With its small-town vibe and inviting atmosphere, one thing’s certain: you’re sure to feel at ease in Pigeon Forge (at least, while the kids aren’t testing your patience!). Situated in the heart of the Smoky Mountains, this outdoorsy destination is all about experiencing the Appalachian wilderness hands-on. In other words, it’s a toddler’s dream-come-true. Explore the dense forests on foot, bike along nature paths, or take a dip in the local swimming holes. If that’s not your thing, downtown Pigeon Forge boasts family-friendly theme parks, unique attractions, and the sounds of country music on almost every street corner, ensuring a good time is had by all.

Top kid-friendly attraction: The Coaster at Goats on the Roof

See all Pigeon Forge vacation rentals from FlipKey!

Stowe, Vermont

Play outdoors during a vacation to Vermont.

Located just miles from Smugglers Notch, one of Vermont’s largest state parks, Stowe boasts countless kid-friendly hikes, scenic byways, and undiscovered attractions. Translation: Stowe is the ultimate natural playground for toddlers. Let your children run free, climbing over twisted roots, playing hide-and-go-seek among the trees, and breathing in the fresh mountain air. Once everyone’s all tired out, retreat to your spacious cabin rental, and spend the evening cuddled on the couch watching movies and reading bedtime stories. Sometimes the best vacation for toddlers is one that involves minimal plans and a place to let loose.

Top kid-friendly attraction: Stowe Bowl

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Orlando, Florida

Orlando best vacation for toddlers

It goes without saying that Orlando is one of the best vacations for toddlers. Home to the world-famous Disney theme parks, happiness fills the air here. Explore a lush, African savanna at Disney’s Animal Kingdom, stay cool at the Typhoon Lagoon Water Park, or watch your children’s eyes light up while hugging Mickey Mouse. The fun doesn’t have to end when you exit the park’s gates, though! Many Orlando vacation rentals bring the magic home with Disney-themed rooms, fabulous pools, and lots of space to play. Visit Orlando and even adults will feel like kids again!

Top kid-friendly attraction: Crayola Experience Orlando

See all Orlando vacation rentals from FlipKey!

Lake Ozark, Missouri

Lake Ozark, MO retreat

With miles of scenic lakefront, world-class boating, and a convenient location in the center of Missouri, Lake Ozark is a fabulous vacation spot for families, especially those with toddlers. Let the hours slip by swimming, strolling, or simply relaxing on the picturesque shores. For toddlers, there are endless things to do and no shortage of hiding spots for your inquisitive little one(s) to discover. At the end of the day, kick up your feet at your cabin rental, and watch the sunset over the water. Indoors and outdoors, your whole family will have fun in Lake Ozark!

Top kid-friendly attraction: Miner Mike’s Indoor Family Fun Center

See all Lake Ozark vacation rentals from FlipKey!

Washington, DC

With so much to do, Washington, DC is one of the best vacations for toddlers.

Washington, DC is loaded with captivating attractions your toddlers will love: the park-like National Zoo, several museums with interactive exhibits, and plenty of sprawling parks perfect for playing and picnicking, to name a few. Rent an apartment downtown or stay along the city’s outskirts—it’s easy to get around Washington, DC, even with toddlers in tow. Hop on the metro and breeze from destination to destination, or climb into a pedicab for an open-air ride through the city’s unique neighborhoods. Your wee ones will be awe-struck by the city’s massive monuments, historic buildings, and iconic landmarks looming in the skyline.

Top kid-friendly attraction: The International Spy Museum

See all Washington, DC vacation rentals from FlipKey!

San Diego, California

Beachside in San Diego, California.

San Diego is a laid-back beach town that’s fun to visit, with or without kids! When you arrive, make your first stop Balboa Park. It’s home to a large playground, nearly 20 museums, the San Diego Zoo, and so much more that will keep your little ones entertained for hours. Along the coast, soak up sun at Mission Beach or visit La Jolla Cove where seals and sea lions perch on the rocks all day long (cuteness overload!). FlipKey has plenty of San Diego rentals just steps from the beach, so you won’t have to tote your toddlers and beach toys too far for fun in the sun.

Top kid-friendly attraction: San Diego Children’s Discovery Museum

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Lake Placid, New York

Boaters explore Lake Placid, NY

Travelers describe a vacation to Lake Placid as “a true Adirondack experience” and an “unbeatable, peaceful retreat.” Although it’s famous for being the site of the 1980 Winter Olympic Games and a hub for snow sports, this quiet city nestled in the mountains offers year-round activities the whole family will enjoy. During the summer, splash in the lake or sit by the fire pit as frogs croak and fireflies flit by. When winter rolls around, try skiing and ice skating, or climb Whiteface Mountain in the Cloudsplitter Gondola for sweeping views of Lake Placid. You’ll find this fabulous destination is as breathtakingly beautiful and full of adventure as it is toddler-friendly.

Top kid-friendly attraction: Whiteface Adventure Zone

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Philadelphia, Pennsylvania

Philadelphia, Pennsylvania skyline

If you’ve never been to Philadelphia, you’ll quickly see why it’s a fabulous city and one of the best vacations for toddlers. From the massive Smith Memorial Playground & Playhouse to the Philadelphia Zoo, there’s plenty to keep your children amused for hours on end. With little ones constantly on the go, try not to miss the centuries of American history on display throughout the city—the Liberty Bell, Independence Hall, and Reading Terminal Market to name a few. Need another reason to visit Philadelphia? Sesame Place is just across the city line in Langhorne!

Top kid-friendly attraction: Please Touch Museum

See all Philadelphia vacation rentals from FlipKey!

Port Aransas, Texas

Port Aransas, TX is one of the best vacations for toddlers.

Fill your days in Port Aransas searching for seashells, fishing from the pier, and exploring the local nature reserves. The 18 miles of soft-sand beaches here provide a cushiony landing spot for toddlers still getting the hang of walking. Overhead, colorful Roseate Spoonbills and Reddish Egrets fly through the sky, while the sound of whooping cranes carries through the air delighting both young and young at heart. Make it easy on yourself by booking a rental right on the water so you won’t have to lug your beach gear too far. If you’re seeking an island retreat without a hefty price tag (you can rent a home for under $100 per night!) Port Aransas is the perfect place for you and your family.

Top kid-friendly attraction: Port Aransas Sandcastle Guy

See all Port Aransas vacation rentals from FlipKey!

Best Vacations for Families With Toddlers

  • Captiva Island, Florida
  • Pigeon Forge, Tennessee
  • Stowe, Vermont
  • Orlando, Florida
  • Lake Ozark, Missouri
  • Washington, DC
  • San Diego, California
  • Lake Placid, New York
  • Philadelphia, Pennsylvania
  • Port Aransas, Texas