7 Florida Winter Vacation Ideas – With House133 Vacation Rentals

Florida Winter Vacation Ideas
Pier on the port of Key West, Florida at sunset.

With cooler weather, holiday activities, and endless sunshine, Florida is a pleasant place to visit in the winter. Perfect for exploring Florida’s pristine coastline and natural outdoor landscapes, the humidity of summer fades and festivals, fairs, and outdoor adventures take precedence. Whether you’re looking for thrills at one of the many theme parks or just want to soak in the sunshine, discover the top vacation ideas for a winter getaway in Florida.

Key West

Part of The Florida Keys archipelago made up of 1,700 islands, Key West is a popular destination, known for its laid-back tropical vibes, water activities, and key lime pie that can be appreciated even in December. Winter is the perfect time to visit, as the 70-degree weather and cool ocean breeze are all visitors need to kick those winter blues. With all its summer activities still in full swing, here visitors can charter a boat and go diving, deep-sea fishing, or spend a day snorkeling in addition to swimming, sailing, and jet-skiing. Nature lovers will love exploring the crystal clear waters at Dry Tortugas National Park and observing gorgeous winged creatures at the Butterfly and Nature Conservatory, while history and literary enthusiasts will be captivated with the Ernest Hemingway Home and Fort Zachary Taylor Historic Park. Those who want to join the revelry can participate in the fun events held on Duval Street and the famous Sloppy Joe’s bar before watching one of Key West’s famous sunsets at Mallory Square.

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The theme park capital of the world, Orlando is the place to be for thrill-seekers. Here visitors will find shorter lines at big-name parks like Disney World, Universal Studios, SeaWorld, and Islands of Adventure. Not into theme parks? There’s plenty of non-theme park action in Orlando too. Space enthusiasts can explore the world-renown Kennedy Space Center while those intrigued by Florida’s alligators can enjoy Orlando’s oldest major attraction, Gatorland. LEGOLAND is less than an hour away and puts on its annual Christmas Bricktacular, the Dr. Phillips Performing Arts Center has “The Sound of Music” performances, while ICE! at Gaylord Palms boasts an impressive family-friendly holiday event with a display of interactive ice sculptures and displays carved from two million pounds of ice.

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Sunshine is the best way to treat winter blues, and Miami does it best with its stunning beaches and an extensive list of activities for a range of travelers. South Beach is where to go to be and be seen and get the party started, Ocean Drive and Coral Gables Miracle Mile are a shoppers paradise, and Jungle Island, the Miami Seaquarium, and Zoo Miami are ideal for animal lovers. Art enthusiasts will enjoy the popular Art Basel contemporary art fair with over 250 art galleries from 31 countries and the Art Deco Weekend celebrating South Beach’s Art Deco architecture. Little ones can visit Santa’s Enchanted Forest complete with an insane amount of activities, rides, and entertainment, while those looking for a real adventure can take an airboat ride through the nearby Everglades National Park for a tour of Florida’s grassy wetlands and endangered species.

Florida Winter Vacation Ideas

Disney World

“The Happiest Place on Earth” for both kids and kids at heart, Disney deserves a mention on its own. With cooler weather, smaller crowds, and shorter lines, it is the perfect time to explore this majestically decorated theme park. Epcot puts on its annual Candlelight Processional, displaying a feast for the senses with a full orchestra and mass choir as a backdrop to the Nativity, while Mickey’s Very Merry Christmas Party is perfect for the little ones with live entertainment, character appearances, and festive parades. Epcot also has a World Showcase, providing a storyteller from each country to captivate audiences with their traditional customs, while the nearby quaint town of Celebration puts on its “Now Snowing” event, the closest visitors will get to seeing snow in the Sunshine State. From life-sized gingerbread houses to classic characters made out of treats, miniature trains, and winter wonderland villages, Disney’s long list of luxury hotel properties seemingly compete to create the most impressive festive displays.

Florida Winter Vacation Ideas

St. Augustine

Considered one of America’s most charming cities, St. Augustine is even more lovely during the wintertime. Here visitors can stroll along its 450-year-old cobblestone streets in the historic district through historical landmarks, quaint cafes, and haunted ghost tours, while history buffs can explore the Castillo de San Marcos Fort, stroll through the Colonial Quarter to watch the famous re-enactments, and drink from the Fountain of Youth that dates back to 1565. St. Augustine also boasts an award-winning annual holiday lights display rated in the “Top 10 Best Holiday Lighting Displays in the World” by National Geographic. This popular Night of Lights celebration brightens this charismatic city with more than 2 million dazzling lights strung towards a towering Christmas tree.

Florida Winter Vacation Ideas


Offering a range of fun-filled activities and mild temperatures, Tampa is a perfect winter getaway destination for all types of travelers. Art enthusiasts will be fascinated with Dali’s most comprehensive collection of paintings outside of Europe at the Dali Museum. At the same time, animal lovers can visit the Lowry Park Zoo and try to catch a glimpse of Florida’s treasured manatees at the Tampa Electric Manatee Viewing Center. Busch Gardens holds its annual Christmas Town event, turning the park into a magical winter wonderland with holiday shopping, festive treats, and a Santa House with elves, Mrs. Clause, and photo opportunities for the family. Visitors can also take a run on Tampa’s annual outdoor ice skating rink set up at the Curtis Hixon Waterfront Park in downtown, or cheer on their favorite college football team at the winter Outback Bowl at Raymond James Stadium.

Florida Winter Vacation Ideas

Mount Dora

Known equally for its antique shopping and small-town charm, Mount Dora offers visitors an array of diverse shops perfect for finding those unique holiday gifts. Lined with 19th-century clapboard houses amongst antique shops, outdoor cafes, quaint restaurants, art galleries, and bed and breakfast inn’s, Mount Dora is a pleasant town to explore in the wintertime. Visit Menninger’s, the largest antique marketplace in the southeast for unique treasures, attend the annual Christmas Lighted Boat Parade on the downtown waterfront, or hop on the century-old Cannonball Christmas Express for storytelling and singing with Santa. Nearby Scott’s Maze Adventures also provides fun for the entire family with themed corn mazes, hayrides in its 7-acre cornfield, and delicious homemade jam in their country food market.

While you are vacationing in Florida and you need a pocket-friendly charming Vacation apartment, House133 Vacation Rentals is the best plug for you!



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