When temperatures dip and daylight feels scarce, the promise of sunshine becomes hard to resist—especially when it doesn’t come with a sky-high price tag. To identify the cheapest warm-weather destinations to visit this season, we partnered with the team at Kayak, which analyzed flight searches made between Sept. 1 and Dec. 4, 2025, for travel dates spanning Dec. 21, 2025, through Feb. 28, 2026, departing from U.S. airports. Airfare prices reflect round-trip, economy itineraries, while hotel rates are nightly averages based on standard, double-occupancy rooms. All prices are averages, subject to change.
According to Kayak’s travel trends expert Sarah Kennedy, affordability is a major win this season. “Florida offers the best bang for your buck this winter, with seven out of 10 cities landing among the top 10 warm-weather destinations with the lowest trip costs,” she tells Travel + Leisure. “And with Jamaica welcoming visitors after a tough hurricane season, travelers can enjoy the sun while supporting recovery, all on a reasonable budget.”
01 of 10
Orlando, Florida
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An amusement park in Orlando, Florida.
Average flight + hotel cost: $463
In Orlando, the magic lingers well past the holidays, carrying straight through winter with festivals and special events like EPCOT’s International Festival of the Arts, Mardi Gras at Universal Orlando, and the Winter Park Sidewalk Art Festival. Of course, the warm weather also makes winter perfect for exploring the theme parks and Orlando’s walkable downtown. Rent a swan boat at Lake Eola Park, bike or walk the mile-long loop, and enjoy al fresco meals at spots like Grills Lakeside Seafood Deck & Tiki Bar.
02 of 10
Tampa, Florida
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Aerial view of homes along Tampa Bay.
Average flight + hotel cost: $463
Tampa makes an easy case for a warm-weather winter getaway, combining quick access to Gulf Coast beaches with vibrant neighborhoods and a thriving culinary scene. Winter brings a full slate of festivals, including the Gasparilla Pirate Festival and the Gasparilla Music Festival, while cooler, sunny days are ideal for walking or biking the Tampa Riverwalk or sipping cocktails at rooftop bars like M.Bird and Sal Y Mar. Historic Ybor City adds charm with its brick streets, cigar heritage, and lively nightlife. Finally, for beach time, head to nearby St. Petersburg and Clearwater, both known for their sugar-sand shores and clear blue waters.
03 of 10
Fort Myers, Florida
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Colorful umbrellas on a beach in Fort Myers, Florida.
Average flight + hotel cost: $517
With its laid-back vibes and ample outdoor adventure opportunities, Fort Myers makes an excellent warm-weather vacation destination. Days are well spent fishing in Pine Island Sound, kayaking the Calusa Blueway, or spotting manatees and migratory birds at nearby wildlife refuges. The city’s Gulf Coast beaches—especially on Sanibel Island—are famed for exceptional shelling, while palm-lined McGregor Boulevard hints at its past as the winter retreat of Thomas Edison and Henry Ford. Historic estates anchor the downtown River District, lined with brick streets, galleries, and theaters. It also hosts events, like the monthly Art Walk.
04 of 10
Fort Lauderdale, Florida
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A hammock hung between two palm trees on a Fort Lauderdale beach.
Average flight + hotel cost: $538
Long known as a spring break capital, Fort Lauderdale has evolved into a more polished, year-round destination. In addition to its 23 miles of beaches, the city offers standout dining, arts, and culture, along with a vibrant downtown scene centered on Las Olas Boulevard. Winter also marks a wave of new developments, including the brand-new Omni Fort Lauderdale Hotel and Huizenga Park, set to reopen in January 2026 following a $15 million renovation. We’d also be remiss not to mention Pier Sixty-Six, which reopened in January 2025 following a $1 billion renovation, bringing revitalized waterfront dining, marinas, and luxury accommodations to Fort Lauderdale’s iconic harbor.
05 of 10
West Palm Beach, Florida
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A view of downtown West Palm Beach, Florida.
Average flight + hotel cost: $560
Long overshadowed by neighboring Palm Beach, West Palm Beach has emerged as a stylish warm-weather hideaway in its own right. In addition to luxe shopping at CityPlace, there’s an increasingly impressive dining scene, ranging from local favorites like Avocado Grill to Michelin-recognized spots such as Moody Tongue Sushi, cementing the city’s culinary credentials. Plus, the newly revitalized NORA District adds fresh energy with designer boutiques and restaurants, and a growing slate of upscale hotels continues to elevate the city’s profile. Winter is an ideal time to visit, with warm days made for waterfront strolls and Saturdays at the West Palm Beach GreenMarket, one of the country’s top farmers’ markets.
06 of 10
Miami, Florida
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A sand walkway to a Miami beach.
Average flight + hotel cost: $587
Travelers in search of a good time should head straight to Miami, where winter warmth sets the stage for endless ways to experience the city. From art-filled Wynwood and trendy Brickell to the swanky streets of Miami Beach and buzzy South Beach, each neighborhood offers its own distinct vibe. A packed winter events calendar—namely the Miami International Boat Show and the Food Network South Beach Wine & Food Festival—draws chefs, creatives, and travelers from around the world, while outdoor dining, beautiful beaches, cultural festivals, and legendary nightlife keep the energy high long after the events end.
07 of 10
Sarasota, Florida
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Sunset over a park in Sarasota, Florida.
Average flight + hotel cost: $614
A trip to Sarasota is a must for arts and culture lovers. The season brings opera at the historic Sarasota Opera House, ballet and symphony performances at the Van Wezel Performing Arts Hall, and acclaimed productions from Florida Studio Theatre. Be sure to also carve out enough time to explore The John and Mable Ringling Museum of Art, from the ornate Ca’ d’Zan mansion to its expansive art collections and manicured gardens. Between performances, visitors can balance museum-hopping with beach time on Siesta Key or wildlife watching at nearby refuges, where manatees and migratory birds are common in winter.
08 of 10
Santo Domingo, Dominican Republic
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A pedestrian street in Santo Domingo at sunset.
Average flight + hotel cost: $635
Although many travelers head straight to Punta Cana, it’s worth checking out Santo Domingo, too. The country’s capital offers fewer crowds and a deeper look at the country’s history and culture, best experienced in the UNESCO-listed Zona Colonial, where cobblestone streets, historic plazas, and centuries-old landmarks invite exploration on foot. Winter also brings a lively calendar of events, from Grupo Bonyé’s free Sunday concerts to traditional celebrations like the Guloyas Festival and Duarte’s Day. Together, they offer a rewarding way to experience the country beyond the typical resort scene.
09 of 10
Kingston, Jamaica
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Houses on the hills of Kingston, Jamaica.
Average flight + hotel cost: $742
Jamaica is continuing its recovery following Hurricane Melissa, and its capital city, Kingston, is welcoming visitors back with much of its cultural core open and active. Highlights include the Bob Marley Museum and the National Gallery of Jamaica, as well as culturally significant areas like Trench Town, bustling hubs such as Coronation Market, and green spaces like National Heroes Park and Hope Botanical Gardens. Not only does visiting this winter help support local businesses and cultural institutions, but it also offers travelers a more in-depth look at Jamaica beyond the resort areas.
10 of 10
Mexico City, Mexico
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Buildings in Mexico City’s Polanco neighborhood.
Average flight + hotel cost: $764
Sure, it’s not a beach destination like Cancún or Los Cabos, but Mexico City still offers plenty for travelers seeking winter sun and substance. The city is also home to some of the world’s most spectacular food, much of it surprisingly affordable—from casual taquerías and neighborhood fondas to buzzed-about eateries like Contramar. Clear, sunny days are ideal for wandering Chapultepec Park, exploring historic neighborhoods like Roma and Condesa, and visiting world-class museums, including the Museo Nacional de Antropología. Winter also coincides with the monarch butterfly migration, when millions of butterflies gather in nearby mountain reserves such as El Rosario and Sierra Chincua, just a few hours from the city.
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