When winter gets cold and days feel shorter, many people start dreaming of sunshine. The good news is that you don’t need to spend a lot of money to enjoy warm weather this season.
To find the cheapest warm destinations, travel search site Kayak studied flight and hotel prices for trips between December 21, 2025, and February 28, 2026, departing from U.S. airports. Prices include round-trip economy flights and average nightly hotel costs for two people.
According to Kayak’s travel expert, Sarah Kennedy, Florida dominates this winter with several cities offering great value. She also noted that destinations like Jamaica are welcoming tourists again, making it a good time to travel while supporting local recovery.
Here are the 10 most affordable warm-weather destinations this winter:
1. Orlando, Florida
Average cost: $463
Orlando stays lively even after the holidays with festivals, theme parks, and outdoor activities. Winter weather is perfect for visiting Disney, Universal Studios, and downtown spots like Lake Eola Park.
2. Tampa, Florida
Average cost: $463
Tampa offers sunshine, nearby beaches, festivals, and great food. Walk along the Tampa Riverwalk, explore historic Ybor City, or visit Clearwater and St. Petersburg for beach time.
3. Fort Myers, Florida
Average cost: $517
Known for its relaxed vibe, Fort Myers is great for kayaking, fishing, wildlife spotting, and shell collecting on Sanibel Island. The city also has a charming historic downtown.
4. Fort Lauderdale, Florida
Average cost: $538
With long beaches, a lively downtown, and new hotels and parks, Fort Lauderdale is now more than a spring break spot. Las Olas Boulevard is perfect for shopping and dining.
5. West Palm Beach, Florida
Average cost: $560
West Palm Beach has become a trendy destination with great restaurants, shopping, and waterfront walks. Winter is ideal for visiting local markets and enjoying outdoor cafés.
6. Miami, Florida
Average cost: $587
Miami is full of energy in winter, with beaches, nightlife, food festivals, and art districts like Wynwood. Warm weather makes it perfect for outdoor dining and events.
7. Sarasota, Florida
Average cost: $614
Sarasota is ideal for art and culture lovers. Enjoy museums, opera, and theater shows, along with beautiful beaches like Siesta Key and nearby wildlife areas.
8. Santo Domingo, Dominican Republic
Average cost: $635
Santo Domingo offers history, culture, and fewer crowds than resort towns. Explore the historic Zona Colonial, enjoy live music, and experience local festivals.
9. Kingston, Jamaica
Average cost: $742
Kingston is welcoming visitors again after recent storms. Travelers can explore Jamaican culture at the Bob Marley Museum, local markets, and beautiful parks while supporting local businesses.
10. Mexico City, Mexico
Average cost: $764
Mexico City may not have beaches, but it offers sunny weather, amazing food, historic neighborhoods, parks, and world-class museums—all at affordable prices.
If you’re looking to escape the cold without overspending, these destinations offer sunshine, culture, and great value. Florida stands out as the cheapest option, while international cities provide rich experiences on a reasonable budget.