Tired of scraping ice off your windshield or layering up just to fetch the mail? We get it. 

So maybe it’s time to swap your boots for flip-flops and enjoy a warm, affordable winter abroad. We’ve rounded up 20 fantastic destinations where you can live comfortably for less than $2,000 a month while also enjoying a bit of sun during the wintry season. 

From stunning beaches to vibrant cities, nearly every one of these places offers welcoming expat communities, easy visa options, and plenty of sunshine.

1. Oaxaca, Mexico 

Cost of Living: Rent $400-$700/month; total around $1,200. 

Climate: Warm, dry winters with daytime highs around 80°F (27°C). 

Details: Oaxaca is a haven for culture lovers, with its colorful streets, rich traditions, and world-renowned food scene (mole and mezcal!). The city hosts festivals year-round, and expats praise Oaxaca for its welcoming vibe and walkable historic center. Mexico’s Temporary Resident Visa is a solid option if you want to stay long-term, requiring minimal proof of income.

2. Mérida, Mexico 

Cost of Living: Rent $450-$750/month; total around $1,200-$1,500. 

Climate: Hot and sunny year-round; winter highs hover near 90°F (32°C). 

Details: Mérida is the cultural capital of the Yucatán, with stunning colonial architecture, thriving arts, and proximity to Mayan ruins. It’s also one of Mexico’s safest cities. With a growing expat population, Mérida offers a uthenticity and community support, and longer stays are easy with Mexico’s visa options.

3. Medellín, Colombia

Cost of Living: Rent $400-$600/month; total around $1,200-$1,500. 

Climate: “Eternal spring” weather, with temps around 72°F (22°C) year-round. 

Detail: Medellín is a poster child for urban transformation, evolving from troubled to vibrant and modern. With a cutting-edge metro, great co-working spaces, and stunning mountain views, the city has a thriving digital nomad scene. And Colombia’s digital nomad visa, launched in 2022, is a great option for remote workers, while retirees benefit from the pensionado visa.

4. Cartagena, Colombia  

Cost of Living: Rent $500-$800/month; total around $1,400-$1,800. 

Climate: Tropical, with winter highs in the 80s°F (27-30°C). 

Details: Cartagena combines Spanish colonial charm with Caribbean flair. Its UNESCO-listed Old Town is a maze of colorful streets, historic churches, and lively plazas. Nearby are pristine beaches and idyllic islands like Isla Barú. Visa options mirror those in Medellín.

5. Tamarindo, Costa Rica

Cost of Living: Rent $600-$1,000/month; total around $1,700-$2,000. 

Climate: Tropical; dry and sunny in winter with highs around 85°F (29°C). 

Details: Tamarindo is Costa Rica’s quintessential beach town, attracting surfers, yogis, and digital nomads. Known for its golden sands and lively nightlife, it’s a bit pricier than other Costa Rican spots, but offers a wealth of amenities. Costa Rica’s “rentista” and “pensionado” visas are tailored for long-term stays, requiring proof of income or retirement funds.

6. Atenas, Costa Rica  

Cost of Living: Rent $500-$800/month; total around $1,200-$1,500. 

Climate: Mild and warm, with daytime highs in the 80s°F (27°C). 

Details: Nestled in the Central Valley, Atenas is a tranquil retreat known for its small-town charm and stunning mountain views. The town is ideal for retirees and expats looking to escape the hustle, while its central location makes it easy to explore Costa Rica’s beaches and national parks. Visa options include the same “rentista” and “pensionado” schemes.

7. Salinas, Ecuador

Cost of Living: Rent $400-$600/month; total around $1,000-$1,500. 

Climate: Coastal and warm, with winter highs around 75°F (24°C). 

Details: Often dubbed “Little Miami,” Salinas offers beachfront living without breaking the bank. The Malecon is a hub of activity, with restaurants, shops, and ocean views. Ecuador’s Retirement Visa is popular among expats, requiring modest proof of income. For digital nomads, a six-month tourist visa can be extended.

8. Manta, Ecuador

Cost of Living: Rent $300-$600/month; total around $1,000-$1,400. 

Climate: Tropical and breezy; winter highs in the 80s°F (27°C). 

Details: Manta, a bustling port city, is known for its fresh seafood, beautiful beaches, and laid-back atmosphere. It’s quieter than Salinas, making it perfect for those seeking tranquility. Long-term stays are supported by Ecuador’s visas, among the most flexible in South America.

9. Chiang Mai, Thailand 

Cost of Living: Rent $300-$500/month; total around $1,000-$1,500. 

Climate: Cool and dry in winter, with temps in the 70s-80s°F (21-27°C). 

Details: Chiang Mai is a digital nomad mecca, blending affordability, ancient temples, and a thriving expat scene. Monthly coworking memberships are as low as $50, making it ideal for remote workers. Thailand’s Long Stay Visa (O-A) and the new Long-Term Resident Visa cater to retirees and digital nomads.

Read More like this: Buying Property in Thailand

10. Krabi, Thailand

Cost of Living: Rent $400-$800/month; total around $1,200-$1,800. 

Climate: Tropical, with sunny winter days around 88°F (31°C). 

Details: With its postcard-perfect limestone cliffs and turquoise waters, Krabi is paradise. Life here revolves around beaches, kayaking, and jungle adventures. Like Chiang Mai, Krabi benefits from Thailand’s visa options for long-term stays.

Read more like this: The Top Five Cities to Consider for a Winter Move

11. Ho Chi Minh City, Vietnam 

Cost of Living: Rent $300-$500/month; total around $1,000-$1,300. 

Climate: Dry and warm in winter, with temps around 85°F (29°C). 

Details: HCMC is Vietnam’s bustling economic hub, with a dynamic mix of street food, skyscrapers, and culture. Its expat community is one of Southeast Asia’s largest, and Vietnam recently launched a digital nomad visa.

12. Da Nang, Vietnam

Cost of Living: Rent $300-$600/month; total around $1,000-$1,400. 

Climate: Mild winters, with temps in the 70s°F (21-26°C). 

Details: A coastal gem, Da Nang has miles of sandy beaches and a relaxed vibe. It’s a favorite for those seeking a quieter alternative to HCMC, with plenty of coworking options and a budding expat community, plus the same visa options.

13. Penang, Malaysia

Cost of Living: Rent $400-$700/month; total around $1,200-$1,600. 

Climate: Tropical, with winter temps around 85°F (29°C). 

Details: Penang is a foodie’s paradise, known for its fusion cuisine and UNESCO-listed George Town. Malaysia’s MM2H (Malaysia My Second Home) visa is expat-friendly, making it an excellent choice for long stays.

14. Langkawi, Malaysia  

Cost of Living: Rent $400-$800/month; total ~$1,500-$1,800. 

Climate: Warm and humid year-round, with winter highs in the 80s°F (27-30°C). 

Details: Langkawi offers island living at its finest, complete with duty-free shopping. It’s perfect for nature lovers, with its lush rainforests and pristine beaches.

15. Madeira, Portugal 

Cost of Living: Rent $600-$900/month; total ~$1,500-$2,000. 

Climate: Mild and sunny winters, with highs around 70°F (21°C). 

Details: Madeira is a subtropical paradise offering hiking, wine, and ocean views. Portugal’s D7 visa is ideal for digital nomads and retirees, requiring proof of passive income.

16. The Algarve, Portugal 

Cost of Living: Rent $600-$1,000/month; total ~$1,500-$2,000. 

Climate: Mild winters, with highs around 65°F (18°C). 

Details: Situated at the southwestern corner of Europe, where the Atlantic meets the Mediterranean, the Algarve’s golden beaches and golf courses attract nomads and retirees from around the world. In addition, Portugal’s welcoming visa options and established expat communities make it a top pick.

17. Marrakesh, Morocco

Cost of Living: Rent $300-$500/month; total ~$1,000-$1,300. 

Climate: Mild and sunny, with winter highs around 70°F (21°C). 

Details: One of the more mysterious and exotic cities of the Arab world, Marrakesh’s bustling souks and stunning riads offer an exotic escape. Morocco’s visa system is straightforward, with extensions available for stays beyond 90 days.

18. Essaouira, Morocco 

Cost of Living: Rent $300-$500/month; total ~$1,000-$1,300. 

Climate: Warm and breezy, with winter highs around 68°F (20°C). 

Details: Known for its laid-back vibe, Essaouira is a stunning coastal gem and a favorite among artists, surfers, and nomads. Its slower pace is complemented by Morocco’s accessible visas.

19. Izmir, Turkey 

Cost of Living: Rent $300-$500/month; total, around $1,200-$1,500. 

Climate: Mild winters, with daily highs around 60°F (15°C). 

Details: Turkey’s Aegean coast tends to be under-appreciated because of the popularity of nearby Greek islands. But Izmir blends modern amenities with ancient history and a lovely waterfront, and is close to the resort towns of Cesme and Alacati. To top it off, Turkey’s new digital nomad visa makes it easy for remote workers to settle in.

20. Antalya, Turkey 

Cost of Living: Rent $400-$700/month; total ~$1,200-$1,800. 

Climate: Mediterranean winters, with highs in the mid-60s°F (18°C). 

Details: Nestled along the glittering Mediterrean, Antalya is famous for its turquoise waters and Roman ruins. Expats appreciate its affordability and strong community, as well as its Lycean hiking trails. Turkey’s flexible visa options make it easy to stay. 

Read More like this: 6 Countries Easy Get Residency Visa

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With all these options, you may want to do a bit more research to decide where to take your flip-flops this winter. But now you know what’s out there. Happy hunting, and bon voyage.