5 Winter Escapes That Cost Less Than $1,000 Round-Trip

We may receive a commission on purchases made from links.

If you're looking for a good way to beat the winter blues, peruse Expedia's "Vacations Under $1000" packages, which bundle round-trip airfare with a range of accommodations to warm-weather destinations. Some of the best options are popular beach locations near the U.S., as round-trip flights to these areas from America are usually inexpensive due to how frequently the routes are flown. Expedia combines these low-cost airfares with deals on affiliated hotels that partner directly with the travel company. As a result, you can get discounted prices and spend under a grand on stays of up to six or seven nights.

Of course, prices are tentative and subject to change. Costs depend on a number of factors, including your travel dates, whether or not those dates are flexible, and your departure airport. Before booking, do your research on which destinations interest you the most, and read up on the latest best practices for finding cheap flights. Using Expedia's tool, each vacation package allows you to fly into a major airport, pick from optional add-ons like car rentals, and choose accommodations across a range of budgets, from luxury apartment-style stays to family-run guesthouses. For further customization, use Expedia's filters to sort results by total price, neighborhood, and accommodation type. Plus, before finalizing your selections, you can read guest reviews to see what suits you best.

These packages invite everyone to chase the sunshine, from tropical hotspots in Colombia to Dominica, a stunning "Nature Island" in the Caribbean. Among all the winter escapes that cost less than $1,000 round-trip (using Miami International Airport as the departure point), we're highlighting five affordable winter getaways that pair warm climates with gorgeous beaches, outdoor experiences, and cultural sites.

For $624, you can visit the vibrant city of Cartagena, Colombia. The trip includes round-trip tickets to and from Cartagena's Rafael Nunez International Airport and a seven-night stay at contemporary-style oceanfront property Bondo Estudio (rated 9.2 out of 10 on Expedia). To reach the area, take an official taxi just a few miles from the airport or use a rideshare app like InDrive. It'll cost as little as $5. Once you arrive, the city is very easy to explore on foot.

Located in the Marbella neighborhood, near the city's historic center, Bondo Estudio will put you up in a standard room with a light, airy, beachy aesthetic. On the building's rooftop, enjoy a pool, bohemian-style bar area, and terrace overlooking the nearby beach. For a beach day, however, skip the shores in the city. Instead, head to the Rosario Islands, which host numerous pristine beaches scattered over nearly 30 islands within San Bernardo National Natural Park. Local tour operators offer day trips to the area. For an unforgettable experience, try snorkeling or scuba diving to see the protected coral reefs and marine life.

Within the city, explore trendy neighborhoods like the colorful Getsemaní neighborhood. It's lined with street art, pastel-hued colonial-era buildings, lively bars, and food stalls. Also worth a visit is the nearby Castillo San Felipe de Barajas, a historic Spanish castle built in the 17th century. Next, watch the sunset over the ocean while enjoying a cocktail at Baluarte de Santo Domingo, a restaurant within the walled fort.

Santo Domingo is the major point of entry for most travelers who visit the Dominican Republic, one of the five Caribbean countries where the U.S. dollar goes furthest. Currently, a six-night package with round-trip tickets to Santo Domingo in early February 2026 costs $755. Once you arrive, find the sun-drenched beaches of Punta Cana by renting a car and driving along the island's scenic eastern coast for about two and a half hours.

As you head out of the city, you'll approach the luxurious accommodation included in your vacation package. Xeliter Cana Rock Punta Cana, located in the Cana Bay area north of some of the island's best beaches, is a gated residential property just a stone's throw from local golf courses. Guests stay in a one-bedroom deluxe apartment, which features a living room, king-size bed, and kitchen, plus a balcony overlooking an infinity pool. You'll also have access to a rooftop hot tub, but the real perk of this apartment-style stay is that it allows you to save some money by preparing meals at home in between outings. 

Cooking your own food might help you save the $90 it takes to tour the iguana-packed Reserva Ecológica Ojos Indígenas, a 1,500-acre nature reserve full of trails and hidden lagoons. It's also home to cenotes you can swim in and rich biodiversity. Tours run twice a day, with one at 10 a.m. and another at 2 p.m., so it's recommended to book in advance. Afterward, visit nearby Bavaro Beach, which is lined with tour guides ready to take you boating, snorkeling, or paragliding.

For $713, you can book a six-night, late February 2026 trip from Florida to Vieques, Puerto Rico. Travelers flock here for the warm weather, as winter temperatures are usually around 80 degrees Fahrenheit. From San Juan, you can reach Vieques via either a roughly 45-minute ferry ride from Ceiba (a town on the east coast about an hour's drive from the capital) or a 30-minute flight from Fernando Luis Ribas Dominicci Airport (just 7 miles from the San Juan International Airport). Flights are usually affordable, ranging from $130 to $160 round-trip through regional carriers like Vieques Air Link.

Located under 5 miles from Antonio Rivera Rodríguez Airport in Vieques, the Seagate Hotel is a highly rated guesthouse included in your bundled offer. You'll enjoy a clean and basic room with one queen bed at the family-run hotel, which is the oldest hotel still in operation in the city. Within walking distance, you can easily reach restaurants, beaches like Sea Glass Beach, and shops. A light breakfast is available every morning, and the staff can assist you with car rentals and tours to explore the island. One Tripadvisor user loved the friendly staff and the location: "Kelly our hostess went out of her way to make sure our trip was flawless! We enjoyed the cottage and surrounding amenities. We walked into town to have dinner at a recommended local restaurant and enjoyed the surrounding location nestled right above the historic Fort Conde de Mirasol and overlooking the town."

The island is known for its pristine beaches where wild horses roam freely, and for some of the best beaches to watch bioluminescent waves. A tour to Mosquito Bay is a must to see the ocean lit up by microscopic organisms. Other popular beaches include Playa La Chiva, Black Sand Beach, and Caracas Beach, all scenic beaches located on the southern side of the island, to get that vacation tan.

Along Mexico's Caribbean coast in Quintana Roo, Cancun offers frequent, affordable flights on Expedia due to its short distance from the states. When we used Expedia's "Vacations Under $1000" search tool, we found round-trip tickets to Cancun from February 22 to 28, 2026, including one room for six nights priced at $617. It's recommended to rent a car at the Cancun airport, which is just 35 miles from Playa del Carmen. The attractions are spread across the region, so this is the best way to travel at your own pace and visit the spots that interest you the most

The package offers a stay in a basic but comfortable room with a terrace at the Tukan Hotel Playa del Carmen. It's located right on the main drag within walking distance of shops, restaurants, and beaches like Playa Mamitas and Coco Beach. The hotel features two pools and a Jacuzzi, but most travelers use it as a perfect jumping-off point to explore the nearby attractions without long hours on the road. One Expedia reviewer raved about the great location, saying, "I loved that El Tukan is an oasis in the middle of a busy city. We could sit by the pool with its beautiful gardens surrounding us. The rooms were comfortable and clean with a king sized bed."

Your first stop should be the Zona Arqueológica de Playa del Carmen, which offers a look at Mayan ruins somewhat hidden in plain sight. When the heat hits, check out the turquoise Cenote Azul located just 15 miles from the city. The region is dotted with cenotes, caverns full of turquoise water usually surrounded by limestone and tropical plants. Another day can be spent in the Reserva de la Biósfera Sian Ka'an, a UNESCO-designated wetland reserve. For a calm trip down the crystalline Mayan Canal, book a snorkeling tour.

For travelers who prefer outdoor-focused trips over all-inclusive type vacations, visit the island of Dominica. For around $834 at the time of writing, including round-trip tickets to Douglas-Charles Airport in Marigot, Dominica, you can stay in late January 2026 for six nights with basic accommodation. Your stay at the Hibiscus Valley Inn includes a room in a comfortable bungalow that comes with a fan and a porch with a hammock, surrounded by manicured gardens. Not only is there a swimming hole on site, but there is also a nearby secret beach. There's also a restaurant at the accommodation that serves up locally sourced ingredients; you can even join the chef to collect the freshly caught fish of the day. The owners can also organize tours on your behalf around the island to some of the most famous attractions as well as lesser-known destinations on the island. One Expedia reviewer described it as a gem: "Hibiscus Valley Inn makes it very easy to explore the island, and at the same time has none of the 'corporate' feel that you get in resorts. It's a family-run business, using local guides and growing much of its own food right on site – it's one of those places that is so hard to come by, and I would warmly recommend it."

Outdoor types will love exploring Morne Trois Pitons National Park, which includes the stunning Trafalgar Falls and Emerald Pool, both reached by short walks through the rainforest. Or visit the village of Wotten Waven to soak in its hot springs, perfect for relaxing after a long day of activities. Located about 6 miles away from the inn, you can visit Kalinago Barana Aute, a cultural site that explores the island's Indigenous heritage.

Using Expedia's search engine, we selected these winter destinations based on which places offered warm weather, budget-friendly flights, and affordable accommodation packages. Additionally, locations with a wide range of attractions, from beaches and cultural sites to outdoor excursions, were prioritized to ensure every traveler has entertaining attractions to choose from.

To keep costs consistent, totals were calculated assuming a departure from Miami International Airport, which offers year-round flights. (All trips cost $1,000 or less at the time of writing, though they are subject to change.) Then, we hand-selected accommodations based on which options were most highly rated on Expedia. Research also included cross-referencing firsthand experiences in some of these destinations against Tripadvisor and Expedia reviews.

In the end, our five winter escapes were all found in the Caribbean. Prefer to spend your winter in a different part of the world? Consider checking out these warm winter escapes in Europe and these equally wonderful destinations in Asia.