Old San Juan’s pretty blue cobblestone streets are the perfect base camp in Puerto Rico’s largest city because you can always taxi over to Condado Beach (three miles away) or walk to nearby education-oriented attractions (such as San Felipe del Morro Fortress). Rates at Hotel El Convento (a retrofitted former convent with a pool and two restaurants) run $383 per night Dec. 21-26.

If relaxing means never leaving the hotel—but not eating at the same place every night—SLS at Baha Mar is ideal. Rates fall to $345-$370 Jan. 2-6, nearly 50 percent less than Christmas week. This chic hotel in the beachfront Baha Mar development offers access to 19 restaurants (from Japanese at Katsuya to tacos at the El Jefe food truck), six pools, a casino, and bars—plus complimentary water-sports rentals.

Continually ranked one of the Caribbean’s best beaches, Seven Mile Beach (yep, almost seven miles in length) is lined with resorts. Rates in the few days before Christmas fall to $190-$199 at two Seven Mile hotels—Comfort Suites Seven Mile Beach and Sunshine Suites Resort—a deep dive from $749 at Grand Cayman Marriott Beach Resort. The capital city of George Town and a turtle farm are nearby.

While it can be a haul to reach this blissful island—from Belize City (reachable on Southwest Airlines), hop a small plane to San Pedro—it’s worth it. Snorkeling is top notch, including Shark Ray Alley (don’t worry, not the dangerous sharks), on the world’s second-largest reef. Between Dec. 22 and New Year’s, pay between $292-$375 at Playa de Sala (https://www.playadesala.com) on Cayo Espanto (off the coast of Ambergris Caye).

Tulum’s no-frills resorts—90 minutes south of Cancun’s all-inclusives—offer significant savings and you’re still on the beach and near attractions like Mayan ruins and cenotes (underwater caves). L.Hotelito’s rates are only $120 between Christmas and New Year’s while the adults-only Joy Tulum runs $126. (Both boast pools.) This just means you’ll have the budget to explore Tulum’s hip dining scene.

While farther south in the Caribbean, flights to Oranjegstad—Aruba’s capital—are plentiful, including on Southwest Airlines. This is one of the Caribbean’s best islands for dining as options span steakhouses to vegan. Talk of the Town Hotel and Beach Club is a chic spot to hunker down after you open Christmas presents at home; $256 rates provide access to a pool and two restaurants.

Chain and full-service hotels on this lush island—with attractions like the Sulphur Springs for DIY pampering—charge upwards of $350 on Christmas Day but quite a few boutique hotels in Rodney Bay don’t (like Coco Palm, $116, with two restaurants and a pool; or the five-year-old Blu St. Lucia for $106, with packages including a buffet breakfast, plus option to book a spa treatment).

The D.R.’s resort capital—Punta Cana—offers package deals at its resorts over the holidays that are among the Caribbean’s lowest. Christmas Day at the recently renovated Melia Caribe Beach Resort costs $207, and Paradisus Palma Real Golf & Spa Resort, $267. Both are all-inclusives. Culture seekers will enjoy an excursion to Santo Domingo, the capital and largest city, with buildings dating to the 1500s.

FromSapphire Beach to Magens Bay, this U.S. Virgin Island is known for its beautiful beaches. Point Pleasant Resort—four miles from Magens Bay, and close to Coki Beach—runs only $144 on Christmas Day. That’s possibly due to the fact that it reopens from hurricane damage Dec. 17. Three outdoor pools and two restaurants are on property. Charlotte Amalie’s shops, restaurants, and art galleries are a treasure trove.

JetBlue’s flights to Willemsted—the capital of Curacao—put this Southern Caribbean island within budget. Colorful European-style buildings on the waterfront allow for easy strolls. Rates at mid-range chain hotels aren’t terrible: Renaissance Curacao Resort & Casino on Christmas Day is only $259, for example, and the pool at the super-cute, boutique-y Scuba Lodge & Ocean Suites ($161) overlooks the beach.