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There’s something about the holidays that makes us romanticize freezing temperatures. Snow-covered streets, cozy fireplaces, and hot chocolate all sound great in theory. But somewhere between scraping ice off your windshield and fighting over the thermostat at your family’s house, the magic starts to wear off.
Here’s a thought: What if the most wonderful time of the year didn’t have to be the coldest?
While a white Christmas has long been the gold standard of holiday nostalgia, there’s something to be said for celebrating the season with your toes in the sand. Picture oceanfront dinners, tropical cocktails, and afternoons spent by the pool instead of bundled up indoors. The holiday spirit is still very much alive, just with a better forecast.
And it’s not like you have to sacrifice the festivities to get there. Across Hawaii, Mexico, and Puerto Rico, Hilton’s beachfront resorts offer a different approach to the holiday getaway, combining tropical settings with local culture, dining, and experiences that make the trip feel like more than just another vacation.
Best Hilton Beach Resorts for a Warm-Weather Holiday Vacation
In Hawaii, that might mean starting your morning with a swim in the Pacific, exploring the islands’ rich cultural traditions, or catching fireworks over Waikiki Beach. In Los Cabos, it’s oceanfront dining, dramatic coastal views, and a sunset that practically demands a toast.
Puerto Rico, meanwhile, takes its holiday celebrations particularly seriously. The island is known for having one of the longest holiday seasons in the world, with festivities stretching well into January. Between traditional parrandas (Puerto Rico’s version of Christmas caroling), lively music, and Three Kings Day celebrations, there’s no shortage of ways to get into the holiday spirit.
Whether you’re trading holiday routines for a romantic getaway or bringing the entire crew along, there’s no rule that says holiday memories have to be made around a fireplace. After all, the holidays come around every year. You might as well spend this one somewhere you won’t need a winter coat.
Hilton
Hilton Hawaiian Village Waikiki Beach Resort
Some people spend the holidays fighting over the thermostat. Others spend them deciding which pool to visit first. At Hilton Hawaiian Village Waikiki Beach Resort, there are five to choose from, along with waterslides, direct access to Waikiki Beach, and the five-acre Duke Kahanamoku Lagoon. Set across 22 acres in Honolulu, the resort has enough going on to keep everyone entertained, whether you’re traveling with kids, extended family, or someone whose only holiday wish is a lounge chair.
And while lounging by the water is certainly encouraged, there’s plenty worth getting up for. Guests can take part in Hawaiian cultural activities, including hula lessons and lei making, or spend an evening at the Waikiki Starlight Luau, where live music, traditional dance, and an island-inspired feast celebrate the cultures of Hawaii and the Pacific Islands. The resort’s weekly Friday night fireworks are another highlight, proving that holiday celebrations don’t necessarily need snow, sleigh bells, or a single ugly Christmas sweater.
Hilton
Grand Wailea, A Waldorf Astoria Resort
Who says Santa needs reindeer? At Grand Wailea, A Waldorf Astoria Resort, Christmas Eve comes with a particularly memorable entrance: Santa arriving on Wailea Beach aboard an outrigger canoe. The Maui resort takes its holiday celebrations seriously, with a tree-lighting ceremony, a marketplace featuring Made-on-Maui gifts, and seasonal dining that gives the usual Christmas spread some competition. Guests can even join a poke-making class or celebrate with a traditional Hawaiian lūʻau, complete with live performances and island-inspired food celebrating Hawaiian and broader Pacific Island traditions.
When the festivities wind down, the resort’s 40 acres offer plenty of ways to spend the rest of your vacation. There’s the Wailea Canyon Activity Pool, where waterslides and waterfalls make a strong argument for never leaving the water, and the Hibiscus Serenity Pool for a quieter afternoon. Meanwhile, Kilolani Spa draws on Hawaiian culture, local botanicals, and wellness traditions, while Nobu Grand Wailea brings chef Nobu Matsuhisa’s signature Japanese-Peruvian flavors to Maui. Christmas dinner with an ocean view? That’s a tradition we could get behind.
Hilton
Waldorf Astoria Los Cabos Pedregal
Getting to Waldorf Astoria Los Cabos Pedregal is an experience in itself. Guests enter the secluded 24-acre property through the Dos Mares tunnel, which cuts through the rocky mountainside before opening onto sweeping views of the Pacific Ocean. Every room, suite, and villa comes with a private plunge pool, making the resort particularly appealing for travelers looking to escape the usual holiday crowds. But the property isn’t leaving Christmas entirely behind, with seasonal celebrations that include a tree-lighting ceremony, festive dinners, and family-friendly activities.
Food is a major part of the experience, from freshly caught seafood at the cliffside El Farallon to Mexican-inspired dishes at Don Manuel’s. Between meals, guests can unwind at the Waldorf Astoria Spa, lounge beside one of the beachfront infinity pools, or explore Cabo San Lucas with help from the resort’s concierge team. For New Year’s Eve, the resort’s holiday program includes a special dinner at El Farallon, complete with oysters, caviar, Champagne, and live music. It’s the kind of celebration that makes staying home feel considerably less appealing.
Hilton
Caribe Hilton
Puerto Rico doesn’t believe in cutting the holidays short. The island’s festive season stretches well into January, with music, traditional celebrations, and Three Kings Day giving visitors plenty of reasons to extend their stay. At Caribe Hilton, a beachfront landmark in San Juan since 1949, that celebratory spirit comes with ocean views, tropical gardens, and a little cocktail history. Caribe Hilton is the birthplace of the piña colada, created there in 1954 by bartender Ramón “Monchito” Marrero, and guests can still order the island’s signature drink at Caribar.
For the 2026 holiday season, the resort is hosting a Christmas Eve dinner at Néctar del Caribe, followed by New Year’s Eve celebrations featuring live bands, a DJ, and Champagne. Beyond the festivities, guests can explore the property’s 17 acres, relax along its secluded beach, or take advantage of its oceanfront pools and spa. Its location also makes it easy to venture into Old San Juan for historic landmarks, local restaurants, and a closer look at Puerto Rico’s cultural traditions. A holiday with a little history, plenty of music, and a piña colada? Hard to argue with that.
