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Historic Hilton and island resorts

Islands are exotic, mysterious and romantic. Time slows down. Sunsets are memorable, and the stars are brighter. Imagine a getaway to a tropical paradise island where you don’t even need a passport, a foreign currency exchange or a phrase book. Welcome to some of the most picturesque Hilton island resorts. If you’ve been collecting hotel rewards from Hilton HHonors, consider rewarding yourself with a Hilton Hawaii or Hilton Puerto Rico vacation.

Embark on a Hilton Hawaii vacation

On the island of Oahu, the historic Hilton Hawaiian Village Waikiki Beach Resort is a true classic. Even before Hawaii was granted statehood in 1959, the resort (now a 60-year-old Hawaiian icon) was one of the island’s main attractions with its tower rooms, lush gardens and numerous pools. Today, the legendary Hilton Hawaiian Village Waikiki Beach Resort is the only true resort in all of Waikiki thanks to its sprawling oceanfront acres. Rubbing up against Duke Kahanamoku Beach, Hilton Hawaiian Village flaunts one of Honolulu’s most enviable locations — the widest point of South Shore’s sparkling white sands, Duke Kahanamoku Beach, adjacent to the now-popular Waikiki Beach.

And the resort certainly lives up to its “Village” name. On 22 lush acres with ponds, waterfalls and wildlife, guests enjoy a stunning 5-acre lagoon, six swimming pools, 20 restaurants and endless entertainment, like the long-celebrated Starlight Luau. The kids club — Camp Penguin — adds extra kid-friendly fun at this family favorite destination. As fun as it is romantic, Hilton Hawaiian Village is also the perfect place to get married, featuring two charming chapels.

Escape to tropical Hilton Puerto Rico,
home to two Hilton Island resorts:

Caribe Hilton in San Juan

U.S. citizens can leave the passport home when traveling to Puerto Rico’s Hilton island resorts, home to three beautiful Hilton Puerto Rico properties. The historic Caribe Hilton, one of the most famous hotels in all the Caribbean, is only 15 minutes from the airport, so you’ll be sipping on a poolside drink in no time — after all, this is the very place where the Piña Colada was born and first served in 1954.

Nestled between historic Old San Juan and the contemporary Condado area of San Juan, Caribe Hilton blends the old with the new, making this a perfect island resort for family members young and old. In fact, we’ve written an entire article devoted to this Caribbean family resort. (And thanks to its views of Fortín de San Gerónimo del Boquerón — a 17th century fort that juts out into the Condado Lagoon — Caribe Hilton is also is a favorite among brides.)

Condado Plaza Hilton in San Juan

With contemporary guest rooms nestled in this historic island property, The Condado Plaza Hilton features one of Puerto Rico’s largest casinos in a trendy waterfront location only five minutes from Old San Juan and the cruise port, and 10 minutes from the airport. Here, the hotel offers high-stakes gaming 24 hours a day in 12,500 square feet of gambling space in this elegant Art Deco casino.

As the only hotel overlooking the Atlantic Ocean and the Condado Lagoon, this historic resort flaunts panoramic views, gentle breezes and ocean activities. The calm, cove-like beach offers the perfect place to paddle an ocean kayak over artificial and natural reefs. Back at Hilton’s chic pools, guests can take a dip in the saltwater pool, lounge in front of the lagoon pool or enjoy a workout in the lap pool.

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