Unbelievably Cheap Caribbean Hotel Deals You Won’t Want to Miss

The Cayman Islands, famous for its offshore activities like scuba diving, is a marine paradise and—expectedly—an expensive place to visit thanks to the banking elite that pack into Grand Cayman’s capital city. Visitors eager to explore the trio of islands and 365 dive sites teeming with stingrays and healthy coral reefs can take advantage of the annual off-season promotion, “Fall Only in Cayman,” which provides island-wide savings when booking by September 30 for travel before December 15. The many perks include complimentary nights and resort credits at participating luxury hotels including the Kimpton Seafire Resort + Spa (debuting this November) and The Ritz Carlton Grand Cayman. Have a diver in the group? Save on dive trips and rental gear at Sunset House and EPIC Divers, or get out on the water for less with discounts from Cayman Islands Boat Rentals and select watersports operators on everything from Waverunner tours to snorkeling excursions to Stingray City.

If being stranded on a deserted tropical island is your idea of the perfect holiday, Turks and Caicos is the place to go. Pristine Parrot Cay, the last in this northern Caribbean string of isles, is home to COMO Parrot Cay, a 1,000-acre private island retreat with its own banana and coconut plantation and mile-long beach as well as one of the best spas in the world. Thankfully, staying in the lap of luxury is more wallet-friendly in the off-season: when guests book one of the hotel’s private villa residences, they have access to their own beach, a butler, and complimentary full board with the option of dining either in the resort's two restaurants or in the privacy of their villa. (Children under 12 stay and dine for free.) Bragging rights, included.

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The unspoiled white beaches of Montego Bay on Jamaica’s north shore are the well-known stomping grounds for names like James Bond, Jackie Kennedy, and the British Royal family. While it’s a pricey place to visit during winter months, well-heeled travelers can stay for a longer sojourn during off-peak windows at Half Moon, an exclusive colonial-style resort named for its two miles of private beach that wrap around a crescent-shaped bay. Among the many highlights at this 400-acre five-star retreat: the 68,000-square-foot Fern Tree Spa (the largest in Jamaica), four- to seven-bedroom villas overlooking the water, championship golf course, equestrian center with a mini-polo field, and a helipad. This season's Island Escape Package, valid through October 31, includes starting rates at just $185 per night (with a three-night minimum).

This little-known West Indies island previously flew under the radar as St. Kitt’s laid-back other half, but it recently landed in the spotlight when Tony Award-winning actor and composer Lin Miranda Manuel visited to gain inspiration for his Broadway hit Hamilton. (Nevis was the birthplace of Alexander Hamilton.) Those that travel before the high-season crowds can score a quiet seaside getaway for a fraction of the cost at Nisbet Planation Beach Club, whose 36 cottage-style accommodations and 30 tropical acres are an ideal respite for families. Its Suite Family Savings offer includes a complimentary connecting second bedroom during a weeklong holiday, as well as an add-on Alexander Hamilton Take-it-to-the-Bank package that offers 25% savings on an island tour, along with some parental pampering like a candlelit dinner and spa treatments.

If partying like a rock star is high on your list of vacation priorities, head to Macao Beach, in the Dominican Republic, and check into the Hard Rock Hotel & Casino Punta Cana. Studded with memorabilia from music legends like Madonna and Elton John and regularly hosting live performances (past headliners include Ringo Starr and Snoop Dogg), this all-inclusive resort lets guests channel their inner celebrity. Weeklong stays during the off-season come with a $3,600 resort credit, which guests can put towards a room upgrade, anteing up at one of the Caribbean’s largest casinos, dining at one of 10 restaurants, or bottle service at the see-and-be-seen ORO nightclub. Options to splurge are endless, from off-site tours and spa treatments to beachfront dinners, lessons at the Nicklaus-designed golf course, swimming with dolphins, and jam sessions at the newly-launched Music Lab. The sweetest part of the deal? The longer your stay, the larger the credit.

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One of the more tropical destinations in the Caribbean, St. Lucia is home to palm-fringed beaches, botanical gardens, a rainforest, and the UNESCO World Heritage Pitons—two towering peaks on the island’s southwest coast. Luxury travelers looking for adventure (and a place to dock their yacht) moor at The Landings Resort & Spa, an all-suite property with a private 80-slip marina, a 7,000-square foot spa, three swimming pools, tennis court, and preferred tee times at the nearby St. Lucia Golf Resort & Country Club. Those who book before September 30 can take advantage of the resort’s off-season Summer Sale, which extends up to 50% off fully-loaded designer villas (many with private plunge pools) for stays through December 16 and includes additional perks including free airport transfers for five-night stays, a $100 resort credit for seven-night stays, and butler service for select suites.

Barbados is a heady mix of beautiful beaches, British sophistication, and rhythmic calypso beats. The island oozes with local culture, as Bajans fully embrace their colonial heritage (a passion for afternoon tea and cricket is prevalent here). There's also a vibrant nightlife scene and multiple colorful coral reefs perfect for underwater exploration. Couples looking to dash off for a romantic island getaway without breaking the bank would do well to consider the End of Summer Sale at the adults-only The House Barbados, where guests enjoy 40% off their room rate when traveling before September 30 or 35% off when traveling during the month of October. Stays also come with a complimentary 30-minute jet-lag massage upon arrival, champagne breakfast, afternoon tea, and evening canapés.

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The sparkling turquoise waters and picture-perfect beaches of the Bahamas have long lured the international jet set, from Sean Connery and Johnny Depp to Kerry Washington and Bey and Jay. Of its 700 islands, the country’s capital Nassau is the most populous and the most visited thanks to its stunning sands, colorful culture, and historic architecture. Meliá Nassau Beach All-Inclusive stretches over seven scenic north shore acres and features a private beach, freshwater pools, waterfalls, six specialty restaurants, and guest rooms overlooking the sea. Visitors traveling before October 30 can shave 20% off their room rate and enjoy a $200 resort credit when staying at least four nights (or a $400 resort credit for six nights). There’s also an additional bonus for families: when parents book before September 11, kids stay for free and have unlimited access to the daily activities planned by the resort’s signature kid’s club, Kid & Co.

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