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Top Caribbean Islands for a Timeshare Vacation

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Posted on September 26, 2023

The Caribbean, with its pristine beaches, crystalline waters, and warm tropical climate, has long been a sought-after timeshare vacation destination. For many travelers, owning a piece of paradise through a Caribbean timeshare is the perfect solution to ensure a luxurious vacation year after year.

With so many islands to choose from, it can be tough to decide where to go. Here are the top Caribbean islands for a timeshare vacation, offering a mix of adventure, relaxation, culture, and breathtaking scenery.

Where Are The Top Caribbean Islands for a Timeshare Vacation?

Aruba

beach on the Caribbean Island of Aruba

Located in the southern Caribbean near South America, Aruba boasts an arid climate, ensuring sun-soaked days perfect for lounging on its white sandy beaches. A major advantage of Aruba is it lies south of the traditional Caribbean storm zone, so tropical storms do not impact the island.

Timeshare properties in Aruba are popular due to their proximity to areas like Palm Beach, upscale shopping, fabulous natural attractions and world-class dining. The island's consistent trade winds make it ideal for wind and kite surfing. Moreover, with a rich blend of Dutch, African, and Spanish heritages, there's plenty to explore culturally.

Top Aruba Timeshares: Marriott's Aruba Surf Club, Marriott's Aruba Ocean Club, Playa Linda Beach Resort Aruba, Divi Aruba Phoenix Beach Resort

St Maarten/St. Martin

Philipsburg St Maarten

Divided between Dutch and French territories, this island has long been popular for timeshare resorts.

The Dutch side, St. Maarten, is renowned for its lively nightlife, beaches, casinos and vibrant shopping districts. In contrast, the French side, St. Martin, exudes a laid-back vibe with its boutique shops, French cuisine, and secluded beaches. Timeshares are abundant here, catering to both the party-goer and the quiet-seeking traveler.

Top St. Maarten Timeshares: Simpson Bay Resort & Marina, Royal Palm, a Hilton Vacation Club, Oyster Bay Beach Resort, Divi Little Bay Beach Resort

Nassau, Bahamas

Harborside at Atlantis, Paradise Island, Nassau

There is debate whether the Bahamas are actually in the Caribbean or considered within the Atlantic Ocean. Regardless, Nassau, the capital, is a very popular timeshare hub known for its beaches, shopping, dining, and nightlife.

Beyond its iconic pink-hued buildings and historic forts, Nassau has a vibrant arts scene, with native Junkanoo festivals adding bursts of color and rhythm to its streets. Paradise Island and its world-famous Atlantis Resort, complete with casinos, water parks, and marine habitats, are just a drive over the bridge away.

Top Nassau Timeshares: Harborside Resort at Atlantis, Paradise Island Beach Club

St Thomas, U.S. Virgin Islands

Magens Bay St Thomas

A vibrant blend of cosmopolitan charm and tropical splendor, the U.S. territory of St. Thomas is a paradise for both relaxation and adventure.

Charlotte Amalie, the capital of St. Thomas, offers a unique mix of high-end shopping and historic sites, like Fort Christian. Magens Bay, frequently listed among the world's top beaches, is an iconic crescent of sand perfect for sunbathing and watersports. Timeshares in St. Thomas are often hillside, providing panoramic views of the turquoise Caribbean waters, making every sunrise and sunset an event.

Top St. Thomas Timeshares: Ritz Carlton Club Saint Thomas, Marriott's Frenchman's Cove, Limetree Beach Resort by Club Wyndham, Bluebeard's Castle

St Croix, U.S. Virgin Islands

Carina Bay on the Caribbean Island of St Croix

The largest of the U.S. Virgin Islands, St. Croix is a mosaic of various landscapes, from rainforests and mountains to white-sand beaches. Its rich history is evident in the well-preserved architecture of Christiansted and Frederiksted. Buck Island, with its underwater national park, is a snorkeler's dream. Timeshares in St. Croix cater to those who want a blend of nature, history, and beachfront luxury.

Top St. Croix Timeshares: Divi Carina Bay All Inclusive Beach Resort, Hotel on the Cay

Puerto Rico

Old San Juan, Puerto Rico

As a U.S. territory, Puerto Rico offers a blend of Caribbean charm and modern conveniences without the need for Americans to take their passports. Old San Juan, with its cobblestone streets and Spanish colonial architecture, transports visitors back in time. Meanwhile, the El Yunque National Forest offers a different kind of retreat, being the only tropical rainforest in the U.S. National Forest System. With an array of timeshare options available, Puerto Rico caters to a variety of vacation styles.

Top Perto Rico Timeshares: Wyndham Rio Mar, Hyatt Hacienda del Mar

Grand Cayman, Cayman Islands

seven mile beach, Grand Cayman

Grand Cayman is the largest of the three Cayman Islands and is a hub for fun. Famous for its Seven Mile Beach, it's a haven for divers with the Cayman Trench offering breathtaking coral reefs and the unique Stingray City where visitors can swim among friendly stingrays. Timeshares in Grand Cayman tend to be luxurious, offering wonderful views of the Caribbean Sea.

Top Grand Cayman Timeshares: Seven Mile Beach Resort, Morritt's Tortuga Club, Wyndham Reef Resort Grand Cayman

Dominican Republic

Punta Cana on the Dominican Republic

The Dominican Republic, particularly Punta Cana, is an emerging timeshare destination and famed for its all-inclusive resorts. Buying a timeshare here means gaining access to miles of sandy beaches, golf courses designed by legends, and National Parks with activities like zip-lining and horseback riding. The cultural mosaic of Taino, Spanish, and African influences also provides a unique backdrop for travelers.

Top Dominican Republic Timeshares: Bahia Principe Grand, Lifestyle Holidays Vacation Club at Crown Villas

Barbados

Bridgetown Barbados

With its British colonial history, Barbados offers a unique blend of Caribbean and English charm with one of the highest standards of living in the Caribbean. The west coast, known as the "Platinum Coast," is famous for its luxurious resorts and calm turquoise waters, making it an ideal spot for timeshares. The island's rich culture, world-class golf courses, and renowned Crop Over Festival are added attractions.

Top Barbados Timeshares: Residences at the Crane, Divi Southwinds Beach & Racquet Club

Points to Ponder As You Consider a Caribbean Timeshare

Accessibility and Connectivity: Islands like St. Thomas, Puerto Rico and Nassau have good domestic and international flight options, often resulting in better flight deals and more direct routes. The infrastructure in these and other more well-established timeshare destinations such as St. Maarten, Barbados and Grand Cayman means the phone and internet connections shouldn’t be as much of an issue as in emerging destinations.

Local Festivals: Nearly all Caribbean islands host local festivals, which can be a major attraction for tourists. For instance, the Crucian Christmas Carnival in St. Croix is a vibrant celebration of music, dance, and culture, while Pirates Fest in Grand Cayman is a rollicking good time.

Water Activities: The crystal-clear waters of the Caribbean make it a hotspot for water-based activities. Consider proximity to renowned snorkeling, diving, and swimming spots when choosing a timeshare location.

Local Culture: Even though many visitors may have a standard image of what a Caribbean Island looks like, each island has its own unique history and culture. Exploring these aspects can add depth to your vacations.

Storm Season: The Caribbean can be prone to tropical storms and hurricanes. It's wise to consider insurance options, buying timeshare outside of the August-October prime storm season or opting for islands outside the main hurricane belt.

Other Factors When Considering Timeshares in the Caribbean

Maintenance Fees: Ensure that you're aware of how and where annual maintenance fees associated with the timeshare are paid, since these can be considered international transactions. Many companies with Caribbean timeshares are based in the States, but not all of them.

Exchange Opportunities: Nearly every timeshare company offers external exchange options. However, some branded programs like Divi and Marriott offer internal exchanges within their networks for other Caribbean locations.

Local Amenities: Think about the proximity to attractions, beaches, dining, shopping, and other amenities that can enhance the vacation experience.

How About Buying a Caribbean Timeshare?

The Caribbean is a paradise filled with diverse cultures, fun activities, and incredible landscapes. Choosing a timeshare on one of these top islands guarantees annual escapes to some of the world's most idyllic locations. Whether seeking adventure, relaxation, or a mix of both, there's a Caribbean Island timeshare that is perfect for every vacation dream.

With so many islands and options to choose from, it may be tough to know where to begin. Thankfully, our licensed agents are experts in helping you decide on the right destination for you and your family.

Call us on 877-624-6889 or send us your questions through the form on our Contact Us page and our agents will help in any way they can.

Author

Author Pic
Steve Luba
Chief Communications Officer

Steve manages the public relations and content creation efforts of the company. Previously the Chief Operating Officer for Perspective Magazine, he provided oversight and contributed articles for the five regional vacation ownership trade magazines under the Perspective Magazine banner. 

A contributor for industry publications such as Resort Trades and Developments Magazine, Steve Luba has 36 years of experience in various roles in radio and television, sales and marketing, public relations, media and government liaison initiatives. 

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