Caribbean Timeshare

Caribbean timeshare prices typically range from a few thousand dollars on the resale market to $24,000 or more when buying directly from a developer, based on 2025 ARDA averages. The island, brand, season, and unit size all move the number. On the resale market, owners set their own asking prices — so you’ll often find postings for considerably less than you’d pay at a sales presentation.

Annual maintenance fees are an ongoing cost of ownership. According to ARDA, the national average is $1,550 per weekly interval, though your exact amount will vary depending on your resort and ownership type.

If you’re looking for the most popular timeshare resorts in the Caribbean, the first place you should look is the most popular islands. That said, some of the best Caribbean resorts can be found on Aruba, the Dominican Republic, Barbados, the US Virgin Islands, and the Bahamas.

The best time to visit the Caribbean depends on what you’re looking to get from your vacation. If it’s dry, comfortable weather, December through April offer plenty of sunshine and low humidity. However, this is considered peak season. So, if lower rates and smaller crowds are a priority, consider vacationing in the shoulder seasons of May through June or November.

The biggest names in Caribbean vacation ownership include Marriott Vacation Club (Aruba, St. Kitts, U.S. Virgin Islands), Hilton Grand Vacations, Wyndham Destinations, Hyatt Vacation Club, Bluegreen Vacations, and Holiday Inn Club Vacations.

Each one works differently — points systems, exchange programs, and resort access all vary by brand. Browse current owner postings on Timeshares Only to compare what’s available.

Many Caribbean islands have timeshare resorts — Aruba, Jamaica, The Bahamas, Puerto Rico, Barbados, St. Maarten, and the U.S. Virgin Islands among them.

• Aruba – Near-perfect weather year-round
• St. Maarten / Sint Maarten – One island, two countries, great food
• Jamaica – Iconic resorts along Montego Bay and Negril
• The Bahamas – Close to the U.S. mainland, with water that looks almost unreal
• Puerto Rico – A U.S. territory, no passport required
• U.S. Virgin Islands – Same passport-free perk, different vibe
• Barbados – Refined west-coast beaches and upscale resort options

Browse the Timeshares Only marketplace to see what owners are advertising across these destinations.

Yes — some Caribbean timeshare resorts are all-inclusive, and Jamaica and the Dominican Republic are your best starting points. The model is deeply embedded in how those destinations operate.

That said, plenty of Caribbean timeshares skip the all-inclusive model entirely — many come with full kitchens, so you eat on your own terms. If all-inclusive matters to you, check the resort details carefully when browsing, or ask one of our associates to help you narrow it down.

To sell a Caribbean timeshare, create an advertisement on a marketplace like Timeshares Only — set your asking price, your posting goes live, and interested buyers come to you.

How it works:

1. Submit your details — resort, season, unit type, and asking price
2. Your posting goes live — visible to buyers actively searching for Caribbean timeshares
3. Review offers — you decide what to accept
4. Close the sale — we can refer you to a licensed real estate brokerage to handle the transfer

Ready to move on from yours? Our associates can walk you through the process.