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3 Caribbean Resorts for Families Who Really Love the Holidays

by Kimberly Inlander

Dec 15, 2025

© Denis Moskvinov | Dreamstime.com

Hotels

If you’re planning family travel during the holiday season and you’re looking for warm weather plus plenty of holiday cheer, consider these three Caribbean resorts.

 

The Strand

Ring in the holidays as this property celebrates its one-year anniversary this month. This Leading Hotels of The World resort, in Turks & Caicos, is nestled on the serene shores of Cooper Jack Bay. The Strand’s collection of all ocean-facing, three-story, three-bedroom villas, as well as private residences that sleep 10–16, are perfect for multi-gen families. All are near the ocean with heated infinity pools, V.I.P. services, kids club access and more.

 

Buoy Haus Beach Resort St. Thomas, Autograph Collection

On the U.S. Virgin Island of St. Thomas, Buoy Haus Beach Resort St. Thomas, Autograph Collection is a boutique resort experience in a passport-free Caribbean destination. Travelers enjoy a lineup of holiday programming that highlights the rich culture, lively music and unique colors of the island, including weekly themed events like Carnival Quadrille Nights with Caribbean food and traditional folk dancing, guestrooms outfitted with holiday decor, Caribbean storytelling sessions in the lobby, a sunset sail with Santa, and more.

 

The Westin St. Thomas

Another passport-free destination perfect for families looking to travel this winter: The Westin St. Thomas, offering 392 guestrooms, three ocean-view pools, an on-site spa and programming for all ages like Westin FAMILY Kids Club. This year, holiday offerings include Santa’s Workshop, a hub for games, crafts and interactive experiences; a month-long elf scavenger hunt; kids-only New Year’s Eve party; and s’mores and bedtime stories read by Santa.

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