Top 15 Caribbean Luxury Resort Offers 2026

Top 10 Caribbean Luxury Resort Offers 2023

The Caribbean is a tempting getaway. While you won't find service that will equal that of the top Asian and Maldivian resorts, the proximity and ease of getting to the Caribbean and Bermuda make these resorts popular for U.S. and Canadian visitors, especially from the East Coast. Here are the top 15 Caribbean and Bermuda luxury resort offers in 2026:

1. Rosewood Le Guanahani, St. Barth: 4th Night Free + Rosewood Elite Benefits

Offer and Dates: Enjoy a complimentary fourth night on stay dates May-October 2026. Alternatively, enjoy a fifth night complimentary for stay dates until April 2026.

2. Amanera, Dominican Republic: 4th Night Free + Virtuoso Benefits

Offer: Stay 4+ nights to enjoy 4th night free. This is combinable with Virtuoso benefits:

Upgrade on arrival, subject to availability
Daily breakfast for up to two guests per bedroom, served in the restaurant (already included in property rates)
$100 USD equivalent Food & Beverage credit to be utilized during stay (not combinable, not valid on room rate, no cash value if not redeemed in full)
Early Check-In / Late Check-Out, subject to availability
Complimentary Wi-Fi

Dates: Available for select dates until 3/17/26; excludes the Two Bedroom Casita, holidays and certain high occupancy blackout dates.

3. Eden Roc Cap Cana: 25% Off Early Booking

Offer: Book 150 days in advance and enjoy 25% off your stay at Eden Roc Cap Cana.

Dates: Throughout 2026

4. Four Seasons Anguilla: 5th or 6th Night Free + Four Seasons Preferred Partner Benefits

Four Seasons Anguilla is often our clients' top choice for extended family getaways in the Caribbean, as it has fantastic villas and Anguilla has beautiful white sand beaches. Keep in mind that our Four Seasons Preferred Partner benefits, in addition to top priority for an upgrade and daily breakfast for two guests per bedroom includes a $200 per bedroom per stay resort credit for suites and villas, so a four bedroom villa would enjoy an $800 resort credit for the stay.

Dates: 5th night free valid for select stay dates 5/25/26-12/15/26; 6th night free valid for select stay dates until 5/29/26 and 1/5/27-12/17/27, some blackout dates apply.

5. Rosewood Le Guanahani: 4th or 5th Night Free + Rosewood Elite Benefits

Dates: 5th night free for select dates until April 2026; 4th night free for select dates May through October 2026.

6. Rosewood Little Dix Bay, British Virgin Islands: 4th Night or 5th Night Free + Rosewood Elite Benefits

Dates: Selected dates in 2026 (mainly late spring-fall), some blackout dates apply.

7. Ritz-Carlton Grand Cayman: Up to 25% Off + STARS Benefits

Offer and Dates: Enjoy 25% off on a 7+ night stay for stay dates until 8/15/26, plus enjoy STARS benefits as a TravelSort Client. 6-night stays enjoy 20% off while 5-night stays enjoy 15% off. STARS benefits include:

Priority for a room upgrade, if available at check-in
Welcome amenity
Daily breakfast for up to two guests per room
$100 resort credit per room per stay
Early check-in and late check-out, subject to availability

8. Hamilton Princess & Beach Club, Bermuda: 3rd Night or 4th Night Free + Virtuoso Benefits

Enjoy a third or fourth night complimentary.

Offer and Dates: Enjoy a 3rd night free for stay dates until 4/6/26 or 9/7/26-3/29/27, or 4th night free for stay dates 4/7/26-9/6/26, inclusive of Virtuoso benefits.

Virtuoso Benefits

Upgrade on arrival, subject to availability
Daily Buffet Breakfast for up to two guests per bedroom, served in Restaurant
$100 USD equivalent Food & Beverage credit utilized during stay (not combinable, not valid on room rate, no cash value)
Early Check-In / Late Check-Out, subject to availability
Complimentary Wi-Fi

9. The Ocean Club (Four Seasons Bahamas): 4th Night Free + Guaranteed Upgrade + FSPP Benefits

Offer also includes complimentary roundtrip transfers from the airport (or private air strip). Guaranteed upgrade depends on availability at time of booking and excludes suites, bungalows, and villas. Eligible upgrade: Garden-View Room to Ocean-View Room, and Ocean-View Room to Luxury Oceanfront Room.

Dates: Ongoing for 4th night free offer, some blackout dates apply. Guaranteed one-category upgrade offer is for new reservations for travel from May 1 to November 15, 2026, when booked by February 28, 2026.

10. Wymara Resort, Turks & Caicos: Up to 25% Off + Virtuoso Benefits

Enjoy up to 25% off on all room categories, excluding One Bedroom Villas, new bookings only.

Dates: Selected stay dates April 16-June 30, 2026

Visit the resort with our Wymara Resort and Villas video review:

11. Four Seasons Nevis: 4th Night Free + Preferred Partner Benefits

Enjoy a complimentary fourth night for selected stay dates throughout 2026.

Dates: Selected stay dates until 12/31/26.

12. Malliouhana Resort, Anguilla: 5th Night Free + $250-$500 Resort Credit

Enjoy a 5th night complimentary, plus a $250 resort credit in guest rooms or a $500 resort credit in suites to use while on property.

Dates: Stay dates until 12/20/26

13. Ambergris Cay: 20% Off Beachfront Bungalow + 30-Minute Couples' Massage

A four-night minimum stay is required for this offer. Alternatively, for families and couples traveling together, there's 20% off Neptune and Poseidon Villas and the Seabreeze Two-Bedroom Bungalow, with a 3-night minimum stay. This offer also includes a shared sunset cruise.

Visit Ambergris Cay with our Ambergris Cay video review:

14. Rosewood Bermuda: 3rd Night Free + Rosewood Elite Benefits

Dates: Selected dates through March 2026 and from September 7, 2026, some blackout dates apply.

15. Dorado Beach, a Ritz-Carlton Reserve: Save up to 20% on 4+ Nights

Offer and Dates: Save up to 20% on a 4+ night stay at Dorado Beach, a Ritz-Carlton Reserve, for stay dates until April 30, 2026 when reserved by April 24, 2026