Top Caribbean Luxury Resort Offers 2026-2027

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 2026-2027:

1. Rosewood Le Guanahani, St. Barth: 4th Night or 5th Night Free + Rosewood Elite Benefits

Offer and Dates: Enjoy a complimentary fourth night on stay dates through October 2026. Alternatively, enjoy a fifth night complimentary for stay dates November to December 15, 2026 and January to April, 2027.

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 3/17/27; excludes the Two Bedroom Casita, holidays and certain high occupancy blackout dates.

3. Four Seasons Anguilla: 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: Valid for select stay dates 1/5/27-12/17/27, some blackout dates apply. Includes our Four Seasons Preferred Partner benefits.

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

Dates: Selected dates until 12/17/26 and 3/28 to 6/30/27. Includes our Rosewood Elite benefits.

5. 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 3/31/27, plus enjoy STARS benefits as a TravelSort Client. 6-night stays enjoy 20% off while 5-night stays enjoy 15% off. Blackout dates include June 13-17, 2026; November 23-28, 2026; December 18, 2026-January 3, 2027; January 13-17, 2027.

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

6. 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 9/7/26-3/29/27, or a 4th night free for stay dates 3/29-9/6/27, 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

Visit the resort with our Hamilton Princess & Beach Club Bermuda video review:

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

Save 25% off Studios and Suites, new bookings only, for 2+ night stays.

Dates: Selected stay dates until October 31, 2026.

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

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

Offer also includes complimentary roundtrip transfers from the airport (or private air strip).

Dates: Ongoing for 4th night free offer, some blackout dates apply.

9. 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 8/15/27

10. Ambergris Cay: Save 15% by Prepaying

Save 15% by making a full, non-refundable prepayment. Combines with current offers, some blackout dates apply, and excludes the Dream Villa Estate.

Visit Ambergris Cay with our Ambergris Cay video review:

11. Rosewood Bermuda: 3rd Night or 4th Night Free + Rosewood Elite Benefits

Dates: Selected dates until 12/31/26, some blackout dates apply.

12. 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 December 18, 2026. Includes our STARS benefits.