Caribbean Luxury Holidays

The Caribbean Luxury Collection

This page lists our favourite luxury hotels in the Caribbean, as hand-selected by our destination specialists. These accommodations really are the cream of the crop for high end holidays in this island paradise. Flights are included in the price as standard, and you also get something extra that faceless booking engines simply can’t provide – peerless expertise, local knowledge and friendly personalised service from the trusted travel professionals here at Kenwood Travel.

Browse below for the best luxury hotels in one of world travel’s most authentic destinations. The Caribbean is awash with spectacular hotels where butler service, swim-up suites, gourmet cuisine, sumptuous spas and breath-taking oceanfront scenery add luxury to every stay. From family-friendly breaks and couples retreats to honeymoons and weddings, the luxury amenities on offer at our expertly hand-crafted holidays below will elevate your holiday with the art of escape. Drink in the culture, dive the coral reefs, soak up the scenery or enjoy some old fashioned R&R; when you stay at a Kenwood Travel luxury hotel in the Caribbean, you won’t have to lift a finger.

Barbados Luxury Holidays

Fairmont Royal Pavilion #5238

5* out of 5 stars
  • Up to 55% saving
Airline Virgin Atlantic
Board Basis Bed and Breakfast
Nights 7
Date 14 Sep 2025
Price per person
Adult
£2,465

Sandy Lane #4983

5* out of 5 stars
  • Complimentary Room upgrade from Orchid Room to Luxury Ocean Room
  • Added Value
  • Stay 7 pay 6
Airline Virgin Atlantic
Board Basis Bed and Breakfast
Nights 7
Date 14 Sep 2025
Price per person
Adult
£3,945

Cancun & Riviera Maya Luxury Holidays

Fairmont Mayakoba #4660

5* out of 5 stars
  • Up to 20% saving
Airline British Airways
Board Basis All Inclusive
Nights 7
Date 9 Sep 2025
Price per person
Adult
£3,200

Conrad Tulum Riviera Maya #5921

5* out of 5 stars
  • Complimentary All Inclusive from Half Board
  • 20% saving
Airline British Airways
Board Basis All Inclusive
Nights 7
Date 13 Jun 2025
Price per person
Adult
£4,604

Dominican Republic Luxury Holidays

Casa de Campo Resort & Villas #6742

5* out of 5 stars
  • Up to 62% saving
  • Complimentary Room Upgrade*
  • One Free Child*
Airline British Airways
Board Basis Room Only
Nights 7
Date 22 Sep 2025
Price per person
Adult
£1,746

Sanctuary Cap Cana, a Luxury Collection Adult All-Inclusive Resort #6755

5* out of 5 stars
Airline British Airways
Board Basis All Inclusive
Nights 7
Date 22 Sep 2025
Price per person
Adult
£2,416

Grenada Luxury Holidays

Calabash Hotel #975

5* out of 5 stars
  • Complimentary Private Dinner on the New Jetty & Airport Transfers
  • Complimentary upgrade to Half Board
Airline Virgin Atlantic
Board Basis Half Board
Nights 7
Date 20 May 2025
Price per person
Adult
£2,886

Spice Island Beach Resort #984

5* out of 5 stars
  • 14% saving
Airline Virgin Atlantic
Board Basis All Inclusive
Nights 7
Date 9 Sep 2025
Price per person
Adult
£3,237

Jamaica Luxury Holidays

Jamaica Inn #4842

5* out of 5 stars
  • 20% saving
Airline British Airways
Board Basis Room Only
Nights 7
Date 5 May 2025
Price per person
Adult
£2,176

Mustique Luxury Holidays

The Cotton House #5167

5* out of 5 stars
  • Complimentary late check out until 13:00
Airline British Airways
Board Basis Bed and Breakfast
Nights 7
Date 28 May 2025
Price per person
Adult
£3,745
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