A tropical beach with clear turquoise waters, lush green hills, and a small red building on a hill.

Caribbean Luxury Vacations

Book a Luxury Hotel + Flight or Car together to unlock savings

Top Luxury vacation packages in Caribbean

Price found within the past 48 hours. Click for updated prices.
  • Aug 29 - Sep 3

    Casa de Campo Resort and Villas + Flight

    La Romana
    5 nights
    5.0 star property
    9.6/10 - Exceptional (1,042 reviews)
    Roundtrip New York (EWR) - Punta Cana (PUJ)
    EWR - PUJNonstop PUJ - EWR1 stop
    Save 100% on your flight
    $2,102
    $1,009
    per traveler
    found 1 day ago
    Casa de Campo Resort and Villas
  • Oct 4 - Oct 9

    Ocean Eden Bay - Adults Only - All inclusive + Flight

    Falmouth
    5 nights
    5.0 star property
    8.4/10 - Very Good (3,894 reviews)
    "very calm clean and great vibes"
    Reviewed July 30, 2026
    Roundtrip New York (EWR) - Montego Bay (MBJ)
    EWR - MBJNonstop MBJ - EWRNonstop
    $2,726
    $1,175
    per traveler
    found 1 day ago
    Ocean Eden Bay - Adults Only - All inclusive
  • Oct 4 - Oct 9

    Ocean Coral Spring - All Inclusive + Flight

    Falmouth
    5 nights
    5.0 star property
    8.4/10 - Very Good (4,194 reviews)
    "Very poor service Rude staff Incompetence and common sense missing Not organized for groups Not able to accommodate family dinners 2-3 hour wait for diner Disorganized no leadership Room tenants hit or missing of they give you towel or replenish Staff only give attention if you give money"
    Reviewed July 30, 2026
    Roundtrip New York (EWR) - Montego Bay (MBJ)
    EWR - MBJNonstop MBJ - EWRNonstop
    $2,489
    $1,097
    per traveler
    found 1 day ago
    Ocean Coral Spring - All Inclusive
  • Oct 3 - Oct 8

    Finest Punta Cana by The Excellence Collection - All Inclusive + Flight

    Uvero Alto
    5 nights
    5.0 star property
    9.0/10 - Wonderful (2,249 reviews)
    "Lovely resort! Enjoyed my stay"
    Reviewed July 30, 2026
    Roundtrip New York (EWR) - Punta Cana (PUJ)
    EWR - PUJNonstop PUJ - EWRNonstop
    Save 100% on your flight
    $2,295
    $1,191
    per traveler
    found 1 day ago
    Finest Punta Cana by The Excellence Collection - All Inclusive
  • Oct 3 - Oct 8

    Excellence El Carmen - Adults Only All Inclusive + Flight

    Uvero Alto
    5 nights
    5.0 star property
    9.0/10 - Wonderful (3,241 reviews)
    "Good staff"
    Reviewed July 30, 2026
    Roundtrip New York (EWR) - Punta Cana (PUJ)
    EWR - PUJNonstop PUJ - EWRNonstop
    Save 100% on your flight
    $2,318
    $1,252
    per traveler
    found 2 days ago
    Excellence El Carmen - Adults Only All Inclusive

Discover the most popular places to visit in Caribbean

Top Luxury Caribbean Hotels

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

All you need to know about luxury vacations in Caribbean

What can I expect from a luxury Caribbean vacation?

Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Caribbean vacation. Sip handcrafted cocktails by an infinity pool, sink into bliss at a full-service spa with a massage cabana on the beach, and chat, cheers, and laugh through exquisite breakfasts, lunches, and dinners with spectacular views. 

How can I find all-inclusive luxury vacation packages in Caribbean?

By refining your filters, the most opulent all-inclusive vacation packages will appear before your eyes. Check the 5* filter to find truly sensational stays. You barely need to lift a finger. 

Can I book a cheap Caribbean luxury vacation?

Affordable luxury is only ever a few clicks away. Enter your travel dates and sort the grandiose getaways on offer by price to see the most fiscally friendly retreats first. Filter by budget, too, to find your perfect balance of luxury. Right now, luxury vacations start at $1,009. Prices and availability are subject to change. Additional terms may apply.

How can I book a luxury family vacation in Caribbean?

Tailor your luxury family escape by checking the filters that set the whole family’s hearts a-flutter. Whether that’s wet and wild water parks, heavenly hot tubs, or the kid-quieting magic of free Wi-Fi. 

Can I book a package in Caribbean with a luxury vacation home?

A private paradise is true luxury! Filter by property type for houses, villas, and apartments. For an amazingly affordable all-in-one luxury experience, book your accommodation, airfare, and car rental as a package.   

How can I find the best luxury vacation deals in Caribbean?

Find absolute delight in the dropdown! Simply sort your tempting search results by deals to find that lean-budget luxury. For a budget conscious stay, consider booking a stay away from big cities or outside the peak months.

Can I book a luxury holiday in Caribbean with free cancellation and/or flexible dates?

Freedom and flexibility are the greatest luxuries of all. Get both when you filter by payment option and book a trip with free cancellation or on a buy now, pay later plan. 

Why should I book my luxury trip to Caribbean with Expedia?

A luxurious trip follows a stress-free booking experience. Find, build, and book the most glorious of getaways in seconds—with ATOL protection for added peace of mind.

What are some of the best things to do in the Caribbean for budget travelers?

The Caribbean is much more than a luxury getaway experience. If you want to plan one of the best Caribbean vacations for cheap, make the most of self-guided street food tours and sample local delicacies such as Barbados' cou-cou and flying fish and Antigua's bread pudding. For a very modest entry fee, hike through tropical forests and cloud-capped mountains in Jamaica's Blue and John Crow Mountains National Park. And of course, enjoy a bounty of free beaches and the always stunning spectacle of the sun going down over the horizon.