Caribbean Islands Luxury Vacations

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

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3 Night Luxury vacations in Caribbean Islands

Price found within the past 48 hours. Click for updated prices.
Casa de Campo Resort and Villas
Hotel Riu Palace Aruba - All Inclusive
West Bay Club
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4 Night Luxury vacations in Caribbean Islands

Price found within the past 48 hours. Click for updated prices.
Casa de Campo Resort and Villas
Hotel Riu Palace Aruba - All Inclusive
West Bay Club
Don't see what you're looking for?
See all available trips from Columbus to Caribbean Islands
View all trips

All you need to know about luxury vacations in Caribbean Islands

What can I expect from a luxury Caribbean Islands vacation?

Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Caribbean Islands 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 Islands?

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 Islands 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 $592. Prices and availability are subject to change. Additional terms may apply.

How can I book a luxury family vacation in Caribbean Islands?

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 Islands 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 Islands?

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 Islands 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 Islands 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.

Top Luxury Caribbean Islands Hotels

Condado Vanderbilt Hotel
Condado Vanderbilt Hotel
5 out of 5
1055 Ashford Avenue, San Juan
  • 17 hours drive from Windward Islands
Condado Vanderbilt Hotel is a San Juan luxury 5-star beach property where you can treat yourself to 24-hour room service, pillowtop beds, and more. Deluxe amenities ...
9/10 Wonderful! (1,525 reviews)
"This is my 3rd stay here. Other than the $200 nightly incidental fee (you can either get it back at then end of your trip, or use it on spa, room service , drinks or any either of their ON SITE restaurants) and night hotel tariff fee it is truly a luxury experience. You won’t get that, “out of the ..."

Reviewed on Jun 29, 2025

Condado Vanderbilt Hotel
Bahia Principe Luxury Runaway Bay - Adults Only - All Inclusive
Bahia Principe Luxury Runaway Bay - Adults Only - All Inclusive
4.5 out of 5
Salt Coppers, Runaway Bay, Saint Ann
  • 36 hours drive from Windward Islands
Bahia Principe Luxury Runaway Bay - Adults Only - All Inclusive is one of the Runaway Bay sumptuous 4.5-star all-inclusive properties where you can pamper yourself ...
8.2/10 Very Good! (2,503 reviews)
"Second time staying at this resort, this time around there didn’t seem to be a lot of entertainment. They closed the nightclub and the white party was lack luster! Doesn’t negate from the the fact that the staff is EXTREMELY nice and accommodating!"

Reviewed on Jul 1, 2025

Bahia Principe Luxury Runaway Bay - Adults Only - All Inclusive
Majestic Elegance Punta Cana - All Inclusive
Majestic Elegance Punta Cana - All Inclusive
4.5 out of 5
Playa Bavaro - Punta Cana, Punta Cana, La Altagracia
  • 21 hours drive from Windward Islands
Majestic Elegance Punta Cana - All Inclusive is one of the Punta Cana lavish 4.5-star all-inclusive properties where you can treat yourself to jetted bathtubs ...
8.8/10 Excellent! (4,150 reviews)
"My stay at Majestic Elegance Punta Cana was beyond exceptional. Arling Amador, my butler, made my birthday unforgettable—thoughtful surprises, personalized attention, and genuine care that turned a great trip into a perfect one. Arling made sure to proactively check in each during our stay, and went ..."

Reviewed on Jul 1, 2025

Majestic Elegance Punta Cana - All Inclusive
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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.