Caribbean Islands Luxury Vacations 2026

Top Luxury vacation packages in Caribbean Islands

Price found within the past 48 hours. Click for updated prices.

Bahia Principe Escape Runaway Bay - Hyatt Inclusive Collection - Adults Only - All Inclusive

Save 100% on your flight

$966

per person

Dec 7 - Dec 11

found 19 hours ago

Roundtrip flight included

Atlanta (ATL) to Montego Bay (MBJ)

8.4/10 Very Good! (2,519 reviews)

Majestic Elegance Punta Cana - All Inclusive

Bávaro

$1,020

per person

Nov 6 - Nov 9

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Punta Cana (PUJ)

9/10 Wonderful! (5,163 reviews)

Excellence Punta Cana - Adults Only All Inclusive

Uvero Alto

Save 100% on your flight

$1,047

per person

Dec 7 - Dec 10

found 12 hours ago

Roundtrip flight included

Atlanta (ATL) to Punta Cana (PUJ)

9.2/10 Wonderful! (2,887 reviews)

Hotel Riu Palace Aruba - All Inclusive

Palm Beach

Save 100% on your flight

$1,998

per person

Nov 6 - Nov 10

found 1 day ago

Roundtrip flight included

Fort Lauderdale (FLL) to Oranjestad (AUA)

8.4/10 Very Good! (1,860 reviews)

Excellence Carmen Punta Cana - Adults Only All Inclusive

Uvero Alto

Save 100% on your flight

$1,179

per person

Dec 7 - Dec 10

found 12 hours ago

Roundtrip flight included

Atlanta (ATL) to Punta Cana (PUJ)

9.2/10 Wonderful! (3,406 reviews)

The property was very clean and very well kept. The entire staff was very courteous, helpful and ready and willing to assist or accommodate with whatever was asked of them. They even offered assistance if it wasn’t requested. They exceeded my expectations. They made my stay absolutely wonderful!! Excellent!

Reviewed on Oct 7, 2026

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5* Luxury vacations in Caribbean Islands

Price found within the past 48 hours. Click for updated prices.

Excellence Punta Cana - Adults Only All Inclusive

Uvero Alto

Save 100% on your flight

$1,047

per person

Dec 7 - Dec 10

found 12 hours ago

Roundtrip flight included

Atlanta (ATL) to Punta Cana (PUJ)

9.2/10 Wonderful! (2,887 reviews)

Excellence Carmen Punta Cana - Adults Only All Inclusive

Uvero Alto

Save 100% on your flight

$1,179

per person

Dec 7 - Dec 10

found 12 hours ago

Roundtrip flight included

Atlanta (ATL) to Punta Cana (PUJ)

9.2/10 Wonderful! (3,406 reviews)

Reviewed on Oct 7, 2026

Majestic Mirage Punta Cana, All Suite Resort - All Inclusive

Bávaro

Save 100% on your flight

$1,227

per person

Dec 7 - Dec 10

found 12 hours ago

Roundtrip flight included

Atlanta (ATL) to Punta Cana (PUJ)

9.2/10 Wonderful! (6,593 reviews)

Don't see what you're looking for?

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3 Night Luxury vacations in Caribbean Islands

Price found within the past 48 hours. Click for updated prices.

Majestic Elegance Punta Cana - All Inclusive

Bávaro

$1,020

per person

Nov 6 - Nov 9

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Punta Cana (PUJ)

9/10 Wonderful! (5,163 reviews)

Excellence Punta Cana - Adults Only All Inclusive

Uvero Alto

Save 100% on your flight

$1,047

per person

Dec 7 - Dec 10

found 12 hours ago

Roundtrip flight included

Atlanta (ATL) to Punta Cana (PUJ)

9.2/10 Wonderful! (2,887 reviews)

Excellence Carmen Punta Cana - Adults Only All Inclusive

Uvero Alto

Save 100% on your flight

$1,179

per person

Dec 7 - Dec 10

found 12 hours ago

Roundtrip flight included

Atlanta (ATL) to Punta Cana (PUJ)

9.2/10 Wonderful! (3,406 reviews)

Reviewed on Oct 7, 2026

Don't see what you're looking for?

See all available trips from Singapore to Caribbean Islands

View all trips

4 Night Luxury vacations in Caribbean Islands

Price found within the past 48 hours. Click for updated prices.

Excellence Punta Cana - Adults Only All Inclusive

Uvero Alto

Save 100% on your flight

$1,214

per person

Dec 7 - Dec 11

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Punta Cana (PUJ)

9.2/10 Wonderful! (2,887 reviews)

Majestic Mirage Punta Cana, All Suite Resort - All Inclusive

Bávaro

Save 100% on your flight

$1,376

per person

Dec 7 - Dec 11

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Punta Cana (PUJ)

9.2/10 Wonderful! (6,593 reviews)

Excellence Carmen Punta Cana - Adults Only All Inclusive

Uvero Alto

Save 100% on your flight

$1,270

per person

Nov 6 - Nov 10

found 17 hours ago

Roundtrip non-stop flight included

Oranjestad (AUA) to Punta Cana (PUJ)

9.2/10 Wonderful! (3,406 reviews)

Reviewed on Oct 7, 2026

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See all available trips from Singapore to Caribbean Islands

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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 $966. 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

1055 Ashford Avenue San Juan

7 hours drive from Oyster Bay Marina

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 ...

Bahia Principe Escape Runaway Bay - Hyatt Inclusive Collection - Adults Only - All Inclusive

Salt Coppers Runaway Bay Saint Ann

32 hours drive from Oyster Bay Marina

Bahia Principe Escape Runaway Bay - Hyatt Inclusive Collection - Adults Only - All Inclusive is one of the Runaway Bay sumptuous 4.5-star all-inclusive properties ...

Majestic Elegance Punta Cana - All Inclusive

Playa Bavaro - Punta Cana Punta Cana La Altagracia

13 hours drive from Oyster Bay Marina

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 ...

See all 88,900 properties in Caribbean Islands

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.