Caribbean Islands Luxury Vacations 2026

Top Luxury vacation packages in Caribbean Islands

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

Majestic Elegance Punta Cana - All Inclusive

Bávaro

Save 100% on your flight

$716

per person

Oct 19 - Oct 22

found 1 day ago

Roundtrip flight included

New York (JFK) to Punta Cana (PUJ)

9/10 Wonderful! (4,936 reviews)

Majestic Elegance is definitely the place to be! 🌴✨ The staff is incredibly friendly, helpful, and attentive. The resort is beautiful, clean, and constantly kept nice and tidy. The entertainment team is AMAZING—they really know how to get the crowd going! 🎶💃 We had the time of our lives and made so many wonderful memories. ❤️ We will definitely be back! Highly recommend Majestic Elegance! ⭐️⭐️⭐️⭐️⭐️

Reviewed on Aug 18, 2026

Excellence Punta Cana - Adults Only All Inclusive

Uvero Alto

Save 100% on your flight

$805

per person

Oct 19 - Oct 22

found 1 day ago

Roundtrip flight included

New York (JFK) to Punta Cana (PUJ)

9.2/10 Wonderful! (2,802 reviews)

I travel once per month to an all inclusive. This is hands down the worst one ever. They “upgraded” my room to a room with no view. Said garden but the trees were grown up to the balcony so you couldn’t see anything. Horrid. Tiny pools compared to others. No activity around the pools. Usually there is entertainment. Music. Something. Expensive if you elect to buy or do anything at the resort. $400 massage. $70 for sunscreen. 10 restaurants but only 2 open at a time and only at 6pm. Mini bar broken. 2 out of 10 overall.

Reviewed on Aug 18, 2026

Casa de Campo Resort and Villas

Save 100% on your flight

$944

per person

Oct 19 - Oct 21

found 3 hours ago

Roundtrip flight included

San Juan (SJU) to Punta Cana (PUJ)

9.6/10 Exceptional! (1,032 reviews)

Water pressure very low and one of the AC in a room didn’t cool much. The rest was fine. Rosa was amazing at the villa.

Reviewed on Aug 18, 2026

Excellence Carmen Punta Cana - Adults Only All Inclusive

Uvero Alto

Save 100% on your flight

$900

per person

Oct 19 - Oct 22

found 1 day ago

Roundtrip flight included

New York (JFK) to Punta Cana (PUJ)

9/10 Wonderful! (3,267 reviews)

Not a 5 star hotel. Staff was helpful if tipped well. Room was not clean upon arrival but was cleaned well the next morning. The resort was clean and pool staff was great. Download the app for the hotel or you will have trouble with any of the amenities, including meals.

Reviewed on Aug 18, 2026

Hotel Riu Palace Aruba - All Inclusive

Palm Beach

Save 100% on your flight

$1,418

per person

Oct 19 - Oct 22

found 21 hours ago

Roundtrip non-stop flight included

Nashville (BNA) to Oranjestad (AUA)

8.2/10 Very Good! (1,744 reviews)

The Riu Palace was recently renovated and just opened a week before we arrived. Everything was in perfect shape. The amenities were great.

Reviewed on Aug 18, 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

$805

per person

Oct 19 - Oct 22

found 1 day ago

Roundtrip flight included

New York (JFK) to Punta Cana (PUJ)

9.2/10 Wonderful! (2,802 reviews)

Reviewed on Aug 18, 2026

Casa de Campo Resort and Villas

Save 100% on your flight

$944

per person

Oct 19 - Oct 21

found 3 hours ago

Roundtrip flight included

San Juan (SJU) to Punta Cana (PUJ)

9.6/10 Exceptional! (1,032 reviews)

Water pressure very low and one of the AC in a room didn’t cool much. The rest was fine. Rosa was amazing at the villa.

Reviewed on Aug 18, 2026

Excellence Carmen Punta Cana - Adults Only All Inclusive

Uvero Alto

Save 100% on your flight

$900

per person

Oct 19 - Oct 22

found 1 day ago

Roundtrip flight included

New York (JFK) to Punta Cana (PUJ)

9/10 Wonderful! (3,267 reviews)

Reviewed on Aug 18, 2026

Don't see what you're looking for?

See all available trips from Columbus to Caribbean Islands

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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

Save 100% on your flight

$756

per person

Oct 19 - Oct 22

found 1 day ago

Roundtrip flight included

New York (JFK) to Punta Cana (PUJ)

9.6/10 Exceptional! (1,032 reviews)

Water pressure very low and one of the AC in a room didn’t cool much. The rest was fine. Rosa was amazing at the villa.

Reviewed on Aug 18, 2026

Sanctuary Cap Cana, a Luxury Collection Resort, Dominican Republic, Adult All-Inclusive

$1,618

per person

Sep 18 - Sep 21

found 1 day ago

Roundtrip non-stop flight included

Charlotte (CLT) to Punta Cana (PUJ)

9.2/10 Wonderful! (1,010 reviews)

Clean room and statt

Reviewed on Aug 18, 2026

Excellence Punta Cana - Adults Only All Inclusive

Uvero Alto

Save 100% on your flight

$805

per person

Oct 19 - Oct 22

found 1 day ago

Roundtrip flight included

New York (JFK) to Punta Cana (PUJ)

9.2/10 Wonderful! (2,802 reviews)

Reviewed on Aug 18, 2026

Don't see what you're looking for?

See all available trips from Columbus to Caribbean Islands

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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

$1,018

per person

Oct 19 - Oct 23

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Punta Cana (PUJ)

9.2/10 Wonderful! (2,802 reviews)

Reviewed on Aug 18, 2026

Excellence Carmen Punta Cana - Adults Only All Inclusive

Uvero Alto

Save 100% on your flight

$1,147

per person

Oct 19 - Oct 23

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Punta Cana (PUJ)

9/10 Wonderful! (3,267 reviews)

Reviewed on Aug 18, 2026

Majestic Mirage Punta Cana, All Suite Resort - All Inclusive

Bávaro

Save 100% on your flight

$1,347

per person

Oct 19 - Oct 23

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Punta Cana (PUJ)

9.2/10 Wonderful! (6,395 reviews)

this was hands down the best resort i have ever stood at in my entire life. literally spotless, the staff treat you amazing, the pool is so clean and the food is delicious!

Reviewed on Aug 18, 2026

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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 $716. 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 ...

8.4/10 Very Good! (2,474 reviews)

"The property was beautiful, well-maintained, and very inviting. The pool area was definitely a highlight—the mid-morning and afternoon poolside activities were lit and brought great energy to the resort! The Xaymaca show was amazing and easily one of the highlights of my stay. Most of the wait and ..."

Reviewed on Aug 18, 2026

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 ...

9/10 Wonderful! (4,949 reviews)

"Majestic Elegance is definitely the place to be! 🌴✨ The staff is incredibly friendly, helpful, and attentive. The resort is beautiful, clean, and constantly kept nice and tidy. The entertainment team is AMAZING—they really know how to get the crowd going! 🎶💃 We had the time of our lives and made ..."

Reviewed on Aug 18, 2026

See all 86,636 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.