Caribbean Luxury Holidays 2026

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Top flight + Luxury hotel deals in Caribbean

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

Hotel El Convento

Old San Juan

₹104,367

per person

22 Nov - 25 Nov

found 1 day ago

Return direct flight included

Chicago (ORD) to San Juan (SJU)

9.2/10 Wonderful! (1,005 reviews)

The beautiful building and historic structure

Reviewed on 13 Sept 2026

Condado Vanderbilt Hotel

Condado

₹113,192

per person

22 Nov - 25 Nov

found 1 day ago

Return direct flight included

Chicago (ORD) to San Juan (SJU)

9.4/10 Exceptional! (1,837 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Caribbean

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5* Luxury holidays in Caribbean

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

Condado Vanderbilt Hotel

Condado

₹113,192

per person

22 Nov - 25 Nov

found 1 day ago

Return direct flight included

Chicago (ORD) to San Juan (SJU)

9.4/10 Exceptional! (1,837 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Caribbean

View all trips

3 Night Luxury holidays in Caribbean

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

Hotel El Convento

Old San Juan

₹104,367

per person

22 Nov - 25 Nov

found 1 day ago

Return direct flight included

Chicago (ORD) to San Juan (SJU)

9.2/10 Wonderful! (1,005 reviews)

The beautiful building and historic structure

Reviewed on 13 Sept 2026

Condado Vanderbilt Hotel

Condado

₹113,192

per person

22 Nov - 25 Nov

found 1 day ago

Return direct flight included

Chicago (ORD) to San Juan (SJU)

9.4/10 Exceptional! (1,837 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Caribbean

View all trips

Top Luxury Caribbean Hotels

Condado Vanderbilt Hotel

1055 Ashford Avenue San Juan

₹29,528

₹39,331 total

20 Sept - 21 Sept

includes taxes & fees

Stay at this luxury hotel in San Juan. Enjoy free Wi-Fi, 4 outdoor pools and a full-service spa. Our guests praise the helpful staff and the clean rooms in their ...

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

Salt Coppers Runaway Bay Saint Ann

₹31,527

₹31,527 total

14 Oct - 15 Oct

includes taxes & fees

Stay at this luxury resort in Runaway Bay. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the pool and the helpful staff in their reviews. ...

8.4/10 Very good! (2,492 reviews)

"Pro: Beautiful hotel right on the beach. Beautiful pool and grounds. Food was delicious with great variety. My room was clean and spacious. The staff were helpful, friendly and professional. Con: the hotel gift shop charges US$20 for a bottle of 16 ounces GATORADE!!! Even though it is an all inclusive ..."

Reviewed on 14 Sept 2026

Hotel El Convento

100 Cristo St San Juan

₹16,662

₹21,794 total

16 Sept - 17 Sept

includes taxes & fees

Stay at this luxury hotel in San Juan. Enjoy free Wi-Fi, breakfast (surcharge) and room service. Our guests praise the helpful staff and the clean rooms in their ...

9.2/10 Wonderful! (1,005 reviews)

"The beautiful building and historic structure"

Reviewed on 13 Sept 2026

See all 88,844 properties in Caribbean

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.