Greater Antilles Vacation Packages 2026 from $569

Add multiple dates or destinations

Plan, book, travel with confidence
Better together
Save up to $2,000 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

Top destinations in Greater Antilles

A beach lined with palm trees and beach chairs under a clear blue sky.

The Latest Greater Antilles Vacation Packages

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

Sep 13 - Sep 17
Palm Green Vacations Whitesands + Flight
Bávaro
4 nights
3.5 star property
5.4/10 - (3 reviews)
"I like this property. I had a problem with the lady renting me the apartment. It was a big property and I tried to get clarification but she was very un accommodating and rude. On day of check out I tried to ask why I was moved last minute as soon as I arrived to the country they changed my reservation and only told me once I arrived to property. The place was very beautiful but I was disappointed with the lady I communicated with. She was unprofessional and did not want to help at all "
Reviewed April 1, 2022
Roundtrip • New York (EWR) - Punta Cana (PUJ)
EWR - PUJ • Nonstop PUJ - EWR • Nonstop
~~$2,642~~
$569
per traveler
found 2 days ago
Palm Green Vacations Whitesands
Oct 2 - Oct 6
Compass Point Dive Resort + Flight
East End
4 nights
3.5 star property
9.8/10 - Exceptional (320 reviews)
"Beautiful beach view. Dining staff, front desk staff, cleaning staff, excursion staff, all very kind, helpful & great! The room was super clean, everything we needed to have a wonderful stay. There is an all day bar & grill, wonderful breakfast. We found a little Mexican restaurant down the road, it was great as well. I do wish there was a store walking distance, but the fairly was perfect!"
Reviewed July 22, 2026
Roundtrip • New York (EWR) - Grand Cayman (GCM)
EWR - GCM • 1 stop GCM - EWR • 1 stop
~~$4,453~~
$1,439
per traveler
found 1 day ago
Compass Point Dive Resort
Oct 2 - Oct 6
NEW Oceanfront Condo in George Town + Flight
George Town
4 nights
2.0 star property
Roundtrip • New York (EWR) - Grand Cayman (GCM)
EWR - GCM • 1 stop GCM - EWR • 1 stop
~~$4,576~~
$1,519
per traveler
found 1 day ago
NEW Oceanfront Condo in George Town
Oct 2 - Oct 6
S2 BP Steps to Beach Entire Apartment + Flight
West Bay
4 nights
3.0 star property
Roundtrip • New York (EWR) - Grand Cayman (GCM)
EWR - GCM • 1 stop GCM - EWR • 1 stop
~~$4,632~~
$1,640
per traveler
found 1 day ago
S2 BP Steps to Beach Entire Apartment
Oct 2 - Oct 6
The Grove 33 in Grand Cayman + Flight
Seven Mile Beach
4 nights
2.0 star property
Roundtrip • New York (EWR) - Grand Cayman (GCM)
EWR - GCM • 1 stop GCM - EWR • 1 stop
~~$4,828~~
$1,731
per traveler
found 1 day ago
The Grove 33 in Grand Cayman