Vacation Packages to Portland for 2026
Top Hotel Deals
Sea Cliff Resort
Ross Craig Long Bay Portland
Stay at this hotel in Long Bay. Enjoy free WiFi, breakfast (surcharge), and room service. Popular attractions Long Bay Beach and Reach Falls are located ...
Jamaica Palace Hotel
Williamsfield Port Antonio Portland
Book a stay at this business-friendly hotel in Port Antonio. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property ...
Match Resort Hotel
Dolphin Bay Port Antonio
Stay at this hotel in Port Antonio. Enjoy free WiFi, free parking, and 2 bars/lounges. Our guests praise the helpful staff in our reviews. Popular attractions ...
Great Huts
8-10 Boston Bay Port Antonio Portland
Book a stay at this beach resort in Port Antonio. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. Popular ...
Geejam
San San, Port Antonio Port Antonio Portland
Book a stay at this luxury hotel in Port Antonio. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
LF Jungle Retreat
Lots 32-40, Willamsfield Port Antonio
Stay at this hotel in Port Antonio. Enjoy free WiFi, free parking, and a rooftop terrace. Popular attractions Trident Castle and Frenchman's Cove Beach are located ...
Goblin Hill Villas at San San
San San Port Antonio Portland
Stay at this resort in Port Antonio. Enjoy breakfast (surcharge), room service, and in-room massages. Popular attractions Blue Lagoon and San San Beach are located ...
Jamaica Colors Eco-Retreat Hotel and Spa
A4 Rural Hill Portland Parish
Book a stay at this beach hotel in Rural Hill. Enjoy free WiFi, free parking, and a private beach. Popular attractions Long Bay Beach and Reach Falls are located ...
All Nations Guesthouse
Skipper Blvd, San San Port Antonio
Book a stay at this family-friendly guesthouse in Port Antonio. Enjoy free WiFi, free parking, and private pools. Popular attractions Blue Lagoon and Frenchman's ...
Frenchman's Cove Resort
Main Rd into Frenchman's Cove Port Antonio Portland
Book a stay at this beach hotel in Port Antonio. Enjoy a private beach, daily housekeeping, and a garden. Popular attractions Blue Lagoon and Frenchman's Cove ...
Moon San Villa at the Blue Lagoon
Blue Hole Road, Drapers Port Antonio Portland
Book a stay at this beach hotel in Port Antonio. Enjoy free parking, room service, and an airport shuttle (surcharge). Our guests praise the helpful staff in ...
Inn The Town
1 Allan Avenue Port Antonio Portland
Book a stay at this business-friendly guesthouse in Port Antonio. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff ...
Sky's Villa Resort
1 Sixth Ave Buff Bay Portland Parish
Stay at this guesthouse in Buff Bay. Enjoy free WiFi, free parking, and an airport shuttle (surcharge). Popular attractions Blue and John Crow Mountains National ...
Bay View Eco Resort & Spa
Anchovy Port Antonio Portland
Book a stay at this spa resort in Port Antonio. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Trident Castle and Folly Ruins are ...
Tropical Lagoon Resort
Blue Hole Road Port Antonio Portland
Book a stay at this beach hotel in Port Antonio. Enjoy free parking, 2 outdoor pools, and room service. Popular attractions Blue Lagoon and San San Beach are ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Tue, Nov 10 - Fri, Mar 26
JFK
New York
KIN
Kingston
$389
Roundtrip
found 5 days ago
Sat, Oct 17 - Sun, Oct 18
JFK
New York
KIN
Kingston
$397
Roundtrip
found 18 hours ago
Tue, Jan 12 - Thu, Jan 28
JFK
New York
KIN
Kingston
$446
Roundtrip
found 5 days ago
Thu, Nov 26 - Tue, Dec 8
LGA
New York
KIN
Kingston
$486
Roundtrip
found 3 days ago
Fri, Mar 5 - Tue, Mar 16
EWR
New York
KIN
Kingston
$518
Roundtrip
found 3 days ago