Vacation Packages to Portland for 2026

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Top Hotel Deals

Sea Cliff Resort

Sea Cliff Resort

3 out of 5
Ross Craig Long Bay Portland
18.92 km from city center
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

Jamaica Palace Hotel

3.5 out of 5
Williamsfield Port Antonio Portland
2.97 km from city center
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 ...
Geejam

Geejam

4.5 out of 5
San San, Port Antonio Port Antonio Portland
4 km from city center
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. ...
Great Huts

Great Huts

3 out of 5
8-10 Boston Bay Port Antonio Portland
9.7 km from city center
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 ...
Jamaica Colors Eco-Retreat Hotel and Spa

Jamaica Colors Eco-Retreat Hotel and Spa

3.5 out of 5
A4 Rural Hill Portland Parish
19.79 km from city center
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 ...
Match Resort Hotel

Match Resort Hotel

3 out of 5
Dolphin Bay Port Antonio
2.25 km from city center
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 ...
Goblin Hill Villas at San San

Goblin Hill Villas at San San

3 out of 5
San San Port Antonio Portland
5.69 km from city center
Stay at this resort in Port Antonio. Enjoy breakfast (surcharge), room service, and in-room massages. Popular attractions San San Beach and Blue Lagoon are located ...
LF Jungle Retreat

LF Jungle Retreat

3 out of 5
Lots 32-40, Willamsfield Port Antonio
3.46 km from city center
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 ...
All Nations Guesthouse

All Nations Guesthouse

3 out of 5
Skipper Blvd, San San Port Antonio
4.14 km from city center
Book a stay at this family-friendly guesthouse in Port Antonio. Enjoy free WiFi, free parking, and private pools. Popular attractions Frenchman's Cove Beach ...
Moon San Villa at the Blue Lagoon

Moon San Villa at the Blue Lagoon

3 out of 5
Blue Hole Road, Drapers Port Antonio Portland
6.28 km from city center
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 ...
Bay View Eco Resort & Spa

Bay View Eco Resort & Spa

3 out of 5
Anchovy Port Antonio Portland
2.3 km from city center
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 ...
Inn The Town

Inn The Town

3 out of 5
1 Allan Avenue Port Antonio Portland
0.03 km from city center
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 ...
Frenchman's Cove Resort

Frenchman's Cove Resort

3 out of 5
Main Rd into Frenchman's Cove Port Antonio Portland
4.79 km from city center
Book a stay at this beach hotel in Port Antonio. Enjoy a private beach, daily housekeeping, and a garden. Popular attractions Frenchman's Cove Beach and San ...
Tropical Lagoon Resort

Tropical Lagoon Resort

3 out of 5
Blue Hole Road Port Antonio Portland
6.4 km from city center
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 ...
Hotel Tim Bamboo

Hotel Tim Bamboo

3 out of 5
5 Eveleigh Park Road Port Antonio Portland
0.24 km from city center
Stay at this hotel in Port Antonio. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions ...
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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.

Delta
Wed, Jan 27 - Fri, Feb 12
JFK
New York
KIN
Kingston
$487 Roundtrip, found 6 days ago
$487
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Jan 27 from New York to Kingston, returning Fri, Feb 12, priced at $487 found 6 days ago
American Airlines
Sun, Jan 24 - Fri, Jan 29
JFK
New York
KIN
Kingston
$512 Roundtrip, found 3 days ago
$512
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sun, Jan 24 from New York to Kingston, returning Fri, Jan 29, priced at $512 found 3 days ago
Copa
Wed, Jan 20 - Sun, Jan 24
MCO
Orlando
KIN
Kingston
$535 Roundtrip, found 7 hours ago
$535
Roundtrip
found 7 hours ago
Select Copa flight, departing Wed, Jan 20 from Orlando to Kingston, returning Sun, Jan 24, priced at $535 found 7 hours ago
JetBlue Airways
Mon, Nov 23 - Fri, Nov 27
FLL
Fort Lauderdale
KIN
Kingston
$540 Roundtrip, found 5 days ago
$540
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Mon, Nov 23 from Fort Lauderdale to Kingston, returning Fri, Nov 27, priced at $540 found 5 days ago
United
Mon, Nov 2 - Wed, Dec 2
JFK
New York
KIN
Kingston
$734 Roundtrip, found 1 day ago
$734
Roundtrip
found 1 day ago
Select United flight, departing Mon, Nov 2 from New York to Kingston, returning Wed, Dec 2, priced at $734 found 1 day ago