Vacation Packages to Portland for 2025

Choose two or more items and save on your trip:

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 3-star 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
Stay at this 3.5-star business-friendly hotel in Port Antonio. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
Match Resort Hotel

Match Resort Hotel

3 out of 5
Dolphin Bay, Port Antonio
2.25 km from city center
Stay at this 3-star 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

Great Huts

3 out of 5
8-10 Boston Bay, Port Antonio, Portland
9.7 km from city center
Stay at this 3-star 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

Geejam

4.5 out of 5
San San, Port Antonio, Port Antonio, Portland
4 km from city center
Stay at this 4.5-star luxury hotel in Port Antonio. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. ...
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
Stay at this 3.5-star beach hotel in Rural Hill. Enjoy free WiFi, free parking, and a private beach. Popular attractions Long Bay Beach and Reach Falls are located ...
Frenchman's Cove Resort

Frenchman's Cove Resort

3 out of 5
Main Rd into Frenchman's Cove, PO Box 101, Port Antonio, Portland
4.79 km from city center
Stay at this 3-star beach hotel in Port Antonio. Enjoy a private beach, daily housekeeping, and a garden. Popular attractions Frenchman's Cove Beach and San ...
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 3-star hotel in Port Antonio. Enjoy free WiFi, free parking, and a rooftop terrace. Popular attractions Trident Castle and Frenchman's Cove Beach ...
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 parking (surcharge). Popular attractions San San Beach and Blue Lagoon are ...
Bay View Eco Resort & Spa

Bay View Eco Resort & Spa

3 out of 5
Anchovy, Turtle Harbour, Port Antonio, Portland
2.3 km from city center
Stay at this 3-star spa resort in Port Antonio. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Trident Castle and Folly Ruins are ...
Sky's Villa Resort

Sky's Villa Resort

3 out of 5
1 Sixth Ave, Buff Bay, Portland Parish
23.62 km from city center
Stay at this 3-star guesthouse in Buff Bay. Enjoy free WiFi, free parking, and an airport shuttle (surcharge). Popular attractions Blue and John Crow Mountains ...
Inn The Town

Inn The Town

3 out of 5
1 Allan Avenue, Port Antonio, Portland
0.03 km from city center
Stay at this 3-star business-friendly guesthouse in Port Antonio. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff ...
S Hotel Kingston

S Hotel Kingston

4.5 out of 5
1 St Lucia Avenue, Kingston, Saint Andrew
40.34 km from city center
Stay at this 4.5-star luxury hotel in Kingston. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. ...
ROK Hotel Kingston, Tapestry Collection by Hilton

ROK Hotel Kingston, Tapestry Collection by Hilton

4 out of 5
2-4 King Street, Kingston
43.62 km from city center
Stay at this 4-star business-friendly hotel in Kingston. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful ...
R Hotel Kingston

R Hotel Kingston

4 out of 5
2 Renfrew Road , Kingston 10, Jamaica, Kingston, Jamaica
40.73 km from city center
Stay at this 4-star hotel in Kingston. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the breakfast and the restaurant in our reviews. ...
Don't see what you're looking for?
See all available properties in Portland
View all properties
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.

Spirit Airlines
Mon, Nov 3 - Thu, Nov 20
FLL
Fort Lauderdale
KIN
Kingston
$253 Roundtrip, found 11 hours ago
$253
Roundtrip
found 11 hours ago
Select Spirit Airlines flight, departing Mon, Nov 3 from Fort Lauderdale to Kingston, returning Thu, Nov 20, priced at $253 found 11 hours ago
JetBlue Airways
Thu, Nov 6 - Tue, Nov 18
FLL
Fort Lauderdale
KIN
Kingston
$356 Roundtrip, found 11 hours ago
$356
Roundtrip
found 11 hours ago
Select JetBlue Airways flight, departing Thu, Nov 6 from Fort Lauderdale to Kingston, returning Tue, Nov 18, priced at $356 found 11 hours ago
Delta
Thu, Nov 6 - Mon, Nov 17
FLL
Fort Lauderdale
KIN
Kingston
$392 Roundtrip, found 11 hours ago
$392
Roundtrip
found 11 hours ago
Select Delta flight, departing Thu, Nov 6 from Fort Lauderdale to Kingston, returning Mon, Nov 17, priced at $392 found 11 hours ago
Caribbean Airlines
Tue, Nov 11 - Sat, Nov 15
JFK
New York
KIN
Kingston
$401 Roundtrip, found 5 days ago
$401
Roundtrip
found 5 days ago
Select Caribbean Airlines flight, departing Tue, Nov 11 from New York to Kingston, returning Sat, Nov 15, priced at $401 found 5 days ago
American Airlines
Thu, Nov 20 - Mon, Feb 9
EWR
New York
KIN
Kingston
$446 Roundtrip, found 1 day ago
$446
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Nov 20 from New York to Kingston, returning Mon, Feb 9, priced at $446 found 1 day ago