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 ...
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. ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 guesthouse in Buff Bay. Enjoy free WiFi, free parking, and an airport shuttle (surcharge). Popular attractions Blue and John Crow Mountains National ...
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 ...
S Hotel Kingston

S Hotel Kingston

4.5 out of 5
1 St Lucia Avenue Kingston Saint Andrew
40.34 km from city center
Book a stay at this 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
Book a stay at this 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 hotel in Kingston. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the breakfast and the restaurant in our reviews. Popular ...
AC Hotel by Marriott Kingston, Jamaica

AC Hotel by Marriott Kingston, Jamaica

4.5 out of 5
38 Lady Musgrave Rd Kingston St. Andrew Parish
39.81 km from city center
Book a stay at this luxury hotel in Kingston. Enjoy free WiFi, free parking, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our ...
The Courtleigh Hotel and Suites

The Courtleigh Hotel and Suites

4 out of 5
85 Knutsford Boulevard Kingston Saint Andrew
40.91 km from city center
Book a stay at this spa hotel in Kingston. Enjoy free breakfast, free WiFi, and a full-service spa. Our guests praise the breakfast and the helpful staff in ...
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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.

JetBlue Airways
Thu, Mar 26 - Mon, Apr 6
FLL
Fort Lauderdale
KIN
Kingston
$348 Roundtrip, found 3 days ago
$348
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Thu, Mar 26 from Fort Lauderdale to Kingston, returning Mon, Apr 6, priced at $348 found 3 days ago
Spirit Airlines
Tue, Dec 9 - Tue, Dec 16
ATL
Atlanta
KIN
Kingston
$360 Roundtrip, found 2 days ago
$360
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Tue, Dec 9 from Atlanta to Kingston, returning Tue, Dec 16, priced at $360 found 2 days ago
Caribbean Airlines
Thu, May 14 - Sat, May 30
JFK
New York
KIN
Kingston
$392 Roundtrip, found 5 days ago
$392
Roundtrip
found 5 days ago
Select Caribbean Airlines flight, departing Thu, May 14 from New York to Kingston, returning Sat, May 30, priced at $392 found 5 days ago
American Airlines
Mon, Jan 26 - Thu, Feb 5
JFK
New York
KIN
Kingston
$415 Roundtrip, found 3 days ago
$415
Roundtrip
found 3 days ago
Select American Airlines flight, departing Mon, Jan 26 from New York to Kingston, returning Thu, Feb 5, priced at $415 found 3 days ago
Delta
Mon, Jan 26 - Thu, Feb 5
JFK
New York
KIN
Kingston
$415 Roundtrip, found 3 days ago
$415
Roundtrip
found 3 days ago
Select Delta flight, departing Mon, Jan 26 from New York to Kingston, returning Thu, Feb 5, priced at $415 found 3 days ago