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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
Villa Juanita

Villa Juanita

3.5 out of 5
Hector's River Happy Grove Portland
26.43 km from city center
Book a stay at this family-friendly hotel in Happy Grove. Enjoy free WiFi, a nightclub, and a rooftop terrace. Popular attraction Reach Falls is located ...
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 ...
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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.

American Airlines
Sun, Jan 18 - Fri, Jan 23
MIA
Miami
KIN
Kingston
$298 Roundtrip, found 4 days ago
$298
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sun, Jan 18 from Miami to Kingston, returning Fri, Jan 23, priced at $298 found 4 days ago
Spirit Airlines
Mon, Jan 12 - Thu, Jan 22
ATL
Atlanta
KIN
Kingston
$317 Roundtrip, found 2 days ago
$317
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Mon, Jan 12 from Atlanta to Kingston, returning Thu, Jan 22, priced at $317 found 2 days ago
Delta
Wed, Jan 21 - Thu, Jan 22
MIA
Miami
KIN
Kingston
$333 Roundtrip, found 4 days ago
$333
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Jan 21 from Miami to Kingston, returning Thu, Jan 22, priced at $333 found 4 days ago
JetBlue Airways
Sat, Jan 24 - Wed, Feb 4
JFK
New York
KIN
Kingston
$400 Roundtrip, found 1 day ago
$400
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, Jan 24 from New York to Kingston, returning Wed, Feb 4, priced at $400 found 1 day ago
Caribbean Airlines
Tue, Jan 20 - Wed, Jan 28
JFK
New York
KIN
Kingston
$422 Roundtrip, found 1 day ago
$422
Roundtrip
found 1 day ago
Select Caribbean Airlines flight, departing Tue, Jan 20 from New York to Kingston, returning Wed, Jan 28, priced at $422 found 1 day ago