Vacation Packages to Portland for 2026
Portland Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Teal Horizon Oceanfrontcaribbean Escape Tower Isle
Price was $1,068, price is now $939 per person
$939
per person
Mar 8 - Mar 13
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Book a stay at this beach apartment in Tower Isle. Enjoy free parking and a beach locale. Popular attractions Turtle Beach and Dunn's River Falls are located nearby.
Ocho Rios Skyview Guest Apartment
Save 100% on your flight
Price was $3,479, price is now $2,339 per person
$2,339
per person
Mar 13 - Mar 20
found 4 hours ago
Roundtrip flight included
Burlington (BTV) to Ocho Rios (OCJ)
Book a stay at this business-friendly villa in Tower Isle. Enjoy free WiFi, free parking, and a 24-hour fitness center. Popular attractions Turtle Beach and Dunn's River Falls are located nearby.
Panoramic Cliffside Luxe Villa
Save 100% on your flight
Price was $11,735, price is now $9,690 per person
$9,690
per person
Mar 13 - Mar 20
found 4 hours ago
Roundtrip flight included
Burlington (BTV) to Ocho Rios (OCJ)
Stay at this vacation home in Tower Isle. Enjoy free parking. Popular attractions Turtle Beach and Rio Nuevo Battle Site are located nearby.
Sea Shell Palms
Price was $1,250, price is now $1,136 per person
$1,136
per person
Mar 13 - Mar 20
found 4 hours ago
Roundtrip flight included
Burlington (BTV) to Ocho Rios (OCJ)
Book a stay at this business-friendly hotel in Tower Isle. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Turtle Beach and Coral Reef are located nearby.
Seapalms
Price was $1,425, price is now $1,316 per person
$1,316
per person
Mar 13 - Mar 20
found 4 hours ago
Roundtrip flight included
Burlington (BTV) to Ocho Rios (OCJ)
Book a stay at this beach apartment in Tower Isle. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Turtle Beach and Dunn's River Falls are located nearby.
The Dream Nest At Csompo Silver Manor
Price was $1,270, price is now $1,176 per person
$1,176
per person
Mar 13 - Mar 20
found 4 hours ago
Roundtrip flight included
Burlington (BTV) to Ocho Rios (OCJ)
Stay at this apartment in Tower Isle. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Turtle Beach and Rio Nuevo Battle Site are located nearby.
Top Hotel Deals
Sea Cliff Resort
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
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
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
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
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 ...
Jamaica Colors Eco-Retreat Hotel and Spa
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 ...
LF Jungle Retreat
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 ...
Frenchman's Cove Resort
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 ...
Goblin Hill Villas at San San
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
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
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 ...
Paradise Inn
Snow Hill Port Antonio Portland
6.27 km from city center
Stay at this hotel in Port Antonio. Enjoy free WiFi, free parking, and room service. Popular attractions Sharshy Beach and Bikini Beach are located nearby.
S Hotel Kingston
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. ...
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, Mar 10 - Fri, Mar 27
FLL
Fort Lauderdale
KIN
Kingston
$309 Roundtrip, found 2 days ago
$309
Roundtrip
found 2 days ago
Sat, Feb 21 - Wed, Mar 4
FLL
Fort Lauderdale
KIN
Kingston
$334 Roundtrip, found 2 days ago
$334
Roundtrip
found 2 days ago
Sun, Mar 22 - Mon, Apr 6
MCO
Orlando
KIN
Kingston
$353 Roundtrip, found 1 day ago
$353
Roundtrip
found 1 day ago
Mon, Feb 16 - Tue, Feb 24
FLL
Fort Lauderdale
KIN
Kingston
$410 Roundtrip, found 4 days ago
$410
Roundtrip
found 4 days ago
Fri, Feb 20 - Fri, Mar 13
JFK
New York
KIN
Kingston
$422 Roundtrip, found 3 days ago
$422
Roundtrip
found 3 days ago