Portland Vacations

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Top destinations in Portland

A beach with clear turquoise water, a rocky coastline, and a small structure on a cliff.

Port Antonio

Port Antonio
A waterfall cascading over a rock formation into a clear pool of water.

Reach

Reach

Portland Hotel Deals

Sea Cliff Resort

Sea Cliff Resort

Ross Craig Long Bay Portland
Fully refundable
AED 408
AED 514 total
13 Sep - 14 Sep
includes taxes & fees
8/10 Very Good! (222 reviews)
"We visited in early August 2026 and had a delightful time. Terrence and Monique were super helpful and the rest of the staff were friendly and courteous. Had a wonderful 3 night stay and as a bonus, got lulled to sleep with the ocean waves and woke up to spectacular sunrises.👍😄🇯🇲"

Reviewed on 11 August 2026

Sea Cliff Resort
Jamaica Palace Hotel

Jamaica Palace Hotel

Williamsfield Port Antonio Portland
Fully refundableReserve now, pay when you stay
AED 506
AED 564 total
18 Aug - 19 Aug
includes taxes & fees
8.2/10 Very Good! (346 reviews)
"The property was magnificient! Clean room, lovely breakfast, friendly staff. Beautiful ladscape and scenery. We enjoyed the cool relaxing ambiance and the drive into the nearby town. A perfect getaway from the busy city life."

Reviewed on 8 August 2026

Jamaica Palace Hotel
Match Resort Hotel

Match Resort Hotel

Dolphin Bay Port Antonio
Fully refundableReserve now, pay when you stay
AED 392
AED 435 total
13 Sep - 14 Sep
includes taxes & fees
8/10 Very Good! (237 reviews)
"Good afternoon, I was invited to a wedding in Portland and I wanted somewhere to stay so I went on Google and began to search and while searching what I saw was way over my budget. And then my friend send me match resort and when I check it out it was the perfect place. When I arrived there the customer ..."

Reviewed on 7 August 2026

Match Resort Hotel
See all 1,956 properties in Portland
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.

Stay near popular Portland attractions

Three boats docked at a calm, turquoise body of water surrounded by lush greenery.

Blue Lagoon

9.2/10 (229 reviews)
Why not spend a carefree afternoon at Blue Lagoon during your travels in Port Antonio? You can enjoy the restaurants while in the area.
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A woman walking on a sandy beach with turquoise water and lush green foliage.

Frenchman's Cove Beach

9.2/10 (164 reviews)
Why not spend a carefree afternoon at Frenchman's Cove Beach during your travels in Port Antonio? You can enjoy the restaurants while in the area.
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A turquoise coastal bay with clear waters, surrounded by lush green hills and a rocky coastline.

Boston Bay Beach

9.0/10 (132 reviews)
If a restful vacation is part of your travel plans, Boston Bay Beach might be the perfect place to seek out during your trip to Port Antonio. You can enjoy the restaurants while in the area.
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A large white colonial-style building with multiple towers and a staircase leading to the entrance, surrounded by lush greenery and a body of water.

Trident Castle

8.6/10 (77 reviews)
After visiting Trident Castle, make a plan to see the other sights and activities in Port Antonio. Wander the waterfront and beaches in the area.
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A beach with clear water, a sandy shore, and dense green foliage in the background.

Winnifred Beach

9.0/10 (117 reviews)
If a restful vacation is part of your travel plans, Winnifred Beach might be the perfect place to seek out during your trip to Port Antonio. You can enjoy the restaurants while in the area.
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A beach with clear turquoise water, a large tree trunk in the sand, and a small island in the distance.

San San Beach

8.4/10 (47 reviews)
If a restful vacation is part of your travel plans, San San Beach might be the perfect place to seek out during your trip to Port Antonio. You can enjoy the restaurants while in the area.
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Portland Parish Church

8.2/10 (32 reviews)
Portland Parish Church is just one of the places to see in Titchfield Peninsula, so why not enjoy the other things to explore during your travels? Wander the waterfront and beaches in the area.
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Port Antonio Square

8.0/10 (99 reviews)
Learn about the local history of Titchfield Peninsula when you take a trip to Port Antonio Square. Wander the waterfront and beaches in the area.
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