A clear turquoise sea, a small island with dense green foliage, and a clear blue sky.

Portland Holiday Rentals

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Our top choices for Portland holiday rentals

A wooden bed with intricate carvings, a bedside lamp, and a robe hanging on the wall.

1. Windbreak Villa

Windbreak Villa
3.5 star property
Buff Bay
10.0 out of 10, Exceptional, (1 review)
The price is S$138
includes taxes & fees
2 Nov - 3 Nov
Windbreak Villa
A large house with a swimming pool surrounded by lush greenery.

2. Norse Hill Estate & Botanic Gardens

Norse Hill Estate & Botanic Gardens
3.5 star property
Port Antonio
The price is S$2,668
includes taxes & fees
2 Nov - 3 Nov
Norse Hill Estate & Botanic Gardens
A cozy living room with wicker furniture, a coffee table, and a patterned rug.

3. The Grand Sinopia Inn Portland

The Grand Sinopia Inn Portland
3.5 star property
Port Antonio
The price is S$722
includes taxes & fees
2 Nov - 3 Nov
The Grand Sinopia Inn Portland
A balcony with white balustrades, three wooden chairs with green cushions, and a solar panel on the wall.

4. Pearl Ocean Villa

Pearl Ocean Villa
3.5 star property
Saint Margarets Bay
10.0 out of 10, Exceptional, (1 review)
"Cleanest the hoast was superb"
United States
Michael
The price is S$378
includes taxes & fees
16 Nov - 17 Nov
Pearl Ocean Villa
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.
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Top Portland Hotel Reviews

R Hotel Kingston

R Hotel Kingston

8/10 Good
"I really loved the customer service and the support provided when needed. The room was clean and breakfast was delicious. I appreciated that breakfast was included in the room."
Danielia Sereta 1-night trip
Posted 3 hours ago
R Hotel Kingston