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$124
includes taxes & fees
17 Sept - 18 Sept
Windbreak Villa
A deck with outdoor seating and a view of the ocean at dusk.

2. Ridge Bay Chateau

Ridge Bay Chateau
3.0 star property
Port Antonio
The price is S$586
includes taxes & fees
30 Sept - 1 Oct
Ridge Bay Chateau
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$719
includes taxes & fees
17 Sept - 18 Sept
The Grand Sinopia Inn Portland
A wooden deck with a table and chairs, surrounded by lush greenery and a view of distant mountains.

4. Reggae Legends Estate

Reggae Legends Estate
3.5 star property
Jack's Hill
9.8 out of 10, Exceptional, (6 reviews)
"A really amazing find! Stunning location with fantastic views. Quiet and relaxing. The cabin was a great experience and we were so well looked after by Anne-Marie."
United Kingdom
Nicola
The price is S$207
includes taxes & fees
17 Sept - 18 Sept
Reggae Legends Estate
A modern hotel room with a large bed, a dark headboard, a small round table, a brown sofa, and a view of greenery through the window.

5. The Gardens

The Gardens
3.0 star property
Barbican
7.8 out of 10, Good, (67 reviews)
"The place was very clean, the bed was comfortable and the bathroom was very modern. Loved the place!"
United States
Jelani
The price is S$122
includes taxes & fees
18 Sept - 19 Sept
The Gardens
A two-story house with a red-tiled roof, surrounded by lush greenery and trees.

6. Can sleep 7 people with private parking

Can sleep 7 people with private parking
2.5 star property
Aeolus Valley
The price is S$192
includes taxes & fees
16 Oct - 17 Oct
Can sleep 7 people with private parking
A wooden deck with benches, a small blue structure, and a view of the sea and mountains.

7. Deanery Apartments - Pool - AC - 24hrs

Deanery Apartments - Pool - AC - 24hrs
3.0 star property
Eden Gardens
The price is S$367
includes taxes & fees
26 Sept - 27 Sept
Deanery Apartments - Pool - AC - 24hrs
A deck with blue lounge chairs and a small blue boat, overlooking a river with a forested hillside in the background.

8. Tapioca Village Retreat

Tapioca Village Retreat
3.0 star property
Castleton
6.0 out of 10, (2 reviews)
"There is so much nature and friendliness! "
United States
Günter
The price is S$118
includes taxes & fees
30 Sept - 1 Oct
Tapioca Village Retreat
A modern kitchen with a built-in oven, a refrigerator, and a dining area with a table set for four.

9. Phoenix Park Villas Portmore

Phoenix Park Villas Portmore
4.0 star property
Portmore
9.8 out of 10, Exceptional, (6 reviews)
"I will definitely recommend that you stay here is so peaceful security are strictly on point with everything and the comfort of the home is great will be staying back for sure ."
United States
Kimoya
The price is S$427
includes taxes & fees
17 Sept - 18 Sept
Phoenix Park Villas Portmore
A rectangular swimming pool with a metal safety railing, surrounded by a concrete deck and a green wall.

10. 1BR Comfort City Apartment with pool

1BR Comfort City Apartment with pool
2.0 star property
Kingston
The price is S$331
includes taxes & fees
17 Sept - 18 Sept
1BR Comfort City Apartment with pool
A swimming pool with a clear water surface reflecting surrounding buildings, a covered area with stairs, and a metal railing along the pool's edge.

11. 1BR Premium Apartments Nitram

1BR Premium Apartments Nitram
2.0 star property
Kingston
The price is S$428
includes taxes & fees
17 Sept - 18 Sept
1BR Premium Apartments Nitram
A rocky beach with clear blue water and a steep cliff.

12. Charming 1-bedroom House in St Thomas Jamaica

Charming 1-bedroom House in St Thomas Jamaica
3.5 star property
Port Morant
2.0 out of 10, (1 review)
"The room was not in the house as shown. It was not gated parking. The bathroom was dirty There was a frog in the toilet. The bed looked unmade and dusty. Decor was not welcoming and homey "
Canada
Sherry
Charming 1-bedroom House in St Thomas Jamaica
A modern indoor swimming pool with glass walls, a wooden deck, and a multi-level building with balconies and hanging lights.

13. Apartment with roof top pool

Apartment with roof top pool
2.0 star property
Half Way Tree
7.2 out of 10, Good, (10 reviews)
"Rooms were excellent, really loved the roof was a beautiful view. People were friendly and kind couldnt have asked for a better stay!!"
United States
Jacqueline
The price is S$486
includes taxes & fees
17 Sept - 18 Sept
Apartment with roof top pool
A kitchen with a granite countertop, stainless steel faucet, and a coffee machine.

14. Modern 1BR Condo in Kingston

Modern 1BR Condo in Kingston
2.0 star property
Half Way Tree
10.0 out of 10, Exceptional, (1 review)
"Excellent location absolutely loved it. The only thing was they had ants… everywhere"
United States
Robin
The price is S$310
includes taxes & fees
17 Sept - 18 Sept
Modern 1BR Condo in Kingston
A modern living room with a sofa, a dining table with chairs, a ceiling fan, and a TV mounted on the wall.

15. Premium Suite at The Vineyards

Premium Suite at The Vineyards
2.0 star property
Kingston
2.0 out of 10, (1 review)
The price is S$407
includes taxes & fees
17 Sept - 18 Sept
Premium Suite at The Vineyards
A hotel room with a bed, a window with curtains, a desk with a computer, and a chair.

16. Abacus Jamaica the Zana Suite

Abacus Jamaica the Zana Suite
3.0 star property
Constant Spring
7.8 out of 10, Good, (74 reviews)
"This was the worst rental I've ever had . I reserved"
United States
Teri
The price is S$130
includes taxes & fees
1 Oct - 2 Oct
Abacus Jamaica the Zana Suite
A modern living room with a sectional sofa, a mounted TV, and a window with natural light.

17. Kingston Comfy 1BR Apartment with pool

Kingston Comfy 1BR Apartment with pool
2.0 star property
Half Way Tree
The price is S$390
includes taxes & fees
17 Sept - 18 Sept
Kingston Comfy 1BR Apartment with pool
A modern kitchen with stainless steel appliances, white cabinetry, and a built-in microwave.

18. VIA Braemar Suites - with roof-top pool

VIA Braemar Suites - with roof-top pool
2.0 star property
New Kingston
10.0 out of 10, Exceptional, (1 review)
The price is S$428
includes taxes & fees
17 Sept - 18 Sept
VIA Braemar Suites - with roof-top pool
A living room with a flat-screen TV on a dark wooden stand, a small table with a vase of flowers, and a grey sofa.

19. Stylish 1-Bed Condo with Views in Harloe

Stylish 1-Bed Condo with Views in Harloe
3.0 star property
Half Way Tree
10.0 out of 10, Exceptional, (1 review)
"Property was very comfortable and clean. Close to everything. Whenever I am in Jamaica will I will stay there."
United States
Cordell
The price is S$391
includes taxes & fees
15 Oct - 16 Oct
Stylish 1-Bed Condo with Views in Harloe
A living room with two cream-colored sofas, a wooden staircase, and a large window with blue curtains.

20. Sweet Kensville

Sweet Kensville
4.0 star property
New Kingston
8.8 out of 10, Excellent, (5 reviews)
"Great stay"
United States
Steve
The price is S$262
includes taxes & fees
30 Sept - 1 Oct
Sweet Kensville
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

Jamaica Palace Hotel

Jamaica Palace Hotel

10/10 Excellent
"Our stay was very nice. The food was delicious. Our servers Dominic and Travaughn were amazing. The entire staff was wonderful. The rooms could use a little upgrade. The property is huge and has a lot of space. It would be nice if some lounge chairs could be added on the property grounds. Overall it was a great experience and we will definitely return."
Deneisha 2-night trip
Posted 1 day ago
Jamaica Palace Hotel