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

4 bedrooms, Egyptian cotton sheets, premium bedding, down duvets

1. 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$380
includes taxes & fees
6 Aug - 7 Aug
Pearl Ocean Villa
View from property

2. Ridge Bay Chateau

Ridge Bay Chateau
3.0 star property
Port Antonio
The price is S$590
includes taxes & fees
3 Aug - 4 Aug
Ridge Bay Chateau
Living area

3. The Grand Sinopia Inn Portland

The Grand Sinopia Inn Portland
3.5 star property
Port Antonio
The price is S$852
includes taxes & fees
3 Aug - 4 Aug
The Grand Sinopia Inn Portland
Premium bedding, bed sheets

4. Windbreak Villa

Windbreak Villa
3.5 star property
Buff Bay
10.0 out of 10, Exceptional, (1 review)
The price is S$125
includes taxes & fees
3 Aug - 4 Aug
Windbreak Villa
Private kitchen

5. 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$481
includes taxes & fees
3 Aug - 4 Aug
Phoenix Park Villas Portmore
1 bedroom, premium bedding, in-room safe, laptop workspace

6. Abacus Jamaica the Zana Suite

Abacus Jamaica the Zana Suite
3.0 star property
Constant Spring
7.8 out of 10, Good, (73 reviews)
"This was the worst rental I've ever had . I reserved"
United States
Teri
The price is S$129
includes taxes & fees
30 Aug - 31 Aug
Abacus Jamaica the Zana Suite
Terrace/patio

7. Apartment with roof top pool

Apartment with roof top pool
2.0 star property
Half Way Tree
7.4 out of 10, Good, (9 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$560
includes taxes & fees
3 Aug - 4 Aug
Apartment with roof top pool
2 bedrooms, hypo-allergenic bedding, in-room safe, iron/ironing board

8. 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$118
includes taxes & fees
3 Aug - 4 Aug
The Gardens
Interior

9. 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$411
includes taxes & fees
9 Aug - 10 Aug
Premium Suite at The Vineyards
Full-sized fridge, microwave, oven

10. PH 1

PH 1
3.0 star property
Half Way Tree
The price is S$208
includes taxes & fees
3 Aug - 4 Aug
PH 1
Terrace/patio

11. 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$119
includes taxes & fees
8 Aug - 9 Aug
Tapioca Village Retreat
Private kitchen

12. 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$322
includes taxes & fees
4 Aug - 5 Aug
Modern 1BR Condo in Kingston
Terrace/patio

13. Can sleep 7 people with private parking

Can sleep 7 people with private parking
2.5 star property
Aeolus Valley
The price is S$163
includes taxes & fees
3 Aug - 4 Aug
Can sleep 7 people with private parking
Terrace/patio

14. Serenity Oasis Apartment

Serenity Oasis Apartment
2.0 star property
Spanish Town
The price is S$156
includes taxes & fees
5 Aug - 6 Aug
Serenity Oasis Apartment
Terrace/patio

15. Deanery Apartments - Pool - AC - 24hrs

Deanery Apartments - Pool - AC - 24hrs
3.0 star property
Eden Gardens
The price is S$367
includes taxes & fees
3 Aug - 4 Aug
Deanery Apartments - Pool - AC - 24hrs
Free WiFi

16. Kensington Place New Kingston Apartment

Kensington Place New Kingston Apartment
2.0 star property
New Kingston
2.0 out of 10, (1 review)
"This is a scam they will take your money and will deny you the access to the property. They stole my money till now I dont get my money and I was denied the access to the property. Thats a scam."
Canada
Luz Carmel
The price is S$293
includes taxes & fees
3 Aug - 4 Aug
Kensington Place New Kingston Apartment
Free WiFi

17. Stylish Studio in Chelsea Manor

Stylish Studio in Chelsea Manor
2.0 star property
New Kingston
8.0 out of 10, Very good, (2 reviews)
"I loved that it was private and the staff was very welcoming everything was exactly what i wanted. I definitely would book agsin everything was so clean and neat"
United States
DONNA
The price is S$365
includes taxes & fees
4 Aug - 5 Aug
Stylish Studio in Chelsea Manor
Living area

18. 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$438
includes taxes & fees
25 Aug - 26 Aug
Stylish 1-Bed Condo with Views in Harloe
Exterior

19. Cozy Apartments

Cozy Apartments
2.5 star property
Barbican
2.0 out of 10, (1 review)
"This property was doble booked"
United States
Michael
The price is S$252
includes taxes & fees
4 Aug - 5 Aug
Cozy Apartments
Property grounds

20. Lovely 2 Bedroom House in St Thomas Jamaica

Lovely 2 Bedroom House in St Thomas Jamaica
3.0 star property
Port Morant
2.0 out of 10, (1 review)
"Don’t book here even if you are tempted; unless you are friends with the owner or you will have many, many problems to deal with …. Expedia helps resolve problems very well. But save yourself the energy. Ya understand. "
Canada
Arlene
The price is S$201
includes taxes & fees
31 Aug - 1 Sept
Lovely 2 Bedroom House in St Thomas Jamaica
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

Sea Cliff Resort

Sea Cliff Resort

8/10 Good
"The hotel provided a clean room, pleasant staff, and great view from the balcony. The breakfast does need a vegetarian/vegan option. Otherwise, it was good and well cooked. The pool area did need a bit of tidying, but it's good for an early morning swim."
Shawna-Kay 2-night trip
Posted 7 hours ago
Sea Cliff Resort