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

Portland Vacation Rentals

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Our top choices for Portland vacation rentals

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1. Windbreak Villa

Windbreak Villa
3.5 star property
Buff Bay
10.0 out of 10, Exceptional, (1 review)
The price is P5,136
P5,967 total
includes taxes & fees
Aug 13 - Aug 14
Windbreak Villa
View from property

2. Ridge Bay Chateau

Ridge Bay Chateau
3.0 star property
Port Antonio
The price is P19,993
P28,180 total
includes taxes & fees
Aug 13 - Aug 14
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 P33,532
P40,340 total
includes taxes & fees
Aug 13 - Aug 14
The Grand Sinopia Inn Portland
Living area

4. New Kingston Comfy 2BR Apartment

New Kingston Comfy 2BR Apartment
2.0 star property
New Kingston
The price is P11,027
P17,337 total
includes taxes & fees
Aug 22 - Aug 23
New Kingston Comfy 2BR Apartment
WiFi (free)

5. Kingston Comfy 2BR Apartment

Kingston Comfy 2BR Apartment
2.0 star property
Half Way Tree
The price is P12,865
P19,450 total
includes taxes & fees
Aug 24 - Aug 25
Kingston Comfy 2BR Apartment
Private kitchen

6. VIA Braemar Suites - with roof-top pool

VIA Braemar Suites - with roof-top pool
2.0 star property
New Kingston
The price is P9,189
P15,223 total
includes taxes & fees
Aug 24 - Aug 25
VIA Braemar Suites - with roof-top pool
Property grounds

7. Kingston Comfy 1BR Apartment with pool

Kingston Comfy 1BR Apartment with pool
2.0 star property
Half Way Tree
The price is P9,189
P15,223 total
includes taxes & fees
Aug 15 - Aug 16
Kingston Comfy 1BR Apartment with pool
Property grounds

8. 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 P8,298
P9,604 total
includes taxes & fees
Aug 31 - Sep 1
Lovely 2 Bedroom House in St Thomas Jamaica
Exterior

9. Finest Accommodation Renfrew Place

Finest Accommodation Renfrew Place
3.0 star property
New Kingston
7.0 out of 10, Good, (2 reviews)
"The property was double booked the first two days leaving us without a place to stay. The property manager said he booked another place when we got there that was also not available. We spent several hours late in the evening until we were finally able to get a temporary booking. Communication was extremely poor overall it was hard initially to get a hold of the property owner although we had paid in advance our accommodations was not available first two days. "
United States
cornel
The price is P5,467
P10,600 total
includes taxes & fees
Sep 8 - Sep 9
Finest Accommodation Renfrew Place
Full-size fridge, microwave, oven

10. PH 1

PH 1
3.0 star property
Half Way Tree
The price is P8,930
P10,330 total
includes taxes & fees
Aug 19 - Aug 20
PH 1
Terrace/patio

11. Can sleep 7 people with private parking

Can sleep 7 people with private parking
2.5 star property
Aeolus Valley
The price is P4,901
P8,515 total
includes taxes & fees
Sep 12 - Sep 13
Can sleep 7 people with private parking
Terrace/patio

12. Modern Luxury 1BR Condo in Kingston

Modern Luxury 1BR Condo in Kingston
2.0 star property
Barbican
2.0 out of 10, (1 review)
"It’s fraud stay away. "
United States
sheldeen
The price is P7,314
P14,906 total
includes taxes & fees
Aug 22 - Aug 23
Modern Luxury 1BR Condo in Kingston
1 bedroom, premium bedding, in-room safe, laptop workspace

13. 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 P3,436
P6,156 total
includes taxes & fees
Aug 13 - Aug 14
Abacus Jamaica the Zana Suite
Terrace/patio

14. Deanery Apartments - Pool - AC - 24hrs

Deanery Apartments - Pool - AC - 24hrs
3.0 star property
Eden Gardens
The price is P11,578
P17,971 total
includes taxes & fees
Aug 22 - Aug 23
Deanery Apartments - Pool - AC - 24hrs
Private kitchen

15. 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 P4,742
P12,635 total
includes taxes & fees
Aug 13 - Aug 14
Modern 1BR Condo in Kingston
Exterior

16. 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 P8,656
P12,704 total
includes taxes & fees
Sep 9 - Sep 10
Cozy Apartments
Balcony

17. 1 Bedroom Mountain Retreat New Kingston

1 Bedroom Mountain Retreat New Kingston
2.0 star property
New Kingston
2.0 out of 10, (1 review)
"Place was nice but some of the workers had a nasty attitude and made us go to the basement to get on elevator. The bathroom toilet wasn’t flushing I had to fill up the toilet with water for every flush. I will not be staying there again "
United States
Darnell
The price is P5,966
P13,355 total
includes taxes & fees
Sep 11 - Sep 12
1 Bedroom Mountain Retreat New Kingston
Beach

18. 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
The price is P7,159
P8,294 total
includes taxes & fees
Aug 31 - Sep 1
Charming 1-bedroom House in St Thomas Jamaica
50-inch LED TV with cable channels, Netflix, streaming services

19. 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 P7,135
P12,518 total
includes taxes & fees
Sep 1 - Sep 2
Sweet Kensville
WiFi (free)

20. 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 P4,595
P15,300 total
includes taxes & fees
Sep 7 - Sep 8
Stylish Studio in Chelsea Manor
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

S Hotel Kingston

S Hotel Kingston

10/10 Excellent
"The grounds, staff and hotel were well kept and professional. Love the hotel decor and theme. The ambiance was very nice. The rooms were clean and very well maintained. Breakfast is a bit underwhelming but it served its purpose."
Sophia 1-night trip
Posted less than an hour ago
S Hotel Kingston

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Holiday Apartments in Portland

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