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 beach scene with clear turquoise water, a person on a swing, and lush greenery in the background.

1. Private Oasis - Portland’s Coastal Gated Hideaway

Private Oasis - Portland’s Coastal Gated Hideaway
Fair Prospect
10.0 out of 10, Exceptional, (1 review)
"The listing didn’t really represent this quant hideaway. I grew up in this community so it was great visiting and have this place to decompress and chill. Very cute spot, the host was super, asked if I needed anything at the store and he was very available to assist as needed, I had my ex to assist so didn’t need him, but he checked if I needed anything and was available if I did. And the view from the gazebo was my favourite. You will not be disappointed perfect for couples or just friends...
Canada
Janet
The price is HK$353
HK$846 total
includes taxes & fees
27 Oct - 28 Oct
Private Oasis - Portland’s Coastal Gated Hideaway
A beach with clear turquoise water, a rocky cliff with vegetation, and a person standing in the water.

2. Ahh! (Ocean View Studio with Private Bath)

Ahh! (Ocean View Studio with Private Bath)
Boston Bay
10.0 out of 10, Exceptional, (2 reviews)
"Not the easiest drive up to the place, but the view is magnificent. The place is clean, and the hosts are friendly and helpful. If you're looking for an inexpensive decent studio in Portland with air conditioning, hot water, and a terrific view, consider this place."
United States
Jerry B.
The price is HK$580
HK$1,388 total
includes taxes & fees
27 Oct - 28 Oct
Ahh! (Ocean View Studio with Private Bath)
A bedroom with a bed, a ceiling fan, a window with a view, and a door.

3. Views from every angle - 2nd floor cozy villa

Views from every angle - 2nd floor cozy villa
Port Antonio
Views from every angle - 2nd floor cozy villa
A bedroom with a bed, white curtains, a wooden wardrobe, and an air conditioning unit.

4. DreamEscape in Fairy Hill p.o : Your Getaway Near Frenchman cove ,Blue Lagoon

DreamEscape in Fairy Hill p.o : Your Getaway Near Frenchman cove ,Blue Lagoon
Fairy Hill
8.0 out of 10, Very good, (1 review)
"The host was very welcoming, and miss Mariana was very kimd and friendly. Great place to stay "
United States
Suzette
DreamEscape in Fairy Hill p.o : Your Getaway Near Frenchman cove ,Blue Lagoon
A two-story house with a balcony, surrounded by lush greenery.

5. Downstairs Bedroom at Robin Hood guesthouse

Downstairs Bedroom at Robin Hood guesthouse
Port Antonio
Downstairs Bedroom at Robin Hood guesthouse
A balcony with a view of the ocean, a lounge chair, and two drinks on a table.

6. Purevibe 2 BR/2 BA, Ocean View Villa, Private Rooftop, Near Port Antonio

Purevibe 2 BR/2 BA, Ocean View Villa, Private Rooftop, Near Port Antonio
Snow District
10.0 out of 10, Exceptional, (3 reviews)
"Randy's place is clean and is exactly as seen online. Must come back here"
Canada
Max L.
The price is HK$1,765
HK$2,257 total
includes taxes & fees
2 Nov - 3 Nov
Purevibe 2 BR/2 BA, Ocean View Villa, Private Rooftop, Near Port Antonio
A bright, sunlit room with a glass door leading outside, a small round table, and a chair.

7. Port Antonio East Side Villa

Port Antonio East Side Villa
Port Antonio
Port Antonio East Side Villa
A two-story house with a balcony, surrounded by lush greenery.

8. Bright Country Apartment at Robin Hood guesthouse

Bright Country Apartment at Robin Hood guesthouse
Port Antonio
Bright Country Apartment at Robin Hood guesthouse
A sunlit room with wicker furniture, large windows, and a view of the sea.

9. One Bedroom Sea View Villa, Frenchman's Cove Resort

One Bedroom Sea View Villa, Frenchman's Cove Resort
Drapers
6.0 out of 10, (1 review)
"The property has a unique cove and the beach area was very clean and well maintained. The staff there were very polite and helpful. The Villa itself was tidy but showed signs of massive wear and tear. It was more a lack of maintenance rather than true heritage status."
Canada
David
One Bedroom Sea View Villa, Frenchman's Cove Resort
A wooden bed with intricate carvings, a bedside lamp, and a robe hanging on the wall.

10. Windbreak Villa

Windbreak Villa
3.5 star property
Buff Bay
10.0 out of 10, Exceptional, (1 review)
The price is HK$657
HK$764 total
includes taxes & fees
26 Oct - 27 Oct
Windbreak Villa
A room with a table and chairs, a window with a decorative metal grill, and a view of greenery outside.

11. Rockery Villa is a cozy 1 Bedroom Townhouse an ideal space for a getaway.

Rockery Villa is a cozy 1 Bedroom Townhouse an ideal space for a getaway.
Port Antonio
Rockery Villa is a cozy 1 Bedroom Townhouse an ideal space for a getaway.
A room with a tiled floor, a table with a vase of sunflowers, two chairs, and a decorative metal gate.

12. Rockery Villa a Cozy hideaway and retreat.Perfect Romantic Getaway for couples.

Rockery Villa a Cozy hideaway and retreat.Perfect Romantic Getaway for couples.
Port Antonio
The price is HK$283
HK$818 total
includes taxes & fees
12 Nov - 13 Nov
Rockery Villa a Cozy hideaway and retreat.Perfect Romantic Getaway for couples.
A large house with a swimming pool surrounded by lush greenery.

13. Norse Hill Estate & Botanic Gardens

Norse Hill Estate & Botanic Gardens
3.5 star property
Port Antonio
The price is HK$10,823
HK$16,375 total
includes taxes & fees
26 Oct - 27 Oct
Norse Hill Estate & Botanic Gardens
A window with a view of a lush landscape and the ocean.

14. 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 HK$1,961
HK$2,321 total
includes taxes & fees
28 Oct - 29 Oct
Pearl Ocean Villa
A cozy living room with wicker furniture, a coffee table, and a patterned rug.

15. The Grand Sinopia Inn Portland

The Grand Sinopia Inn Portland
3.5 star property
Port Antonio
The price is HK$4,329
HK$5,208 total
includes taxes & fees
26 Oct - 27 Oct
The Grand Sinopia Inn Portland
A covered outdoor area with white columns, potted plants, and a tiled floor.

16. Charming 3-bedroom house in enchanting Fairy Hill with WiFi, AC

Charming 3-bedroom house in enchanting Fairy Hill with WiFi, AC
Fairy Hill
10.0 out of 10, Exceptional, (2 reviews)
"I spent the weekend with my family for my brothers birthday and it was a lovely experience , the ambiance was great and the rooms were spacious and beautiful! I would definitely come back ! Big up !"
United States
Sheneker R.
The price is HK$2,470
HK$2,823 total
includes taxes & fees
26 Oct - 27 Oct
Charming 3-bedroom house in enchanting Fairy Hill with WiFi, AC
A wooden staircase leading to an outdoor patio area with white railings, surrounded by lush greenery and a sign that reads "Spicy Portland."

17. Spicy Hill Villa, One Of Jamaica's Best-Kept Secrets.

Spicy Hill Villa, One Of Jamaica's Best-Kept Secrets.
Port Antonio
9.4 out of 10, Exceptional, (15 reviews)
"The staff made the visit memorable. "
United States
Eric
The price is HK$7,058
HK$8,062 total
includes taxes & fees
26 Oct - 27 Oct
Spicy Hill Villa, One Of Jamaica's Best-Kept Secrets.
A bedroom with a view of the ocean, a bed with white bedding, a nightstand with a lamp, and a window with a view of trees and the sea.

18. 2 Bedroom Sea View Villa, Frenchman's Cove Resort

2 Bedroom Sea View Villa, Frenchman's Cove Resort
Drapers
2 Bedroom Sea View Villa, Frenchman's Cove Resort
A wooden staircase leading to a small wooden building with a white door and windows.

19. Jamaica House - The Blue Mountain Wilderness Retreat

Jamaica House - The Blue Mountain Wilderness Retreat
Bangor Ridge
Jamaica House - The Blue Mountain Wilderness Retreat
A spacious room with a stone wall, wooden ceiling, and large windows. There is a dining table with chairs, a sofa, and a blue chair.

20. Luxury Three Bedroom Sea View Villa, Frenchman's Cove Resort

Luxury Three Bedroom Sea View Villa, Frenchman's Cove Resort
Drapers
Luxury Three Bedroom Sea View Villa, Frenchman's Cove Resort
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

Goblin Hill Villas at San San

Goblin Hill Villas at San San

10/10 Excellent
"Goblin Hill Villas is a spectacular property, with a perfect balance between lush greenery and amazing ocean views. Our villa was spacious, clean, and comfortable with a great retro vibe. We loved watching the waves roll into San San beach, sunrise and sunset, and floating in the pool surrounded by palms and flowers. The bird life is active and varied: one evening we even had a visit from a Jamaican Owl. The staff are professional and friendly, exceptionally helpful, and the food is fantastic. We love Jamaican food in general and theirs is so fresh and flavourful. Blue Lagoon, San San Beach and Frenchman’s Cove are all an easy walk from the villas and wonderful places to enjoy swimming and nature."
Gillian 11-night trip
Posted 21 hours ago
Goblin Hill Villas at San San