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

Vacation Rentals in Portland

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Our top choices for Portland vacation 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 ￥6,997
￥16,882 total
includes taxes & fees
Oct 14 - Oct 15
Private Oasis - Portland’s Coastal Gated Hideaway
A wooden bed with intricate carvings, a bedside lamp, and a robe hanging on the wall.

2. Windbreak Villa

Windbreak Villa
3.5 star property
Buff Bay
10.0 out of 10, Exceptional, (1 review)
The price is ￥13,272
￥15,420 total
includes taxes & fees
Oct 14 - Oct 15
Windbreak Villa
A beach with clear turquoise water, a rocky cliff with vegetation, and a person standing in the water.

3. 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 ￥11,715
￥28,338 total
includes taxes & fees
Nov 10 - Nov 11
Ahh! (Ocean View Studio with Private Bath)
A balcony with a view of the ocean, a lounge chair, and two drinks on a table.

4. 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 ￥35,694
￥45,649 total
includes taxes & fees
Oct 16 - Oct 17
Purevibe 2 BR/2 BA, Ocean View Villa, Private Rooftop, Near Port Antonio
A dining area with a table and chairs, a decorative partition, and a view through a window with a metal grill.

5. 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 ￥5,657
￥16,342 total
includes taxes & fees
Oct 14 - Oct 15
Rockery Villa a Cozy hideaway and retreat.Perfect Romantic Getaway for couples.
A bedroom with two beds, a chair, a staircase, and a large painting on the wall.

6. Norse Hill Estate & Botanic Gardens

Norse Hill Estate & Botanic Gardens
3.5 star property
Port Antonio
The price is ￥218,468
￥330,551 total
includes taxes & fees
Oct 26 - Oct 27
Norse Hill Estate & Botanic Gardens
A window with a view of a lush landscape and the ocean.

7. 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 ￥39,578
￥46,860 total
includes taxes & fees
Oct 31 - Nov 1
Pearl Ocean 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
The price is ￥15,198
￥18,364 total
includes taxes & fees
Nov 10 - Nov 11
Bright Country Apartment at Robin Hood guesthouse
A bedroom with a bed, white curtains, a wooden wardrobe, and an air conditioning unit.

9. 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
The price is ￥15,862
￥20,938 total
includes taxes & fees
Oct 14 - Oct 15
DreamEscape in Fairy Hill p.o : Your Getaway Near Frenchman cove ,Blue Lagoon
A bedroom with a bed, a ceiling fan, a window with a view, and a door.

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

Views from every angle - 2nd floor cozy villa
Port Antonio
The price is ￥18,275
￥24,621 total
includes taxes & fees
Oct 16 - Oct 17
Views from every angle - 2nd floor cozy villa
A bright, sunlit room with a glass door leading outside, a small round table, and a chair.

11. Port Antonio East Side Villa

Port Antonio East Side Villa
Port Antonio
The price is ￥15,831
￥22,955 total
includes taxes & fees
Nov 10 - Nov 11
Port Antonio East Side Villa
A garden with various plants and a metal fence.

12. 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 two-story house with a balcony, surrounded by lush greenery.

13. Downstairs Bedroom at Robin Hood guesthouse

Downstairs Bedroom at Robin Hood guesthouse
Port Antonio
The price is ￥7,124
￥11,240 total
includes taxes & fees
Nov 8 - Nov 9
Downstairs Bedroom at Robin Hood guesthouse
A cozy living room with wicker furniture, a coffee table, and a patterned rug.

14. The Grand Sinopia Inn Portland

The Grand Sinopia Inn Portland
3.5 star property
Port Antonio
The price is ￥81,270
￥97,786 total
includes taxes & fees
Oct 16 - Oct 17
The Grand Sinopia Inn Portland
A deck with outdoor seating and a view of the ocean at dusk.

15. Ridge Bay Chateau

Ridge Bay Chateau
3.0 star property
Port Antonio
The price is ￥51,666
￥72,823 total
includes taxes & fees
Oct 26 - Oct 27
Ridge Bay Chateau
A sunlit room with wicker furniture, large windows, and a view of the sea.

16. 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
The price is ￥47,592
￥61,552 total
includes taxes & fees
Oct 14 - Oct 15
One Bedroom Sea View Villa, Frenchman's Cove Resort
A wooden staircase leading to a small wooden building with a white door and windows.

17. Jamaica House - The Blue Mountain Wilderness Retreat

Jamaica House - The Blue Mountain Wilderness Retreat
Bangor Ridge
The price is ￥11,105
￥15,388 total
includes taxes & fees
Oct 14 - Oct 15
Jamaica House - The Blue Mountain Wilderness Retreat
A covered outdoor area with white columns, potted plants, and a tiled floor.

18. 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 ￥49,972
￥57,111 total
includes taxes & fees
Oct 14 - Oct 15
Charming 3-bedroom house in enchanting Fairy Hill with WiFi, AC
A group of people standing near a small structure by the beach, surrounded by palm trees and ocean views.

19. Charming Beach Front 2-bedroom house with WiFi, AC in nice Long Bay, Portland

Charming Beach Front 2-bedroom house with WiFi, AC in nice Long Bay, Portland
Long Bay
The price is ￥22,163
￥39,260 total
includes taxes & fees
Oct 23 - Oct 24
Charming Beach Front 2-bedroom house with WiFi, AC in nice Long Bay, Portland
A wooden staircase leading to an outdoor patio area with white railings, surrounded by lush greenery and a sign that reads "Spicy Portland."

20. 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 ￥142,479
￥162,743 total
includes taxes & fees
Oct 22 - Oct 23
Spicy Hill Villa, One Of Jamaica's Best-Kept Secrets.
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

8/10 Good
"We had a nice stay. The property was very well maintained and clean. The beds were rounded so were a bit odd an"
Tina 1-night trip
Posted 1 hour ago
Jamaica Palace Hotel

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Vacation Apartments in Portland

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