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 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 ￥13,360
￥15,523 total
includes taxes & fees
Aug 30 - Aug 31
Windbreak Villa
A beach scene with clear turquoise water, a person on a swing, and lush greenery in the background.

2. 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 ￥6,731
￥14,555 total
includes taxes & fees
Aug 30 - Aug 31
Private Oasis - Portland’s Coastal Gated Hideaway
A bedroom with a bed, white curtains, a wooden wardrobe, and an air conditioning unit.

3. 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 ￥15,934
￥21,034 total
includes taxes & fees
Aug 30 - Aug 31
DreamEscape in Fairy Hill p.o : Your Getaway Near Frenchman cove ,Blue Lagoon

4. 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 ￥5,850
￥16,900 total
includes taxes & fees
Sep 3 - Sep 4
Rockery Villa a Cozy hideaway and retreat.Perfect Romantic Getaway for couples.
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
The price is ￥7,171
￥11,314 total
includes taxes & fees
Aug 30 - Aug 31
Downstairs Bedroom at Robin Hood guesthouse
A two-story house with a balcony, surrounded by lush greenery.

6. Bright Country Apartment at Robin Hood guesthouse

Bright Country Apartment at Robin Hood guesthouse
Port Antonio
The price is ￥15,299
￥18,486 total
includes taxes & fees
Aug 30 - Aug 31
Bright Country Apartment at Robin Hood guesthouse
A garden with various plants and a metal fence.

7. 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
The price is ￥7,583
￥18,633 total
includes taxes & fees
Sep 5 - Sep 6
Rockery Villa is a cozy 1 Bedroom Townhouse an ideal space for a getaway.
A bedroom with a bed, a ceiling fan, a window with a view, and a door.

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

Views from every angle - 2nd floor cozy villa
Port Antonio
The price is ￥18,358
￥24,732 total
includes taxes & fees
Aug 30 - Aug 31
Views from every angle - 2nd floor cozy villa

9. 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, (2 reviews)
"As someone who will only stay at a property that has white sheets & presents as very updated/clean, this property was 10/10. Coming from someone who spent several hours looking for the perfect airbnb for our stay in Portland, to get a 10/10 from me is pretty wild. My husband and I booked last minute and the owner Randy and his team were responsive and helpful from the beginning. The property was exactly as pictured but better. At the time of booking, they didn't have any many photos that really...
United States
Matthew N.
The price is ￥35,856
￥46,334 total
includes taxes & fees
Aug 30 - Aug 31
Purevibe 2 BR/2 BA, Ocean View Villa, Private Rooftop, Near Port Antonio
A living room with a television, a fan, a sofa, and a red chair. There is a door with a window and a refrigerator.

10. Horse Shoe Villa Port Antonio air conditioned close to it all family friendly

Horse Shoe Villa Port Antonio air conditioned close to it all family friendly
Port Antonio
The price is ￥15,936
￥21,514 total
includes taxes & fees
Aug 30 - Aug 31
Horse Shoe Villa Port Antonio air conditioned close to it all family friendly
A wooden deck with a swimming pool, a covered seating area, and a view of the ocean.

11. Ahh! (Pool/Ocean View Room w/ Private Bath)

Ahh! (Pool/Ocean View Room w/ Private Bath)
Boston Bay
The price is ￥13,147
￥30,039 total
includes taxes & fees
Aug 30 - Aug 31
Ahh! (Pool/Ocean View Room w/ Private Bath)
A wooden staircase leading to a small wooden building with a white door and windows.

12. Jamaica House - The Blue Mountain Wilderness Retreat

Jamaica House - The Blue Mountain Wilderness Retreat
Bangor Ridge
The price is ￥11,155
￥15,458 total
includes taxes & fees
Aug 30 - Aug 31
Jamaica House - The Blue Mountain Wilderness Retreat
A bright, sunlit room with a glass door leading outside, a small round table, and a chair.

13. Port Antonio East Side Villa

Port Antonio East Side Villa
Port Antonio
The price is ￥15,936
￥23,107 total
includes taxes & fees
Aug 30 - Aug 31
Port Antonio East Side Villa
A deck with outdoor seating and a view of the ocean at dusk.

14. Ridge Bay Chateau

Ridge Bay Chateau
3.0 star property
Port Antonio
The price is ￥52,247
￥73,641 total
includes taxes & fees
Aug 30 - Aug 31
Ridge Bay Chateau
A pebbled beach with dense greenery and a calm body of water.

15. Teejay's rustic retreat

Teejay's rustic retreat
Port Antonio
9.0 out of 10, Wonderful, (2 reviews)
"Best ever home the host Brenon was amazing. Brennon made sure me and my family was comfortable and felt at home. Beautiful home, parking was safe and good. Hot water, air conditioner comfort all around"
United States
Andrea W.
The price is ￥18,326
￥39,043 total
includes taxes & fees
Aug 31 - Sep 1
Teejay's rustic retreat
A beach with pebbles, waves, and dense green foliage.

16. Charming 2-bedroom house with AC, WiFi in enchanting Port Antonio, Portland

Charming 2-bedroom house with AC, WiFi in enchanting Port Antonio, Portland
Port Antonio
The price is ￥12,908
￥22,470 total
includes taxes & fees
Sep 1 - Sep 2
Charming 2-bedroom house with AC, WiFi in enchanting Port Antonio, Portland
A living room with a television, a fan, a sofa, and a refrigerator.

17. Horse Shoe Villas A family friendly 2 bedroom villa near to it all

Horse Shoe Villas A family friendly 2 bedroom villa near to it all
Port Antonio
The price is ￥15,936
￥23,267 total
includes taxes & fees
Aug 30 - Aug 31
Horse Shoe Villas A family friendly 2 bedroom villa near to it all
A sunlit room with wicker furniture, large windows, and a view of the sea.

18. 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 ￥47,808
￥61,832 total
includes taxes & fees
Aug 30 - Aug 31
One Bedroom Sea View Villa, Frenchman's Cove Resort
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 ￥24,223
￥42,071 total
includes taxes & fees
Sep 1 - Sep 2
Charming Beach Front 2-bedroom house with WiFi, AC in nice Long Bay, Portland
A cozy living room with wicker furniture, a coffee table, and a patterned rug.

20. The Grand Sinopia Inn Portland

The Grand Sinopia Inn Portland
3.5 star property
Port Antonio
The price is ￥87,967
￥105,824 total
includes taxes & fees
Aug 30 - Aug 31
The Grand Sinopia Inn Portland
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
"Great atmosphere, clean rooms...Great breakfast"
David 1-night trip
Posted 1 day ago
S Hotel Kingston

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