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

Portland Holiday Rentals

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Top Cities in Portland

A tropical beach with clear blue waters, sandy shore, and lush greenery.
Holiday RentalsHoliday Rentals

Long Bay

Long Bay

Our top choices for Portland holiday rentals

A bright, sunlit room with a glass door leading outside, a small round table, and a chair.

1. Port Antonio East Side Villa

Port Antonio East Side Villa
Port Antonio
The price is NZ$231
includes taxes & fees
14 Nov - 15 Nov
Port Antonio East Side 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 NZ$218
includes taxes & fees
6 Nov - 7 Nov
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.

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 NZ$290
includes taxes & fees
6 Nov - 7 Nov
Ahh! (Ocean View Studio with Private Bath)
A two-story house with a balcony, surrounded by lush greenery.

4. Downstairs Bedroom at Robin Hood guesthouse

Downstairs Bedroom at Robin Hood guesthouse
Port Antonio
The price is NZ$112
includes taxes & fees
6 Nov - 7 Nov
Downstairs Bedroom at Robin Hood guesthouse
A bedroom with a bed, a ceiling fan, a window with a view, and a door.

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

Views from every angle - 2nd floor cozy villa
Port Antonio
The price is NZ$262
includes taxes & fees
6 Nov - 7 Nov
Views from every angle - 2nd floor cozy villa
A room with a table and chairs, a window with a decorative metal grill, and a view of greenery outside.

6. 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 NZ$180
includes taxes & fees
16 Nov - 17 Nov
Rockery Villa a Cozy hideaway and retreat.Perfect Romantic Getaway for couples.
A bedroom with a bed, white curtains, a wooden wardrobe, and an air conditioning unit.

7. 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 NZ$222
includes taxes & fees
6 Nov - 7 Nov
DreamEscape in Fairy Hill p.o : Your Getaway Near Frenchman cove ,Blue Lagoon
A balcony with a view of the ocean, a lounge chair, and two drinks on a table.

8. 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.
Purevibe 2 BR/2 BA, Ocean View Villa, Private Rooftop, Near Port Antonio
A room with a table and chairs, a window with a decorative metal grill, and a view of greenery outside.

9. 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 NZ$192
includes taxes & fees
4 Dec - 5 Dec
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.

10. Bright Country Apartment at Robin Hood guesthouse

Bright Country Apartment at Robin Hood guesthouse
Port Antonio
The price is NZ$193
includes taxes & fees
3 Dec - 4 Dec
Bright Country Apartment at Robin Hood guesthouse
A large house with a swimming pool surrounded by lush greenery.

11. Norse Hill Estate & Botanic Gardens

Norse Hill Estate & Botanic Gardens
3.5 star property
Port Antonio
The price is NZ$3,734
includes taxes & fees
9 Nov - 10 Nov
Norse Hill Estate & Botanic Gardens
A sunlit room with wicker furniture, large windows, and a view of the sea.

12. 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.

13. Windbreak Villa

Windbreak Villa
3.5 star property
Buff Bay
10.0 out of 10, Exceptional, (1 review)
The price is NZ$192
includes taxes & fees
6 Nov - 7 Nov
Windbreak Villa
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 NZ$526
includes taxes & fees
16 Nov - 17 Nov
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 NZ$1,010
includes taxes & fees
6 Nov - 7 Nov
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 NZ$592
includes taxes & fees
6 Nov - 7 Nov
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 NZ$1,720
includes taxes & fees
3 Dec - 4 Dec
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
The price is NZ$158
includes taxes & fees
14 Nov - 15 Nov
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

Match Resort Hotel

Match Resort Hotel

10/10 Excellent
"The staff was very helpful and caring they stopped what they were doing to help us with our luggages. The breakfast was well presented and tasty."
Carlene 1-night trip
Posted 8 hours ago
Match Resort Hotel

Find out more about Portland

Everything you need to know about Portland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Portland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Portland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Portland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Portland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Portland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Portland holiday rentals we have selected for you start as low as NZ$166 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Portland rentals

At Expedia, we put the best Portland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Portland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Portland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Portland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.