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

Portland Vacation Rentals

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Top Cities in Portland

A beach with clear turquoise water, a rocky coastline, and a small structure on a cliff.
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Port Antonio

Port Antonio
A tropical beach with clear blue waters, sandy shore, and lush greenery.
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Long Bay

Long Bay

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 CA $119
CA $138 total
includes taxes & fees
Sep 27 - Sep 28
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 CA $57
CA $135 total
includes taxes & fees
Oct 12 - Oct 13
Private Oasis - Portland’s Coastal Gated Hideaway
A two-story house with a balcony, surrounded by lush greenery.

3. Downstairs Bedroom at Robin Hood guesthouse

Downstairs Bedroom at Robin Hood guesthouse
Port Antonio
The price is CA $64
CA $100 total
includes taxes & fees
Sep 27 - Sep 28
Downstairs Bedroom at Robin Hood guesthouse
A garden with various plants and a metal fence.

4. 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 CA $51
CA $146 total
includes taxes & fees
Sep 27 - Sep 28
Rockery Villa is a cozy 1 Bedroom Townhouse an ideal space for a getaway.
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 CA $51
CA $146 total
includes taxes & fees
Sep 27 - Sep 28
Rockery Villa a Cozy hideaway and retreat.Perfect Romantic Getaway for couples.
A beach with pebbles, waves, and dense green foliage.

6. 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 CA $125
CA $210 total
includes taxes & fees
Sep 27 - Sep 28
Charming 2-bedroom house with AC, WiFi in enchanting Port Antonio, Portland
A two-story house with a balcony, surrounded by lush greenery.

7. Bright Country Apartment at Robin Hood guesthouse

Bright Country Apartment at Robin Hood guesthouse
Port Antonio
The price is CA $136
CA $164 total
includes taxes & fees
Sep 27 - Sep 28
Bright Country Apartment at Robin Hood guesthouse
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 CA $163
CA $219 total
includes taxes & fees
Sep 27 - Sep 28
Views from every angle - 2nd floor cozy villa
A wooden deck with a swimming pool, a covered seating area, and a view of the ocean.

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

Ahh! (Pool/Ocean View Room w/ Private Bath)
Boston Bay
The price is CA $117
CA $264 total
includes taxes & fees
Sep 28 - Sep 29
Ahh! (Pool/Ocean View Room w/ Private Bath)
A bright, sunlit room with a glass door leading outside, a small round table, and a chair.

10. Port Antonio East Side Villa

Port Antonio East Side Villa
Port Antonio
The price is CA $141
CA $205 total
includes taxes & fees
Sep 27 - Sep 28
Port Antonio East Side Villa
A wooden staircase leading to a small wooden building with a white door and windows.

11. Jamaica House - The Blue Mountain Wilderness Retreat

Jamaica House - The Blue Mountain Wilderness Retreat
Bangor Ridge
The price is CA $99
CA $137 total
includes taxes & fees
Sep 27 - Sep 28
Jamaica House - The Blue Mountain Wilderness Retreat
A cozy living room with wicker furniture, a coffee table, and a patterned rug.

12. The Grand Sinopia Inn Portland

The Grand Sinopia Inn Portland
3.5 star property
Port Antonio
The price is CA $630
CA $759 total
includes taxes & fees
Oct 2 - Oct 3
The Grand Sinopia Inn Portland
A deck with outdoor seating and a view of the ocean at dusk.

13. Ridge Bay Chateau

Ridge Bay Chateau
3.0 star property
Port Antonio
The price is CA $462
CA $651 total
includes taxes & fees
Sep 30 - Oct 1
Ridge Bay Chateau
A bedroom with a bed, white curtains, a wooden wardrobe, and an air conditioning unit.

14. 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 CA $141
CA $187 total
includes taxes & fees
Sep 30 - Oct 1
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.

15. 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 CA $318
CA $404 total
includes taxes & fees
Sep 27 - Sep 28
Purevibe 2 BR/2 BA, Ocean View Villa, Private Rooftop, Near Port Antonio
A kitchen with dark wooden cabinets, a tiled backsplash, a stove, and a dining table with chairs.

16. Da Villa Juanita

Da Villa Juanita
Hordley
The price is CA $191
CA $362 total
includes taxes & fees
Sep 27 - Sep 28
Da Villa Juanita
A beach with clear turquoise waters, surrounded by dense green forest and hills in the background.

17. One Bedroom Garden View Villa, Frenchman's Cove Resort

One Bedroom Garden View Villa, Frenchman's Cove Resort
Drapers
The price is CA $410
CA $523 total
includes taxes & fees
Sep 27 - Sep 28
One Bedroom Garden View Villa, Frenchman's Cove Resort
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 CA $445
CA $501 total
includes taxes & fees
Sep 27 - Sep 28
Charming 3-bedroom house in enchanting Fairy Hill with WiFi, AC
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.

19. 2 Bedroom Sea View Villa, Frenchman's Cove Resort

2 Bedroom Sea View Villa, Frenchman's Cove Resort
Drapers
The price is CA $636
CA $820 total
includes taxes & fees
Sep 27 - Sep 28
2 Bedroom Sea View Villa, Frenchman's Cove Resort
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 CA $1,273
CA $1,454 total
includes taxes & fees
Sep 27 - Sep 28
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

S Hotel Kingston

S Hotel Kingston

10/10 Excellent
"Cleanliness"
Janette 1-night trip
Posted 16 hours ago
S Hotel Kingston

Find out more about Portland

Everything you need to know about Portland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Portland vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Portland vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Portland vacation rentals we have selected for you start as low as CA $120 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 vacation 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 vacation.

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.