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

Vacation Rentals in Portland

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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 AED 308
AED 358 total
includes taxes & fees
3 Oct - 4 Oct
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 AED 148
AED 375 total
includes taxes & fees
15 Oct - 16 Oct
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 AED 165
AED 261 total
includes taxes & fees
2 Oct - 3 Oct
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 AED 131
AED 379 total
includes taxes & fees
2 Oct - 3 Oct
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 AED 131
AED 379 total
includes taxes & fees
2 Oct - 3 Oct
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 AED 324
AED 544 total
includes taxes & fees
2 Oct - 3 Oct
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 AED 353
AED 426 total
includes taxes & fees
2 Oct - 3 Oct
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 AED 423
AED 570 total
includes taxes & fees
2 Oct - 3 Oct
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 AED 303
AED 689 total
includes taxes & fees
7 Oct - 8 Oct
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 AED 367
AED 533 total
includes taxes & fees
2 Oct - 3 Oct
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 AED 257
AED 356 total
includes taxes & fees
2 Oct - 3 Oct
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 AED 1,689
AED 2,033 total
includes taxes & fees
3 Oct - 4 Oct
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 AED 1,199
AED 1,690 total
includes taxes & fees
2 Oct - 3 Oct
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 AED 367
AED 485 total
includes taxes & fees
2 Oct - 3 Oct
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 AED 826
AED 1,064 total
includes taxes & fees
2 Oct - 3 Oct
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 AED 2,311
AED 3,058 total
includes taxes & fees
2 Oct - 3 Oct
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 AED 1,065
AED 1,335 total
includes taxes & fees
31 Oct - 1 Nov
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 AED 1,157
AED 1,315 total
includes taxes & fees
2 Oct - 3 Oct
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
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 AED 3,306
AED 3,776 total
includes taxes & fees
2 Oct - 3 Oct
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Portland Hotel Reviews

S Hotel Kingston

S Hotel Kingston

10/10 Excellent
"My husband and I have stayed here before in 2018 and the experience was just as amazing in 2026 treated us like we were royalty. Loved all of the kindness. Beautiful place"
Jacqueline 3-night trip
Posted 6 hours ago
S Hotel Kingston