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

Villas in Portland

Compare and save

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Top Cities in Portland

A sunset over a calm sea with a visible horizon line.
VillasVillas

Hope Bay

Hope Bay

Our top choices for Portland villas

A wooden deck with a table and chairs, surrounded by lush greenery and a view of distant mountains.

1. Reggae Legends Estate

Reggae Legends Estate
3.5 star property
Jack's Hill
9.8 out of 10, Exceptional, (6 reviews)
"A really amazing find! Stunning location with fantastic views. Quiet and relaxing. The cabin was a great experience and we were so well looked after by Anne-Marie."
United Kingdom
Nicola
$127 nightly
The price is $147
Oct 14 - Oct 15
Total with taxes and fees
Reggae Legends Estate
A balcony with a red railing, a black chair, and a potted plant.

2. Kai's Place @ Tim Pappies 3rd Floor luxury villa

Kai's Place @ Tim Pappies 3rd Floor luxury villa
Port Antonio
10.0 out of 10, Exceptional, (3 reviews)
"Even though there were some mixup with the booking thru VRBO, and spotty gps, which caused some initial inconveniences. The beautiful settings, comfortable room and Sangela's attentiveness, made it a very pleasant stay!"
Canada
rohan k r.
Kai's Place @ Tim Pappies 3rd Floor luxury villa
A row of single-story houses with tiled roofs, a well-maintained garden, and a clear sky.

3. Sunrise Villa On The Beach

Sunrise Villa On The Beach
3.0 star property
Portmore
8.6 out of 10, Excellent, (10 reviews)
"Quite environment great staff would definitely come again"
United States
Samoya
Sunrise Villa On The Beach
A large, yellow building with a swimming pool and multiple balconies, surrounded by lush greenery and a view of the ocean.

4. The Palms at Oracabessa *Luxury Vacation Rental* Fully Staffed

The Palms at Oracabessa *Luxury Vacation Rental* Fully Staffed
Oracabessa
8.8 out of 10, Excellent, (26 reviews)
"We really enjoyed our stay. The villa is modern and beautiful. The views from the balconies were amazing. The staff were attentive but discreet, Chef Shavon was very accommodating, one of our party was lactose intolerant with other intolerances and he at no point forgot that.We ate the mangoes which had fallen from the trees and they were so sweet and juicy.Our stay was short but memorable - it was very relaxing."
United States
M. S.
$1,717 nightly
The price is $1,717
Oct 14 - Oct 15
Total with taxes and fees
The Palms at Oracabessa *Luxury Vacation Rental* Fully Staffed
A covered outdoor area with a wooden bench and table, surrounded by a railing and lush greenery.

5. Casa Victoria Golf Retreat

Casa Victoria Golf Retreat
4.0 star property
Kingston
9.8 out of 10, Exceptional, (72 reviews)
"Our stay was very comfortable and relaxing,we didn't stay in but it had all the nesscessary things that we were looking for. I would recommend it to anyone who are travelling with their family to stay there.lovely place,!!"
Canada
Desmond
Casa Victoria Golf Retreat
A two-story building with a tiled entrance and a gated driveway.

6. Windbreak Villa

Windbreak Villa
3.5 star property
Buff Bay
10.0 out of 10, Exceptional, (1 review)
$84 nightly
The price is $97
Oct 14 - Oct 15
Total with taxes and fees
Windbreak Villa
A balcony with a view of the ocean, a lounge chair, and two drinks on a table.

7. 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.
$254 nightly
The price is $288
Oct 16 - Oct 17
Total with taxes and fees
Purevibe 2 BR/2 BA, Ocean View Villa, Private Rooftop, Near Port Antonio
A covered outdoor area with a pool, surrounded by potted plants and outdoor furniture.

8. 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
$1,028 nightly
The price is $1,028
Oct 19 - Oct 20
Total with taxes and fees
Spicy Hill Villa, One Of Jamaica's Best-Kept Secrets.
A clear blue pool surrounded by a white fence with palm trees and a 'NO DIVING' sign.

9. The Country Club Villa I

The Country Club Villa I
3.5 star property
Kingston
9.0 out of 10, Wonderful, (10 reviews)
"The management team was awesome, the AC didn’t work in the main room on the first night but Ms Vicki made sure that I didn’t go a second night without it."
United States
Anonymous traveler
The Country Club Villa I
A balcony with a clear view of the sea and a distant island.

10. Heaven Villa - We are not on the water, we are above!

Heaven Villa - We are not on the water, we are above!
Port Antonio
9.2 out of 10, Wonderful, (13 reviews)
"the views of the surrounding area "
United States
Christopher
Heaven Villa - We are not on the water, we are above!
A pool with a clear view of the sea and a distant cityscape during sunset.

11. C-Vue Villa (Pool AC Gated Sea Front )

C-Vue Villa (Pool AC Gated Sea Front )
Portmore
9.6 out of 10, Exceptional, (12 reviews)
"This property exceeded all expectations and we all had a wonderful and comfortable stay. If you are looking for somewhere to relax with the sound of the waves and waking up to the sun rising over the ocean this is it. Beautifully maintained, secure property and grounds, great communication from the host, before, during and after our stay, thank you Michael we will be back"
United Kingdom
Naomi A.
C-Vue Villa (Pool AC Gated Sea Front )
A swimming pool with a white fence, surrounded by buildings with red roofs and palm trees.

12. The Oasis Golf Retreat

The Oasis Golf Retreat
3.0 star property
Kingston
9.6 out of 10, Exceptional, (4 reviews)
"IT WAS WONDERFUL.. VERY CLEAN , QUIET..JUST LOVELY.. "
United States
MARLON
The Oasis Golf Retreat
A waterfront property with a house, a dock, and clear blue water.

13. LillyBelleMar,San San Port Antonio,with pristine views and world class amenities

LillyBelleMar,San San Port Antonio,with pristine views and world class amenities
Fairy Hill
10.0 out of 10, Exceptional, (1 review)
"We had the best time during our stay. It was such a pleasure being back in this home and the staff are truly amazing "
United States
Olivia S.
LillyBelleMar,San San Port Antonio,with pristine views and world class amenities
A covered outdoor seating area with a sofa and a table, surrounded by arches and a railing, overlooking a scenic view.

14. 2 Villas in Jamaica-22 guests-Fully staffed

2 Villas in Jamaica-22 guests-Fully staffed
Galina
10.0 out of 10, Exceptional, (1 review)
"Really appreciated the kindness of the staff and great cooking! Chef Keamary was great at making what we wanted and surprising us with delicious Jamaican cooking. Housekeepers Cavisha and Simone were unobtrusive and got everything tidy. Spacious rooms and nice bathrooms, too. "
United States
Allison W.
2 Villas in Jamaica-22 guests-Fully staffed
A residential area with a house, lush greenery, and a clear sky.

15. Tapioca Village Retreat

Tapioca Village Retreat
3.0 star property
Castleton
6.0 out of 10, (2 reviews)
"There is so much nature and friendliness! "
United States
Günter
$70 nightly
The price is $81
Nov 12 - Nov 13
Total with taxes and fees
Tapioca Village Retreat
A modern kitchen with grey cabinets, stainless steel appliances, and a window with grey curtains.

16. Carter's Nest Villa

Carter's Nest Villa
3.5 star property
New Kingston
$517 nightly
The price is $596
Oct 14 - Oct 15
Total with taxes and fees
Carter's Nest Villa
A balcony with two cushioned chairs and a table, overlooking a beach and ocean.

17. Private Oceanside Luxury Villa Near Ocho Rios, Chef & Staff Included

Private Oceanside Luxury Villa Near Ocho Rios, Chef & Staff Included
Stony Hill
9.0 out of 10, Wonderful, (2 reviews)
"Unbelievable a great place to vacation with friends and family. Staff very accommodating and easy to communicate with. This is my new vacation spot in Jamaica!!"
United States
Dawn S.
Private Oceanside Luxury Villa Near Ocho Rios, Chef & Staff Included
A two-story house with a well-maintained lawn and vibrant red flowers in the front yard.

18. 4-bedroom villa in peaceful Portmore with AC

4-bedroom villa in peaceful Portmore with AC
Greater Portmore
4-bedroom villa in peaceful Portmore with AC
deck looking out at sea

19. "Sought-After" Secluded Private Beach Cove,14 Rooms, Retreat Center Destination

"Sought-After" Secluded Private Beach Cove,14 Rooms, Retreat Center Destination
St Mary
10.0 out of 10, Exceptional, (1 review)
"Strawberry Fields Together is a hidden gem! We stayed for three days with a large group from the United States because our previous travel plans fell through as many of the resorts were under renovation due to Hurricane Melissa and, now that we experienced the real Jamaica, I don't think we will ever go back. First of all, the grounds are what I imagine paradise looking like. Beautiful beaches, gardens, views, etc. Second, the accommodations are unique and charming. While they may lack some of...
United States
Mike S.
$6,876 nightly
The price is $8,076
Oct 17 - Oct 18
Total with taxes and fees
"Sought-After" Secluded Private Beach Cove,14 Rooms, Retreat Center Destination
Pool

20. Timeless - Lovely beach cottage. Private pool, ocean view, beach access. R &R !

Timeless - Lovely beach cottage. Private pool, ocean view, beach access. R &R !
Kingston
9.6 out of 10, Exceptional, (4 reviews)
"Excellent stay. Very thorough check in info and attentive communication from the host. Beautiful home in a beautiful location. Can't wait to return."
United States
Amahra S.
Timeless - Lovely beach cottage. Private pool, ocean view, beach access. R &R !
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

Sea Cliff Resort

Sea Cliff Resort

8/10 Good
"Simply / plainly decorated room (not what I was expected based on the displayed photos ) with great view, food and staff / customer service."
Fredricka 2-night trip
Posted 8 hours ago
Sea Cliff Resort

Find out more about Portland

Portland Villas information

Number of reviews
181
Accommodation
98 Villas
Lowest Price
$81
Highest Price
$8,076

Frequently asked questions

Why book your villa in Portland with Expedia?
Expedia makes it a cinch to find your ideal villa in Portland. Vacationing with the kids? Use our helpful filters to look for stays with amenities like free WiFi. If you have a budget in mind, select how much you want to spend and the star rating of the property. We'll help you find the perfect pad that gels with your style and taste.
How can I find cheap villas in Portland?
With Expedia's handy filter tool, booking cheap villas in Portland is easy. To discover options that are easy on the wallet, narrow down your search by amenities, budget and star rating.

Explore a world of travel with Expedia