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

Villas in Portland

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In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Top Cities in Portland

A sunset over a calm sea with a visible horizon line.
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Hope Bay

Hope Bay

Our top choices for Portland villas

Terrace/patio

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
$125 nightly
The price is $145
Oct 8 - Oct 9
Total with taxes and fees
Reggae Legends Estate
Pool

2. 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
$1,023 nightly
The price is $1,023
Sep 9 - Sep 10
Total with taxes and fees
Spicy Hill Villa, One Of Jamaica's Best-Kept Secrets.
Property grounds

3. 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.
$253 nightly
The price is $287
Sep 9 - Sep 10
Total with taxes and fees
Purevibe 2 BR/2 BA, Ocean View Villa, Private Rooftop, Near Port Antonio
Exterior

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 celebrated Mom's 90th birthday and the entire team worked together to make everything PERFECT! From my initial connection with Lewis the owner, who was very responsive to all our questions as we prepared, to the staff Debbi, Cavesha and Arlene..WOW! To top it all off...Chef Kealy and Chef Shavon...best food ever...would definitely recommend "
United States
Andrea W.
$1,717 nightly
The price is $1,717
Sep 9 - Sep 10
Total with taxes and fees
The Palms at Oracabessa *Luxury Vacation Rental* Fully Staffed
Gazebo

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
Exterior

6. 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
Exterior

7. Windbreak Villa

Windbreak Villa
3.5 star property
Buff Bay
10.0 out of 10, Exceptional, (1 review)
$83 nightly
The price is $96
Oct 8 - Oct 9
Total with taxes and fees
Windbreak Villa
Family Villa, 3 Bedrooms, Accessible, Hill View | View from room

8. The Country Club Villa II

The Country Club Villa II
3.5 star property
Kingston
9.4 out of 10, Exceptional, (11 reviews)
"The place overall is okay . I didn’t really have a major problem is was okay for the most part."
United States
Janiel
The Country Club Villa II
Property grounds

9. 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!
Outdoor pool

10. 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
Pool

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)
"We stayed here for our wedding, and it was absolutely magical. The property provided the most stunning backdrop for such a special milestone. The beach view was breathtaking waking up to the sound of the ocean made everything feel so serene. Our host was incredibly accommodating, ensuring everything was perfect for our arrival. It truly felt like a sanctuary during a busy week. We couldn’t have picked a better place to start our new chapter!"
United States
Sashel B.
C-Vue Villa (Pool AC Gated Sea Front )
Outdoor pool

12. 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
Terrace/patio

13. 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
$79 nightly
The price is $92
Oct 8 - Oct 9
Total with taxes and fees
Tapioca Village Retreat
Villa | Private kitchen

14. Carter's Nest Villa

Carter's Nest Villa
3.5 star property
New Kingston
$530 nightly
The price is $596
Oct 8 - Oct 9
Total with taxes and fees
Carter's Nest Villa
Terrace/patio

15. 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
Pool

16. 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 !
Outdoor dining

17. "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.
$6,158 nightly
The price is $7,238
Sep 12 - Sep 13
Total with taxes and fees
"Sought-After" Secluded Private Beach Cove,14 Rooms, Retreat Center Destination
Property grounds

18. 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
Property grounds

19. 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
Exterior

20. Premium Suite at The Vineyards

Premium Suite at The Vineyards
2.0 star property
Kingston
2.0 out of 10, (1 review)
$276 nightly
The price is $318
Oct 8 - Oct 9
Total with taxes and fees
Premium Suite at The Vineyards
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
"My stay with my family was wonderful, every thing was correct"
Alastair 2-night trip
Posted 14 hours ago
S Hotel Kingston

Find out more about Portland

Portland Villas information

Number of reviews
181
Accommodation
98 Villas
Lowest Price
$92
Highest Price
$7,238

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