Portland Villas

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Villas in Portland

Tapioca Village Retreat

Tapioca Village Retreat

3 out of 5
Devon Pen Castleton St. Mary Parish
$80 nightly
The price is $93 total per night
$93 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
With a stay at Tapioca Village Retreat in Castleton, you'll be steps from Blue and John Crow Mountains National Park and a 3-minute drive from Castleton Gardens.
Pool
Kitchen
Bougan Blu - Beach front cottage , Port Maria , St. Mary

Bougan Blu - Beach front cottage , Port Maria , St. Mary

Port Maria St. Mary Parish
With a stay at this villa in Port Maria, you'll be on the beach, within a 15-minute drive of Jamaica Beaches and James Bond Beach.
Pool
Kitchen
Reggae Legends Estate

Reggae Legends Estate

2.5 out of 5
Skyline Dr Kingston St. Andrew Parish
$269 nightly
The price is $310 total per night
$310 total
Dec 13 - Dec 14
Total with taxes and fees
With a stay at Reggae Legends Estate in Kingston (Jack's Hill), you'll be within a 15-minute drive of Bob Marley Museum and Jamaica House.
Pool
Kitchen
Casa Victoria Golf Retreat

Casa Victoria Golf Retreat

4 out of 5
85C Caymanas Estate Kingston
With a stay at Casa Victoria Golf Retreat in Kingston, you'll be 9.7 mi (15.6 km) from Devon House and 10 mi (16.1 km) from Jamaica House.
Kitchen
Free WiFi
The Palms at Oracabessa *Luxury Vacation Rental* Fully Staffed

The Palms at Oracabessa *Luxury Vacation Rental* Fully Staffed

Oracabessa St. Mary Parish
With a stay at this villa in Oracabessa, you'll be by the sea, within a 10-minute drive of Jamaica Beaches and James Bond Beach.
Pool
Hot Tub
The Country Club Villa I

The Country Club Villa I

3.5 out of 5
44 Ray Wright Drive, Section F Kingston
$238 nightly
The price is $253 total per night
$253 total
Dec 13 - Dec 14
Total with taxes and fees
When you stay at this villa in Kingston, you'll be next to a golf course and within a 5-minute drive of Caymanas Golf and Country Club.
Pool
Kitchen
Spicy Hill Villa, One Of Jamaica's Best-Kept Secrets.

Spicy Hill Villa, One Of Jamaica's Best-Kept Secrets.

Port Antonio Portland Parish
$987 nightly
The price is $987 total per night
$987 total
Dec 14 - Dec 15
Total with taxes and fees
When you stay at this villa in Port Antonio, you'll be by the ocean, within a 15-minute walk of Jamaica Beaches and Frenchman's Cove Beach.
Pool
Hot Tub
Gather,relax, and indulge at Chateau, in your stunning private villa sleeps 12

Gather,relax, and indulge at Chateau, in your stunning private villa sleeps 12

San San Port Antonio
With a stay at this villa in Port Antonio, you'll be on the waterfront, within a 5-minute drive of Jamaica Beaches and Blue Lagoon.
Pool
Kitchen
Authentic Jamaican Family Villa

Authentic Jamaican Family Villa

Kingston St. Andrew Parish
$189 nightly
The price is $189 total per night
$189 total
Dec 13 - Dec 14
Total with taxes and fees
With a stay at this villa in Kingston (Rollington Town), you'll be within a 15-minute drive of Bob Marley Museum and Jamaica House.
Air conditioning
A place in paradise - family villa on a peninsula directly by the sea

A place in paradise - family villa on a peninsula directly by the sea

Port Antonio, Portland
With a stay at this villa in Port Antonio, you'll be on the waterfront, within a 10-minute drive of Jamaica Beaches and Rio Grande.
Pool
Kitchen
Heaven Villa - We are not on the water, we are above!

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

Port Antonio Portland
With a stay at this villa in Port Antonio, you'll be next to a golf course, within a 5-minute drive of Jamaica Beaches and Trident Castle.
Pool
Kitchen
Affordable Way to Wake Up to a Magical Sunrise from our Beach Front Villa

Affordable Way to Wake Up to a Magical Sunrise from our Beach Front Villa

St. Mary St Mary Parish
$492 nightly
The price is $578 total per night
$578 total
Dec 13 - Dec 14
Total with taxes and fees
With a stay at this villa in Robins Bay, you'll be on the beach, within a 5-minute drive of Jamaica Beaches and Mahoe Bay.
Kitchen
Washer
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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.

Portland Villas essential information

Accommodation
122 Villas
Lowest Price
$93
Highest Price
$987
Popular accommodation
Tapioca Village Retreat, Bougan Blu - Beach front cottage , Port Maria , St. Mary, Reggae Legends Estate, Casa Victoria Golf Retreat, The Palms at Oracabessa *Luxury Vacation Rental* Fully Staffed, The Country Club Villa I, Spicy Hill Villa, One Of Jamaica's Best-Kept Secrets., Gather,relax, and indulge at Chateau, in your stunning private villa sleeps 12, Authentic Jamaican Family Villa, A place in paradise - family villa on a peninsula directly by the sea, Heaven Villa - We are not on the water, we are above!, Affordable Way to Wake Up to a Magical Sunrise from our Beach Front Villa

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