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Houses in Portland Parish and Villas – Holiday Lettings - Holiday Rentals Portland Parish

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158 Holiday homes

Holiday home rental

Port Antonio house

4 bedrooms • 2 bathrooms • sleeps 9

from £21 / night

£125 - £1,291 / week

1 / 12

Holiday apartment rental

Buff Bay apartment

2 bedrooms • 1 bathroom • sleeps 4

from £40 / night

£281 / week

1 / 15

Portland Parish holiday villa accommodation

Port Antonio villa

2 bedrooms • 1 bathroom • sleeps 5

“Jamaica jewel!” We adored our stay at Tranquility -- it truly lives up to its name! This elegant, old-school school villa, built in the 1950s, is perched on a mountaintop. The views alone (Port antonio bay one one side, Blue Mountains on the other) are worth the price of admission! The house is small (5 people max but 4 is ideal) but airy and completely private. And the decor -- white wood wainscoting, ceiling fans, teak floors and simple white beds with mosquito netting -- is classic Jamaica (Noel Coward or Ian Fleming would have been very much at home here). Our stay was made even more delightful by a warm and professional staff: Beverly, a gifted cook specializing in Jamaican cuisine, on-property houseman Dennis, and on-call driver Charlie. Frenchman's Cove, a gorgeous private beach, is a 15-20 minute car ride away -- but truthfully, this is the kind of place where you can wile away the hours sitting by the pool and watching the changing views as the light shifts. One issue to take into consideration: the trip from the airport is 2- 21/2 hours through winding mountain roads. But the setting and staff make it well worth the wait!

from £221 / night

£1,662 - £2,011 / week

1 / 11

Holiday guest house in Portland Parish

Long Bay guest house

5 bedrooms • 5 bathrooms • sleeps 8

from £50 / night

£333 / week

1 / 27

Holiday home in Portland Parish

Port Antonio house

4 bedrooms • 2 bathrooms • sleeps 9

from £166 / night

£789 / week

1 / 29

Holiday guest house in Portland Parish

Long Bay guest house

1 bedroom • 1 bathroom • sleeps 3

from £75 / night

£525 / week

1 / 15

Holiday guest house rental

Long Bay guest house

1 bedroom • 1 bathroom • sleeps 3

from £59 / night

£408 / week

1 / 12

Holiday guest house in Portland Parish

Long Bay guest house

1 bedroom • 1 bathroom • sleeps 2

from £38 / night

£263 / week

1 / 12

Villa rental in Portland Parish

Long Bay villa

4 bedrooms • 2 bathrooms • sleeps 8

from £38 / night

£233 - £1,280 / week

1 / 4

Villa rental in Portland Parish

Port Antonio villa

2 bedrooms • 2 bathrooms • sleeps 6

from £291 / night

£1,662 / week

1 / 29

Portland Parish holiday cottage rental

Long Bay cottage

1 bedroom • 1 bathroom • sleeps 2

from £46 / night

£321 / week

1 / 12

Guest house rental in Portland Parish

Long Bay guest house

3 bedrooms • 3 bathrooms • sleeps 10

from £250 / night

£1,249 / week

1 / 15

Holiday apartment rental

Port Antonio apartment

1 bedroom • 1 bathroom • sleeps 6

from £35 / night

£241 / week

1 / 7

Holiday home rental

Boston Bay house

6 bedrooms • 4 bathrooms • sleeps 12

from £71 / night

£496 / week

1 / 4

Holiday cottage in Portland Parish

Port Antonio cottage

2 bedrooms • 1 bathroom • sleeps 4

from £42 / night

£291 / week

1 / 38

Portland Parish holiday apartment rental

Long Bay apartment

2 bedrooms • 1 bathroom • sleeps 4

from £125 / night

£875 - £1,632 / week

1 / 56

Holiday home in Portland Parish

Manchioneal house

4 bedrooms • 7 bathrooms • sleeps 10

from £253 / night

£1,769 / week

1 / 49

Holiday log cabin in Portland Parish

Port Antonio log cabin

1 bedroom • 1 bathroom • sleeps 2

from £42 / night

£250 / week

1 / 14

Holiday log cabin in Port Antonio

Port Antonio log cabin

1 bedroom • 1 bathroom • sleeps 2

from £25 / night

£167 / week

1 / 15

Holiday home with golf nearby in Portland Parish

Boston Bay house

2 bedrooms • 3 bathrooms • sleeps 4

from £54 / night

£366 / week

1 / 40

Holiday home with swimming pool in Portland Parish

Port Antonio house

4 bedrooms • 4 bathrooms • sleeps 10

from £603 / night

£4,218 - £4,799 / week

1 / 21

Villa rental in Port Antonio

Port Antonio villa

7 bedrooms • 6 bathrooms • sleeps 12

“Great & Memorable Vacation in a Beautiful Island” The cottage was ideal place to relax with family & friends,open veranda overlooking the serene,calm ocean is refreshing to the soul.We watched the most beautiful sunrise while sipping into a pure Jamaican blue mountain coffee.The saying in Jamaica "once you go , you know" proved true.Lots of other great places near by for a day trip.We watched sunset at Norma's by the pier...great foods.The cook at RBC makes real, authentic Jamaican foods,lots of variety...Come and see it for yourself, you won't be disappointed...

from £399 / night

£2,792 / week

1 / 44

Villa rental in Portland Parish

Port Antonio villa

3 bedrooms • 3 bathrooms • sleeps 8

from £63 / night

£437 - £671 / week

1 / 81

Home rental in Portland Parish with shared pool

Drapers house

4 bedrooms • 4 bathrooms • sleeps 8

from £63 / night

£466 - £2,103 / week

1 / 40

Portland Parish holiday condo rental

Port Antonio condo

2 bedrooms • 1 bathroom • sleeps 4

from £83 / night

£582 / week

1 / 16

Holiday home in Port Antonio

Port Antonio house

3 bedrooms • 2 bathrooms • sleeps 6

from £63 / night

£437 - £1,020 / week

1 / 18

Holiday home in Portland Parish

Port Antonio house

2 bedrooms • 1 bathroom • sleeps 4

from £68 / night

£475 / week

1 / 22

Holiday villa in Portland Parish

Portland Parish villa

1 bedroom • 1 bathroom • sleeps 2

from £208 / night

£1,455 / week

1 / 13

Portland Parish holiday b&b rental

Port Antonio b&b

1 bedroom • 3 bathrooms • sleeps 2

from £54 / night

£333 / week

1 / 30

Portland Parish holiday villa rental

Port Antonio villa

5 bedrooms • 5 bathrooms • sleeps 10

“Spicy Hill, Port antonio - An unforgettable weekend. I so deser” What a fabulous property! Understated luxury and elegance; separate games house and friendly, solicitous staff and the cuisine was, in a word, 'delectable'! A group of freinds and I went to the villa for a BFF weekend and the bedrooms and bathrooms were beautifully appointed and comfortably accommodated all ten of us. The grounds were lush and manicured at the same time and the entire setting just very conducive to relaxation,cameraderie and rejuvenation. The staff, Chef-Denny; Butler-Keith & Housekeeper-Karen, were just great and spoiled us rotten. We so deserved it:) Anything we wanted to eat they got the ingredients and prepared it. Wonderful weekend. . We would definitely go back to Spicy Hill and highly recommend this villa in Port antonio, Jamaica

from £745 / night

£5,066 / week

1 / 30

Port Antonio holiday home rental

Port Antonio house

1 bedroom • 1 bathroom • sleeps 4

from £63 / night

£408 / week

1 / 11

Villa rental in Port Antonio with swimming pool

Port Antonio villa

2 bedrooms • 1 bathroom • sleeps 5

“Jamaica jewel!” We adored our stay at Tranquility -- it truly lives up to its name! This elegant, old-school school villa, built in the 1950s, is perched on a mountaintop. The views alone (Port antonio bay one one side, Blue Mountains on the other) are worth the price of admission! The house is small (5 people max but 4 is ideal) but airy and completely private. And the decor -- white wood wainscoting, ceiling fans, teak floors and simple white beds with mosquito netting -- is classic Jamaica (Noel Coward or Ian Fleming would have been very much at home here). Our stay was made even more delightful by a warm and professional staff: Beverly, a gifted cook specializing in Jamaican cuisine, on-property houseman Dennis, and on-call driver Charlie. Frenchman's Cove, a gorgeous private beach, is a 15-20 minute car ride away -- but truthfully, this is the kind of place where you can wile away the hours sitting by the pool and watching the changing views as the light shifts. One issue to take into consideration: the trip from the airport is 2- 21/2 hours through winding mountain roads. But the setting and staff make it well worth the wait!

from £230 / night

£1,502 / week

1 / 35

Holiday home in Portland Parish

Port Antonio house

1 bedroom • 2 bathrooms • sleeps 4

from £63 / night

£437 / week

1 / 28

Port Antonio holiday guest house rental

Port Antonio guest house

6 bedrooms • 4 bathrooms • sleeps 8

from £167 / night

£1,164 / week

1 / 24

Holiday villa in Port Antonio

Port Antonio villa

3 bedrooms • 2 bathrooms • sleeps 6

from £452 / night

£3,158 / week

1 / 12

Holiday home in Portland Parish

Port Antonio house

4 bedrooms • 4 bathrooms • sleeps 8

from £871 / night

£7,310 - £8,934 / week

1 / 18

Portland Parish holiday home rental

Port Antonio house

2 bedrooms • 1 bathroom • sleeps 4

from £50 / night

£349 / week

1 / 28

Holiday villa in Portland Parish

Port Antonio villa

4 bedrooms • 7 bathrooms • sleeps 14

“Stunning Experience...” We just returned from our stay at Norse Hill in Jamaica and feel blessed to have stayed in the beautiful experience that this home offers. Norse Hill is a peaceful retreat, the staff is lovely and the grounds are special. My favorite moments were waking up each morning to the turquoise light flooding into the bedroom, and sharing rum punch with my husband while relaxing on the lawn overlooking the ocean...a stunning time.

from £667 / night

£4,670 / week

1 / 74

Villa rental in Portland Parish with shared pool

Port Antonio villa

3 bedrooms • 2 bathrooms • sleeps 6

“Relaxing Jamaican privacy in nature” I had a wonderful week staying at Shotover Gardens with my three friends. It is a beautiful place far away from the ultra-touristy cities and resorts that too many people see. The property is six acres of beautiful gardens with spectacular views, and we spent a lot of time lounging in the pool, watching the birds, and soaking in the views. It's also a great staging ground to see some of the best parts of Jamaica, and we got to spend a lot of time seeing amazing birds, snorkeling, swimming in the Blue Lagoon, going to picturesque beaches, and sitting on the back porch drinking Blue Mountain coffee. We had a great time there, and I would wholeheartedly recommend Shotover Gardens to anyone else.

from £125 / night

£831 / week

1 / 20

Holiday villa with golf nearby in Port Antonio

Port Antonio villa

4 bedrooms • 5 bathrooms • sleeps 8

from £1,081 / night

£7,479 / week

1 / 16

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Top Destination reviews

Harmony Heights - Portland 4 Bedroom villa with a view sleeps 9
Harmony Heights

As a Jamaican descendent, I have been a regular visitor to Jamaica, for over 20 years, however my stay at Harmony Heights, was in fact the most relaxing stress free, and truely Irie (no problem) stay I have ever experienced while in Jamaica. I felt as if I was home from home, I was traveling with my teenage daughter, we were safe comfortable and our belongings secure, all of which were priority. The Local area has a relaxed, welcoming and friendly ambiance, the local beaches are in walking distance and are all distinctively unique, there are local shops and eateries. If you are seeking retreat or sanctuary this is the place to be, with the best of everything, near enough to the local town, beautiful panoramic views, nestled in the lush foliage of Fairy Hill, which did occasionally boast some rare sightings of local birdlife. The facilitator at Harmony Heights is called "Head" he is always at hand to assist if needs be. Authentic Jamaican meals can be provided for a reasonable charge, which was great because we had a daily choice of self catering or not. The Kitchen and all amenities are sufficient.see more

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