50 Best Vacation Rentals in Portland Parish - Holiday Lettings - Cabins

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77 Vacation rentals

7

Villa accommodation in Portland Parish

Portland Parish / Buff Bay

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Child friendly
  • Air conditioning
  • Ask about pets
Windbreak villa is situated in the coastal parish of Portland, within the beautiful, popular housing scheme of Woodstock in the town of buff bay. Windbreak villa is the perfect setting for a family vacation or secluded, quit, romantic getaway. come visit us at windbreak …see more

from $200 / night

$1400 / week

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from $200 / night

(1) Excellent 

29

Villa rental in Portland Parish

Port Antonio / Williamsfield

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Two elegant 1-bedrooms studio apartments, complete with bathroom, living room and kitchen—offer hosting to a maximum of 6 persons. Several outdoor terraces invite you to dine, unwind and relax while savoring idyllic tropical views. Immerse yourself, for nature's thera …see more

from $350 / night

$2000 / week

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from $350 / night

10

Villa rental in Portland Parish

Portland Parish / Long Bay

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
A vacation home away from home with probably the best view in Long bay. With just steps from the beach and a short drive to Port Antonio or other nearby attractions you can enjoy a fun relaxing island vacation. There are 4 spacey bedrooms available for rent (or entire h …see more

from $40 / night

$280 - $490 / week

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from $40 / night

(14) Excellent 

27

Vacation home in Portland Parish

Port Antonio / Blue Lagoon, Port Antonio

4 9 1 night min

  • 4 bedrooms
  • Sleeps 9
  • 1 night min
  • Beach/lakeside relaxation
  • Suitable for children age 5+
  • Car not necessary
Mr Barrys is nestled nicely on a hill in the heart of Fairy HIll, Boston. We welcome visitors from around the world to stay with us and to feel at home here. Mr Barry's White House is in a quiet part of the Island and the locals are very warm and welcoming, there are …see more

from $200 / night

$1050 - $1200 / week

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Responds fast!
avg. 3 hours 19 minutes

from $200 / night

(1)  

26

Vacation guest house in Portland Parish

Portland Parish / Long Bay

5 8 2 nights min

  • 5 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
This is Rasta Villa Guest house with 4 bungalows to choose from, all ocean views Born an Bread in Portland and I still believe its one of the most beautiful place in the world. Lush greenery, peaceful ambiance , some of the friendliest people you will ever meet. Many …see more

from $60 / night

$400 / week

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from $60 / night

16

Vacation villa with golf nearby in Port Antonio

Port Antonio / Blue Lagoon, Port Antonio

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Suitable for children age 5+
  • Air conditioning
Bonne Amie is in the picturesque Blue Lagoon area of Port Antonio, which offers excellent swimming, snorkeling and scuba. The villa has four bedrooms able to satisfy the most discriminating of tastes. Each room has four-poster beds, and tropical paintings compl …see more

from $1300 / night

$9000 / week

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from $1300 / night

7

Vacation guest house in Portland Parish

Portland Parish / Port Antonio

6 6 2 nights min

  • 6 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
The villa consist of 6 double bedrooms and 1 twin bedroom room, 2 bedroom, self-catering apartment. From the dining room and living room areas you will immediately capture the lovely breath taking panoramic view of the ocean and steep lush and fruitful hills. The pr …see more

from $65 / night

$497 / week

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from $65 / night

(30) Excellent 

11

Portland Parish Vacation villa accommodation

Portland Parish / Port Antonio

2 5 4 nights min

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Your Jamaican Home Away from Home ~ Lounge pool side, gaze out at the ocean from your living room or front porch ... watch the colors change over the Blue Mountains from your bedroom balcony - Nestled 1/4 mile up Richmond Hill overlooking Port Antonio & its magnificent …see more

from $265 / night

$1855 / week

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from $265 / night

(5) Excellent 

14

Port Antonio Vacation villa rental

Portland Parish / Port Antonio

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
  • Pet friendly
Heaven is a stunning, fully refurbished villa that seamlessly fuses classic architecture with upscale modern design. Located on the enchanted hill of Fern Cliff in the San San enclave of Port Antonio, Portland, Heaven is the ideal retreat and one of the area’s most cove …see more

from $750 / night

$5250 / week

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from $750 / night

4

Portland Parish Vacation villa rental

Portland Parish / Port Antonio

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Air conditioning
Apart from its panoramic views, SINOPIA INN has a large lounge/living area, TV, wireless internet, bathroom essentials, air conditioning, free parking on premises, onsite security, housekeeper, washing machine and complete privacy. Additionally, its outdoor patio, man-m …see more

from $113 / night

$786 - $1012 / week

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from $113 / night

12

Vacation home rental

Portland Parish / Port Antonio

4 9 2 nights min

  • 4 bedrooms
  • Sleeps 9
  • 2 nights min
  • Nearest beach 1 mi
  • Child friendly
  • Private garden
Beautiful 2 floor house with big staircase around the house. You have a lot of privacy. Comfortable, pretty rooms and abeautiful garden between 2 Rivers where you can chill and relax. Very near to town and Near to beach. Come and enjoy. And also every sightseeing like b …see more

from $25 / night

$150 - $1550 / week

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from $25 / night

9

Vacation villa in Portland Parish

Portland Parish / Port Antonio

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Child friendly
  • Air conditioning
Apart from its panoramic views, SINOPIA INN has a large lounge/living area, TV, wireless internet, bathroom essentials, air conditioning, free parking on premises, onsite security, housekeeper, washing machine and complete privacy. Additionally, its outdoor patio, man-m …see more

from $123 / night

$858 - $1102 / week

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from $123 / night

83

Villa rental in Port Antonio with golf nearby

Portland Parish / Port Antonio

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Nearest beach 2 mi
  • Child friendly
  • Air conditioning
Apart from its panoramic views, SINOPIA INN has a large lounge/living area, TV, wireless internet, bathroom essentials, air conditioning, free parking on premises, onsite security, housekeeper, washing machine and complete privacy. Additionally, its outdoor patio, man-m …see more

from $497 / night

$3479 - $3864 / week

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from $497 / night

4

Vacation villa in Port Antonio

Portland Parish / Port Antonio

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Air conditioning
Apart from its panoramic views, SINOPIA INN has a large lounge/living area, TV, wireless internet, bathroom essentials, air conditioning, free parking on premises, onsite security, housekeeper, washing machine and complete privacy. Additionally, its outdoor patio, man-m …see more

from $113 / night

$786 - $1012 / week

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from $113 / night

8

Port Antonio Vacation apartment rental

Portland Parish / Port Antonio

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This pied-à-terre apartment is ideal for couples or friends wanting to decompress and indulge in the good life, relaxing and enjoying the awesome view of the Caribbean sea and the bay, without having to share their space with any other. The apartment is within Heaven Vi …see more

from $250 / night

$1750 / week

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from $250 / night

4

Vacation villa rental

Portland Parish / Port Antonio

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Child friendly
  • Air conditioning
SINOPIA is an early twentieth century house refurbished with modern interior decor which is set on two acres of lush green gardens, filled with palm trees - making it a stunning hideaway in Portland, Jamaica. Units are perfect for families, couples or large groups (not …see more

from $123 / night

$862 - $1111 / week

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from $123 / night

(1) Very Good 

28

Portland Parish Vacation home rental

Portland Parish / Port Antonio

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 2 mi
  • Child friendly
  • Car not necessary
Pineapple Hill Sea View Cottage is located within the city limits and within walking distance of quaint yet beautiful Port Antonio. Port Antonio itself is located by the Caribbean sea on the north eastern coast of Jamaica and is the capital of the parish,Portland. The r …see more

from $60 / night

$420 / week

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from $60 / night

(2) Excellent 

39

Portland Parish Vacation bungalow rental

Portland Parish / Long Bay

4 10 2 nights min

  • 4 bedrooms
  • Sleeps 10
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Panoramic Ocean View bungalows, in the picturesque town of Long Bay, Portland. No place else on the island you will be able to enjoy such a true cultural experience. Where the mountain meets the ocean, warm and friendly vibrations of the people and gorgeous white sand b …see more

from $40 / night

$250 - $1370 / week

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from $40 / night

(4) Excellent 

7

Vacation villa in Port Antonio

Portland Parish / Port Antonio

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Built by the Woolworth family in the early 60′s, Birdie ‘ill Villa is described as Jamaican Colonial Architecture with a French flair. Birdie ‘ill Villa formerly named Pixie Hill, is located on 5 acres of lush gardens and pathways overlooking the ocean. The likes of Vog …see more

from $643 / night

$4500 / week

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from $643 / night

57

Vacation home in Portland Parish

Jamaica / Portland Parish

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
  • Air conditioning
San Bar Villa is a beautiful deluxe villa located on the renowned Blue Lagoon. The exquisite new villa in Jamaica is positioned right on the water, a short swim to Pellou or Monkey Island. Situated right on the waters of the Blue Lagoon, this Jamaica villa offers a magi …see more

from $1500 / night

$10500 - $12000 / week

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from $1500 / night

(1) Excellent 

40

Vacation home in Portland Parish

Portland Parish / Boston Bay

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Ask about children
Happy Villa is a guest house situated in Fairy Hill a district in Portland Jamaica West Indies and home to the once Famous Movie Star Errol Flinn. HaPPY Villa is centrally located as it about ten minutes from the major town of Port Antonia and many attractions includin …see more

from $140 / night

$950 / week

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from $140 / night

(1) Excellent 

15

Vacation log cabin in Port Antonio

Portland Parish / Port Antonio

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 16 mi
  • Swimming pool
  • Child friendly
Shotover Gardens Estate offers a one bedroom studio cabin The cabin is set in 6 acres of forests, lawns, gardens and pool. It is 1000 feet up in the hills outside Port Antonio, Jamaica, It is a 20 minute drive from downtown Port Antonio. The property is secure and ver …see more

from $30 / night

$200 / week

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from $30 / night

28

Vacation home in Port Antonio

Portland Parish / Port Antonio

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Crystal Cove villa in Jamaica, Port Antonio, For Vacationers looking for a unspoiled beauty and away from the tourist hub, perfect hideaway, very private 3 bedrooms, 3 bathrooms Housekeeper/cook, handyman, house maid Air conditioning, ceiling fans in all bedrooms Cable …see more

from $660 / night

$4200 - $6930 / week

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from $660 / night

(14) Very Good 

22

Vacation home rental

Portland Parish / Port Antonio

3 7 1 night min

  • 3 bedrooms
  • Sleeps 7
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
Here you'll find some of the most captivating natural environment Jamaica has to offer. Whether you like to soak up the sun or enjoy the view, Winifred Beach is the place for you (5 Mins walk). There's also Boston Bay where surfers go to rest or to dine on Jamaica's mos …see more

from $105 / night

$735 / week

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Responds fast!
avg. 1 hour 3 minutes

from $105 / night

(1)  

9

Vacation villa with shared pool in Port Antonio

Portland Parish / Port Antonio

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Villa B is a spacious one bedroom villa. View of the pool and the Caribbean sea. The villa balcony is most ideal for the glorious sunset gazing. Equipped with wifi, daily maid service, balcony with outside seating area & private pool entrance. ROOM AMENITIES Sea view Ga …see more

from $100 / night

$700 / week

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Responds fast!
avg. 2 hours 27 minutes

from $100 / night

5

Condo rental in Port Antonio

Portland Parish / Port Antonio

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Ask about pets
Are you LooKing for the Tru Jamaican Experience, a chance to live like a local or a tourists? Then, Tha GreeN CoVe @ ThA LaGooN Spot is your place. Nestled right off the back entrance of the Blu Lagoon(300m), on a private drive, where you can enjoy our Blue Mountain Co …see more

from $85 / night

$490 - $665 / week

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from $85 / night

30

Home rental in Portland Parish

Port Antonio / Blue Lagoon, Port Antonio

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
It a beach front house four bed rooms three bathrooms two kitchens two living rooms two pouches up stairs downstairs sleep 8 highj speed internet each room have it own tv breakfast in the morning beach towels and beach chairs free parking and a maid …see more

from $120 / night

$850 - $2530 / week

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Responds fast!
avg. 1 hour 10 minutes

from $120 / night

(1) Excellent 

26

Vacation home with shared pool in Portland Parish

Portland Parish / Port Antonio

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Brand new luxury villa on the Blue Lagoon in Jamaica! Avalon is located on famous Blue Lagoon, famous for is beauty, waterfront edge villas and crystalline blue waters! Avalon is one of the newest additions to the list of private luxury villas and the nearest to the fam …see more

from $850 / night

$5950 - $8400 / week

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from $850 / night

(2) Excellent 

12

Port Antonio Vacation guest house rental

Portland Parish / Port Antonio

6 5 1 night min

  • 6 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Car not necessary
  • Private garden
Pearl Ocean villa has 5 double bedroom with en-suite. room, Each bedroom is tastefully decorated for your comfort and relaxation. There is a large open lounge area and dining room leasing onto the patio allowing you to immediately capture the lovely breath taking pa …see more

from $85 / night

$595 / week

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from $85 / night

(2) Excellent 

48

Vacation guest house with shared pool in Portland Parish

Portland Parish / Port Antonio

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Suitable for children age 5+
We are a small Guest House Overlooking the entire town of Port Antonio, the Harbours, piers, Navy Island(once owned by Errol Flynn) , Mountains and surrounding areas. Very peaceful, romantic surroundings with the feel of home away from home. We have a total of 4 bedroo …see more

from $125 / night

$875 / week

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from $125 / night

26

Portland Parish Vacation home rental

Jamaica / Portland Parish

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
Brand new luxury villa on the Blue Lagoon in Jamaica! Avalon is located on famous Blue Lagoon, famous for is beauty, waterfront edge villas and crystalline blue waters! Avalon is one of the newest additions to the list of private luxury villas and the nearest to the fam …see more

from $1000 / night

$7000 - $8400 / week

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from $1000 / night

16

Portland Parish Vacation condo rental

Portland Parish / Port Antonio

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Are you LooKing for the Tru Jamaican Experience, a chance to live like a local or a tourists? Then, The Lagoon Spot is your place. Nestled in Jamaica's Blue Mountains,off of a private drive, where you can enjoy our Blue Mountain Coffee in seclusion, or go off to some of …see more

from $85 / night

$450 / week

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from $85 / night

13

Vacation home rental

Portland Parish / Long Bay

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 0.5 mi
  • Child friendly
  • Car not necessary
For a relaxed vacation in contact with nature, nice people, safe environment, beautiful beaches, best jerk food, then this is the spot to be.Get to know the real Jamaica, you will love it. The house is on the hill side of Long Bay, 10 minutes walk from the 1 mile white …see more

from $50 / night

$350 / week

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from $50 / night

(35) Excellent 

Certificate of Excellence

35

Vacation cottage in Portland Parish

Portland Parish / Port Antonio

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 0 mi
  • Child friendly
  • Car not necessary
three secluded cottages nestled in the jungled foothills overlooking the sleepy market town of port antonio on jamaicas northeast coast.Walking distance to craft and produce markets and the transportation center where local route taxis take you to nearby beaches..or hi …see more

Certificate of Excellence

from $50 / night

$350 / week

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from $50 / night

26

Portland Parish Vacation b&b rental

Portland Parish / Port Antonio

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Suitable for children age 5+
  • Ask about pets
Need luxury getaway with a jaw-dropping view at a reasonable cost? Then Pier View Heights Villa is the right place. Beautiful King Size Bed...Big spacious Bedroom and bathroom. Unlimited Internet Access. This beautiful Beach House is nestled upon the hills of Passley Ga …see more

from $60 / night

$350 / week

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Responds fast!
avg. 3 hours 43 minutes

from $60 / night

11

Port Antonio Vacation home rental

Portland Parish / Port Antonio

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Ask about pets
Welcome to Fransica, a very homely hideaway nestled in the hills above St. Margarets Bay, Portland. This House boasts one of the most magnificent view of the Caribbean Sea.., while the beach is only 12 minutes away. If you are looking for a real secure Jamaican livin …see more

from $75 / night

$490 / week

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from $75 / night

(5) Very Good 

14

Vacation log cabin in Portland Parish

Portland Parish / Port Antonio

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 16 mi
  • Swimming pool
  • Child friendly
Shotover Gardens Estate offers a one bedroom cottage. The cottage is set in 6 acres of forests, lawns, gardens and pool. It is 1000 feet up in the hills outside Port Antonio, Jamaica, It is a 20 minute drive from downtown Port Antonio. The property is secure and very …see more

from $50 / night

$300 / week

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from $50 / night

13

Vacation villa in Portland Parish

Jamaica / Portland Parish

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
  • Pet friendly
Beautiful one bedroom villa with small private beach just steps away from the verandah located near Folly at the edge of Port Antonio. A large Grocery store is within walking distance and only 10 minutes drive to the famous Frenchman’s Cove Beach and the Blue Lagoon. Th …see more

from $250 / night

$1750 / week

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from $250 / night

10

Portland Parish Vacation villa rental

Jamaica / Portland Parish

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
In this luxurious villa located in Jamaica's world-renowned Port Antonio, you'll never want to leave. This luxurious 6 bedroom villa sleeps a total of 8 adults and 6 children. Relax in exotic comfort & style. Sun tan on the beautiful deck, dine in our gorgeous dining ro …see more

from $1500 / night

$10500 - $12000 / week

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from $1500 / night

12

Vacation villa in Port Antonio

Portland Parish / Port Antonio

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
Bolt Hole Villa is located in Port Antonio on a one acre estate overlooking the spectacular Caribbean Sea. With its beautiful breathtaking ocean front view, you can escape all your cares and unwind in the peaceful and tranquil atmosphere. The villa is of Jamaican Colon …see more

from $543 / night

$3800 / week

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from $543 / night