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

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140 Vacation rentals

(1) Excellent 

29

Villa rental in Portland Parish

Port Antonio / Williamsfield

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • 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

$2,000 / week

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from $350 / night

4

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 $45 / night

$280 - $1,540 / week

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from $45 / night

(1)  

27

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

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 - $1,550 / week

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from $25 / 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

$1,050 - $1,099 / week

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Responds fast!
avg. 3 hours 9 minutes

from $200 / 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 $1,300 / night

$9,000 / week

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from $1,300 / 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

$1,855 / week

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from $265 / night

12

Portland Parish Vacation cottage rental

Portland Parish / Long Bay

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Private garden
We offer you a newly built one bedroom cabin that sleeps up to two guests, a private toilet with shower and balcony equipped with hammock to enjoy the amazing sea view and ocean breeze. There are steps to get up to the cabins. Guest access: to the villa, terrace, ro …see more

from $60 / night

$420 / week

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from $60 / night

4

Vacation villa in Port Antonio

Portland Parish / Port Antonio

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night 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 $122 / night

$853 / week

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from $122 / 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 $133 / night

$931 / week

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from $133 / night

15

Vacation apartment rental

Portland Parish / Buff Bay

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Private garden
Ray & Perry welcome you to The Windsor Retreat. A self catering luxury Guesthouse located in Portland on the Northeast coast side of Jamaica. The parish of Portland is well visited and borders the Blue Mountains National Park. There is plenty to explore in the surroundi …see more

from $49 / night

$343 / week

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from $49 / 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 $133 / night

$936 / week

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from $133 / night

(1) Excellent 

4

Portland Parish Vacation villa rental

Portland Parish / Port Antonio

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night 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 $122 / night

$853 / week

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from $122 / night

(2) Very Good 

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 $552 / night

$3,864 / week

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from $552 / night

(4) Excellent 

41

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. Price is based on 2 people to each bungalow so book accordingly. The best place on the island you will be able to enjoy such a true cultural experience. Where the mountain meets the ocean, w …see more

from $40 / night

$250 - $1,370 / week

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from $40 / night

(35) Excellent 

Certificate of Excellence

38

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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Responds fast!
avg. 3 hours 45 minutes

from $50 / night

(2) Excellent 

9

Vacation villa in Portland Parish

Jamaica / Portland Parish

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
There's no place like a villa on the sea. In this elegant villa at Jamaica's world-renowned Port Antonio, you'll never want to leave. This luxurious 4 bedroom villa sleeps a total of 8 guests. Relax in comfort & style. Sun tan on the beautiful deck, dine in our gorgeo …see more

from $1,000 / night

$7,000 - $8,000 / week

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from $1,000 / night

10

Portland Parish Vacation villa rental

Jamaica / Portland Parish

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
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 …see more

from $1,500 / night

$10,500 - $12,000 / week

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from $1,500 / 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 $100 / night

$700 / week

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from $100 / night

45

Portland Parish Vacation apartment rental

Portland Parish / Long Bay

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Car not necessary
  • Private garden
The property is located in the peaceful seaside village of Long Bay Portland. It is a self contained apartment with its own entrance located on the second floor of my home. We are metres away from the ocean and the apartment offers an excellent ocean view and a spectac …see more

from $30 / night

$150 - $360 / week

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Responds fast!
avg. 1 hour 9 minutes

from $30 / night

(2) Excellent 

17

Port Antonio Vacation guest house rental

Portland Parish / Port Antonio

6 10 1 night min

  • 6 bedrooms
  • Sleeps 10
  • 1 night min
  • Nearest beach 3 mi
  • Child friendly
  • Car not necessary
This villa is a splendid holiday rental that has 3 large double bedroom with en-suite and 1 twin bedroom, 4 Bedrooms. Also a 1 communal bathroom shower/bathroom. This include a 1 bedroom self-contained apartment on the ground floor of the property. All bedroom is airy …see more

from $60 / night

$420 / week

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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

(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

(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

(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 36 minutes

from $105 / night

(4) Very Good 

41

Port Antonio Vacation b&b rental

Portland Parish / Port Antonio

5 14 1 night min

  • 5 bedrooms
  • Sleeps 14
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
This villa offers daily COMPLIMENTARY BREAKFAST FOR 10, FREE USE OF BOAT WITH CAPTAIN for snorkeling and sightseeing to San San Beach, Monkey Island and Blue Lagoon. You also receive COMPLIMENTARY PASSES TO THE BLUE MOUNTAIN BICYCLE TOUR, #1 tour in Portland(If you stay …see more

from $905 / night

$6,335 - $7,175 / week

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Responds fast!
avg. 40 minutes

from $905 / night

7

Villa rental in Portland Parish with shared pool

Jamaica / Portland Parish

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
Originally owned by a member of Alexander Graham Bell's family, one of the first owners at San San, this magnificent family-friendly villa is located immediately above San San beach near Port Antonio. Halcyon is a casual and elegant 4 bedroom, 4 bathroom villa that ent …see more

from $1,000 / night

$7,000 - $10,500 / week

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from $1,000 / night

(17) Excellent 

30

Portland Parish Vacation villa rental

Portland Parish / Port Antonio

5 10 1 night min

  • 5 bedrooms
  • Sleeps 10
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Swimming pool
Spicy Hill Villa, one of Jamaica's best-kept secrets. In a secluded tropical setting surround yourself in luxury. Spend romantic candle lit moments dining around the pool or watch the sunrise on the bay.  Spicy Hill Villa is a Jamaica Tourist Board approved Villa, this …see more

from $900 / night

$6,125 / week

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from $900 / night

(4) Very Good 

28

Vacation home in Portland Parish

Portland Parish / Port Antonio

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Private garden
Located in the beautiful parish of Portland, this vacation rental has all the comforts of home. The home is located 5-7 minutes from downtown Port Antonio, and 10-15 Minutes from all beaches. If rafting on the Rio Grand is on your agenda, we are only a 10-minute drive a …see more

from $75 / night

$525 / week

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Responds fast!
avg. 3 hours 25 minutes

from $75 / night

39

B&b rental in Portland Parish with shared pool

Portland Parish / Port Antonio

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
All Nations Guesthouse is suitable for all type of travelers visiting Jamaica. Our villa is 3 floors, the top floor is reserved for the luxury rooms with pvt terrace, the middle floor for the common spaces as kitchen and living room, and at the first floor 2 double room …see more

from $125 / night

$875 / week

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from $125 / night

22

Vacation apartment in Portland Parish

Portland Parish / Port Antonio

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 1 mi
  • Child friendly
  • Car not necessary
The Cove is a spacious two bedroom apartment located a quiet upscale neighborhood of Harmony Heights. The space boasts large r bedrooms, spacious kitchen dining and living room with sliding glass doors which leads out to a warp around balcony with a panoramic view of th …see more

from $55 / night

$320 / week

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from $55 / 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 $100 / night

$700 / week

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from $100 / night

(3) 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

(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

18

Vacation home in Port Antonio

Portland Parish / Port Antonio

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Private garden
The perfect off the beaten track beach house perched in the midst of Portland natural green vegetation on one side and the sea on the other, you literally hear the sound of the waves from the rooms facing the sea. The place to be, to have your entire body and soul reju …see more

from $75 / night

$525 - $1,225 / week

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from $75 / 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 - $2,530 / week

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Responds fast!
avg. 1 hour 47 minutes

from $120 / night

22

B&b rental in Portland Parish

Portland Parish / Port Antonio

1 5 1 night min

  • 1 bedroom
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Pet friendly
The Upstairs Master Bedroom has 2 rooms and is on the top floor of Moon San and has the best view of all the rooms. This room has a private bathroom, queen bed, 40" TV with 5 pay per view channels, a/c, and coffee maker with Blue Mountain Coffee. There is also a second …see more

from $210 / night

$1,470 - $2,310 / week

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Responds fast!
avg. 40 minutes

from $210 / night

(1) Excellent 

40

Vacation home with golf nearby in Portland Parish

Portland Parish / Boston Bay

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
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 $65 / night

$440 / week

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from $65 / night

31

Vacation home in Portland Parish

Portland Parish / Port Antonio

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
Sea Star is the latest addition to the ultra luxurious villas located on the world famous Blue Lagoon in romantic Port Antonio. This exquisite newly built 5-bedroom waterfront villa is nestled in between the lush vegetation of Portland and the sparkling Caribbean Sea. Y …see more

from $1,300 / night

$9,100 - $11,500 / week

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from $1,300 / night

45

Vacation home in Portland Parish

Portland Parish / Manchioneal

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Child friendly
  • Car not necessary
  • Private garden
Built in late 1970’s, Serendipity represents the classical architecture of its era, with original Terrazzo floors and classic iron work. Private and spacious, it offers the perfect intimate getaway as well as a fabulous family vacation. Serendipity is off the beaten-pa …see more

from $200 / night

$1,400 / week

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from $200 / night