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

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Portland Parish

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75 Vacation rentals

18

Portland Parish / Long Bay

3 4 2 nights min

  • 3 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 0.1 mi
  • Child friendly
  • Private garden

from $100 / night

$700 / week

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from $100 / 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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from $200 / 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 $35 / night

$220 - $490 / week

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from $35 / night

(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 $200 / night

$1400 / week

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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

(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

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

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

20

Portland Parish / Long Bay

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 0.1 mi
  • Child friendly
  • Private garden

from $65 / night

$455 / week

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from $65 / night

18

Portland Parish / Long Bay

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 0.1 mi
  • Child friendly

from $45 / night

$315 / week

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from $45 / night

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 $1100 / night

$7700 / week

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from $1100 / night

25

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 $159 / night

$1111 - $1174 / week

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from $159 / night

30

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
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 $158 / night

$1102 - $1220 / week

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from $158 / night

40

Villa rental in Port Antonio with golf nearby

Portland Parish / Port Antonio

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Private garden
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 $540 / night

$3780 - $4235 / week

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from $540 / night

23

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
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 $145 / night

$1012 - $1129 / week

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from $145 / night

26

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
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 $145 / night

$1012 - $1129 / week

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from $145 / night

(34) Excellent 

35

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

from $50 / night

$350 / week

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from $50 / night

16

Portland Parish / Port Antonio

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary

from $85 / night

$450 / week

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from $85 / night

(1) Excellent 

9

Portland Parish / Port Antonio

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

from $400 / night

$2800 - $2975 / week

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from $400 / night

31

Portland Parish / Port Antonio

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children

from $1300 / night

$9100 - $11500 / week

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from $1300 / night

18

Portland Parish / Port Antonio

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children

from $1000 / night

$7000 - $8000 / week

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from $1000 / night

(14) Very Good 

22

Portland Parish / Port Antonio

3 7 1 night min

  • 3 bedrooms
  • Sleeps 7
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi

from $105 / night

$735 / week

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from $105 / night

36

Portland Parish / Port Antonio

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly

from $68 / night

$476 / week

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from $68 / night

13

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

from $50 / night

$350 / week

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from $50 / night

(4) Very Good 

28

Portland Parish / Port Antonio

1 4 5 nights min

  • 1 bedroom
  • Sleeps 4
  • 5 nights min
  • Child friendly
  • Private garden

from $50 / night

$300 / week

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from $50 / night

(5) Very Good 

14

Portland Parish / Port Antonio

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 16 mi
  • Swimming pool
  • Child friendly

from $50 / night

$300 / week

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from $50 / night

(1) Excellent 

15

Portland Parish / Port Antonio

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 16 mi
  • Swimming pool
  • Child friendly

from $30 / night

$200 / week

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from $30 / night

(1) Very Good 

28

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

from $60 / night

$420 / week

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from $60 / night

5

Portland Parish / Port Antonio

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Ask about pets

from $85 / night

$490 - $665 / week

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from $85 / night

(2) Excellent 

40

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

from $40 / night

$250 - $1370 / week

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from $40 / night

(2) Excellent 

12

Portland Parish / Port Antonio

6 5 1 night min

  • 6 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Car not necessary
  • Private garden

from $85 / night

$595 / week

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from $85 / night

11

Portland Parish / Port Antonio

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Ask about pets

from $75 / night

$490 / week

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from $75 / night

(2) Excellent 

48

Portland Parish / Port Antonio

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Suitable for children age 5+

from $125 / night

$875 / week

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from $125 / night

30

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

from $120 / night

$850 - $2530 / week

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from $120 / night

(1) Excellent 

40

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

from $140 / night

$950 / week

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from $140 / night

13

Jamaica / Portland Parish

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
  • Pet friendly

from $250 / night

$1750 / week

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from $250 / night

(2) Excellent 

18

Port Antonio / Blue Lagoon, Port Antonio

5 10 2 nights min

  • 5 bedrooms
  • Sleeps 10
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

from $850 / night

$5250 / week

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from $850 / night

(1) Excellent 

15

Portland Parish / Port Antonio

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

from $1000 / night

$7000 - $70000 / week

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from $1000 / night

(33) Excellent 

34

Portland Parish / Port Antonio

2 5 4 nights min

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool

from $260 / night

$1800 - $2315 / week

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from $260 / night

1