30 Best Vacation Rentals in Oracabessa - Holiday Lettings - Cabins

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37 Vacation rentals

22

Vacation home in Oracabessa

Saint Mary Parish / Oracabessa

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 3 mi
  • Private garden
Quaint 2 bedroom, 2 1/2 bathroom cottage with lots of character located on 3/4 acre lot with a few fruit trees and blooming plants. A perfect location with much land space. A decorator's potential dream can be realized as this 2-storey house offers many nooks and …see more

from $125 / night

$750 / week

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from $125 / night

16

Oracabessa Vacation villa rental

Saint Mary Parish / Oracabessa

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Ask about children
One bedroom villa located right beside the famous GoldenEye Hotel & Resort, original home of author Ian Fleming who wrote many of the James Bond novels while living in Oracabessa. Property has 24hr security. There is no beach however there are steps leading down to the …see more

from $65 / night

$378 / week

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from $65 / night

14

Cottage accommodation in Oracabessa

Saint Mary Parish / Oracabessa

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
The Space 1 bedroom, 1 bath single or double occupancy cottage available off the beaten path, in the hills of St. Mary. Minutes from world renowned James Bond Beach with easy access to highway to local cities. Property includes a pool with a beautiful view of the …see more

from $50 / night

$300 / week

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from $50 / night

24

Oracabessa Vacation home rental

Saint Mary Parish / Oracabessa

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
4 Waterfront villas with 4 luxury bedrooms for a total of 16 bedrooms! Great for weddings, family reunions, special events! Newly refurbished waterfront luxury villas! Enjoy the luxury and peaceful surroundings of these four luxury villas with your own beachfront, sea k …see more

from $785 / night

$5500 - $7000 / week

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from $785 / night

(22) Excellent 

40

Cottage rental in Oracabessa

Saint Mary Parish / Oracabessa

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 24 mi
The cosy newly built cottage in the traditional Jamaican style is located on a vast property with stunning sea views and tropical garden, just above a rocky cliff. From your front porch or lying in the hammock you will enjoy the beautiful view of the sea, or discover ex …see more

from $95 / night

$585 - $675 / week

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from $95 / night

15

Vacation villa in Oracabessa

Saint Mary Parish / Oracabessa

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
Your room is a spacious king size with private family sized bathroom and access to huge balcony and dining space shared with one other room! Stunning panoramic views of the mountains, ocean and golden eye island! Fantastic in the mornings! Access to shared pool area, l …see more

from $45 / night

$315 / week

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from $45 / night

24

Home rental in Oracabessa

Saint Mary Parish / Oracabessa

12 24 Min stay varies

  • 12 bedrooms
  • Sleeps 24
  • Min stay varies
  • Child friendly
  • Air conditioning
4 Waterfront villas with 4 luxury bedrooms for a total of 16 bedrooms! Great for weddings, family reunions, special events! Newly refurbished waterfront luxury villas! Enjoy the luxury and peaceful surroundings of these four luxury villas with your own beachfront, sea k …see more

from $2357 / night

$16500 - $21000 / week

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from $2357 / night

21

Oracabessa Vacation cottage rental

Saint Mary Parish / Oracabessa

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
Quaint cottage located in the hills of Jamaica's north coast. Ideal for those seeking adventure and/or a peaceful retreat. Minutes from the main road to Ocho Rios and Kingston, pool access, private beach, and many Jamaican attractions. The Space 1 bedroom, …see more

from $45 / night

$270 / week

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from $45 / night

30

Villa rental in Oracabessa with swimming pool

Saint Mary Parish / Oracabessa

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Golden Clouds villa in Jamaica has long been recognized as the pinnacle of excellence among Caribbean villas and resorts. In its 100-year history, our exclusive, award-winning villa has become known for understated luxury and warm Jamaican heart. This legendary property …see more

Pricing unknown

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Pricing unknown

24

Oracabessa Vacation home rental

Saint Mary Parish / Oracabessa

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Child friendly
  • Air conditioning
4 Waterfront villas with 4 luxury bedrooms for a total of 16 bedrooms! Great for weddings, family reunions, special events! Newly refurbished waterfront luxury villas! Enjoy the luxury and peaceful surroundings of these four luxury villas with your own beachfront, sea k …see more

from $1571 / night

$11000 - $14000 / week

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from $1571 / night

10

Vacation villa in Oracabessa

Saint Mary Parish / Oracabessa

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
Your room is a spacious king room with private shower room and great views! Stunning panoramic views of the mountains, ocean and golden eye island! Fantastic in the mornings! Access to shared pool area, lounge/TV area and kitchen if you like to cook! Of course we can o …see more

from $35 / night

$245 / week

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from $35 / night

47

Oracabessa Vacation home rental

Saint Mary Parish / Oracabessa

11 22 Min stay varies

  • 11 bedrooms
  • Sleeps 22
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Situated on a picturesque banana port village of Oracabessa, 15 minutes from Ocho Rios - a luxurious, 6 acre estate, gated and private. Waterfront villa! Golden Clouds Villa is a luxurious estate located on the northern coast of Jamaica, in the picturesque banana port v …see more

from $2071 / night

$14500 - $24000 / week

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from $2071 / night

24

Vacation home in Oracabessa

Saint Mary Parish / Oracabessa

16 32 Min stay varies

  • 16 bedrooms
  • Sleeps 32
  • Min stay varies
  • Child friendly
  • Air conditioning
4 Waterfront villas with 4 luxury bedrooms for a total of 16 bedrooms! Great for weddings, family reunions, special events! Newly refurbished waterfront luxury villas! Enjoy the luxury and peaceful surroundings of these four luxury villas with your own beachfront, sea k …see more

from $3215 / night

$22500 - $29000 / week

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from $3215 / night

(1) Excellent 

33

Oracabessa Vacation villa rental

Saint Mary Parish / Oracabessa

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
Loveland Villa, sits ideally on top of a slope that provides its occupants with a beautiful sea view. The villa comes with a private outdoor swimming pool and private beach access. Ideal getaway for the persons loving nature, privacy and quiet. Yet still ideal for thos …see more

from $200 / night

$1350 - $2120 / week

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from $200 / night

(1) Excellent 

27

Villa rental in Oracabessa with swimming pool

Saint Mary Parish / Oracabessa

4 16 3 nights min

  • 4 bedrooms
  • Sleeps 16
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
Sea side villa sits 80 ft above sea level, panoramic view, 4 bedroom 4.5 bath, pool, wifi, fully staffed, on site management and security. Foodies paradise, 15minutes from Downtown Ocho Rios, Mystic mtn, Dolphins cove, Dunns river falls, James Bond beach, Turtle Mel's …see more

from $900 / night

$6500 / week

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from $900 / night

(2) Excellent 

35

Villa rental in Oracabessa with swimming pool

Saint Mary Parish / Oracabessa

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Take a break from the "hustle and bustle" of life, and experience the taste and sounds of the Jamaican countryside in fine style. Grande Haven Gibraltar is a Mediterranean style villa located in the scenic hills of Oracabessa, St. Mary. This hidden gem is nestled in lu …see more

from $300 / night

$2100 / week

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Responds fast!
avg. 1 hour 6 minutes

from $300 / night

(4) Good 

58

Vacation villa in Oracabessa

Saint Mary Parish / Oracabessa

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Loveland Villa boasts a panoramic view of the Caribbean Sea and a lovely tropical breeze throughout the day. This view is a 180 degrees view can can be see seen from two bedrooms. The third bedroom has a garden view. You can also see the world famous Golden Eye Hotel …see more

from $200 / night

$1300 - $2120 / week

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Responds fast!
avg. 1 hour 17 minutes

from $200 / night

(1) Excellent 

49

Vacation home in Oracabessa

Saint Mary Parish / Oracabessa

10 20 Min stay varies

  • 10 bedrooms
  • Sleeps 20
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Situated on a picturesque banana port village of Oracabessa, 15 minutes from Ocho Rios - a luxurious, 6 acre estate, gated and private. Waterfront villa! Golden Clouds Villa is a luxurious estate located on the northern coast of Jamaica, in the picturesque banana port v …see more

from $2000 / night

$14000 - $22500 / week

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from $2000 / night

(1) Excellent 

40

Vacation villa in Oracabessa

Saint Mary Parish / Oracabessa

11 22 Min stay varies

  • 11 bedrooms
  • Sleeps 22
  • Min stay varies
  • Ask about children
  • Ask about pets
Holiday rates available upon request only Golden Clouds is a magnificent villa located on a sprawling property in the picturesque banana port village of Orcabessa. Sip your favorite drink while lounging on your own private, enclosed beach atop a stone deck upon the ocea …see more

from $2071 / night

$14497 / week

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Responds fast!
avg. 1 hour 22 minutes

from $2071 / night

40

Vacation villa in Oracabessa

Saint Mary Parish / Oracabessa

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Ask about children
  • Ask about pets
Holiday rates available upon request only Golden Clouds is a magnificent villa located on a sprawling property in the picturesque banana port village of Orcabessa. Sip your favorite drink while lounging on your own private, enclosed beach atop a stone deck upon the ocea …see more

from $1715 / night

$11999 / week

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Responds fast!
avg. 1 hour 22 minutes

from $1715 / night

40

Oracabessa Vacation villa rental

Saint Mary Parish / Oracabessa

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
  • Ask about children
  • Ask about pets
Holiday rates available upon request only Golden Clouds is a magnificent villa located on a sprawling property in the picturesque banana port village of Orcabessa. Sip your favorite drink while lounging on your own private, enclosed beach atop a stone deck upon the ocea …see more

from $1857 / night

$12999 / week

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Responds fast!
avg. 1 hour 22 minutes

from $1857 / night

40

Vacation villa in Oracabessa

Saint Mary Parish / Oracabessa

10 20 Min stay varies

  • 10 bedrooms
  • Sleeps 20
  • Min stay varies
  • Ask about children
  • Ask about pets
Holiday rates available upon request only Golden Clouds is a magnificent villa located on a sprawling property in the picturesque banana port village of Orcabessa. Sip your favorite drink while lounging on your own private, enclosed beach atop a stone deck upon the ocea …see more

from $2000 / night

$14000 / week

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Responds fast!
avg. 1 hour 22 minutes

from $2000 / night

12

Vacation home in Oracabessa

Saint Mary Parish / Oracabessa

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
Your room is a spacious king size with private family sized bathroom and access to huge balcony and dining space shared with one other room! Stunning panoramic views of the mountains, ocean and golden eye island! Fantastic in the mornings! Access to shared pool area, l …see more

from $35 / night

$245 / week

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Responds fast!
avg. 2 hours 17 minutes

from $35 / night

14

Vacation home accommodation

Saint Mary Parish / Oracabessa

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Swimming pool
Sleeps 1-12 1-10 in main house, with availability for 1 bedroom/2 guests to stay/use Spanish Elm, cottage at Golden Eye. Secluded five-bedroom private home surrounded by 40 acres of landscaped lawn, fruit trees, and lush, untouched tropical forest, Bolt House is nestl …see more

from $2000 / night

$14000 - $21000 / week

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from $2000 / night

43

Vacation home in Oracabessa

Saint Mary Parish / Oracabessa

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Situated on a picturesque banana port village of Oracabessa, 15 minutes from Ocho Rios - a luxurious, 6 acre estate, gated and private. Waterfront villa! Golden Clouds Villa is a luxurious estate located on the northern coast of Jamaica, in the picturesque banana port v …see more

from $1857 / night

$13000 - $21000 / week

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from $1857 / night

40

Vacation villa in Oracabessa

Saint Mary Parish / Oracabessa

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
  • Ask about pets
Holiday rates available upon request only Golden Clouds is a magnificent villa located on a sprawling property in the picturesque banana port village of Orcabessa. Sip your favorite drink while lounging on your own private, enclosed beach atop a stone deck upon the ocea …see more

from $1428 / night

$9996 / week

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Responds fast!
avg. 1 hour 22 minutes

from $1428 / night

45

Vacation home rental

Saint Mary Parish / Oracabessa

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Situated on a picturesque banana port village of Oracabessa, 15 minutes from Ocho Rios - a luxurious, 6 acre estate, gated and private. Waterfront villa! Golden Clouds Villa is a luxurious estate located on the northern coast of Jamaica, in the picturesque banana port v …see more

from $1343 / night

$9400 - $21000 / week

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from $1343 / night

40

Oracabessa Vacation villa rental

Saint Mary Parish / Oracabessa

12 24 Min stay varies

  • 12 bedrooms
  • Sleeps 24
  • Min stay varies
  • Ask about children
  • Ask about pets
Holiday rates available upon request only Golden Clouds is a magnificent villa located on a sprawling property in the picturesque banana port village of Orcabessa. Sip your favorite drink while lounging on your own private, enclosed beach atop a stone deck upon the ocea …see more

from $2142 / night

$14994 / week

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Responds fast!
avg. 1 hour 22 minutes

from $2142 / night

49

Vacation home with shared pool in Oracabessa

Saint Mary Parish / Oracabessa

12 24 Min stay varies

  • 12 bedrooms
  • Sleeps 24
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Situated on a picturesque banana port village of Oracabessa, 15 minutes from Ocho Rios - a luxurious, 6 acre estate, gated and private. Waterfront villa! Golden Clouds Villa is a luxurious estate located on the northern coast of Jamaica, in the picturesque banana port v …see more

from $2143 / night

$15000 - $25000 / week

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from $2143 / night

40

Oracabessa Vacation villa rental

Saint Mary Parish / Oracabessa

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Ask about pets
Holiday rates available upon request only Golden Clouds is a magnificent villa located on a sprawling property in the picturesque banana port village of Orcabessa. Sip your favorite drink while lounging on your own private, enclosed beach atop a stone deck upon the ocea …see more

from $1342 / night

$9394 / week

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Responds fast!
avg. 1 hour 22 minutes

from $1342 / night

40

Oracabessa Vacation villa rental

Saint Mary Parish / Oracabessa

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Ask about children
  • Ask about pets
Holiday rates available upon request only Golden Clouds is a magnificent villa located on a sprawling property in the picturesque banana port village of Orcabessa. Sip your favorite drink while lounging on your own private, enclosed beach atop a stone deck upon the ocea …see more

from $1571 / night

$10997 / week

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Responds fast!
avg. 1 hour 22 minutes

from $1571 / night

44

Vacation home rental

Saint Mary Parish / Oracabessa

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Situated on a picturesque banana port village of Oracabessa, 15 minutes from Ocho Rios - a luxurious, 6 acre estate, gated and private. Waterfront villa! Golden Clouds Villa is a luxurious estate located on the northern coast of Jamaica, in the picturesque banana port v …see more

from $1429 / night

$10000 - $21000 / week

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from $1429 / night

44

Vacation home rental

Saint Mary Parish / Oracabessa

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Situated on a picturesque banana port village of Oracabessa, 15 minutes from Ocho Rios - a luxurious, 6 acre estate, gated and private. Waterfront villa! Golden Clouds Villa is a luxurious estate located on the northern coast of Jamaica, in the picturesque banana port v …see more

from $1571 / night

$11000 - $21000 / week

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from $1571 / night

47

Oracabessa Vacation home rental

Saint Mary Parish / Oracabessa

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Situated on a picturesque banana port village of Oracabessa, 15 minutes from Ocho Rios - a luxurious, 6 acre estate, gated and private. Waterfront villa! Golden Clouds Villa is a luxurious estate located on the northern coast of Jamaica, in the picturesque banana port v …see more

from $1715 / night

$12000 - $21000 / week

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from $1715 / night

17

Oracabessa Vacation villa rental

Saint Mary Parish / Oracabessa

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning
Stroll across the suspension bridge to another world on a white sand beach next to translucent blue water. Nine remarkable villas form a village on Low Cay Beach. * Daily housekeeping and laundry service * Complimentary Wi-Fi (available in all rooms and th …see more

from $1966 / night

$13760 - $23840 / week

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Responds fast!
avg. 28 minutes

from $1966 / night

23

Vacation villa with swimming pool in Oracabessa

Saint Mary Parish / Oracabessa

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
About GoldenEye Fleming Villa FOR DECADES, The Fleming Villa has been legend for its illustrious past, its celebrity guests, and the lasting works of literature and film that were penned and shot here. Today, it is just as stunning as ever and still filled with the …see more

from $8508 / night

$59550 - $84351 / week

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Responds fast!
avg. 28 minutes

from $8508 / night

10

Vacation villa with swimming pool in Oracabessa

Saint Mary Parish / Oracabessa

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning
On the other side of the peninsula is yet another world: the Lagoon. Created in the days when the village of Oracabessa was a banana port, it is marvelous for swimming and kayaking. * 287-square foot veranda crafted from sustainable Brazilian hardwood * Da …see more

from $956 / night

$6690 - $11430 / week

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Responds fast!
avg. 28 minutes

from $956 / night

1