25 Best Vacation Rentals in Oracabessa - Holiday Lettings - Cabins

Close

View larger map

Oracabessa

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this vacation rental you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

518 Vacation rentals

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

Book View

from $50 / night

(9) 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. This Mediterranean style villa is nestled behind a palm tree lined driveway in the hills of Gibraltar, overlooking the infamous James Bond …see more

from $450 / night

$3,150 / week

Book View

Responds fast!
avg. 1 hour 50 minutes

from $450 / 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

Book View

Responds fast!
avg. 3 hours 16 minutes

from $35 / 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

Book View

from $45 / night

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

Book View

from $125 / night

(5) Good 

58

Vacation villa in Oracabessa

Saint Mary Parish / Oracabessa

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • 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 $250 / night

$1,500 - $1,920 / week

Book View

Responds fast!
avg. 2 hours 34 minutes

from $250 / night

28

Oracabessa Vacation home rental

Saint Mary Parish / Oracabessa

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Blow Hole Villa, is a charming 5 bedroom, 7.5 bathroom seaside villa located on the east side of Ocho Rios on the Jamaican north coast. The 110 ft. veranda of the main house runs the entire length of the building facing the sea, and connects the bedrooms and public spac …see more

from $786 / night

$5,500 - $10,000 / week

Inquire View

from $786 / night

(1) Excellent 

33

Oracabessa Vacation villa rental

Saint Mary Parish / Oracabessa

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • 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

$1,350 - $1,630 / week

Book View

from $200 / night

(23) Excellent 

40

Cottage rental in Oracabessa

Saint Mary Parish / Oracabessa

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • 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 / week

Book View

from $95 / night

(3) Excellent 

47

Villa rental in Oracabessa with swimming pool

Saint Mary Parish / Oracabessa

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 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 $650 / night

$3,200 / week

Book View

from $650 / 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 $2,000 / night

$14,000 - $21,000 / week

Inquire View

from $2,000 / 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
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 ocean. Located in one of the lesser developed …see more

from $2,071 / night

$14,497 / week

Book View

Responds fast!
avg. 2 minutes

from $2,071 / 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
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 ocean. Located in one of the lesser developed …see more

from $1,714 / night

$11,998 / week

Book View

Responds fast!
avg. 2 minutes

from $1,714 / 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
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 ocean. Located in one of the lesser developed …see more

from $2,000 / night

$14,000 / week

Book View

Responds fast!
avg. 2 minutes

from $2,000 / 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
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 ocean. Located in one of the lesser developed …see more

from $1,857 / night

$12,999 / week

Book View

Responds fast!
avg. 2 minutes

from $1,857 / night

44

Oracabessa Vacation villa rental

Saint Mary Parish / Oracabessa

7 15 Min stay varies

  • 7 bedrooms
  • Sleeps 15
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
SPECIAL:  ONE FREE NIGHT WHEN BOOKING A WEEK IN THE "HIGH" SEASON - (Does not apply to holiday weeks like Easter, Thanksgiving, Christmas/New Year) Spectacular 7 bedroom waterfront villa in Oracabessa, 15 minutes from Ocho Rios. Perfect for family reunions and weddings. …see more

from $1,571 / night

$11,000 - $21,000 / week

Inquire View

from $1,571 / night

45

Oracabessa Vacation villa rental

Saint Mary Parish / Oracabessa

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
SPECIAL:  ONE FREE NIGHT WHEN BOOKING A WEEK IN THE "HIGH" SEASON - (Does not apply to holiday weeks like Easter, Thanksgiving, Christmas/New Year) RENTING 5 BEDROOMS ONLY - Golden Clouds Villa is a luxurious estate located on the northern coast of Jamaica, in the pictu …see more

from $1,343 / night

$9,400 - $21,000 / week

Inquire View

from $1,343 / night

44

Oracabessa Vacation villa rental

Saint Mary Parish / Oracabessa

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
SPECIAL:  ONE FREE NIGHT WHEN BOOKING A WEEK IN THE "HIGH" SEASON  - (Does not apply to holiday weeks like Easter, Thanksgiving, Christmas/New Year) Spectacular 6 bedroom waterfront villa in Oracabessa, 15 minutes from Ocho Rios. Perfect for family reunions and weddings …see more

from $1,429 / night

$10,000 - $21,000 / week

Inquire View

from $1,429 / night

40

Oracabessa Vacation villa rental

Saint Mary Parish / Oracabessa

12 26 7 nights min

  • 12 bedrooms
  • Sleeps 26
  • 7 nights min
  • Ask about children
  • Ask about pets
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 ocean. Located in one of the lesser developed …see more

from $2,214 / night

$15,498 / week

Book View

Responds fast!
avg. 2 minutes

from $2,214 / night

43

Oracabessa Vacation villa rental

Saint Mary Parish / Oracabessa

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
SPECIAL:  ONE FREE NIGHT WHEN BOOKING A WEEK IN THE "HIGH" SEASON - (Does not apply to holiday weeks like Easter, Thanksgiving, Christmas/New Year) RENTING 9 BEDROOMS - Golden Clouds Villa is a luxurious estate located on the northern coast of Jamaica, in the picturesqu …see more

from $1,857 / night

$13,000 - $21,000 / week

Inquire View

from $1,857 / 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
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 ocean. Located in one of the lesser developed …see more

from $2,143 / night

$15,001 / week

Book View

Responds fast!
avg. 2 minutes

from $2,143 / 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
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 ocean. Located in one of the lesser developed …see more

from $1,343 / night

$9,401 / week

Book View

Responds fast!
avg. 2 minutes

from $1,343 / night

47

Oracabessa Vacation villa rental

Saint Mary Parish / Oracabessa

11 22 Min stay varies

  • 11 bedrooms
  • Sleeps 22
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
SPECIAL:  ONE FREE NIGHT WHEN BOOKING A WEEK IN THE "HIGH" SEASON  - (Does not apply to holiday weeks like Easter, Thanksgiving, Christmas/New Year) Situated on a picturesque banana port village of Oracabessa, 15 minutes from Ocho Rios - a luxurious, 6 acre estate, gate …see more

from $2,071 / night

$14,500 - $24,000 / week

Inquire View

from $2,071 / 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
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 ocean. Located in one of the lesser developed …see more

from $1,571 / night

$10,997 / week

Book View

Responds fast!
avg. 2 minutes

from $1,571 / night

47

Vacation villa with shared pool in Oracabessa

Saint Mary Parish / Oracabessa

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
SPECIAL:  ONE FREE NIGHT WHEN BOOKING A WEEK IN THE "HIGH" SEASON 2017 and 2018 - (Does not apply to holiday weeks like Easter, Thanksgiving, Christmas/New Year) Spectacular 8 bedroom waterfront villa in Oracabessa, 15 minutes from Ocho Rios. Perfect for family reunions …see more

from $1,714 / night

$12,000 - $21,000 / week

Inquire View

from $1,714 / 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
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 ocean. Located in one of the lesser developed …see more

from $1,429 / night

$10,003 / week

Book View

Responds fast!
avg. 2 minutes

from $1,429 / night

49

Oracabessa Vacation villa rental

Saint Mary Parish / Oracabessa

10 20 Min stay varies

  • 10 bedrooms
  • Sleeps 20
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
SPECIAL:  ONE FREE NIGHT WHEN BOOKING A WEEK IN THE "HIGH" SEASON  - (Does not apply to holiday weeks like Easter, Thanksgiving, Christmas/New Year) Situated on a picturesque banana port village of Oracabessa, 15 minutes from Ocho Rios - a luxurious, 6 acre estate, gate …see more

from $2,000 / night

$14,000 - $22,500 / week

Inquire View

from $2,000 / night