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

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77 properties
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69 properties
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22 properties

Trelawny Parish

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420 Vacation rentals

(4) Excellent 

26

Vacation guest house in Falmouth

Trelawny Parish / Falmouth

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
This is Charmaine's 2 Bedroom guest house. It is a spacious and beautiful private destination that is situated in the middle of Montego Bay and Ocho Rios. The house is newly built in 2015 and is a gated community. The guest house is close to all tourist attractions, ac …see more

from $49 / night

$343 / week

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from $49 / night

(2) Good 

27

Vacation villa with swimming pool in Falmouth

Trelawny Parish / Falmouth

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 10 mi
  • Swimming pool
  • Child friendly
Our beautiful home sits on the hill with a panoramic view of the Caribbean Sea. In this exclusive location in Greenside, Trelawny, you can relax under a Mango tree in the front yard, or a breadfruit tree in the backyard, sipping your favourite drink. We keep the environ …see more

from $50 / night

$200 / week

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from $50 / night

(2) Excellent 

27

Trelawny Parish Vacation villa rental

Trelawny Parish / Duncans

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Location: Things have changed at Yellow Canary Villa, the villa has just had a facelift with a cheerful entrance to the property. A double bedroom has been renovated and added, with a modern fresh decor. All bedrooms have been redecorated adding charm and colour to t …see more

from $150 / night

$1,050 - $1,120 / week

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Responds fast!
avg. 3 hours 12 minutes

from $150 / night

13

Vacation villa in Falmouth

Trelawny Parish / Falmouth

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden
Beautiful newly build 4 bedroom house. Close to the beach, wifi, cable, full kitchen, AC, hot water. Tour guide available, cook available. My place is close to Beach . You’ll love my place because of the outdoors space and the neighborhood. My place is good for couples …see more

from $63 / night

$441 / week

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from $63 / night

54

Trelawny Parish Vacation home rental

Trelawny Parish / Falmouth

2 8 5 nights min

  • 2 bedrooms
  • Sleeps 8
  • 5 nights min
  • Nearest beach 7 mi
  • Child friendly
  • Air conditioning
Welcome to "The Embassy Property." My place is close to the beach, restaurants and dining, family-friendly activities, great views, and nightlife. You’ll love my place because of the cosiness, the high ceilings, the location, and the views. My place is good for couples, …see more

from $70 / night

$490 / week

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from $70 / night

6

Vacation villa in Trelawny Parish

Trelawny Parish / Duncans

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
Je Suis Content Villa is one of only 5 Villas located on the cliffs of the beautiful Silvar Sands Estate and has pride of place of commanding the most picturesque view. As a matter of fact most pictures taken of the white sands stretch of Beach at Silver Sands are taken …see more

from $370 / night

$2,590 / week

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from $370 / night

(3) Very Good 

22

Villa accommodation in Trelawny Parish with swimming pool

Trelawny Parish / Falmouth

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Nearest beach 10 mi
  • Swimming pool
  • Child friendly
Our beautiful home sits on the hill with a panoramic view of the Caribbean Sea. In this exclusive location in Greenside, Trelawny, you can relax under a Mango tree in the front yard, or a breadfruit tree in the backyard, sipping your favourite drink. We keep the environ …see more

from $160 / night

$800 / week

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Responds fast!
avg. 27 minutes

from $160 / night

6

Vacation villa in Trelawny Parish

Trelawny Parish / Duncans

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Je Suis Content Villa is one of only 5 Villas located on the cliffs of the beautiful Silvar Sands Estate and has pride of place of commanding the most picturesque view. As a matter of fact most pictures taken of the white sands stretch of Beach at Silver Sands are taken …see more

from $320 / night

$2,240 / week

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from $320 / night

10

Vacation home in Trelawny Parish

Trelawny Parish / Falmouth

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Private garden
We have a stunning 2 double bedroom bungalow in a newly built gated complex in Falmouth 10 minutes from burwood beach our property has a big back yard for sunbathing and relaxing we have air conditioning units in rooms a fully fitted kitchen and living room with cable t …see more

from $112 / night

$770 - $1,162 / week

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Responds fast!
avg. 45 minutes

from $112 / night

7

Vacation home rental

Trelawny Parish / Falmouth

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Air conditioning
Florence Hall, Falmouth, Trelawny, Jamaica. 1 BR/1 BA available for rent. Located in a gated community with security. 10 minutes to Burrwood Beach. Furnished house with kitchen, dinning room that seats 6, living room, enclosed sunroom/veranda. AC, ceiling fan, intern …see more

from $65 / night

$425 / week

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from $65 / night

(1) Excellent 

6

Duncans Vacation villa rental

Trelawny Parish / Duncans

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Je Suis Content Villa is one of only 5 Villas located on the cliffs of the beautiful Silvar Sands Estate and has pride of place of commanding the most picturesque view. As a matter of fact most pictures taken of the white sands stretch of Beach at Silver Sands are taken …see more

from $470 / night

$3,290 / week

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from $470 / night

21

Trelawny Parish Vacation home rental

Trelawny Parish / Falmouth

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Private garden
Humble Abode is an entire home away from home offering modern spacious facilities. Located in Stonebrook Estate in a secure, small, quiet gated community close to Falmouth Town. There are 3 good size bedrooms. Master bedroom has ensuite jacuzzi bath and air conditioni …see more

from $77 / night

$525 / week

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from $77 / night

29

Vacation villa in Trelawny Parish

Trelawny Parish / Silver Sands

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Dreamin Villa is 75 yards from the Warm clean clear Caribbean Sea. Very comfortably furnished through out. Linens are 800 thread count. Bed rooms are air conditioned with efficient quiet units. Villa is staffed daily 9-5 we cook, clean and do all laundry. All linens an …see more

from $315 / night

$2,206 / week

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from $315 / night

(1) Very Good 

17

Falmouth Vacation villa rental

Trelawny Parish / Falmouth

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Nearest beach 10 mi
  • Swimming pool
  • Child friendly
Does relaxing on the veranda overlooking the caribbean sea sounds great. At the picturesque hillside location in Greenside, Trelawny, you could be sitting on a pool-deck watching the beautiful cruise liners roll into the Falmouth shipping pier. Or, just relax under a ma …see more

from $100 / night

$250 / week

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Responds fast!
avg. 27 minutes

from $100 / night

11

Vacation home in Trelawny Parish

Trelawny Parish / Falmouth

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly
Buzzo's Guest House By the Sea is located on the worlds Famous Glistening Waters Bay in Trelawny. It is located 22 Miles outside of Montego Bay In a little fishing Village called Rock Districk. We offer tours on the lagoon and drop line fishing also come down and have f …see more

from $180 / night

$1,260 / week

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from $180 / night

20

Vacation villa in Trelawny Parish

Trelawny Parish / Silver Sands

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
Oh Boy Villa is a 4-bedroom, 3-bath private villa tucked away in Silver Sands, a private gated villa community built along one of Jamaica's most pristine white sand beaches. While only 45 minutes away from Montego Bay Airport, Oh Boy could not feel further away from the …see more

from $328 / night

$2,296 / week

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from $328 / night

18

Vacation villa with swimming pool in Silver Sands

Trelawny Parish / Silver Sands

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This magnificent 5 bedroom/5bathroom villa commands a spectacular view of the Caribbean sea. Three minutes walk to the lovely silver sand beach. The villa is characterized by large rooms en-suites, soaring ceilings and rich oriental furnishings four of the bedrooms are …see more

from $240 / night

$1,680 - $2,030 / week

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from $240 / night

(13) Excellent 

Certificate of Excellence

39

Falmouth Vacation home rental

Trelawny Parish / Falmouth

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 2 mi
  • Child friendly
  • Air conditioning
The property is situated in a lovely gated community with 24 hr. security in the historic town of Falmouth. Falmouth Oasis is the perfect home away from home while vacationing in Jamaica. This guest house sits elevated above the Trelawny Multi-Purpose Stadium and boa …see more

Certificate of Excellence

from $51 / night

$352 - $462 / week

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Responds fast!
avg. 1 hour 4 minutes

from $51 / night

(2) Excellent 

19

Vacation home in Falmouth

Trelawny Parish / Falmouth

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Air conditioning
New Fully furnished lovely island get away In Falmouth ,Trelawney.Two Bedrooms, 2Bathrooms Vacation Home located just off the highway in Coral Spring Village a Gated Community . Refrigerator, gas stove, microwave, coffee maker. Cable TV. laundry and more. This comfo …see more

from $65 / night

$455 / week

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Responds fast!
avg. 35 minutes

from $65 / night

(5) Excellent 

16

Vacation apartment in Trelawny Parish

Trelawny Parish / Falmouth

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Nearest beach 3 mi
  • Child friendly
  • Car not necessary
Relax and enjoy the awesome view of the Caribbean Sea from the veranda. Watch the cruise ships come in a go out again. We are minutes away from historic Falmouth, Burwood Beach and the luminous Lagoon Only 30 minutes from Montego Bay airport. Feel safe and secure o …see more

from $25 / night

$150 - $410 / week

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from $25 / night

(6) Very Good 

Certificate of Excellence

25

Vacation villa in Trelawny Parish

Trelawny Parish / Falmouth

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 6 mi
  • Child friendly
A newly built 2 Bedroom bungalow is in the exclusive gated-community of Stonebrook Vista - New Falmouth. This property provides an opportunity to experience the 'Real Jamaica' in a friendly community. It is fitted with a variety of modern appliances and Wifi access for …see more

Certificate of Excellence

from $49 / night

$294 / week

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Responds fast!
avg. 2 hours 43 minutes

from $49 / night

(4) Excellent 

12

Vacation home with swimming pool in Trelawny Parish

Trelawny Parish / Silver Sands

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
Mai Tai is one of the newest villas in the Silver Sands resort. This beautiful and spacious 4 bedroom, 4 bathroom home sits on a prime waterfront location with a small beach and is just a few hundred yards from the main Silver Sands, on Jamaica's fabulous North Coast. E …see more

from $686 / night

$4,800 - $6,400 / week

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from $686 / night

(2) Excellent 

24

Falmouth Vacation bungalow rental

Trelawny Parish / Falmouth

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 6 mi
  • Child friendly
  • Air conditioning
This newly re-furnished, two-bedroom bungalow is in the exclusive gated-community of Stonebrook Vista - New Falmouth. The property provides an opportunity to experience the authentic Jamaica' in a friendly community. It is fitted with a variety of modern appliances and …see more

from $49 / night

$322 / week

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Responds fast!
avg. 2 hours 43 minutes

from $49 / night

(1) Good 

16

Vacation apartment rental

Trelawny Parish / Duncans

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 0.1 mi
  • Swimming pool
  • Child friendly
A 2 minute walk from approximately 2 miles long sandy natural beach of Duncans Bay. A few minutes along the beach, Jacob Taylor Beach, with restaurants, bars, fishing boats, woodcarvers and even a small music studio. Built 2016 and opened in January 2017 Beautiful roo …see more

from $75 / night

$450 / week

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from $75 / night

(3) Excellent 

29

Vacation apartment in Duncans

Trelawny Parish / Duncans

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Luxury bedroom apartment can sleep up to 6 persons. Self contained and fully equipped. Two double bedroom with ensuite. Master bedroom with Queen size bed with balcony and A/C. Second bedroom as double bed and single bed ensuite ,A/C and outside balcony Large open p …see more

from $150 / night

$1,050 - $1,330 / week

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from $150 / night

20

Home rental in Silver Sands with shared pool

Trelawny Parish / Silver Sands

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Pineapple Villa is located in the private beach community of Silver Sands approximately 45 minutes from Montego Bay, Pineapple Villas consist of two villas that may be rented together or separately. The houses are situated to provide the convenience of accommodating lar …see more

from $929 / night

$6,500 - $8,000 / week

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from $929 / night

11

Trelawny Parish Vacation villa rental

Trelawny Parish / Duncans

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Sleeps 1-8 Situated on the beautiful property of Silver Sands, Mai Tai Villa is the perfect destination for a vacation. Mai Tai Villa provides a perfect view of the Caribbean Sea and first class, experienced staff who will take care of all you needs. This newly …see more

from $629 / night

$4,399 - $5,999 / week

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from $629 / night

(3) Excellent 

18

Vacation home in Falmouth

Trelawny Parish / Falmouth

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Our home provides all the conveniences of home while being in a desirable location on the North Coast of Jamaica Home is located in a gated community with access to all amenities in the neighborhood including the park, walking and bicycle trails. Local agent will b …see more

from $50 / night

$320 - $600 / week

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from $50 / night

(13) Excellent 

Certificate of Excellence

43

Trelawny Parish Vacation home rental

Trelawny Parish / Falmouth

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 6 mi
  • Suitable for children age 5+
A gated tranquil community with 24 hrs security. Adjacent mountainside encourages a relaxing ambiance, a true getaway, safe & secure. Fully furnished, fully A/C, ceiling fans, fully grilled, insect screen affixed to all external windows and doors, cable, internet (Netfl …see more

Certificate of Excellence

from $55 / night

$350 - $455 / week

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Responds fast!
avg. 1 hour 30 minutes

from $55 / night

11

Vacation home in Trelawny Parish

Trelawny Parish / Falmouth

9 16 1 night min

  • 9 bedrooms
  • Sleeps 16
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden
This beautiful 8 Bedroom suite at Paul's home away from home is located in Green Park,Trelawny Jamaica. It comes with 5 bathrooms, 2 full kitchens, 2 living and dining room area, private balcony,secure parking. The beach is 10 mins away and night life is 5 mins away. W …see more

from $275 / night

$1,925 / week

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from $275 / night

(16) Excellent 

19

Trelawny Parish Vacation villa rental

Trelawny Parish / Silver Sands

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Charming 3-bedroom villa located in the gated community of Silver Sands. Enjoy a 180° view of the ocean from a spacious pool deck or take a 5 minute trek to the beautiful white sand beach. Feel the cool tropical breeze while sitting under the gazebo. Villa sleeps 6. …see more

from $325 / night

$2,800 / week

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Responds fast!
avg. 1 hour 6 minutes

from $325 / night

12

Vacation home in Trelawny Parish

Trelawny Parish / Falmouth

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Nearest beach 7 mi
  • Child friendly
  • Air conditioning
Located in the home of olympic medalist Usain Bolt, this stay located in the safe gated community of Florence Hall Village is your home away from home. This new house boasts a comfortable living space, with 2 bedroom suites, plenty of fenced outdoor space, and all the a …see more

from $80 / night

$560 / week

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from $80 / night

(2) Excellent 

34

Trelawny Parish Vacation home rental

Trelawny Parish / Falmouth

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Relax, put your feet up and enjoy this 2 bed, 2 bathroom family owned property on the North Coast of Jamaica. Situated 25 minutes from Montego Bay Airport and 45 Minutes to the famous Ocho Rios treasures. Located outside Falmouth off the highway 2000 near to the home …see more

from $75 / night

$455 / week

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from $75 / night

15

Apartment rental in Trelawny Parish

Trelawny Parish / Falmouth

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Nearest beach 3 mi
  • Child friendly
  • Car not necessary
Tallest Pier View Villas is located in a secure gated community with 24 hour security guard service in Stonebrook Vista. The veranda overlooks the Caribbean Sea, the mountains and the Community. There is a playground nearby and it is close to public transportation. We …see more

from $30 / night

$200 - $410 / week

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from $30 / night

(5) Excellent 

44

Duncans Vacation villa rental

Trelawny Parish / Duncans

5 8 Min stay varies

  • 5 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
Sleeps 1-10 (8 adults, 2 children in child's room off of Master Bedroom) VILLA KELSO is conveniently located in the town of Duncans only moments from Silver Sands Beach (guests have full access to the beach and bar/restaurant) and within a short drive to Glistening Wat …see more

from $400 / night

$2,800 - $7,000 / week

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from $400 / night

(2) Excellent 

69

Vacation villa in Falmouth

Trelawny Parish / Falmouth

7 14 2 nights min

  • 7 bedrooms
  • Sleeps 14
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
7BR/7BA, 9000 square feet with air conditioning and a pool! Flamingo Beach Guest house, a 7 bedroom home that accommodates 14 guests, is located 20 minutes from the Montego Bay airport. This beautiful 2 storey house is located in a quite Trelawny community. The roof pr …see more

from $400 / night

$3,000 / week

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from $400 / night

(4) Excellent 

Certificate of Excellence

32

Vacation home in Trelawny Parish

Trelawny Parish / Falmouth

2 7 3 nights min

  • 2 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 5 mi
  • Child friendly
  • Air conditioning
This is a family owned property in the parish of Trelawny, Jamaica. It is conveniently located just off the main North Coast Highway at Falmouth, approximately 25 minutes from Montego Bay & 40 minutes from Ochos Rios. The property itself is within a quiet Cul-de …see more

Certificate of Excellence

from $91 / night

$504 - $1,288 / week

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Responds fast!
avg. 2 hours 28 minutes

from $91 / night

21

Home accommodation in Trelawny Parish

Trelawny Parish / Duncans

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 1 mi
  • Child friendly
  • Air conditioning
Luke's Paradise is located in a gated community in Coral spring village 10 minutes from the historic town of Falmouth, 30 minutes from Sangsters Airport, minutes away from the beach, Chukka adventures , rafting on the Martha Brae , Fisherman' …see more

from $66 / night

$461 / week

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from $66 / night

(9) Excellent 

29

Vacation home in Trelawny Parish

Trelawny Parish / Silver Sands

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Sleeps 1-8 w/ 2 daybeds for 2 more children (10 guests in total) + Crib upon request EbbTide is a spacious and comfortable holiday beach villa surrounded by manicured gardens and ideally located on the beach at Silver Sands, Jamaica. EbbTide is a charming home away …see more

from $290 / night

$2,030 - $3,815 / week

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from $290 / night

(6) Excellent 

Certificate of Excellence

26

Vacation home in Trelawny Parish

Trelawny Parish / Falmouth

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 6 mi
  • Child friendly
  • Air conditioning
This is a seaside theme house. It can easily hold a family of 6. We offer a fully furnished home with A/C in each room, a functional kitchen, a dinning area that seats 6. It is located in a gated community with security. We are approximately 3 minutes from Burrwo …see more

Certificate of Excellence

from $45 / night

$630 - $1,890 / week

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from $45 / night