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

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169 Vacation rentals

(1)  

9

Duncans Vacation cottage rental

Trelawny Parish / Duncans

4 10 1 night min

  • 4 bedrooms
  • Sleeps 10
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
This is a 4 bedroom-bedroom fully Furnished house offering spacious living for 10. Children are welcome.Each bedroom has a large double bed and own bathroom.with the master bedroom features a Jacuzzi tub and shower.Some of the bedrooms are air condition with all …see more

from $150 / night

$900 / week

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from $150 / night

18

Silver Sands Vacation guest house rental

Trelawny Parish / Silver Sands

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
3 bedroom guest house with en suite master bedroom; bedroom 1&2 share "walk in shower/wet room " with w/c and wash basin. There is a spacious, tastefully decorated and furnished living area which opens out into the dining room and fully fitted kitchen area. The beauti …see more

from $180 / night

$1260 / week

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Responds fast!
avg. 2 hours 27 minutes

from $180 / night

(2) Excellent 

18

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: The Yellow Canary Villa is a few steps to white sandy beach and is located half way between Montego Bay and Ochio Rios, off the north coast. The villa comes with our gourmet cook/housekeeper Joan and Sandra, Curtis gardener and Johnny our experienced driver. …see more

from $150 / night

$1050 / week

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Responds fast!
avg. 3 hours 23 minutes

from $150 / night

21

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 $65 / night

$455 / week

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from $65 / night

20

Vacation villa with swimming pool in Silver Sands

Trelawny Parish / Silver Sands

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning
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

$2275 / week

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Responds fast!
avg. 41 minutes

from $325 / 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 $104 / night

$715 - $1079 / week

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from $104 / 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

$2206 / week

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Responds fast!
avg. 2 hours 45 minutes

from $315 / night

14

Vacation villa with swimming pool in Silver Sands

Trelawny Parish / Silver Sands

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Sunset 1 is truly the hidden gem of the Silver sands community. This 3 bedroom, 3 bathroom vacation rental is less than a 2 minute stroll from the pristine beaches . Breezy living room, comfortable dinning. Let our onsite housekeeper and butler cater to your eve …see more

from $286 / night

$2700 / week

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from $286 / 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

53

Trelawny Parish Vacation home rental

Trelawny Parish / Falmouth

2 8 2 nights min

  • 2 bedrooms
  • Sleeps 8
  • 2 nights min
  • Nearest beach 7 mi
  • Child friendly
  • Air conditioning
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, solo adventurers, business travele …see more

from $50 / night

$350 / week

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from $50 / 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

$1260 / week

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from $180 / 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 

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 $46 / night

$299 - $475 / week

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Responds fast!
avg. 3 hours 30 minutes

from $46 / night

5

Vacation villa in Duncans

Trelawny Parish / Duncans

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Child friendly
Kelso is located within the private beach community of Silver Sands, which is approximately a 30-minute drive from Montego Bay. The home is located on a hillside and offers spectacular views of one of the most beautiful beaches on the entire island. Kelso is a beautiful …see more

from $500 / night

$3500 - $7000 / week

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from $500 / night

18

Vacation villa with swimming pool in Silver Sands

Trelawny Parish / Silver Sands

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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 $400 / night

$2800 - $5800 / week

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from $400 / night

29

Vacation home rental

Trelawny Parish / Silver Sands

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
3 modern bedrooms and 3 modern bathrooms! One of the largest pool entertaining areas in the whole of Silver Sands! Amazing!! Jacuzzi Tub Swim up pool bar with stools in the pool! Modern island in the pool with relaxing lounge chairs/ sofas - great for cocktails! Outdoor …see more

from $500 / night

$3500 - $5951 / week

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from $500 / night

(11) Excellent 

Certificate of Excellence

38

Falmouth Vacation home rental

Trelawny Parish / Falmouth

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Nearest beach 4 mi
  • Child friendly
  • Air conditioning
Situated in a lovely gated community with 24 hr. security in the historic town of Falmouth, Falmouth Oasis @ Stonebrook Vista is the perfect home away from home while vacationing in Jamaica. This guest house sits elevated above the Trelawny Multi-Purpose Stadium and b …see more

Certificate of Excellence

from $48 / night

$320 / week

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Responds fast!
avg. 1 hour 21 minutes

from $48 / night

30

Silver Sands Vacation home rental

Trelawny Parish / Silver Sands

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Butterfly Villa is a fabulous luxury villa in picturesque Silver Sands! Silver Sands is a beautiful jewel in Jamaica located approximately 60 minutes from the Montego Bay airport. It is this special community of wonderful villas that shares one of Jamaica's most beautif …see more

from $385 / night

$2700 - $3750 / week

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from $385 / night

54

Vacation home with shared pool in Trelawny Parish

Trelawny Parish / Duncans

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Kelso Villa reflects the grand era of Jamaican colonial charm. With that wonderful plantation feeling, this 4 bedrooms plus children's room, 5 bathroom has spectacular views and access to 3 white sandy beaches nearby! Kelso Villa has one of the most spectacular views of …see more

from $500 / night

$3500 - $7000 / week

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from $500 / night

(16) Excellent 

13

Trelawny Parish Vacation villa rental

Trelawny Parish / Silver Sands

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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

$2800 - $3220 / week

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Responds fast!
avg. 37 minutes

from $325 / night

54

Vacation home with shared pool in Trelawny Parish

Trelawny Parish / Duncans

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Kelso Villa reflects the grand era of Jamaican colonial charm. With that wonderful plantation feeling, this 4 bedrooms plus children's room, 5 bathroom has spectacular views and access to 3 white sandy beaches nearby! Kelso Villa has one of the most spectacular views of …see more

from $650 / night

$4550 - $7000 / week

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from $650 / night

(1) Good 

13

Vacation home in Trelawny Parish

Trelawny Parish / Falmouth

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Child friendly
This villa is located in the newly built gated community Coral Springs . This 2 bedroom 2 bathroom villa is a 3 min drive to the beautiful Burwood beach. 10 min from the historic Falmouth, 35 min from Montego Bay airport and 30 min to Ocho Rios . Services include- Air c …see more

from $90 / night

$800 / week

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from $90 / night

24

Home rental in Trelawny Parish with shared pool

Trelawny Parish / Silver Sands

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Je Suis Content Villa is a pleasant luxury villa Jamaica, offering three lovely bedrooms and four bathrooms, and magnificent views of Silver Sands Beach and the Northern Shore of Jamaica. This charming villa in Jamaica provides excellent views of the sparkling Caribbean …see more

from $400 / night

$2800 - $3750 / week

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from $400 / night

18

Silver Sands Vacation villa rental

Trelawny Parish / Silver Sands

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • 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 $472 / night

$3301 - $5800 / week

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from $472 / 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 $930 / night

$6500 - $8000 / week

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from $930 / night

39

Vacation home in Trelawny Parish

Trelawny Parish / Silver Sands

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
Mi Amor is a villa is family friendly and a short walk to the beach. With 5 bedrooms and 5 bathrooms, this Jamaican villa is great for family reunions and can sleep 10 persons comfortably.  Private swimming pool, fully staffed villa and only 35 minutes drive from the Mo …see more

from $459 / night

$3213 - $5033 / week

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from $459 / night

(5) Very Good 

25

Vacation villa in Trelawny Parish

Trelawny Parish / Falmouth

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • 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

from $46 / night

$273 - $475 / week

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Responds fast!
avg. 3 hours 42 minutes

from $46 / night

(4) Very Good 

29

Falmouth Vacation villa rental

Trelawny Parish / Falmouth

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This is a family owned property located in Falmouth, Trelawny, Jamaica. Situated in the birth place of the world's fastest man, Usain Bolt, and 22 minutes from Montego Bay International airport, the home is located in a special yet accessible part of the island. It feat …see more

from $120 / night

$1200 - $1480 / week

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Responds fast!
avg. 2 hours 17 minutes

from $120 / night

17

Silver Sands Vacation home rental

Trelawny Parish / Silver Sands

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Buena vista Villa in Silver Sands is a lovely 3 bedroom villa that has been refurbished to reflect the tropical caribbean decor.  This villa also has its own private swimming pool.  All rooms have ceiling fans and you will sleep comfortably with the air conditioned bedr …see more

from $240 / night

$1680 - $2450 / week

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from $240 / night

(1) Excellent 

39

Silver Sands Vacation home rental

Trelawny Parish / Silver Sands

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
Mi Amor is a villa is family friendly and a short walk to the beach. With 5 bedrooms and 5 bathrooms, this Jamaican villa is great for family reunions and can sleep 10 persons comfortably.  Private swimming pool, fully staffed villa and only 35 minutes drive from the Mo …see more

from $579 / night

$4053 - $5033 / week

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from $579 / night

9

Trelawny Parish Vacation home rental

Trelawny Parish / Silver Sands

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Pineapple Cottage is located in the private beach community of Silver Sands approximately 45 minutes from Montego Bay. This charming cottage has two air conditioned bedrooms each with with its own full bathroom. The cottage is next door to Pineapple Villa, just a short …see more

from $243 / night

$1700 - $2500 / week

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from $243 / night

43

Vacation home rental

Trelawny Parish / Silver Sands

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
Eirie Blue is a sea front cottage with 4 bedrooms, 4 bathrooms - Affordable vacation, yet one of the nicest villas in Silversands.  With your own private swimming pool and outdoor hot tub, this villa enjoys direct northern Caribbean seaviews.  For the main swimming beac …see more

from $605 / night

$4240 - $5540 / week

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from $605 / night

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
  • Swimming pool
  • Ask about children
  • Air conditioning
Windjammer is a very luxurious and spacious 4 bedroom, 4 bathroom home, located just a two minute walk from the sea at Silver Sands, on Jamaica's fabulous North Coast. This gorgeous villa has all the amenities you desire for that dream vacation. There is a large breezy …see more

from $457 / night

$3200 - $3900 / week

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from $457 / night

(2) Excellent 

32

Trelawny Parish Vacation b&b rental

Trelawny Parish / Falmouth

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Swimming pool
Cheap, Clean, Cousy, Friendly staff, Friendly Community and a home away from home. This humble abode is in the same district as Royalyon White Sands and Blue waters, Same District as Mangos Resorts and Blue Waters. Its in the tourism epicenter of Falmouth. You deserve t …see more

from $115 / night

$805 - $1225 / week

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Responds fast!
avg. 3 hours 48 minutes

from $115 / night

(8) Excellent 

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

from $49 / night

$340 - $410 / week

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Responds fast!
avg. 2 hours 8 minutes

from $49 / night

18

Trelawny Parish Vacation villa rental

Trelawny Parish / Silver Sands

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • 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 $600 / night

$4200 - $5800 / week

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from $600 / night

25

Vacation home in Trelawny Parish

Trelawny Parish / Silver Sands

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Air conditioning
2 bedrooms, recently refurbished villa, only a few minutes walk to the beach!!! The charming Dreamin Villa in Silver Sands Jamaica is a delightful two bedroom cottage located less than 100 yards from the pristine white-sand Silver Sands beach and the sparkling Caribbean …see more

from $245 / night

$1716 - $3431 / week

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from $245 / night

30

Vacation home with shared pool in Trelawny Parish

Trelawny Parish / Silver Sands

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Quadrille Villa is a fantastic luxury villa Jamaica situated within the private gated community of Silver Sands on Jamaica's northern shore. The Silver Sands Community is second home to several affluent and wealthy people of Jamaica and offers white sand beaches, sparkl …see more

from $685 / night

$4800 - $7600 / week

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from $685 / night

9

Vacation villa in Duncans

Trelawny Parish / Duncans

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Lovely Villa located in Silver Sands, Trelawny, Jamaica, just a 45 minutes scenic drive from Montego Bay airport. Landfall Villa is well appointed with a commanding view of the Caribbean Sea. The villa is located within a gated community with 24 hr security. The beaut …see more

from $300 / night

$2100 / week

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Responds fast!
avg. 2 hours 0 minutes

from $300 / night

22

Trelawny Parish Vacation home rental

Trelawny Parish / Silver Sands

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Braata Villa in Silver Sands Jamaica is a 3 bedroom, 3 bathroom villa which is fully staffed.  With your own private swimming pool, ourdoor gazebo.  All bedrooms are air conditioned and has your own ensuite bathrooms. As you enter Braata Villa, you walk into a spacious …see more

from $235 / night

$1651 - $2200 / week

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from $235 / night