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70 Holiday homes in Jamaica

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Trelawny
55 properties
Ocho Rios
51 properties
Montego Bay
8 properties
Runaway Bay
8 properties
St Ann
8 properties
Negril
5 properties
Port Antonio
5 properties
Portland, Jamaica
4 properties
Kingston, Jamaica
3 properties
Boscobel
2 properties
Portmore
2 properties
Blue Mountains, Jamaica
1 properties
Cousins Cove
1 properties
Discovery Bay, Jamaica
1 properties
Red Hills
1 properties
Treasure Beach
1 properties
Whitehouse
1 properties

Filters applied: Private pool (70)

70 Results  |  
23 Photos

Villa | 2 Bedrooms | sleeps 4

5 Nights min stay

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from £288 /night

£2013 - £2434 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
Eirie Blue is a spacious luxury 4 bedroom villa with a private pool and hot tub on the sea front at Silver Sands, less than twenty yards from the turquoise waters of the Caribbean Sea. Eirie Blue is the villa that has location, location, location!  …see more

19 Photos

Villa | 4 Bedrooms | sleeps 8

4 Nights min stay

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from £387 /night

£2705 - £3007 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
Rock Hill is a large, luxurious five bedroom villa sprawling across two building lots on the highest point of Silver Sands, yet only a five minute walk to the Silver Sands beach. Tastefully set into the hill, the villa offers total privacy and panoramic sea views.  …see more

24 Photos

Cottage | 2 Bedrooms | sleeps 8

4 Nights min stay

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from £309 /night

£2163 - £2705 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
Summertime Villa is a beautiful 4 bedroom vacation rental with private pool and sea view. Located just a two minute walk to the private white sand beach in the gated community, Silver Sands Jamaica. Included, a talented cook and housekeeper.  …see more

23 Photos

Villa | 5 Bedrooms | sleeps 14

5 Nights min stay

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from £473 /night

£3308 - £5778 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Endless Summer Villa is a luxurious 7 bedroom villa (rent from 4 to 7 bedrooms) on the beach with solar heated swimming pool and hot tub. Enjoy panoramic views of the Caribbean Sea. Perfect for families or groups. Comes with two shifts of staff.  …see more

17 Photos

Villa | 3 Bedrooms | sleeps 6

Short stays welcome

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from £250 /night

£1747 - £2049 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
  • Private garden
Just minutes from the glorious Silver Sands Beach, the magnificent 4 bedroom Honeycomb Villa is an ideal family retreat. The swimming pool and deck to the front of the villa provide a wonderful area for relaxation while admiring the breathtakingly beautiful sea views.  …see more

23 Photos

Villa | 3 Bedrooms | sleeps 6

5 Nights min stay

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from £430 /night

£3007 - £3609 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Moonshine Villa is a three bedroom, three and a half bathroom vacation villa with private infinity pool situated in the gated community of Silver Sands on the North Coast of Jamaica. Moonshine Villa offers a beautiful panoramic view of the Caribbean Sea.  …see more

18 Photos

Villa | 4 Bedrooms | sleeps 10

5 Nights min stay

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from £302 /night

£2109 - £2711 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Primrose Path (a way of life of worldly ease & pleasure) is a very luxurious and spacious 4 bedroom villa, which sleeps 10 persons. Sporting a private swimming pool, spa and lovely sea views. dine outside on a starlit evening with your family and friends.  …see more

21 Photos

House | 3 Bedrooms | sleeps 6

3 Nights min stay

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from £190 /night

£1326 - £1868 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
The Orchid House is a creatively designed 3 bedroom, 3 bathroom villa, featuring an enclosed courtyard with a private pool and dining gazebo. The Orchid House was specially designed to enhance the joy of outdoor living while retaining privacy.  …see more

17 Photos

Villa | 5 Bedrooms | sleeps 10

Excellent 5/5 

5 Nights min stay

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from £278 /night

£1940 - £3037 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
This beautiful villa has 5 large en-suite bedrooms and huge open-plan living space. It is perched on a cliff in three acres of lush tropical gardens, with a perfect 180 degree view of the Caribbean Sea. Private gardens, coral reef, swimming pool, tennis course, daily maid and chef available.  …see more

20 Photos

Villa | 4 Bedrooms | sleeps 10

2 Nights min stay

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from £365 /night

£2555 - £3193 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Set in a natural valley surrounded by mountains, a river and activities including hiking, biking and adventure and historic tours. This artistic, historic and peaceful villa has a pool and a private beach nearby, Delicious food, wonderful service with staff. Treehouse is a unique villa on the magical Good Hope Plantation in Trelawny, 40 minutes form MBJ airport  …see more

20 Photos

Villa | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £1033 /night

£7229 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
Four Winds is a 5 bedroom villa located on beautiful acres of private gardens.  …see more

20 Photos

Villa | 9 Bedrooms | sleeps 18

5 Nights min stay

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from £1377 /night

£9639 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
Golden Clouds is located in the banana port village of Oracabessa, 15 minute drive from Ocho Rios. This villa overlooks its own palm fringed beach and the Caribbean sea.  …see more

20 Photos

Villa | 5 Bedrooms | sleeps 10

Min stay varies

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from £2290 /night

£16025 - £33735 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Air conditioning
  • No pets allowed
Thee Divine Villa Roaring Pavilion is a one of a kind property which has a reputation as the Caribbean's most celebrated estate home. It is the flagship property of Thee Divine Villa, the world's most cutting edge luxury villa management company.  …see more

20 Photos

Villa | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £818 /night

£5723 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
Mount Pleasant is nestled in the hills above Runaway Bay, on 88 acres. Enter through the gates up a long driveway to the villa that parts of the original house date back as far as the 1880's. In the foyer, the walls depict hand-painted tropical foliage. To the right is a powder room, the left is the dining room which features a beautiful table true to the Jamaican style. The dining room leads to a breakfast nook which in turn leads to the kitchen. In the kitchen their is a large fireplace, original to the house made of local cut stone. This villa features an organic garden which helps you to have the freshest of meals during your stay.  …see more

19 Photos

Villa | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £775 /night

£5422 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Emerald Seas is set in a hillside on over 2 acres of tropical grounds near the sea. The villa is near hotels on the main North Coast Road. Next door is the Sans Souci Hotel and Spa where guests can purchase day or evening passes for water sports, sauna, entertainment or use of their restaurants (no children under 16 permitted).  …see more

20 Photos

Villa | 6 Bedrooms | sleeps 12

5 Nights min stay

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from £1420 /night

£9940 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
Located on a wide, sandy beach, Sweet Spot is like a pretty jewel box next to the sea. Its remarkable location is the best of all worlds: a 6,000 sq.ft. private home with a huge lawn and beach, just yards from the Breezes Golf Pro Shop which offers unlimited complimentary green fees to Sweet Spot guests.  …see more

20 Photos

Villa | 10 Bedrooms | sleeps 20

5 Nights min stay

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from £1507 /night

£10543 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Kai Kala is consists of 4 buildings, giving 10 bedrooms sitting on 2½ acres of fruit trees and flowers on a cliff that overlooks the sea. Hideaway Cottage has 1 bedroom and is located right on the cliff’s edge looking down onto the wooden deck entryway into the sea.  …see more

18 Photos

Villa | 5 Bedrooms | sleeps 10

5 Nights min stay

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from £692 /night

£4841 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Scotch On The Rocks (a.k.a. Scotchie) on the coast overlooking Sandy Bay in Ocho Rios. Scotchie is a short walk away from the Royal Plantation where guests may use the resort's beach for $20 per person per day and tennis for $10 per hour. Also guests can use the resort's gym, sauna, steam room and spa for a fee.  …see more

20 Photos

Villa | 6 Bedrooms | sleeps 12

5 Nights min stay

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from £1377 /night

£9639 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
Malatai is a 6 bedroom villa located in Ocho Rios. This villa features an air conditioned family room / office equipped with everything you need to keep you entertained for a day indoors including television, internet, board games and music.  …see more

20 Photos

Villa | 7 Bedrooms | sleeps 14

5 Nights min stay

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from £1291 /night

£9037 / week

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Key info:

  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • No pets allowed
Villa Paradiso sits on a 150 feet white sand beach in Mammee Bay Estates and is surrounded by over an acre of tropical gardens. It is comprised of a 5 bedroom main house and a 2 bedroom cottage. When you enter the villa, the foyer leads into theliving room which has french doors that showcase beautiful ocean views and open on to the covered verandah. Off of the living room is an informal dining room. The first floor vereandah fronts the pool, features and outdoor dining area and has views of the sea and beach. Upstairs their is a family room that overlook the main floor. There is also a fitness room and games room.  …see more

With its own unique historical mix, Jamaica is a unique experience from the beaches of Negril to bustling Montego Bay, the people are warm and friendly and Jamaican music is famous the world over. With both the rich mixture of Kingston and idyllic resorts such Runaway Bay, Port Antonio and Discovery Bay, Jamaica has something for everyone.