50 Best Vacation Rentals in Discovery Bay - Holiday Lettings - Cabins

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111 Vacation rentals

(1) Excellent 

26

Vacation villa accommodation

Saint Ann Parish / Discovery Bay

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Welcome to Fortlands Point on the Beach, one of the world's most exquisite and luxurious 7 bedroom beachfront mansions located on a private promontory with its own private beach, swimming pool extensive gardens. Set amongst stunning landscaped gardens with tropical flow …see more

from $2571 / night

$18000 - $31000 / week

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from $2571 / night

(2) Excellent 

26

Vacation villa rental

Saint Ann Parish / Discovery Bay

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
Welcome to villa Sea Grapes on the Beach, a wonderful 5 bedroom beach front villa on its own sugary white sandy beach lapped by the clear turquoise waters of Discovery Bay. The calm turquoise waters here are excellent for swimming and kayaking. There is complimen …see more

from $1086 / night

$7600 - $18000 / week

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from $1086 / night

(2) Excellent 

24

Vacation home rental

Saint Ann Parish / Discovery Bay

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Welcome to Noble House on the Beach, a luxurious 5 bedroom private beach front villa located in the beautiful Montego Bay. Noble House is perched on one of the most coveted sites on Jamaica's lush north coast. This iconic villa is a unique, sprawling 15,000-square-foot …see more

from $1314 / night

$9200 - $19900 / week

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from $1314 / night

(1) Excellent 

19

Apartment rental in Discovery Bay

Saint Ann Parish / Discovery Bay

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
The Apartment is located 1.6 Km from the town centre & beaches,Its 4 Min's drive & about 20min's walk. Discovery Bay is just 30min's to the larger resort of Ocho Rios & 45 min's to Montego Bay,& 2hours to Negril The apartment as easy access to all amenities, Supe …see more

from $117 / night

$819 / week

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from $117 / night

12

Discovery Bay Vacation apartment rental

Saint Ann Parish / Discovery Bay

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Private garden
A really nice 3 bedroom apartment, located on the north coast of Jamaica, with a lovely garden, Located 1.6 km from town centre and the local beach. 20min walk, 4 min drive, The apartment has easy access to all amenities supermarkets, cam bio, Doctors, Pharmacy, Post o …see more

from $117 / night

$819 / week

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from $117 / night

18

Vacation villa with swimming pool in Discovery Bay

Saint Ann Parish / Discovery Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This 3-bedroom casual cottage shares a delightful waterfront site with its sister property, Coral Cove Villa, on the clear waters of Discovery Bay. Linga-Awile sits on a lovely, long, large lawn. Beyond the lawn and swimming pool is its sugary white sand beach with two …see more

from $429 / night

$3000 - $5300 / week

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from $429 / night

21

Vacation villa with swimming pool in Discovery Bay

Saint Ann Parish / Discovery Bay

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
On its own sugary white sand beach lapped by the clear turquoise waters of Discovery Bay sits the charming home Sea Grapes. The translucent azure waters here are excellent for swimming and kayaking. Surrounding the swimming pool is a spacious grassy lawn, wonderful for …see more

from $1086 / night

$7600 - $18000 / week

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from $1086 / night

14

Vacation villa with swimming pool in Discovery Bay

Saint Ann Parish / Discovery Bay

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Located on a private waterfront acre, Sea Haven is a traditional West Indian cottage dressed in charming periwinkle blue. It sits directly on the edge of beautiful Discovery Bay. * waterfront cottage on beautiful Discovery Bay * 12' floating raft just offs …see more

from $572 / night

$4000 - $8000 / week

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from $572 / night

(1) Excellent 

28

Vacation villa rental

Saint Ann Parish / Discovery Bay

9 18 Min stay varies

  • 9 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Sundown is an exquisite staffed home on a private white sand beach next to the turquoise waters of Discovery Bay. PREMIER 4-bedroom guest house * exquisite 9-bedroom villa on beautiful Discovery Bay * 125' private beach ... 17'x 28' pool with shower …see more

from $2929 / night

$20500 - $35500 / week

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from $2929 / night

(3) Excellent 

35

Villa rental in Discovery Bay

Saint Ann Parish / Discovery Bay

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Child friendly
Coral Cove Estate consists of Coral Cove Villa & Coral Cove Cottage; Descriptions of both properties are noted below. Coral Cove Villa is a delightful beach front property located in the exclusive Fortlands Road section of Discovery Bay. The newly renov …see more

from $842 / night

$5900 - $12900 / week

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from $842 / night

30

Discovery Bay Vacation villa rental

Saint Ann Parish / Discovery Bay

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
A recent renovation has created a second floor, fifth bedroom and updated interiors ~ all without compromising this villa's comfy put-your-feet-up signature. The feeling is an at-home, informal, relaxed lifestyle. * 5-bedroom newly-renovated 2-story villa * …see more

from $843 / night

$5900 - $12900 / week

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from $843 / night

21

Vacation villa rental

Saint Ann Parish / Discovery Bay

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
On its own sugary white sand beach lapped by the turquoise waters of Discovery Bay sits the exquisite home Sugar Bay. Interiors are distinguished by elegant custom-designed furniture, color-washed walls, gleaming breadnut floors, and fascinating objets d`art from around …see more

from $1935 / night

$13545 - $25500 / week

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from $1935 / night

(7) Excellent 

12

Villa rental in Discovery Bay

Saint Ann Parish / Discovery Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
Coral Cove Cottage is a wonderful property located in the exclusive Fortlands Road section of Discovery Bay. This 3 bedrooms cottage has living room (12 x 14), dining room (10 x 14), and an open, covered patio looking out to the bay. The Coral Cove interior is comfortab …see more

from $428 / night

$3000 - $5300 / week

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from $428 / night

(1) Excellent 

30

Discovery Bay Vacation villa rental

Saint Ann Parish / Discovery Bay

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Makana is one of the most glamorous private villas on the precious strip of land that borders Discovery Bay. The site itself is remarkable: a spacious villa with private tennis court and swimming pool on a sugary white sand beach bordering translucent swimming and kayak …see more

from $2358 / night

$16500 - $27000 / week

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from $2358 / night

(1) Excellent 

28

Vacation villa with shared pool in Discovery Bay

Saint Ann Parish / Discovery Bay

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Located on a private coral cove, this pretty yellow stone villa overlooks one of Jamaica's loveliest bodies of water ~ Discovery Bay. Additional amenities include: private chef, poolside shower, snorkel gear, linda smith premier rating, golf available, complimentary ca …see more

from $1929 / night

$13500 - $30000 / week

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from $1929 / night

13

Discovery Bay Vacation villa rental

Saint Ann Parish / Discovery Bay

7 14 4 nights min

  • 7 bedrooms
  • Sleeps 14
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
Located on beautiful Discovery Bay, Amanoka is one of the largest and most stunning villas in this collection. From the spacious veranda and pool, a barefoot stroll leads down a soft lawn to the 70' white sand beach, clear turquoise water and waterfront gazebo with susp …see more

from $4256 / night

$29792 / week

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from $4256 / night

27

Discovery Bay Vacation villa rental

Saint Ann Parish / Discovery Bay

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Located on beautiful Discovery Bay, Amanoka is one of the largest and most stunning villas in this collection. From the spacious verandah and pool, a barefoot stroll leads down a soft lawn to the 70’ white sand beach, clear turquoise water and waterfront gazebo with sus …see more

from $2829 / night

$19800 - $33000 / week

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from $2829 / night

26

Vacation villa with swimming pool in Discovery Bay

Saint Ann Parish / Discovery Bay

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Makana is one of the most glamorous private villas on the precious strip of land that borders Discovery Bay. The site itself is remarkable: a spacious villa with private tennis court and swimming pool on a sugary white sand beach bordering translucent swimming and kayak …see more

from $2358 / night

$16500 - $27000 / week

Inquire View

from $2358 / night

31

Vacation home with shared pool in Discovery Bay

Saint Ann Parish / Discovery Bay

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
One of the newest of the Discovery Bay luxury properties, Fortlands Point is located at the point of land at the entrance to the bay. The villa offers panoramic views of the Caribbean Sea and Discovery Bay from its expansive terraces and dramatic infinity pool area. The …see more

from $2571 / night

$18000 - $31000 / week

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from $2571 / night

18

Discovery Bay Vacation home rental

Saint Ann Parish / Discovery Bay

9 18 4 nights min

  • 9 bedrooms
  • Sleeps 18
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Sundown is an exquisite staffed home on a private white sand beach next to the turquoise waters of Discovery Bay. Interiors are beautifully decorated in rich fabrics on dark wicker and mahogany. Living and dining room floors are marble. Home-cooked meals are served i …see more

from $2643 / night

$18501 / week

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from $2643 / night

(2) Excellent 

40

Vacation villa with shared pool in Discovery Bay

Saint Ann Parish / Discovery Bay

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Located on beautiful Discovery Bay, Amanoka is one of the largest and most stunning villas in this collection. From the spacious verandah and pool, a barefoot stroll leads down a soft lawn to the 70’ white sand beach, clear turquoise water and waterfront gazebo with sus …see more

from $2829 / night

$19800 - $33000 / week

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from $2829 / night

(3) Excellent 

26

Discovery Bay Vacation villa rental

Saint Ann Parish / Discovery Bay

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Located on the beach of Discovery Bay, Coral Cove Villa is a five bedroom, two story villa with a comfy put-your-feet-up signature feeling that allows an at-home, informal, relaxed lifestyle. Additional amenities include: private chef, poolside shower, golf available, …see more

from $843 / night

$5900 - $12900 / week

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from $843 / night

(3) Very Good 

18

Discovery Bay Vacation villa rental

Saint Ann Parish / Discovery Bay

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This 3-bedroom casual cottage shares a delightful waterfront site with its sister property, Coral Cove Villa, on the clear waters of Discovery Bay. Linga-Awile sits on a lovely, long, large lawn. Beyond the lawn and swimming pool is its sugary white sand beach with two …see more

from $429 / night

$3000 - $5300 / week

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from $429 / night

21

Vacation home with shared pool in Discovery Bay

Saint Ann Parish / Discovery Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Pineapple Cottage or Pineapple Villa 2 is a two bedroom luxury villa Jamaica. Luxurious and very comfortable, the villa offers all the facilities needed to make a vacation memorable. This villa in Jamaica is only a short 3 minute walk to Silver Sand's white sandy beach. …see more

from $285 / night

$2000 - $3000 / week

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from $285 / night

33

Vacation villa with swimming pool in Discovery Bay

Saint Ann Parish / Discovery Bay

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
On a stunning promontory, once the site of an old stone fort, sits a remarkable new home named Fortlands Point. From its breathtaking location on the tip of the peninsula, the commanding view encompasses the turquoise water of Discovery Bay on one side and the deep blue …see more

from $2572 / night

$18000 - $31000 / week

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from $2572 / night

34

Vacation home with shared pool in Discovery Bay

Saint Ann Parish / Discovery Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Excellent for families, Seagrapes has everything to complete the experience for your family. Private beachfront villa with 5 airconditioned bedrooms. Seagrapes is a wonderful and charming, waterfront home which is located on the beautiful Discovery Bay. This absolute wa …see more

from $785 / night

$5500 - $18000 / week

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from $785 / night

22

Vacation home with swimming pool in Discovery Bay

Saint Ann Parish / Discovery Bay

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
Located on Bengal beach in Rio Bueno, approximately 50 minutes from Montego Bay, Sleepy Shallows is a spacious and playful family vacation home. Luxurious thunbergia, allamanda, plumbago, palms and various fruit and other trees adorn the gardens and welcome you to your …see more

from $737 / night

$5160 - $9000 / week

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from $737 / night

34

Discovery Bay Vacation villa rental

Saint Ann Parish / Discovery Bay

7 14 4 nights min

  • 7 bedrooms
  • Sleeps 14
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
From the homeowner who created the wonderful villa Keela Wee comes its new sister house, Whispering Waters. Located side by side, these neighboring villas combine to offer 13 bedrooms, two swimming pools, two private beaches, two air conditioned gyms and two tennis cour …see more

from $2500 / night

$17500 / week

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from $2500 / night

50

Villa rental in Discovery Bay

Saint Ann Parish / Discovery Bay

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Child friendly
A Summer Place is a lovely villa located on beautiful, private white sand beach cove in Discovery Bay. Recently renovated, the villa is the perfect setting for family reunions and larger groups. The design of A Summer Place is charming West Indian gingerbread complete w …see more

from $1714 / night

$12000 - $24500 / week

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from $1714 / night

(1) Excellent 

22

Vacation villa in Discovery Bay

Saint Ann Parish / Discovery Bay

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
Located on a private waterfront acre, Sea Haven is a traditional West Indian home dressed in charming periwinkle blue. It sits directly on the edge of beautiful Discovery Bay. The living room is sunshine yellow with a vaulted ceiling painted to match the sky. Antiques i …see more

from $571 / night

$4000 - $8000 / week

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from $571 / night

(9) Excellent 

17

Vacation villa in Discovery Bay

Saint Ann Parish / Discovery Bay

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Ask about pets
Located in Discovery Bay where Columbus is said to have first landed in Jamaica, Sea Haven offers entryway into this tropical paradise that so marveled its first explorers. The periwinkle blue exterior, sunshine yellow interior and barrel vaulted blue sky ceiling within …see more

from $571 / night

$3997 / week

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from $571 / night

(1) Excellent 

20

Discovery Bay Vacation villa rental

Saint Ann Parish / Discovery Bay

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
This three bedroom casual cottage shares a delightful waterfront site with its sister property, Coral Cove Villa, on the clear waters of Discovery Bay. Linga-Awile sits on a lovely, long, large lawn. Beyond the lawn and swimming pool is its sugary white sand beach with …see more

from $400 / night

$2800 / week

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from $400 / night

(1) Excellent 

10

Vacation villa in Discovery Bay

Saint Ann Parish / Discovery Bay

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Blissful baybiew is a well tucked away villa in the hills of Discovery bay. It is equipped with 2 bedrooms,2 private bathroom s and A modern kitchen,air condition and is 3 mins walk to the Puerto Seco beach,free WiFi, a pool,and a basket ball hoop. Blissful Bayview is …see more

from $135 / night

$700 / week

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from $135 / night

30

Vacation villa in Discovery Bay

Saint Ann Parish / Discovery Bay

6 12 4 nights min

  • 6 bedrooms
  • Sleeps 12
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Makana is one of the most glamorous private villas on the precious strip of land that borders Discovery Bay. The site itself is remarkable: a spacious villa with private tennis court and swimming pool on a sugary white sand beach bordering translucent swimming and kayak …see more

from $3857 / night

$26999 / week

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from $3857 / night

27

Vacation home with swimming pool in Discovery Bay

Saint Ann Parish / Discovery Bay

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
Idleawile is a family friendly ocean front villa located on Rio Bueno Harbor near Discovery Bay. The villa sits on a low ridge of coral giving stunning views out to the bay, ocean and of the setting sun. Idleawile is comfortably furnished for a relaxing Caribbean holida …see more

from $857 / night

$6000 - $8500 / week

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from $857 / night

(1) Excellent 

34

Vacation home with shared pool in Discovery Bay

Saint Ann Parish / Discovery Bay

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Excellent for families, Seagrapes has everything to complete the experience for your family. Private beachfront villa with 5 air conditioned bedrooms. Seagrapes is a wonderful and charming, waterfront home which is located on the beautiful Discovery Bay. This absolute w …see more

from $985 / night

$6900 - $18000 / week

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from $985 / night

29

Discovery Bay Vacation home rental

Saint Ann Parish / Discovery Bay

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
Keela Wee Villa, named after the beach paradise of the legendary "Phantom", is located on a private coral cove. The yellow stone villa overlooks the crystal clear Discovery Bay and Keela Wee's own private white sand beach. The villa interior consists of a lovely living …see more

from $1929 / night

$13500 - $30000 / week

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from $1929 / night

27

Vacation home with swimming pool in Discovery Bay

Saint Ann Parish / Discovery Bay

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
Sea Grapes is a charming and well appointed 3-bedroom beach villa with separate 3-bedroom cottage. The villa is located on a private white sand beach on exclusive Fortlands Road in Discovery Bay. The two-story entry leads into a living room with vaulted ceiling and s …see more

from $1086 / night

$7600 - $18000 / week

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from $1086 / night

19

Villa rental in Discovery Bay with swimming pool

Saint Ann Parish / Discovery Bay

5 10 5 nights min

  • 5 bedrooms
  • Sleeps 10
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets
Sugar Bay Villa is a Jamaican house with a colourful and interesting history. Sugar Bay has been a home since the early part of the 1800's to a family from Ireland who cam to Jamaica and developed the natural resources as well as farming the area in order to make a livi …see more

from $1935 / night

$13545 / week

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from $1935 / night

26

Vacation home rental

Saint Ann Parish / Discovery Bay

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
Sugar Bay is one of the jewels of Discovery Bay, a gorgeous 5-bedroom beach front villa designed and built by its present owners to capture the authentic style of a traditional Caribbean villa. Although built only in 1995, the quality of materials and workmanship recall …see more

from $1935 / night

$13545 - $25500 / week

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from $1935 / night

1