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

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87 Vacation rentals

(3) 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

(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

(4) 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

19

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, Po …see more

from $117 / night

$819 / week

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from $117 / night

6

Vacation villa in Discovery Bay

Saint Ann Parish / Discovery Bay

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Even on vacation we all long for comfort, a home, away from home, with a bit of luxury. Well this residence is definitely the place to spend your vacation. It is a 8 bedroom unit Located on the beautiful island of Jamaica, on Discovery Bay harbor, 45mins from Sangsters …see more

from $80 / night

$400 - $680 / week

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from $80 / night

5

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 $1571 / night

$11000 - $24500 / week

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from $1571 / 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

38

Discovery Bay Vacation villa rental

Saint Ann Parish / Discovery Bay

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Child friendly
Located on the Discovery Bay, sits this magnificent 7 bedroom home-the ultimate in comfort and luxury. Set on its own large and completely private white sand beach cove, Whispering Waters is an elegant, 12000 square foot, two story home with seven air-conditioned bedroo …see more

from $2214 / night

$15500 - $36000 / week

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from $2214 / night

(2) Excellent 

33

Vacation home with swimming pool in Discovery Bay

Saint Ann Parish / Discovery Bay

5 18 Min stay varies

  • 5 bedrooms
  • Sleeps 18
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
Sundown Villa epitomizes what an exquisite, vacation villa should be. This beautiful, totally renovated in 2012, nine-bedroom villa nestled in the secluded Discovery Bay, on Jamaica's North Coast, is spread across 5.500 square feet of gorgeous, Caribbean-styled living. …see more

from $2929 / night

$20500 - $35500 / week

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from $2929 / 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

31

Discovery Bay Vacation villa rental

Saint Ann Parish / Discovery Bay

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Child friendly
Makana is a deluxe beachfront villa located on the white sands of beautiful Discovery Bay. It offers a gorgeous setting and private pool, private tennis court and full staff. Built on two levels, the interiors are both stylish and comfortable. An expansive living room a …see more

from $2071 / night

$14501 - $27000 / week

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from $2071 / night

(2) Excellent 

28

Villa rental in Discovery Bay

Saint Ann Parish / Discovery Bay

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
  • Ask about pets
Keela Wee is a majestic villa that sits proudly atop its own cozy coral cove. Whether you are swimming in the crystal clear swimming pool, soaking in the bubbling Jacuzzi or frolicking in the turquoise sea, you may, from time to time, recall the rich history of this are …see more

from $1928 / night

$13496 / week

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avg. 19 minutes

from $1928 / night

21

Vacation home with swimming pool, tennis court 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
A Summer Place is a beautiful 7 bedroom villa located on sparkling Discovery Bay. The villa has its own private white sand beach, swimming pool and tennis court and is perfect for family reunions and larger groups. The villa interiors are decorated in Caribbean fabrics …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 $428 / night

$3000 - $8000 / week

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avg. 3 minutes

from $428 / night

15

Vacation villa in Discovery Bay

Saint Ann Parish / Discovery Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Ask about pets
Amanoka is a lush villa in Jamaica inspired by East Asian splendor. The property was named after the Indonesian word for “peaceful home.” Many of the lush wooden features throughout the villa were indeed imported from Bali. Close to the outdoor museum Columbus Park that …see more

from $2514 / night

$17598 / week

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Responds fast!
avg. 19 minutes

from $2514 / night

22

Vacation villa 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
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 $1350 / night

$9450 - $25500 / week

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from $1350 / night

(2) Very Good 

19

Vacation home rental

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
Sun Kissed Villa is a beautiful new 4 bedroom, 4 ½ bathroom, beachfront villa completed in the spring of 2014. Situated on Bengal Beach, just east of the small town of Rio Bueno and west of Discovery Bay, Sun Kissed offers guests the benefits of a lovely house and setti …see more

from $714 / night

$5000 - $9500 / week

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from $714 / 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

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

(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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avg. 19 minutes

from $571 / night

(1) Excellent 

32

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 $2072 / night

$14501 - $27000 / week

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from $2072 / 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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avg. 3 hours 42 minutes

from $135 / night

21

Vacation villa in Discovery Bay

Saint Ann Parish / Discovery Bay

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Ask about pets
Located in Discovery Bay, where Columbus is first said to have landed in Jamaica, Sea Grapes is a comfortable and unpretentious villa that accommodates up to twelve guests. The pool area leads directly to the clear Caribbean Sea via a quaint wooden dock. Close to the hi …see more

from $865 / night

$6049 / week

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avg. 19 minutes

from $865 / night

21

Vacation villa in Discovery Bay

Saint Ann Parish / Discovery Bay

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Ask about children
  • Ask about pets
Located in Discovery Bay, where Columbus is first said to have landed in Jamaica, Sea Grapes is a comfortable and unpretentious villa that accommodates up to twelve guests. The pool area leads directly to the clear Caribbean Sea via a quaint wooden dock. Close to the hi …see more

from $1194 / night

$8358 / week

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Responds fast!
avg. 19 minutes

from $1194 / night

(1) Excellent 

13

Vacation home rental

Saint Ann Parish / Discovery Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
Linga-Awile at Coral Cove is located in the exclusive Fortlands Road section of Discovery Bay. This popular beach front cottage has 3 bedrooms, living room (12 x 14), dining room (10 x 14), and a lovely open, covered patio looking out to the bay. The cottage is comforta …see more

from $429 / night

$3000 - $5300 / week

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from $429 / night

(9) Excellent 

30

Villa rental in Discovery Bay

Saint Ann Parish / Discovery Bay

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Ask about children
  • Ask about pets
Your own brilliant piece of white sand beach awaits you at Whispering Waters. This villa is located along Discovery Bay, where it is generally believed that Columbus first arrived to Jamaica’s wondrous shores. During your stay at Whispering Waters, you will also experie …see more

from $2500 / night

$17500 / week

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Responds fast!
avg. 19 minutes

from $2500 / night

(2) Excellent 

20

Vacation home 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
Sugar Bay is one of the most elegant villas in Jamaica. Beachfront Luxury villa, Tennis court, sea kayaks, butler service. First class service! Sugar Bay Villa is a luxurious Jamaica villa with a very interesting and colorful history. The divine property has been a home …see more

from $1935 / night

$13545 - $25500 / week

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from $1935 / 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

28

Discovery Bay Vacation villa rental

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, A Summer Place has much to offer. Whether you are lounging in the stand-alone hammock, playing a set of night tennis or enjoying the hundred foot expanse of private white sand beach, you a …see more

from $1571 / night

$10997 / week

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avg. 19 minutes

from $1571 / night

17

Vacation villa in Discovery Bay

Saint Ann Parish / Discovery Bay

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Harmony lives here…the house keeps you in touch with the surrounding elements in such subtle ways that you wonder why you feel so good . A spacious verandah waits to accommodate your drifting moods and a large green cushion of a lawn extends down to your own private bea …see more

Pricing unknown

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Pricing unknown

34

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
From the homeowner who created the wonderful villa Keela Wee comes its new sister house, Whispering Waters. Located immediately next door to Keela Wee, this brand new villa offers seven bedrooms and en-suite bathrooms. Whispering Waters overlooks one of Jamaica’s loveli …see more

from $2215 / night

$15500 - $36000 / week

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from $2215 / 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

(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 $643 / night

$4500 - $12900 / week

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from $643 / 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 $1716 / night

$12000 - $30000 / week

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from $1716 / night

(2) Excellent 

25

Vacation villa in Discovery Bay

Saint Ann Parish / Discovery Bay

6 10 7 nights min

  • 6 bedrooms
  • Sleeps 10
  • 7 nights min
  • Child friendly
Set on its own private white sand beach on the shores of a perfect horseshoe bay, Sea Grapes is a standard but charming three-bedroom villa with a separate two-bedroom cottage offering a total of five bedrooms. In the main house are two bedrooms upstairs and one downsta …see more

from $885 / night

$6201 - $7600 / week

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avg. 3 minutes

from $885 / night

(3) Excellent 

37

Vacation villa rental

Saint Ann Parish / Discovery Bay

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Child friendly
Fortlands Point is a fabulous villa located at the lookout point where Discovery Bay meets the Caribbean Sea. Two old canons still remain on the shore of this property providing testimony to the role the land of this wonderful property once played in the defense of Jama …see more

from $2000 / night

$14000 - $31000 / week

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from $2000 / night

21

Vacation villa in Discovery Bay

Saint Ann Parish / Discovery Bay

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
  • Ask about pets
Located in Discovery Bay, where Columbus is first said to have landed in Jamaica, Sea Grapes is a comfortable and unpretentious villa that accommodates up to twelve guests. The pool area leads directly to the clear Caribbean Sea via a quaint wooden dock. Close to the hi …see more

from $1084 / night

$7588 / week

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Responds fast!
avg. 19 minutes

from $1084 / night

(7) Excellent 

10

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 

0

Villa rental in Discovery Bay

Saint Ann Parish / Discovery Bay

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
  • Ask about pets
Located in the historic Discovery Bay where Columbus is said to have first landed on the sunny shores of Jamaica, Makana is a waterfront villa sure to impress. The private white sand beach, just steps from the main house, is only the beginning. Whether you are lounging …see more

from $2357 / night

$16499 / week

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Responds fast!
avg. 19 minutes

from $2357 / night

36

Vacation villa with swimming pool in Discovery Bay

Saint Ann Parish / Discovery Bay

7 14 5 nights min

  • 7 bedrooms
  • Sleeps 14
  • 5 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets
The seven bedroom villa rests on a private cove with pristine white sand beach in Discovery Bay, an exclusive resort area along Jamaica’s picturesque North Coast. At Amanoka the best of Caribbean beauty and hospitality abounds. Within the villa’s walled compound, colour …see more

from $2828 / night

$19800 / week

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from $2828 / night