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

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629 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 $2,571 / night

$18,000 / week

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from $2,571 / night

(4) 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 $1,086 / night

$7,600 - $10,100 / week

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from $1,086 / night

(1) Excellent 

16

Apartment rental in Discovery Bay

Saint Ann Parish / Discovery Bay

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 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 $128 / night

$895 / week

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from $128 / night

(6) 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 $1,314 / night

$9,200 - $12,000 / week

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from $1,314 / night

15

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 $128 / night

$895 / week

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from $128 / 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. 1 hour 46 minutes

from $135 / night

(1) Excellent 

22

Vacation villa with shared 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 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. Antique …see more

from $571 / night

$4,000 - $8,000 / week

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from $571 / 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

$3,000 - $5,300 / week

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from $429 / night

33

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
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 $2,571 / night

$17,997 - $31,000 / week

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from $2,571 / night

30

Discovery Bay Vacation villa accommodation

Saint Ann Parish / Discovery Bay

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
A Secluded Villa situated on a 5 acres property with a breath taking view of the ocean and surrounding valleys. This private Retreat enjoys 24 hours of continuous sea breeze. Get wake up call from our domestic chickens in the morning. You could chose to take a dip in th …see more

from $200 / night

$1,400 / week

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from $200 / night

20

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
Sea Haven Villa is located on the beautiful and popular Discovery Bay between Montego Bay and Ocho Rios. This comfortable 4-bedroom waterfront villa has been completely renovated. The villa comes with a full staff to tend to your every need. Decorated in rich tropical f …see more

from $571 / night

$4,500 - $8,000 / week

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from $571 / night

(1) Excellent 

26

Home rental in Discovery Bay with swimming pool

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
Makana Villa , completed in December 2006, continues the tradition of Discovery Bay as having the finest collection of luxurious homes in Jamaica, and possibly the Caribbean. This beautiful 6-bedroom villa is designed to provide an unforgettable setting for a memorable …see more

from $2,543 / night

$17,800 - $29,000 / week

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from $2,543 / night

32

Vacation home with swimming 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
Whispering Waters Villa was completed in December 2006 and continues the tradition of Discovery Bay luxury. This super luxury 7 bedroom villa offers the finest in appointments; from the extensive use of tropical woods featuring bamboo ceilings, to the tasteful decor and …see more

from $2,500 / night

$17,500 - $36,000 / week

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from $2,500 / night

29

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 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 $2,500 / night

$17,500 - $36,000 / week

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from $2,500 / night

(3) Excellent 

37

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
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 $2,571 / night

$18,000 - $31,000 / week

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from $2,571 / night

21

Vacation villa with shared 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
Many comfortable moments will be spent here on the lovely wicker chaises, draped with flowering vines and overlooking the spectacular blue waters of the Caribbean Sea. Sea Haven is a private waterfront Jamaica villa located near Discovery Bay. Discovery Bay is magnific …see more

from $570 / night

$4,000 - $8,000 / week

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from $570 / night

(3) Excellent 

35

Villa rental in Discovery Bay with shared pool

Saint Ann Parish / Discovery Bay

8 10 Min stay varies

  • 8 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
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 $843 / night

$5,900 - $12,900 / week

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from $843 / night

(8) Excellent 

10

Villa rental in Discovery Bay with shared pool

Saint Ann Parish / Discovery Bay

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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 $429 / night

$3,000 - $5,300 / week

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from $429 / night

33

Villa rental in Discovery Bay with shared pool

Saint Ann Parish / Discovery Bay

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
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 …see more

from $1,714 / night

$12,000 - $24,500 / week

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from $1,714 / 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 $2,828 / night

$19,796 - $33,000 / week

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from $2,828 / 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 $1,086 / night

$7,602 / week

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avg. 2 minutes

from $1,086 / night

(10) Very Good 

39

Vacation villa with swimming pool in Discovery Bay

Saint Ann Parish / Discovery Bay

7 18 1 night min

  • 7 bedrooms
  • Sleeps 18
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Beach front villa at Discovery Bay on the beautiful Carribean Sea. BOOK TWO WEEKS AND GET THE THIRD WEEK FREE!!!! This private and exclusive villa is located on 2 acres of land in the quiet atmosphere of Discovery Bay overlooking the blue waters of the Caribbean Sea. …see more

from $675 / night

$4,725 / week

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Responds fast!
avg. 3 hours 13 minutes

from $675 / night

33

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 $2,215 / night

$15,500 - $36,000 / week

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from $2,215 / 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 $1,935 / night

$14,500 - $25,500 / week

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from $1,935 / night

14

Vacation villa with shared 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 $571 / night

$3,997 - $8,000 / week

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from $571 / 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

$5,300 - $9,000 / 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

$3,997 / week

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Responds fast!
avg. 2 minutes

from $571 / night

(1) Excellent 

33

Villa rental 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 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 $2,357 / night

$16,499 / week

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Responds fast!
avg. 2 minutes

from $2,357 / 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 $786 / night

$5,502 / week

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Responds fast!
avg. 2 minutes

from $786 / 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 $2,571 / night

$18,000 - $31,000 / week

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from $2,571 / night

36

Vacation home rental

Saint Ann Parish / Discovery Bay

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Makana Villa is a luxurious beachfront villa and a stunning new addition to Millionaires' Row in picturesque Discovery Bay. This fabulous luxury villa Jamaica has its own private cove and sandy beach for the exclusive use of its guests. An epitome of luxury, the fabulou …see more

from $2,543 / night

$17,800 - $29,000 / week

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from $2,543 / night

18

Vacation villa 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
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 $428 / night

$2,996 - $5,300 / week

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from $428 / night

(5) Excellent 

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

$3,000 - $5,300 / week

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from $429 / 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 $986 / night

$6,902 / week

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Responds fast!
avg. 2 minutes

from $986 / 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 $2,515 / night

$17,600 - $33,000 / week

Inquire View

from $2,515 / night

21

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 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 $886 / night

$6,202 / week

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Responds fast!
avg. 2 minutes

from $886 / night

33

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 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 $2,071 / night

$14,497 / week

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Responds fast!
avg. 2 minutes

from $2,071 / night

15

Vacation villa with shared pool in Discovery Bay

Saint Ann Parish / Discovery Bay

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Situated in Discovery Bay, Paradise Villas features accommodation with a hot tub, complimentary wifi is offered throughout the property. All units come with a living room, a seating area with a sofa, flat-screen TV with satellite channels, a fully equipped kitchen and a …see more

from $270 / night

$1,890 / week

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Responds fast!
avg. 3 hours 56 minutes

from $270 / night

21

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
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 $1,085 / night

$7,595 - $18,000 / week

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from $1,085 / night

(11) Excellent 

34

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
Named in reference to the colonial era, Fortlands Point villa resides at the site of the original military fortification leading into Discovery Bay. Indeed, the pronounced geography of the landscape sprawling around this magnificent estate remains a testament to the pur …see more

from $2,571 / night

$17,997 / week

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Responds fast!
avg. 2 minutes

from $2,571 / night