50 Best Jamaica Estates on Holiday Lettings - Villas

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2,467 Vacation rentals

(6) Very Good 

27

Negril Vacation villa rental

Westmoreland Parish / Negril

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to the Villa 3, your Jamaican vacation beach home. Just steps from the sea, Villa 3 sleeps and entertains groups of 2 to 10 comfortably. The villa is located in the gated Little Bay Country Club: an exquisite, brand new, beachfront community in Negril. Vi …see more

from $628 / night

$4,391 / week

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from $628 / night

20

Vacation b&b rental

Saint Thomas Parish / Yallahs

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Child friendly
Ready to try something different? Need a quiet haven? Come to Jenny's Retreat the farm house on Black's Farm in Yallahs. You and your family and friends will always find a warm welcome waiting for you. You can watch the sun rise and set from our panoramic views, while s …see more

from $30 / night

$210 / week

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from $30 / night

(34) Very Good 

19

Vacation apartment with shared pool in Ocho Rios

Saint Ann Parish / Ocho Rios

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This accommodation is a fully air-conditioned two bedroom apartment situated on the 3rd floor, you may rent this apartment as a one, or two bedroom see table rates. FREE INTERNET ACCESS The Apartment is tastefully furnished to a high standard, within the …see more

from $111 / night

$778 / week

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from $111 / night

7

Vacation home in Rose Hall

Montego Bay / Rose Hall

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Nearest beach 2 mi
  • Child friendly
  • Air conditioning
This property is a two bedroom cozy house, home away from home that is tastefully decorated. It is situated in a scenic community of Rosehall, Montego Bay. This beautiful home has seaview scenery, and is just 20 minutes from the airport. This house is a open plan wit …see more

from $72 / night

$503 / week

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from $72 / night

15

Vacation apartment rental

Portland Parish / Buff Bay

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child friendly
  • Private garden
Ray & Perry welcome you to The Windsor Retreat. A self catering luxury Guesthouse located in Portland on the Northeast coast side of Jamaica. The parish of Portland is well visited and borders the Blue Mountains National Park. There is plenty to explore in the surroundi …see more

from $46 / night

$321 / week

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from $46 / night

(3) Very Good 

26

Vacation villa in Runaway Bay

Saint Ann Parish / Runaway Bay

4 6 3 nights min

  • 4 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Topaz Villa is situated in the quiet residential area of Cardiff Hall in Runaway Bay, St Ann's. The Villa boasts a large private swimming pool overlooking the golf club. The bedrooms are large and airy with ensuite and fans. There is a large lounge/diner for inside din …see more

from $79 / night

$471 / week

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avg. 3 hours 13 minutes

from $79 / night

(2) Very Good 

24

St. Ann's Bay Vacation home rental

Saint Ann Parish / St. Ann's Bay

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Enjoy your holidays in the tropical paradise of Jamaica We offer you a newly built freestanding 140 sq m single house in a gated community. The house offers all comfort you need, 2 bedrooms with queen size and 1 bedroom with double bed and 2 Bathrooms. All rooms …see more

from $131 / night

$915 / week

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Responds fast!
avg. 2 hours 26 minutes

from $131 / night

(1) Excellent 

38

Vacation home in Mandeville

Manchester Parish / Mandeville

3 7 1 night min

  • 3 bedrooms
  • sleeps 7
  • 1 night min
  • Nearest beach 24 mi
  • Child friendly
  • Private garden
A rustic space for you to unwind & rejuvenate in total tranquility & privacy. To quiet your mind, open your heart, and allow your body temple to return to a more relaxed state. Reconnect with the natural rhythms of nature and allow yourself this space to transform, a …see more

from $40 / night

$236 / week

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from $40 / night

(17) Very Good 

21

Vacation condo with shared pool in Ocho Rios

Saint Ann Parish / Ocho Rios

1 3 3 nights min

  • 1 bedroom
  • sleeps 3
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
A romantic peaceful setting but only ten minutes walk away from shops, restaurants and tourist attractions. Beautiful self catering condo, with stunning sea views overlooking the bay of Ocho Rios. Set in 14 acres of scenic landscaped gardens. This property is suitable f …see more

from $53 / night

$366 / week

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Responds fast!
avg. 24 minutes

from $53 / night

14

Vacation condo with shared pool, golf nearby in Rose Hall

Montego Bay / Rose Hall

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Marriott SeaCastles Penthouse is a modern luxury condo overlooking the ocean. The property is peaceful and perfect for a relaxing vacation away from all the hustle and bustle found on many tourist resorts in the area. Our guests have the option of enjoying quiet relax …see more

from $149 / night

$1,190 / week

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avg. 33 minutes

from $149 / night

(1) Excellent 

12

Apartment rental in Jamaica

Saint Thomas Parish / Yallahs

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Child friendly
Ready to try something different? Need a quiet haven? Come to Jenny's Retreat the farm house on Black's Farm in Yallahs. You and your family and friends will always find a warm welcome waiting for you. You can watch the sun rise and set from our panoramic views, while s …see more

from $40 / night

$280 / week

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from $40 / night

(8) Excellent 

30

Vacation villa in Ocho Rios

Saint Ann Parish / Ocho Rios

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Eden Sands Villa is a fully air conditioned property that is located 15 feet away from its very own beach. The approximately 1600 sq ft property is a hidden gem that has been contemporarily renovated. Our master bedroom is equipped with a custom King Size Guango bed, …see more

from $458 / night

$3,202 / week

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from $458 / night

(2) Excellent 

24

Runaway Bay Vacation villa rental

Saint Ann Parish / Runaway Bay

4 10 3 nights min

  • 4 bedrooms
  • sleeps 10
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Private garden
It doesn’t get much better than this! Our new private 6000 square foot villa has been meticulously built and designed to ensure you have the best of the best with air conditioning in all of our sleeping areas. Boasting two full size bedrooms each with queen beds and one …see more

from $299 / night

$2,000 / week

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avg. 1 hour 46 minutes

from $299 / night

(8) Excellent 

12

Vacation bungalow with shared pool, golf nearby in Portmore

Saint Catherine Parish / Portmore

2 5 3 nights min

  • 2 bedrooms
  • sleeps 5
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Swimming pool
This Beautifully located property consists of two bedrooms and 1 bathroom. Located within the beautiful secured community of Caymanas Country Club Estate, just off the the Mandela Highway. It is nestled in the foothills of St. Catherine. The house is located 15 minu …see more

from $59 / night

$412 / week

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from $59 / night

33

Ocho Rios Vacation villa rental

Saint Ann Parish / Ocho Rios

8 19 4 nights min

  • 8 bedrooms
  • sleeps 19
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Swimming pool
Garden House is located in the prestigious area of Shaw Park, in Ocho Rios. This historical property comes fully staffed and is easily reached by either airport, car or taxi. Approx. 3mins drive from Ocho Rios main street, 10mins walk. On arrival guests will gain en …see more

from $525 / night

$4,550 / week

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from $525 / night

(12) Excellent 

54

Treasure Beach Vacation home rental

Saint Elizabeth Parish / Treasure Beach

5 8 2 nights min

  • 5 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 12 mi
  • Child friendly
The White House is located in Rose Hall St. Elizabeth, Jamaica. This holiday home is set 5km from Junction/Southfield. Lovers leap is 6km and 11km from Treasure beach. Be sure to check out the exclusive Pelican Bar and YS Falls as well as The Black River Safari Tours. T …see more

from $131 / night

$686 / week

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from $131 / night

(8) Excellent 

27

Vacation apartment with golf nearby in Kingston

Kingston Parish / Kingston

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Child friendly
  • Air conditioning
The Pentwood is a newly renovated apartment with everything brand spanking new!!!!. It's decorated in a modern ultra chic style, with beautiful lighting, wooden blinds, wooden floors, air conditioning, modern kitchen appliances, a classy modern bathroom, and a comfortab …see more

from $75 / night

$480 / week

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Responds fast!
avg. 2 hours 32 minutes

from $75 / night

(5) Excellent 

24

Vacation villa in Mammee Bay

Saint Ann Parish / Mammee Bay

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly
Morning Glory Villas occupies 1.5 acres of beautifully manicured tropical garden is just a stroll (2 minute) from the beautiful private Mammee Bay beach with its powdery soft sands and beach club. This large property "Over the Moon" and "Sanora" offers 2 or 4 be …see more

from $138 / night

$961 / week

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from $138 / night

16

Vacation home with shared pool in St. Ann's Bay

Saint Ann Parish / St. Ann's Bay

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Close to the world famous attractions of Dunn's River and Mystic Mountain is this peaceful Villa in a gated community with 24 hour security. Ideal for individuals and families looking for a unique experience of the Caribbean in a relaxed, comfortable, secure environmen …see more

from $94 / night

$634 - $1,085 / week

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Responds fast!
avg. 34 minutes

from $94 / night

31

Apartment rental in Old Harbour with shared pool

Saint Catherine Parish / Old Harbour

1 6 5 nights min

  • 1 bedroom
  • sleeps 6
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Whole top floor home with one bedroom but can sleep 4; open plan kitchen, lounge, and dinging. Access to three balconies - two private and private pool with sheltered, sunny and shaded areas to relax. Rural location but easy access to old harbour with numerous bars, res …see more

from $66 / night

$458 / week

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from $66 / night

(11) Very Good 

22

Vacation villa in Treasure Beach

Saint Elizabeth Parish / Treasure Beach

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Private garden
Modern spacious fully furnished 2 double bedrooms (sleeps up to six) villa to rent in the town of Junction, St Elizabeth, in Jamaica's Countryside on the South Coast of the Island. Light bright and airy. Located on a private hill with breath taking views all around. …see more

from $62 / night

$430 - $869 / week

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avg. 1 hour 37 minutes

from $62 / night

(12) Very Good 

41

Runaway Bay Vacation apartment rental

Saint Ann Parish / Runaway Bay

1 3 3 nights min

  • 1 bedroom
  • sleeps 3
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
Cozy Tropical Paradise Vacation Apt! Spend the summer vacation in paradise, or escape the cold winter at Dreamy Haven, where it is sunny all year round, and sunbathing on white sand beaches sipping margaritas in the middle of winter is the norm. Experience home away fro …see more

from $60 / night

$420 / week

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avg. 3 hours 42 minutes

from $60 / night

8

Apartment rental in Kingston

Kingston Parish / Kingston

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Child friendly
  • Air conditioning
Perfectly situated at the top of Jack's Hill over looking beautiful Kingston Jamaica, The Great Escape is the ultimate get away experience. A Cool environment with air conditioned rooms, wifi access, cable TV along with secure parking shows that the Great Escape is a mu …see more

from $36 / night

$154 / week

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avg. 1 hour 30 minutes

from $36 / night

(48) Very Good 

Certificate of Excellence

140

Vacation villa with swimming pool, golf nearby in Ocho Rios

Saint Ann Parish / Ocho Rios

3 10 1 night min

  • 3 bedrooms
  • sleeps 10
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
Beautiful North Coast Jamaican villa with private swimming pool, BBQ pit also spa retreat. Only 5 minutes walk away from the most fabulous beach. This is in my opinion the best location on the island In comparison to our competitors our property is head and should …see more

Certificate of Excellence

from $196 / night

$1,174 / week

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from $196 / night

(6) Very Good 

21

Villa rental in Negril Beach with shared pool

Negril / Negril Beach

1 3 min stay varies

  • 1 bedroom
  • sleeps 3
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
*** Our $450 per week special start April 1st and ends December 1st ***** Located on Norman Manley Blvd, Negril hip strip, directly across the street from Negril's famous 7 miles white sand beach. Access to the beach right across the street just a few steps away. We …see more

from $65 / night

$400 / week

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from $65 / night

(3) Excellent 

21

Vacation villa in Runaway Bay

Saint Ann Parish / Runaway Bay

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Nearest beach 0.5 mi
  • Swimming pool
  • Child friendly
This two bedroom, sweet spot gem has spectacle views of the mountain on one side and the ocean on the other. There’s a gentle breeze with a large patio set in a tropical garden; the front lawn was used in the filming of the 2016 Season 20 finale of the Bachelor with Ben …see more

from $175 / night

$1,225 / week

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from $175 / night

(2) Very Good 

35

Mammee Bay Vacation villa rental

Saint Ann Parish / Mammee Bay

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
With the beauty of nature as its backdrop, Island Treasure Villas offer its guests a tranquil island escape that provides all the comfort of home with the flair and amenities of a 5 star hotel. A stay at this luxurious 3 bed, 2 baths villa provide guests with access to …see more

from $120 / night

$840 / week

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Responds fast!
avg. 1 hour 17 minutes

from $120 / night

(12) Excellent 

26

Vacation villa with shared pool in Ocho Rios

Saint Ann Parish / Ocho Rios

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Complimentary excursion for stays over two weeks. Ideal location for Rebel Solute in January 2018. Situated on Jamaica's north coast, Gated twenty four hour security. Nearby attractions include: Dunn's River Falls, Dolphin Cove and Mystic Mountain. Onsite pool, gym, …see more

from $130 / night

$910 / week

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avg. 2 hours 1 minutes

from $130 / night

20

Spanish Town Vacation home rental

Saint Catherine Parish / Spanish Town

3 4 3 nights min

  • 3 bedrooms
  • sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 16 mi
  • Child friendly
Comfortzone-retreat is a self contain accommodation located in Ensom City St Catharine . This retreat will provide you with 1 ,2, 3 bedrooms units full kitchen with all appliances .free WiFi ,Cable and mush more, grocery laundry and island tour can be arranged .We ar …see more

from $100 / night

$700 / week

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from $100 / night

(2) Excellent 

22

Vacation villa with swimming pool in White House

Westmoreland Parish / White House

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Palm Trees is an imposing hillside villa and guest house with a large private pool. It is located within it’s own grounds on the gated Anchor Estate near Whitehouse on Jamaica’s South Coast. Whitehouse is a very safe area. The villa is about 200 ft above sea level and 4 …see more

from $250 / night

$1,750 / week

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from $250 / night

(3) Excellent 

7

Vacation apartment with shared pool in Ocho Rios

Saint Ann Parish / Ocho Rios

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly
Beautiful newly decorated one bedroom Suite. This is your home away from home. You can walk easily to the town for restaurants and entertainment. But, you really have no need as there is restaurant and pool onsite. The beaches are a short drive or walk away and many …see more

from $92 / night

$588 / week

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from $92 / night

(5) Very Good 

34

Villa rental in St. Ann's Bay with golf nearby

Saint Ann Parish / St. Ann's Bay

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
With the beauty of nature as its backdrop, Island Treasure Villas offer its guests a tranquil island escape that provides all the comfort of home with the flair and amenities of a luxury hotel. A stay at this luxurious 3 bed, 2 baths villa provide guests with access to …see more

from $120 / night

$840 / week

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avg. 3 hours 36 minutes

from $120 / night

17

Westmoreland Parish Vacation guest house rental

Jamaica / Westmoreland Parish

4 16 1 night min

  • 4 bedrooms
  • sleeps 16
  • 1 night min
  • Suitable for children age 5+
  • Car not necessary
Blue Paradise Farms is an Embryonic Permaculture Resort (eco-farm) set in 18.5 acres of lush Jamaican countryside, yet just 10 minutes away from Savanna-la-Mar, the parish capital and close to the main road from Savanna-la-Mar to Montego Bay. The accent here is on sust …see more

from $36 / night

$247 / week

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from $36 / night

(2) Very Good 

19

Runaway Bay Vacation guest house rental

Saint Ann Parish / Runaway Bay

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Richmond Estate Is Located On A Northern Coastal Property near the Resort Town Of St Anns Bay. It Is nestled between Runaway Bay and Priory, With A Breathtaking View Of The Caribbean Sea. Richmond St. Ann is an easy 50-minute drive from the Sangster International Ai …see more

from $144 / night

$1,098 - $4,025 / week

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from $144 / 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

(2) Excellent 

18

Ocho Rios Vacation apartment rental

Saint Ann Parish / Ocho Rios

1 3 min stay varies

  • 1 bedroom
  • sleeps 3
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Chrisanns Beach Resort is a complex of beach front vacation apartments located four miles east of Ocho Rios that offer any holidaymaker an experience of Jamaica they could never forget. This enchanting property has its own private pool and beach with gazebo that overloo …see more

from $92 / night

$718 / week

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Responds fast!
avg. 3 hours 54 minutes

from $92 / night

(4) Very Good 

8

Vacation home in Boscobel

Saint Mary Parish / Boscobel

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child friendly
  • Car not necessary
Modern Large cool onsuite rooms with Amercian windjammer fans. . A relaxing through lounge lei, dining room and modern fitted kitchen. If you book all 3 rooms you will have the entire downstairs to yourself. You have a view of the sea from the front of house and lush g …see more

from $40 / night

$262 / week

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from $40 / night

(5) Good 

21

Vacation villa in Ironshore

Montego Bay / Ironshore

7 14 min stay varies

  • 7 bedrooms
  • sleeps 14
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Welcome to Chateau Gloria Luxury Villa, your home away from home. Looking for place to relax? To enjoy the Jamaican spirit? Then this villa is perfect for you. The property offers its guests a private outdoor pool with bar, ocean view and is surrounded by a tropical g …see more

from $728 / night

$5,096 - $6,664 / week

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from $728 / night

(13) Excellent 

40

Runaway Bay Vacation bungalow rental

Saint Ann Parish / Runaway Bay

3 6 4 nights min

  • 3 bedrooms
  • sleeps 6
  • 4 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly
Contemporary stylish beach villa located along Jamaica's picturesque north coast Runaway Bay :) Villa is located in a secure upmarket gated community called Richmond. The community is quiet and safe with 24 hour security. There is also a supermarket located on the com …see more

from $80 / night

$560 / week

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Responds fast!
avg. 2 hours 56 minutes

from $80 / night

(6) Very Good 

19

St James, Montego Bay Vacation condo rental

Montego Bay / St James, Montego Bay

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0.6 mi
  • Swimming pool
WELL APPOINTED LUXURY 1BEDROOM APARTMENT ON JAMAICA'S GOLD COAST, ROSE HALL IS WITHIN 5 MINUTES FROM MONTEGO BAY AIRPORT. AMENITES INCL GRANITE COUNTER TOPS IN KITCHEN & BATHROOMS, BREATHTAKING VIEW FROM BALCONIES OF THE CARIBBEAN SEA/POOL AREA, OTHER ON PROPERTY AMENIT …see more

from $150 / night

$1,050 / week

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from $150 / night