50 Best Jamaica Estates on Holiday Lettings - Villas

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Saint Ann Parish
670 properties
Saint James Parish
628 properties
Kingston Parish
343 properties
Westmoreland Parish
175 properties
Trelawny Parish
175 properties
Portland Parish
96 properties
Saint Mary Parish
93 properties
Saint Catherine Parish
84 properties
Hanover Parish
54 properties
Saint Elizabeth Parish
53 properties
Manchester Parish
27 properties
Saint Andrew Parish
12 properties
Saint Thomas Parish
7 properties
Cabins Blue Mountains National Park
6 properties

Jamaica

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2,428 Vacation rentals

21

Vacation home with swimming pool in White House

Westmoreland Parish / White House

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Ballets Negres is a stunning, architecturally modern villa, situated in the idyllic fishing village of Whitehouse on the South Coast of Jamaica. Newly built in 2016, the villa’s luxurious and contemporary surroundings provide a peaceful and tropical haven with bea …see more

from $700 / night

$4,900 / week

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from $700 / night

8

Home rental in Old Harbour

Saint Catherine Parish / Old Harbour

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 30 mi
  • Child friendly
  • Car not necessary
2 Bedrooms, 1 Bathroom, Sleeps 4 This Beautiful Two Bedroom House Is Nestled In The Foothills Of New Harbour, St. Catherine. The House Is Located 25 Minutes from Kingston,45 minutes from Norman Manley Airport, 20 mins to Hellshire Beach, 25 mins to Caymanas Race Track …see more

from $63 / night

$343 - $1,078 / week

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avg. 1 hour 13 minutes

from $63 / night

(33) 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 $119 / night

$833 / week

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from $119 / 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 $140 / night

$735 / week

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from $140 / night

(3) Excellent 

28

Vacation apartment in Kingston

Kingston Parish / Kingston

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Air conditioning
The Apartment is fully furnished, centrally located, safe, quiet and very well kept, it also provides a nice view of surrounding areas. It is located across from the world famous Devon House, where the world comes for ice cream. It is within walking distance of the Bob …see more

from $44 / night

$370 / week

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avg. 2 hours 53 minutes

from $44 / 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 $49 / night

$392 / week

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avg. 1 hour 14 minutes

from $49 / night

(4) 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 $147 / night

$1,029 / week

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from $147 / night

31

Vacation villa in Montego Bay

Saint James Parish / Montego Bay

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Ask about children
  • Air conditioning
  • Private garden
Pleasant View is a unique and immaculate air conditioned 3 bedroom villa luxuriously furnished with modern furnishings. Including outdoor bar, barbecue, large pool & other amenities. Seven miles west of Sangsters International Airport is Pleasant View, rapturo …see more

from $350 / night

$2,380 / week

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avg. 2 hours 13 minutes

from $350 / night

(10) 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 $66 / night

$461 - $931 / week

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avg. 2 hours 51 minutes

from $66 / night

(1) Excellent 

29

Villa rental in Port Antonio

Port Antonio / Williamsfield

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Two elegant 1-bedrooms studio apartments, complete with bathroom, living room and kitchen—offer hosting to a maximum of 6 persons. Several outdoor terraces invite you to dine, unwind and relax while savoring idyllic tropical views. Immerse yourself, for nature's thera …see more

from $350 / night

$2,000 / week

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from $350 / 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 $42 / night

$252 / week

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from $42 / night

(4) Excellent 

26

Vacation guest house in Falmouth

Trelawny Parish / Falmouth

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
This is Charmaine's 2 Bedroom guest house. It is a spacious and beautiful private destination that is situated in the middle of Montego Bay and Ocho Rios. The house is newly built in 2015 and is a gated community. The guest house is close to all tourist attractions, ac …see more

from $49 / night

$343 / week

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from $49 / night

(3) Excellent 

15

Vacation apartment rental

Montego Bay / St James, Montego Bay

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Child friendly
Apartment comprises 2 double bedrooms both with double beds and one bedroom has a single additional bed. Lounge/dinning room comprise sofa and a double sofa bed. TV with dinning table and chairs. Now also with WiFi. The kitchen is fully working with cooker, fridge and M …see more

from $70 / night

$280 - $567 / week

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Responds fast!
avg. 1 hour 38 minutes

from $70 / night

(6) Excellent 

14

Vacation apartment in Tower Isle

Saint Mary Parish / Tower Isle

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 1 mi
  • Swimming pool
  • Car not necessary
Comfortable one bedroom apartment. Fully air conditioned and overlooking the warm waters of the aquamarine Caribbean Sea. Direct access to the beach or if you prefer ,a large swimming pool. Other amenities include water sports,Golf courses.boating and fishing. Within …see more

from $121 / night

$280 / week

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avg. 1 hour 18 minutes

from $121 / 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. 13 minutes

from $149 / 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 24th ***** 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

16

Vacation guest house in Treasure Beach

Saint Elizabeth Parish / Treasure Beach

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 0 mi
  • Child friendly
Kudehya is nestled beachfront, at the end of a quiet street in the peaceful Old Wharf district of Treasure Beach. It's majestic location allows for spectacular views of the Caribbean Sea, the Great Bay Bluff and the Santa Cruz mountains. Is an easy walk to restaurants, …see more

from $250 / night

$1,750 / week

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from $250 / night

(4) Excellent 

20

Vacation villa with swimming pool, golf nearby in Runaway Bay

Saint Ann Parish / Runaway Bay

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
Villa Pegasus is a stunning villa which can be found in the Upscale area of Cardiff Hall in the sleepy resort town of Runaway Bay. The property boasts 4 large bedrooms, 3 large reception rooms, a freeform swimming poo and a summer house (gazebo) with all the mod-cons o …see more

from $224 / night

$1,232 / week

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from $224 / 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 $70 / night

$455 - $1,064 / week

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avg. 1 hour 30 minutes

from $70 / 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

26

Vacation apartment rental

Saint Ann Parish / Ocho Rios

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
Fishermans point resort is a one Bedroom beach apartment (living room, bedroom, kitchen, bath room), beach 3 minutes walk, with ocean view, located in Ocho Rios Turtle Street Mahogany Beach. The spacious apartments sleeps 4 (2 adults + 2 children or 3 adults), Cable TV. …see more

from $100 / night

$600 - $700 / week

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from $100 / night

22

Vacation villa in Negril

Westmoreland Parish / Negril

11 24 Min stay varies

  • 11 bedrooms
  • Sleeps 24
  • Min stay varies
  • Child friendly
ABOVE THE HISTORIC CITY OF NEGRIL, ROOF TOP TERRACE, 20 PERSONS INFINITY POOL, PRIVATE GARDENS, ACTIVITIES FOR THE WHOLE FAMILY. FULL SERVICE ALL INCLUSIVE TAPS FORMAT MEALS. VACATION YOUR WAY. POOL TABLE TENNIS LOUNGE AREAS. ROOF TOP BAR. EXCURSIONS, GYM, YOGA SPA T …see more

from $170 / night

$1,190 / week

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Responds fast!
avg. 2 hours 28 minutes

from $170 / night

(1) Excellent 

20

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 $195 / night

$1,365 / week

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from $195 / 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. 3 hours 0 minutes

from $80 / night

(1) Very Good 

Certificate of Excellence

26

Ocho Rios Vacation studio rental

Saint Ann Parish / Ocho Rios

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Nearest beach 1 mi
  • Swimming pool
  • Car not necessary
Pimento is a delightful spacious studio, one of three apartments overlooking the pool at Almond Tree Villa. Quiet upscale area, one of the nicest locations in Ocho Rios. Only 3 miles from the center of town and close to postcard perfect beaches. Lovely swimming pool and …see more

Certificate of Excellence

from $59 / night

$378 / week

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Responds fast!
avg. 2 hours 14 minutes

from $59 / 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 $97 / night

$770 / week

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from $97 / night

(6) Very Good 

Certificate of Excellence

20

Vacation apartment in Ocho Rios

Saint Ann Parish / Ocho Rios

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Child friendly
  • Private garden
Imagine a villa which has fabulous views, in a quiet location, with a spacious indoor Jacuzzi. This is a superb 3 bedroom holiday villa, in a quiet location yet minutes away from the fun and activities which the Ocho Rios scene can offer, such as Reggae Beach, Jet Ski r …see more

Certificate of Excellence

from $84 / night

$588 / week

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Responds fast!
avg. 1 hour 42 minutes

from $84 / night

(4) Excellent 

Certificate of Excellence

32

Vacation studio in Ocho Rios

Saint Ann Parish / Ocho Rios

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Car not necessary
Cinnamon Apartment is one of three lovely studios sharing the grounds and swimming pool with Tamarind and Pimento apartments together with Almond Tree Villa. Cinnamon is built at the rear of the villa and looks out over the swimming pool terrace. The apartment is design …see more

Certificate of Excellence

from $54 / night

$350 / week

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Responds fast!
avg. 2 hours 14 minutes

from $54 / night

(2) Excellent 

29

Villa rental in Jamaica with swimming pool, golf nearby

Saint James Parish / Montego Bay

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to Calypso Shores, a luxurious contemporary 4-bedroom beachfront villa located on its own private beach on a calm lagoon in Montego Bay in Jamaica. Calypso Shores, located in a stunning California-style residential neighbourhood named Lagoons, is possibl …see more

from $855 / night

$5,985 / week

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from $855 / 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 

13

Vacation apartment in Tower Isle

Saint Mary Parish / Tower Isle

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
This newly built Villa complex has a breath taking ocean views and is 10mins away from downtown Ocho Rios. The studio has AC, wifi, hot water, cable, private parking and security. There is daily housekeeping a pool and hot tub. It is close to beaches, restaurants, hor …see more

from $126 / night

$882 / week

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from $126 / night

(44) Very Good 

141

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

from $210 / night

$1,260 / week

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from $210 / night

(1) Excellent 

65

Mammee Bay Vacation apartment rental

Saint Ann Parish / Mammee Bay

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 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 Location, quality and the price for what you receiving for your …see more

from $112 / night

$700 / week

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from $112 / night

12

Mandeville Vacation b&b rental

Manchester Parish / Mandeville

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Nearest beach 25 mi
  • Child friendly
  • Car not necessary
Bed and breakfast in an eco friendly environment in rural Jamaica and walking distance to Mandeville Town Center. Home located up in the cool hills of Manchester. Comfortable self contained facilities with electronic / remote controlled security gate. Laid back environ …see more

from $36 / night

$252 - $952 / week

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from $36 / night

27

Apartment rental in Ocho Rios with shared pool

Saint Ann Parish / Ocho Rios

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
These one Bedroom apartments are in Ocho Rios Main Street Mahogany Beach. The spacious apartments sleeps 4. Wi-fi and cable TV. The living and dining area area have extra sleeping facilities for 2. The independent kitchen is fully tiled with hand made pine units, and …see more

from $98 / night

$546 / week

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from $98 / night

(1) Excellent 

14

Apartment rental in Tower Isle with shared pool

Saint Mary Parish / Tower Isle

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 0.5 mi
  • Swimming pool
  • Child friendly
Hidden Coral is located on the North Coast. Set within Sea Palms Complex, and surrounded by a well maintained green garden and the beautiful Caribbean Sea and Private Beach. Only a mile from the centre of Ocho Rios. 24 hour security. House Keeper Service. The apartment …see more

from $112 / night

$784 - $2,352 / week

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from $112 / night

(7) Very Good 

34

Vacation villa rental

Saint Ann Parish / Runaway Bay

5 7 3 nights min

  • 5 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 7 mi
  • Swimming pool
  • Child friendly
The beautiful Santai Villa Hibiscus is off the beaten track nestled in the cool hills of Mount Pleasant Runaway Bay. The Villa/Guest house is within a 5 minute drive to the centre of Runaway and beaches. The views of the sea, mountains and surrounding areas from the Vil …see more

from $252 / night

$1,540 - $1,834 / week

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from $252 / night

(7) Excellent 

29

Vacation home in St. Ann's Bay

Saint Ann Parish / St. Ann's Bay

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning
Located along Jamaica's scenic Northern Coast, Richmond St. Ann is an easy one hours drive from the Sangster International Airport in Montego Bay. Near by attractions: * Dunn's River * Mystic Mountains * Dolphin Cove * Cranbrook Flower Forest * Seville Great House * …see more

from $180 / night

$1,260 / week

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from $180 / night

(4) Excellent 

46

Ocho Rios Vacation villa rental

Saint Ann Parish / Ocho Rios

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
If you've ever dreamed of paradise then Grande Haven Gibraltar is simply your ultimate dream come true. This modern and magnificently designed villa is nestled amidst a lush, tropically landscaped, palm tree-lined driveway, with dazzling ocean views of the famous James …see more

from $450 / night

$3,150 / week

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avg. 1 hour 31 minutes

from $450 / night

14

Vacation bungalow rental

Saint Ann Parish / Runaway Bay

3 4 3 nights min

  • 3 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
Householder with special breakfast service in a secure and clean accommodation. It is for very favourable cost and a central start point for many activities. Support from natives will be offered. Beach is 10 minutes walking away so as shops and bus stop. Diving school a …see more

from $31 / night

$215 - $860 / week

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from $31 / night