50 Best Jamaica Estates on Holiday Lettings - Villas

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Saint Ann Parish
637 properties
Saint James Parish
567 properties
Kingston Parish
347 properties
Westmoreland Parish
165 properties
Trelawny Parish
120 properties
Portland Parish
89 properties
Saint Mary Parish
81 properties
Saint Catherine Parish
72 properties
Saint Elizabeth Parish
55 properties
Hanover Parish
31 properties
Manchester Parish
23 properties
Saint Andrew Parish
12 properties
Cabins Blue Mountains National Park
6 properties
Saint Thomas Parish
5 properties

Jamaica

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2,217 Vacation rentals

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

(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 - $470 / week

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from $65 / 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

(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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avg. 2 hours 16 minutes

from $119 / night

(1) Very Good 

8

Cottage rental in Negril Beach

Negril / Negril Beach

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden
Firefly is located on the famous seven miles beach in Negril Jamaica the only small Negril Hotel for couples, children and singles •Our friendly family and staff are here to invite you to be a part of our wonderful atmosphere. Step out of your cottage, apartment or p …see more

from $210 / night

$1,505 / week

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from $210 / night

(1) 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 30 minutes

from $121 / night

(3) 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 $300 / night

$2,100 / week

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Responds fast!
avg. 2 hours 29 minutes

from $300 / night

19

Vacation villa with swimming pool in Ocho Rios

Saint Ann Parish / Ocho Rios

4 12 3 nights min

  • 4 bedrooms
  • Sleeps 12
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
On 2 1/2 acres overlooking Ocho Rios & St. Ann's Bay, Villa Barbary has the seclusion of a private estate just minutes from Ocho Rios and Jamaica's north shore. The best of the Island and it's offerings! • 4 Bedrooms for 2+ people in each! • 4 Bathrooms • F …see more

from $475 / night

$3,200 - $3,900 / week

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avg. 1 hour 22 minutes

from $475 / 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 $70 / night

$490 / week

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from $70 / night

(6) Very Good 

27

Negril Vacation villa rental

Westmoreland Parish / Negril

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • 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 $672 / night

$4,704 / week

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from $672 / 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

(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 6 minutes

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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avg. 1 hour 39 minutes

from $70 / night

12

Vacation townhouse with shared pool in Negril

Westmoreland Parish / Negril

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
Little Bay Country Club: An upscale gated community in Negril. This spacious one bedroom apartment features a full kitchen, bath and amenities to make you feel like you never left home! It has wifi, hot water, cable and AC. Short walk to the infinity pool and beach. Thi …see more

from $150 / night

$1,050 / week

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from $150 / 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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avg. 2 hours 16 minutes

from $80 / 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

(2) Excellent 

18

Ocho Rios Vacation apartment rental

Saint Ann Parish / Ocho Rios

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • 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 $107 / night

$770 / week

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from $107 / night

(3) Excellent 

24

Vacation villa rental

Saint James Parish / Montego Bay

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Welcome to Scotch on the Rocks a stunning 5 bedroom ocean front villa with wonderful views of the Caribbean Sea, just minutes from lively Ocho Rios. Scotch on the Rocks is a charming 5 bedroom villa overlooking the Caribbean Sea. Its ideal location is a privately …see more

from $936 / night

$6,535 - $8,350 / week

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from $936 / 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

(6) Very Good 

17

Home rental in Jamaica with golf nearby

Montego Bay / St James, Montego Bay

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 1 mi
  • Child friendly
  • Private garden
Tthis is a 2 bedroom fully furnished house, most of our furniture has been imported with influence from the UK. At our home in Montego Bay, there is a good size kitchen/dining area and a bathroom. We live in a small community which is local to shops. Montego Bay is …see more

from $63 / night

$441 / week

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from $63 / 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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avg. 2 hours 7 minutes

from $120 / 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 $180 / night

$1,260 / week

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avg. 3 hours 15 minutes

from $180 / 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

(4) Very Good 

31

Ocho Rios Vacation apartment rental

Saint Ann Parish / Ocho Rios

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
Hotel Features. This 2bed Penthouse apartment in a resort, features a pool attached to a swim-up bar and an eight-person jetted tub. Beach 7 minutes away.One king bed, two-person jetted Jacuz tub, vanity sink in master bedroom located in loft with peaked wood ceili …see more

from $140 / night

$826 - $966 / week

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from $140 / night

(10) Excellent 

Certificate of Excellence

25

Vacation studio with shared pool in Ocho Rios

Saint Ann Parish / Ocho Rios

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Tamarind Apartment is one of three lovely studios sharing the grounds and swimming pool with Pimento and Cinnamon apartments together with Almond Tree Villa. Only 10 mins from Ocho Rios centre and close to some beautiful beaches. Tamarind is on the ground floor below P …see more

Certificate of Excellence

from $56 / night

$364 / week

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Responds fast!
avg. 2 hours 16 minutes

from $56 / 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

(11) Very Good 

Certificate of Excellence

21

Ocho Rios Vacation condo rental

Saint Ann Parish / Ocho Rios

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Ask about children
Carib Condominiums are located on a private beach on Main street, Ocho Rios. This privately owned and managed apartment is located on the top floor of this 2 storey apartment building. Here you can see magnificant views of the Caribbean Sea from your condo's ba …see more

Certificate of Excellence

from $87 / night

$574 - $770 / week

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Responds fast!
avg. 1 hour 59 minutes

from $87 / 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 47 minutes

from $66 / night

(2) Very Good 

30

Vacation apartment with shared pool in Ocho Rios

Saint Ann Parish / Ocho Rios

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
The Resort is situated on 19 acres of lush landscaped gardens with 90 story residences surrounding a freshwater swimming pool, swim-up bar, whirlpool and bar. There are also two tennis courts and a Spa. Beach 7 minutes walk from apartment. The resort offers Restaura …see more

from $112 / night

$546 - $644 / week

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from $112 / 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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Responds fast!
avg. 2 hours 24 minutes

from $350 / night

(12) Excellent 

Certificate of Excellence

49

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
  • Nearest beach 0.1 mi
  • Swimming pool
This refreshingly bright self-contained apartment is everything you might need to relax after a wonderful day at the beach. Located in the heart of Ocho Rios and strategically positioned for you to enjoy the ideal beachfront location. The area is teeming with mouthwate …see more

Certificate of Excellence

from $98 / night

$735 - $882 / week

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Responds fast!
avg. 3 hours 33 minutes

from $98 / 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

(40) 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

(3) Very Good 

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 $148 / night

$1,037 / week

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from $148 / night

(1) Excellent 

69

Ocho Rios Vacation studio rental

Saint Ann Parish / Ocho Rios

Studio 4 1 night min

  • Studio
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
This property is located on one of the most prestigious locations in Jamaica This villa is set in one and a half acres of landscaped gardens boasting a verity of indigenous plants, flowers, and fruit bearing trees. The Studio has its own swimming pool, gazebo, spa …see more

from $84 / night

$420 / week

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from $84 / night

12

Vacation cottage rental

Negril / Negril Beach

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Firefly is the only small Negril Hotel for couples, children and singles that offers beach experience •Our friendly family and staff are here to invite you to be a part of our wonderful atmosphere. Wear your swimsuit family friendly beach. Step out of your c …see more

from $160 / night

$1,120 / week

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from $160 / 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 16 minutes

from $54 / night

10

Vacation apartment rental

Saint James Parish / Montego Bay

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
Modern, simple, fully equipped newly built studio. This centrally located studio is minutes from the beach, restaurants, recreation activities and nightlife. Visit the gardens, caves, luminous lagoons, go snorkeling, catamaran sailing and scuba diving. Water falls, h …see more

from $69 / night

$483 / week

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from $69 / 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 - $2,500 / week

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from $350 / night

(3) Very Good 

24

Vacation condo with shared pool in Ocho Rios

Saint Ann Parish / Ocho Rios

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Location Location Location...If you would like to stay at the best location in Ocho Rios..this is the condo to visit, this condo is so well located no need to spend money on taxi's everything is in walking distance, the golden beach is through the back entrance of the …see more

from $84 / night

$546 - $684 / week

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from $84 / night