50 Best Jamaica Estates on Holiday Lettings - Villas

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Saint Ann Parish
680 properties
Saint James Parish
596 properties
Kingston Parish
350 properties
Trelawny Parish
182 properties
Westmoreland Parish
171 properties
Portland Parish
89 properties
Saint Catherine Parish
82 properties
Saint Mary Parish
74 properties
Hanover Parish
55 properties
Saint Elizabeth Parish
55 properties
Manchester Parish
28 properties
Saint Andrew Parish
16 properties
Cabins Blue Mountains National Park
16 properties
Saint Thomas Parish
6 properties

Jamaica

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2,329 Vacation rentals

(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 $128 / night

$670 / week

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from $128 / 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 $109 / night

$759 / week

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from $109 / night

(47) Very Good 

140

Vacation villa with swimming pool, golf nearby in Ocho Rios

Saint Ann Parish / Ocho Rios

3 10 min stay varies

  • 3 bedrooms
  • sleeps 10
  • min stay varies
  • 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 $191 / night

$1,145 / week

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from $191 / 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 $71 / night

$491 / week

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from $71 / 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 $35 / night

$241 / week

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from $35 / 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 $54 / night

$378 / week

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avg. 3 hours 22 minutes

from $54 / night

37

Vacation apartment rental

Saint Catherine Parish / Old Harbour

4 12 3 nights min

  • 4 bedrooms
  • sleeps 12
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Enjoy the private pool is safe gardens. with safe area for children. We have hot water and wifi The house is a family home on a 3 acre small holding. The rooms are large and cool. There is a large lounge and kitchen with numerous balconies and verandas to relax on. Th …see more

from $74 / night

$518 / week

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avg. 3 hours 33 minutes

from $74 / 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

(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 $39 / night

$230 / week

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from $39 / 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 $51 / night

$357 / week

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avg. 26 minutes

from $51 / 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 $45 / night

$313 / week

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from $45 / night

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 $638 / night

$4,464 / week

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from $638 / night

(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 $613 / night

$4,285 / week

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from $613 / 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 $120 / night

$840 / week

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avg. 2 hours 2 minutes

from $120 / night

(14) Excellent 

27

Vacation home in Port Antonio

Port Antonio / Blue Lagoon, Port Antonio

4 9 1 night min

  • 4 bedrooms
  • sleeps 9
  • 1 night min
  • Beach/lakeside relaxation
  • Suitable for children age 5+
  • Car not necessary
Mr Barrys is nestled nicely on a hill in the heart of Fairy HIll, Boston. We welcome visitors from around the world to stay with us and to feel at home here. Mr Barry's White House is in a quiet part of the Island and the locals are very warm and welcoming, there are …see more

from $200 / night

$1,050 - $1,099 / week

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avg. 3 hours 20 minutes

from $200 / night

(3) 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 $185 / night

$1,295 / week

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from $185 / night

(18) Excellent 

Certificate of Excellence

36

Vacation townhouse rental

Westmoreland Parish / Negril

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
This newly built two bedroom, two and a half bathroom townhouse, located on the cliffs, overlooking the ocean, is the perfect home away from home for your holiday, or stay in Negril, Jamaica. It easily sleeps 6 guests. The king bedroom can be separated into 2 twin bed …see more

Certificate of Excellence

from $199 / night

$1,750 - $2,170 / week

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avg. 1 hour 3 minutes

from $199 / night

(2) Very Good 

13

Villa accommodation in Runaway Bay with swimming pool, golf nearby

Saint Ann Parish / Runaway Bay

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
Private fully furnished villa located in the heart of Runaway Bay. Reef Winds boasts great proximity to the beach in addition to local shops and restaurants, whilst maintaing the privacy of guests. Each of the three double bedrooms feature a separate bathroom and can ac …see more

from $140 / night

$1,000 - $1,200 / week

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from $140 / 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

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 $65 / night

$452 / week

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avg. 3 hours 33 minutes

from $65 / night

(14) Excellent 

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

from $96 / night

$670 - $804 / week

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avg. 3 hours 41 minutes

from $96 / 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 $134 / night

$935 / week

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from $134 / 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 $77 / night

$498 - $623 / week

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from $77 / night

(5) 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 $204 / night

$1,123 / week

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from $204 / 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) Very Good 

13

Mandeville Vacation b&b rental

Manchester Parish / Mandeville

3 4 2 nights min

  • 3 bedrooms
  • sleeps 4
  • 2 nights min
  • Nearest beach 25 mi
  • Child friendly
  • Car not necessary
Property located up in the cool hills of Manchester, with (A) master bedroom with en suite bathroom available with breakfast. (B) annexed to the main house is a private self-contained independent apartment (no breakfast included) set in an eco-friendly environment and …see more

from $15 / night

$105 - $455 / week

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from $15 / 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 $39 / night

$255 / week

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from $39 / 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

(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

(20) Excellent 

24

Vacation villa with swimming pool in Ocho Rios

Saint Ann Parish / Ocho Rios

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
If you are looking for high standard, self-catering accommodation in Jamaica at a budget price you have just found the perfect holiday retreat. We offer everything you might possibly need for that perfect Jamaican vacation and please just compare our prices to what else …see more

from $102 / night

$574 - $896 / week

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avg. 1 hour 44 minutes

from $102 / night

(5) Excellent 

24

Villa rental in Runaway Bay with swimming pool, golf nearby

Saint Ann Parish / Runaway Bay

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Welcome! **We have a summer sale from the end of May to the end of August. We are offering 1-free night on 4+ night bookings , please inquire for more info!** Villa Turrasann (formally known as Las Palmas) is a beachfront villa located in Runaway Bay 70 kilometers eas …see more

from $498 / night

$3,482 - $8,481 / week

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from $498 / 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 53 minutes

from $299 / night

(2) Excellent 

16

St. Ann's Bay Vacation home rental

Saint Ann Parish / St. Ann's Bay

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Sophia is a lush green taste of paradise. It is a single family vacation home. It is located in Ochio Rios, Jamaica (North Coast), in the gated community of Drax Hall Manor. The property has 24 hrs security. It has a pool, club house, and a tennis court. Nearby …see more

from $125 / night

$775 - $1,140 / week

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from $125 / night

(3) Excellent 

20

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 $64 / night

$255 - $517 / week

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avg. 1 hour 39 minutes

from $64 / night

(9) Very Good 

37

Vacation apartment with shared pool in Port Royal

Kingston / Port Royal

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
My place is close to family-friendly activities, nightlife, public transport, the airport, and the beach. You’ll love my place because of the views, the location,, the people, the cosiness, the high ceilings. My place is good for couples, solo adventurers, business trav …see more

from $100 / night

$700 / week

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avg. 52 minutes

from $100 / night

18

Studio rental in Portmore

Saint Catherine Parish / Portmore

Studio 2 2 nights min

  • Studio
  • sleeps 2
  • 2 nights min
ARE YOU VISITNG JAMAICA FROM OVERSEAS? ATTENDING A CRICKET MATCH AT THE FAMOUS SABINA PARK? ON A BUDGET? ADVENTUROUS? INTO HISTORICAL RESEARCH? WANT SOMEPLACE OFF THE BEATEN PATH & AWAY FROM IT ALL? WANT TO ENJOY THE REAL JAMAICA? Don't waste your $$ money at …see more

from $30 / night

$210 / week

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avg. 2 hours 5 minutes

from $30 / 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

12

Long Bay Vacation cottage rental

Portland Parish / Long Bay

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Child friendly
  • Private garden
We offer you a newly built one bedroom cabin that sleeps up to two guests, a private toilet with shower and balcony equipped with hammock to enjoy the amazing sea view and ocean breeze. There are steps to get up to the cabins. Guest access: to the villa, terrace, ro …see more

from $60 / night

$420 / week

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from $60 / night

(14) 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 $79 / night

$523 - $804 / week

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Responds fast!
avg. 30 minutes

from $79 / 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 $75 / night

$484 - $967 / week

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avg. 30 minutes

from $75 / night