50 Best Vacation Rentals in Saint Mary Parish - Holiday Lettings - Cabins

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Tower Isle
32 properties
Oracabessa
28 properties
Apartments Boscobel
18 properties

Saint Mary Parish

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624 Vacation rentals

(4) Very Good 

8

Vacation home in Saint Mary Parish

Saint Mary Parish / Boscobel

3 10 2 nights min

  • 3 bedrooms
  • Sleeps 10
  • 2 nights min
  • Child friendly
  • Car not necessary
Modern Large cool onsuite rooms with Amercian windjammer fans. There is a plug in kingsizet blow up bed if there is more than six guests. A relaxing through lounge which seats up to 10 peoplei, dining room and modern fitted kitchen. If you book all 3 rooms you will have …see more

from $40 / night

$266 - $824 / week

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from $40 / night

(6) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from $67 / night

$266 / week

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avg. 1 hour 10 minutes

from $67 / 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 $107 / night

$744 - $2,232 / week

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from $107 / night

15

Vacation apartment in Tower Isle

Saint Mary Parish / Tower Isle

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
Apartment details: Fully furnished 2 bedroom - sleeps 4 persons Hot water, wall and ceiling fans present, Mosquito nets to windows Secure Gated community - 24 hour security provided Facilities available - Cooker, Fridge Freezer, Washing machine, Ironing board/Iron ,Micr …see more

from $85 / night

$595 / week

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from $85 / night

(5) Very Good 

12

Vacation apartment with shared pool in Saint Mary Parish

Saint Mary Parish / Tower Isle

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Delicately designed, one bedroom apartment to rent in, Ocho Rios Jamaica. Turtle Beach Towers, is in the midst of all that is Ocho Rios, with the local beach opposite the rear gateway to the complex and popular attractions including The Hard Rock Cafe, Island Village an …see more

from $87 / night

$505 - $551 / week

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from $87 / night

14

Home accommodation in Saint Mary Parish with shared pool

Saint Mary Parish / Boscobel

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
The accommodation is a 3 bedroom, 2 bathroom property with an en-suite bathroom to the master bedroom. There is a small verandah at the front of the property. All bedrooms are fully furnished with modern furnishings, including air conditioning in the master bedroom and …see more

from $81 / night

$602 / week

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avg. 1 hour 10 minutes

from $81 / night

(1) Very Good 

26

Robin's Bay Vacation cottage rental

Saint Mary Parish / Robin's Bay

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
Secrets and Dreams! With a large bedroom with a Queen-size bamboo bed and double Fulton bamboo couch bed you can sleep up to 4 persons. The bathroom has a tub with the bay window opening right to the sea as well. Stroll outside on your deck with an outside shower made f …see more

from $200 / night

$1,300 - $1,510 / week

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avg. 2 hours 19 minutes

from $200 / night

(12) Excellent 

63

Vacation villa with swimming pool, golf nearby in Saint Mary Parish

Saint Mary Parish / Tower Isle

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Take a break from the 'hustle and bustle' of life, and experience the taste and sounds of the Jamaica. Only the very best… Jamaican Ocean View Villas offer you a full on-site staff, including chef, butler, chauffeur*, and housekeeper/ house manager, who focus on making …see more

from $700 / night

$4,900 - $6,510 / week

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avg. 2 hours 5 minutes

from $700 / night

12

Vacation home in Oracabessa

Saint Mary Parish / Oracabessa

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
Your room is a spacious king size with private family sized bathroom and access to huge balcony and dining space shared with one other room! Stunning panoramic views of the mountains, ocean and golden eye island! Fantastic in the mornings! Access to shared pool area, l …see more

from $35 / night

$245 / week

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avg. 2 hours 58 minutes

from $35 / night

14

Cottage accommodation in Saint Mary Parish

Saint Mary Parish / Oracabessa

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
The Space 1 bedroom, 1 bath single or double occupancy cottage available off the beaten path, in the hills of St. Mary. Minutes from world renowned James Bond Beach with easy access to highway to local cities. Property includes a pool with a beautiful view of the …see more

from $50 / night

$300 / week

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from $50 / night

18

Vacation apartment with golf nearby in Boscobel

Saint Mary Parish / Boscobel

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
This is a beautiful, fully furnished apartment, located only 10 minutes from the lovely tourist mecca of Ocho Rios and in proximity to the lovely Dunn's River Falls and Mystic Mountains attractions. Only 2 minutes away from the James Bond beach. It is in a gated compl …see more

from $80 / night

$500 - $640 / week

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from $80 / night

(9) Excellent 

35

Villa rental in Saint Mary Parish with swimming pool

Saint Mary Parish / Oracabessa

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Take a break from the "hustle and bustle" of life, and experience the taste and sounds of the Jamaican countryside in fine style. This Mediterranean style villa is nestled behind a palm tree lined driveway in the hills of Gibraltar, overlooking the infamous James Bond …see more

from $450 / night

$3,150 / week

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avg. 1 hour 50 minutes

from $450 / night

(7) Excellent 

42

Saint Mary Parish Vacation villa rental

Saint Mary Parish / Oracabessa

12 22 Min stay varies

  • 12 bedrooms
  • Sleeps 22
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Golden Clouds is a luxurious, six acre gated estate located in the picturesque banana port village of Orcabessa, just a 15-minute drive from Ocho Rios. The villa sits directly above the sea overlooking its own palm fringed beach and the Caribbean Sea. Entrance is down a …see more

from $2,071 / night

$14,500 - $24,000 / week

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from $2,071 / night

34

Vacation apartment with shared pool in Saint Mary Parish

Saint Mary Parish / Tower Isle

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
My place is close to restaurants and dining, the beach, nightlife, family-friendly activities, and public transport. You’ll love my place because of the people, the ambiance, the outdoors space, and the neighborhood. My place is good for couples and solo adventurers,ITS …see more

from $55 / night

$385 / week

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avg. 1 hour 12 minutes

from $55 / night

(4) Very Good 

18

Vacation villa rental

Saint Mary Parish / Robin's Bay

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Beach/lakeside relaxation
Our newest renovation is the “Moonlight Magic" and "Secrets and Dreams“ or “deluxe cottage” boasts of its very own little beach cove! Moonlight Magic boasts of a whirlpool bath encased in natural chalk stone with a bay window opening right to the sea! The Queen size bam …see more

from $220 / night

$1,500 / week

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avg. 2 hours 19 minutes

from $220 / night

15

Saint Mary Parish Vacation villa rental

Saint Mary Parish / Boscobel

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
Secluded Villa For Up To 8 Persons With A Panoramic View Of The Caribbean Sea Built on a cliff overlooking the sea, guests enjoy exquisite comfort, safety and privacy. Its spacious 4 bedrooms/4 bathrooms are tastefully decorated with a wonderful Balinese ambienc …see more

from $395 / night

$2,765 / week

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from $395 / night

34

Vacation villa with shared pool in Saint Mary Parish

Jamaica / Saint Mary Parish

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Surrounded by 50 acres of landscaped lawn, fruit trees, and lush, untouched tropical forest, Bolt House is nestled on a hill overlooking Port Maria's beautiful blue harbor on the island of Jamaica. Augmenting this secluded five-bedroom private home, is a one-bedroom cot …see more

from $2,400 / night

$16,800 - $21,000 / week

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from $2,400 / night

21

Oracabessa Vacation cottage rental

Saint Mary Parish / Oracabessa

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
Quaint cottage located in the hills of Jamaica's north coast. Ideal for those seeking adventure and/or a peaceful retreat. Minutes from the main road to Ocho Rios and Kingston, pool access, private beach, and many Jamaican attractions. The Space 1 bedroom, …see more

from $45 / night

$270 / week

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from $45 / night

14

Vacation home accommodation

Saint Mary Parish / Oracabessa

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Swimming pool
Sleeps 1-12 1-10 in main house, with availability for 1 bedroom/2 guests to stay/use Spanish Elm, cottage at Golden Eye. Secluded five-bedroom private home surrounded by 40 acres of landscaped lawn, fruit trees, and lush, untouched tropical forest, Bolt House is nestl …see more

from $2,000 / night

$14,000 - $21,000 / week

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from $2,000 / night

11

Home rental in Saint Mary Parish

Saint Mary Parish / Boscobel

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
Townhouse located 15 minutes outside of the town of Ocho Rios. Close to Sandals and Breezes Resorts, with public beach access just 10 minutes away. Nearby Beaches include - Bamboo Beach, Bay Beach. The townhouse is a fifteen minutes drive to the world famous Dunn's Riv …see more

from $60 / night

$400 / week

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avg. 2 hours 23 minutes

from $60 / night

(1) Excellent 

33

Saint Mary Parish Vacation villa rental

Saint Mary Parish / Oracabessa

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
Loveland Villa, sits ideally on top of a slope that provides its occupants with a beautiful sea view. The villa comes with a private outdoor swimming pool and private beach access. Ideal getaway for the persons loving nature, privacy and quiet. Yet still ideal for thos …see more

from $200 / night

$1,350 - $1,630 / week

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from $200 / night

(1) Very Good 

11

Vacation villa in Saint Mary Parish

Saint Mary Parish / Boscobel

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
Sapphire Reef (formerly Windjammer) is located in Boscobel approximately 6 miles east of the resort town of Ocho Rios and is perched on a one acre bluff with 200 feet of frontage on the Caribbean Sea. The villa is located close to the road to maximize the front yard and …see more

from $429 / night

$3,000 - $5,000 / week

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from $429 / night

14

Saint Mary Parish Vacation apartment rental

Saint Mary Parish / Tower Isle

3 11 2 nights min

  • 3 bedrooms
  • Sleeps 11
  • 2 nights min
  • Child friendly
Sea Palms is a very quiet, well maintained, and not to mention beautiful property located in St. Mary. My apartment has a full view of the sea. If you want somewhere peaceful and relaxing, this is the place for you. With a housekeeper available, the apartment is cleaned …see more

from $215 / night

$1,505 / week

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from $215 / night

22

Vacation home in Saint Mary Parish

Saint Mary Parish / Oracabessa

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 3 mi
  • Private garden
Quaint 2 bedroom, 2 1/2 bathroom cottage with lots of character located on 3/4 acre lot with a few fruit trees and blooming plants. A perfect location with much land space. A decorator's potential dream can be realized as this 2-storey house offers many nooks and …see more

from $125 / night

$750 / week

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from $125 / night

13

Vacation guest house in Tower Isle

Saint Mary Parish / Tower Isle

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Located 15 minutes from the town of Ocho Rios and 10 minutes from the world renown James Bond Beach in Oracabessa St.Mary ,this lovely home away from home guest house (shared space) comprise of 3 individual bedrooms with ensuite bathrooms free wi-fi internet, cable t.v …see more

from $60 / night

$420 / week

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from $60 / night

(2) Excellent 

19

Vacation villa in Saint Mary Parish

Saint Mary Parish / Tower Isle

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
  • Ask about pets
The exclusive stately ambiance of Frankfort makes it one of the most sought after villas in Jamaica. Historically graced by royalty, celebrities and politicians such as Winston Churchill, Pierre Trudeau and Henry Kissinger, the private white sands at this converted eigh …see more

from $3,023 / night

$21,161 / week

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avg. 2 minutes

from $3,023 / night

27

Vacation apartment in Tower Isle

Saint Mary Parish / Tower Isle

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Private garden
Spring Palm Estate Your Vacation Home located in the Gated Community of tower isle Estate; 5 min Drive to Ocho Rios. Ocho Rios makes an excellent base for active, solvent travelers who wish to explore the north coast and partake in slick, well-managed adventures such as …see more

from $70 / night

$490 / week

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avg. 1 hour 12 minutes

from $70 / night

23

Home rental in Saint Mary Parish

Saint Mary Parish / Boscobel

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Nearest beach 0.003 mi
  • Car not necessary
  • Air conditioning
Our stylish, modern space has all the flavours of a Jamaican home. This Vacation Rental has a beautiful 3 bedroom ocean view private suite with Air conditioning, fully equipped kitchen and Free WiFi. Relax in our unique Boscobel living space, or stroll down to our loca …see more

from $60 / night

$360 - $672 / week

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Responds fast!
avg. 44 minutes

from $60 / night

(33) Excellent 

Certificate of Excellence

32

Saint Mary Parish Vacation villa rental

Saint Mary Parish / Tower Isle

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Nearest beach 6 mi
  • Ask about children
  • Car not necessary
Your stay at The Orchids Villa promises to be most relaxing and memorable. Picture this just 15 minutes from Ocho Rios in the hills of St. Mary with its magnificent view of the coast line and the surrounding hills is the Orchids Villa .The villa is beautifully designed …see more

Certificate of Excellence

from $40 / night

$280 - $560 / week

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Responds fast!
avg. 1 hour 21 minutes

from $40 / night

7

Vacation apartment rental

Saint Mary Parish / Tower Isle

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Swimming pool
  • Child friendly
  • Private garden
Ocho rios Your Vacation Home Located in the Gated Community of tower isle Estate,5 min Drive to Ocho Rios.Ocho Rios makes an excellent base for active, solvent travelers who wish to explore the north coast and partake in slick, well-managed adventures� such as zip-line …see more

from $55 / night

$385 / week

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avg. 1 hour 12 minutes

from $55 / night

28

Saint Mary Parish Vacation home rental

Saint Mary Parish / Oracabessa

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Blow Hole Villa, is a charming 5 bedroom, 7.5 bathroom seaside villa located on the east side of Ocho Rios on the Jamaican north coast. The 110 ft. veranda of the main house runs the entire length of the building facing the sea, and connects the bedrooms and public spac …see more

from $786 / night

$5,500 - $10,000 / week

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from $786 / night

(6) Excellent 

22

Vacation villa with swimming pool in Saint Mary Parish

Saint Mary Parish / Tower Isle

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
LaCaye villa is a beautiful waterfront villa. Our four bedroom villa offers the serenity of a secluded villa with the convenience of being only minutes away from Ocho Rios and a number of attractions. The villa brings outdoor living indoors with its open living room w …see more

from $550 / night

$3,850 / week

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from $550 / night

(23) Excellent 

40

Cottage rental in Saint Mary Parish

Saint Mary Parish / Oracabessa

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 24 mi
The cosy newly built cottage in the traditional Jamaican style is located on a vast property with stunning sea views and tropical garden, just above a rocky cliff. From your front porch or lying in the hammock you will enjoy the beautiful view of the sea, or discover ex …see more

from $95 / night

$585 / week

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from $95 / night

(1) Very Good 

17

Vacation villa rental

Saint Mary Parish / Tower Isle

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Located 1 ½ hours from Montego Bay, this 1930’s Tudor house is the holiday escape that is totally spoilt, relaxing and unique. This quintessential historical abode is equipped with modern day amenities. The main house has four wonderfully furnished and air-co …see more

from $1,210 / night

$8,500 - $14,000 / week

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from $1,210 / night

(1) Excellent 

18

Vacation villa with swimming pool in Saint Mary Parish

Saint Mary Parish / Boscobel

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Air conditioning
Endless Summer is a beautiful seafront property with a breathtaking view of the Caribbean Sea. We are located 10 to 15 minutes east of Ocho Rios, so we are close to several major attractions, beaches, nightlife, family-friendly activities and dining. You’ll love my pl …see more

from $160 / night

$1,008 / week

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from $160 / night

12

Apartment rental in Saint Mary Parish with swimming pool

Saint Mary Parish / Tower Isle

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Private garden
Spring Palm Estate Your Vacation Home located in the Gated Community of tower isle Estate; 5 min Drive to Ocho Rios. Ocho Rios makes an excellent base for active, solvent travelers who wish to explore the north coast and partake in slick, well-managed adventures such a …see more

from $60 / night

$420 / week

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avg. 1 hour 12 minutes

from $60 / night

(2) Excellent 

12

Boscobel Vacation home rental

Saint Mary Parish / Boscobel

3 12 2 nights min

  • 3 bedrooms
  • Sleeps 12
  • 2 nights min
  • Nearest beach 2 mi
  • Ask about children
  • Car not necessary
Seaviews from a wrap around veranda providing shade all day long in Boscobel Jamaica. Our hillside property offers constant tradewinds in this comfortable, quiet, and diverse neighborhood. The rooms are large with clean contempory furnishing. The suites all have their …see more

from $75 / night

$400 - $5,405 / week

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from $75 / night

45

Vacation apartment with swimming pool in Saint Mary Parish

Saint Mary Parish / Tower Isle

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
My place is close to restaurants and dining, the beach, nightlife, family-friendly activities, and public transport. You’ll love my place because of the people, the ambiance, the outdoors space, and the neighborhood. My place is good for couples and solo adventurers.My …see more

from $48 / night

$336 / week

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avg. 1 hour 12 minutes

from $48 / night

(3) Excellent 

77

Vacation villa with swimming pool in Port Maria

Saint Mary Parish / Port Maria

9 16 Min stay varies

  • 9 bedrooms
  • Sleeps 16
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Affordable- Relax & enjoy the sun, sea and activities For large groups- please submit your request and contact owner to discuss discount options. Thank you All events or special occasion must receive approval by the owner. This includes weddings and private parties …see more

from $250 / night

$1,750 / week

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Responds fast!
avg. 3 hours 48 minutes

from $250 / night

(1)  

25

Saint Mary Parish Vacation home rental

Saint Mary Parish / Tower Isle

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
Become one with Jamaica! Come and experience the life of a typical Jamaican family. Be immersed in our culture, food , music and our 'One love' way of living. Our home boasts a beautiful sea view which is perfect for couples and those that enjoy the little things in li …see more

from $47 / night

$326 / week

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avg. 3 hours 51 minutes

from $47 / night