50 Best Vacation Rentals in St. Ann's Bay - Holiday Lettings - Cabins

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734 Vacation rentals

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 $67 / night

$432 - $1,010 / week

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avg. 1 hour 29 minutes

from $67 / night

(5) Very Good 

34

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

Saint Ann Parish / St. Ann's Bay

3 8 3 nights min

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

from $120 / night

$840 / week

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Responds fast!
avg. 3 hours 22 minutes

from $120 / night

(1) Very Good 

13

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

Saint Ann Parish / St. Ann's Bay

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Nearest beach 13 mi
  • Swimming pool
  • Child friendly
Island Vibz is located in close proximity to Ocho Rios Center, Dunn's River Falls, Dolphin Cove, Chukka Cove, Blue Hole, Konoko Falls, Marguaritaville, Duty Free Shops and many more local attractions....... This is the ideal vacation home for couples, solo adventurers, …see more

from $120 / night

$800 / week

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Responds fast!
avg. 2 hours 50 minutes

from $120 / 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 $130 / night

$850 - $1,140 / week

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from $130 / night

(2) Very Good 

24

St. Ann's Bay Vacation home rental

Saint Ann Parish / St. Ann's Bay

3 6 3 nights min

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

from $133 / night

$930 / week

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Responds fast!
avg. 1 hour 26 minutes

from $133 / 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

13

St. Ann's Bay Vacation private room rental

Saint Ann Parish / St. Ann's Bay

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 4 mi
Teresina is a unique chalet located inside the foot-hills of the Sussex Estate Road, St Ann. With seven acres of privacy your chalet is only 13.2 km or 20 minutes drive to the world famous DUNN'S RIVER FALLS, MYSTIC MOUNTAIN RAIN FOREST a 700 feet drop bobsledding and z …see more

from $86 / night

$602 / week

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from $86 / night

(4) Excellent 

17

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

Saint Ann Parish / St. Ann's Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 3 mi
  • Swimming pool
  • Child friendly
Warm and inviting 3BR/3BA vacation home with all the amenities of home in the exclusive gated community of Drax Hall Manor. The property set in the heart of the garden parish of St. Ann, this vacation home is only minutes away from Dunn's River Falls and many other attr …see more

from $115 / night

$725 - $1,005 / week

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from $115 / night

22

Vacation home in St. Ann's Bay

Saint Ann Parish / St. Ann's Bay

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Private garden
It is located in a gated community. Ten minutes to ochi Rios and 50 mins to Montego Bay Airport. It's available in 1,2,3 bedroom rental. The place is good for couples and families with kids. You will enjoy the location,ambiance and the outdoor space. You will have aces …see more

from $120 / night

$840 / week

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from $120 / night

16

Vacation home in St. Ann's Bay

Saint Ann Parish / St. Ann's Bay

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Swimming pool
  • Child friendly
3 Bedrooms, 2 Bathrooms, 6 Sleeps This is a Beautifully decorated 3 bedroom, 2 bathroom home located in an exclusive gated community with 24 hour security. It is located less than 10 minutes from Ocho Rios Town and all major attractions (Dolphin's Cove, Mystic Mounta …see more

from $160 / night

$1,116 / week

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from $160 / night

5

Vacation home with golf nearby in St. Ann's Bay

Saint Ann Parish / St. Ann's Bay

6 2 1 night min

  • 6 bedrooms
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Pet friendly
This is a beautiful family home that is located in priory st ann Jamaica. It has beautiful views from every window spectacular views overlooking the ocean and 15mins drive to ocho Rios town centre and a local beach 4 mins away. This home is in the perfect location and …see more

from $93 / night

$651 / week

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from $93 / night

44

Villa rental in St. Ann's Bay with shared pool

Saint Ann Parish / St. Ann's Bay

3 7 2 nights min

  • 3 bedrooms
  • Sleeps 7
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
Beautiful and spacious 3 bedroom home in a modern, eco-friendly, gated community in the Ocho Rios area. There is a gorgeous master bedroom and a master bath. There are high arched ceilings and plantation shutters on every window. Home is fully equipped with all the amen …see more

from $155 / night

$1,085 / week

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Responds fast!
avg. 1 hour 39 minutes

from $155 / night

7

Vacation home in St. Ann's Bay

Saint Ann Parish / St. Ann's Bay

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
Best area to be. Quiet, comfy, secure and affordable. Major spots are just 10 mins away and car rental and chauffeur services are available for an extra fee so just hit me up and let me know. AC room cable TV and everything at your convenience. Overall it is a 4 bedroom …see more

from $40 / night

$280 / week

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from $40 / night

13

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
Experience Jamaica in your own Private Villa located in a Gated Community with 24 Hour Security Ideally located in Drax Hall St Ann close to Ocho Rios Center, Dunn's River Falls, Dolphin Cove, Chukka Cove, Blue Hole, Konoko Falls, Mystic Mountain, Helicopter Tours, Marg …see more

from $119 / night

$828 / week

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from $119 / night

4

Vacation apartment in St. Ann's Bay

Saint Ann Parish / St. Ann's Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Air conditioning
Its a very cosy studio apartment just 5 mins drive to Ocho Rios town center 24 hour security in the complex self contained kitchen with a flat screen Tv on the wall .We can arrange for your meals to be cooked and shopping delivered for a extra fee .This studio is ext …see more

from $75 / night

$525 / week

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Responds fast!
avg. 1 hour 39 minutes

from $75 / night

(2) Excellent 

27

Vacation home rental

Saint Ann Parish / St. Ann's Bay

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 1 mi
  • Child friendly
  • Air conditioning
Rickets Cottage is situated near the sandy beaches of the North Coast, (5 min drive) with many tourist attractions and other places of interest to visit. The Cottage/small house is newly refurbished, self contained with a kitchen, open planned living/dining area, it has …see more

from $60 / night

$400 / week

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from $60 / night

(7) Very Good 

Certificate of Excellence

60

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

Saint Ann Parish / St. Ann's Bay

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The ideal villa for a super vacation, a garden like paradise situeated in a gated community with 24/7 security at Richmond Estate in the Garden Parish of St. Ann. The villa comprise 3 bed rooms and 2 bath rooms , all bed rooms have air conditions and celing fans. It ha …see more

Certificate of Excellence

from $120 / night

$790 - $1,630 / week

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from $120 / night

28

Vacation home with golf nearby in St. Ann's Bay

Saint Ann Parish / St. Ann's Bay

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Nearest beach 3 mi
  • Child friendly
Affordable resort living. The ideal tropical getaway. Suitable for families or business travel. The space Resort living affordably Guest access Pool & Recreational area House Rules No smoking Not suitable for pets No parties or events Check in is anytime after 3PM …see more

from $150 / night

$1,050 / week

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from $150 / night

(17) Excellent 

49

St. Ann's Bay Vacation home rental

Saint Ann Parish / St. Ann's Bay

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
Vibrant and inspirational 3 bedroom Villa to kick start your holiday. This 3 bedroom Villa in The Palms can also be rented as a 1, 2 or 3 bedroom rental, comfortably sleeps up-to 7 guests. The property is located in the gated community of Richmond Estates in Priory on t …see more

from $120 / night

$700 - $1,200 / week

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from $120 / night

(3) Excellent 

73

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

Saint Ann Parish / St. Ann's Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
A scenic community nested between the Caribbean Sea and the lush mountain side in St Ann's Bay. Enjoy the comforts of modern living, the serenity and security of a suburban retreat in the place you can vacation. Veranda overlook the Clear Crystal Waters of the Caribbe …see more

from $230 / night

$1,610 / week

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Responds fast!
avg. 3 hours 32 minutes

from $230 / night

17

Vacation home in St. Ann's Bay

Saint Ann Parish / St. Ann's Bay

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
This brand new property is situated in a safe, gated community nestled in the Drax Hall Community just 10 minutes from Ocho Rios. On the property is a wonderful pool, tennis court, gym, and clubhouse all open for guest use; beaches only minutes away. When you're hungry …see more

from $80 / night

$550 / week

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from $80 / night

7

Apartment accommodation in St. Ann's Bay with swimming pool

Saint Ann Parish / St. Ann's Bay

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Our Villa in Montego Bay St. James has 11 bedrooms to host multiple parties of guests. It is just 15 minutes from the airport with a spectacular view of the Caribbean Sea. Swimming pool/Hot tub and basketball court access included. Our Villa is special because it is fam …see more

from $80 / night

$600 / week

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from $80 / night

36

Vacation home in St. Ann's Bay

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
A destination retreat ideal for individuals, couples or families! (with accommodations for up to six people). The house has 3 bedrooms and 2 baths, including a master bedroom with ensuite. Enjoy a relaxing space in a gated community with 24 hr security while still being …see more

from $91 / night

$637 / week

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avg. 1 hour 38 minutes

from $91 / night

(1) Very Good 

18

St. Ann's Bay Vacation apartment rental

Saint Ann Parish / St. Ann's Bay

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning
Montego Bay Club is a high–rise resort actually built into the side of a mountain, and best of all, it's right across the street from the world–famous Doctor's Cave Beach. Guests can lounge by the top pool and take in the magnificent ocean views. This small apartment h …see more

from $135 / night

$945 / week

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Responds fast!
avg. 3 hours 7 minutes

from $135 / night

12

St. Ann's Bay Vacation apartment rental

Saint Ann Parish / St. Ann's Bay

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Child friendly
My place is close to The heart of Ocho Rios and a short walk from fabulous beaches. . You’ll love my place because of It's security and privacy. It's the perfect location to experience the best of Jamaica. A true local Experience with a perfect mix of the comfort we lov …see more

from $40 / night

$280 / week

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from $40 / night

(3) Very Good 

32

St. Ann's Bay Vacation villa rental

Saint Ann Parish / St. Ann's Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Richmond Estate is an easy 50-minute drive from the airport in Montego Bay, and 15 minutes to Ocho Rios. With captivating views of the mountains and the Caribbean Sea, this green community estate boasts country charm with urban conveniences.--Interaction with Guests--Th …see more

from $85 / night

$955 - $1,830 / week

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Responds fast!
avg. 2 hours 57 minutes

from $85 / night

39

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

Saint Ann Parish / St. Ann's Bay

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Richmond Estate This is an excellent choice for visitors looking for a safe, clean, plush home away from home that will surpass your expectations. Its a fantastic retreat for couples, friends or family. Its definitely one of the best locations on the island! The spac …see more

from $114 / night

$798 / week

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Responds fast!
avg. 2 hours 30 minutes

from $114 / night

(11) Excellent 

31

St. Ann's Bay ski villa to rent.

Saint Ann Parish / St. Ann's Bay

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 6 mi
  • Swimming pool
The community is very safe with 24hr security and mobile patrol to ensure you are safe in walking or jogging around our community. This 3 bedroom villa comes equipped with all the modern amenities and conveniences of a modern home. It is beautifully decorated with vib …see more

from $105 / night

$750 - $1,170 / week

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Responds fast!
avg. 2 hours 0 minutes

from $105 / night

17

St. Ann's Bay Vacation villa rental

Saint Ann Parish / St. Ann's Bay

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Your own Cozy 2 bedroom Villa situeated in a Gated community of Drax Hall Country club with 24 hr security and only 5 to 10 minutes away from major tourist attractions such as, Dunn's River Falls, Dolphin Cove, Mystic Mountain, Chukka Cove, Blue Hole, White River , Shaw …see more

from $75 / night

$525 - $665 / week

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from $75 / night

(1) Excellent 

16

St. Ann's Bay Vacation bungalow rental

Saint Ann Parish / St. Ann's Bay

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 2 mi
  • Child friendly
  • Air conditioning
Sunshine Villa is home away from home. You will feel welcome from the time you enter the complex. This homely villa is close to Mammee Bay, approximately 10 minutes drive from Ocho Rios and 10.6 miles from Runaway Bay. You can be sure to relax in a spacious comfortabl …see more

from $110 / night

$770 / week

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from $110 / night

2

St. Ann's Bay Vacation home rental

Saint Ann Parish / St. Ann's Bay

4 1 night min

  • Sleeps 4
  • 1 night min
  • Child friendly
Enjoy Jamaica in true form. Our comfortable 2 bedroom,2 bathroom home in the historic town Falmouth sleeps five. The house is located in the gated community of Florence Hall Village, a stone throw from the home of Air Jamaica Jazz & Blue Festival. Our home provides al …see more

from $57 / night

$342 / week

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from $57 / night

15

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
  • Child friendly
  • Car not necessary
  • Air conditioning
A three bedroom two bathroom house in Jamaica overlooking the blue Caribbean Sea . This property has access to a private beach approximately five minutes across the main road. Sandals Whitehouse is about ten minutes drive from the house and about one hours drive from th …see more

from $93 / night

$465 - $2,139 / week

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from $93 / night

(4) Very Good 

38

Vacation villa 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
Richmond Estate is an easy 50-minute drive from the airport in Montego Bay, and 15 minutes to Ocho Rios. With captivating views of the mountains and the Caribbean Sea, this green community estate boasts country charm with urban conveniences.--Interaction with Guests--Th …see more

from $145 / night

$1,015 / week

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Responds fast!
avg. 2 hours 57 minutes

from $145 / night

25

St. Ann's Bay Vacation cottage rental

Saint Ann Parish / St. Ann's Bay

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Ask about children
  • Ask about pets
Stay once and you will never want to leave. You will spend a glorious vacation in a totally romantic, private, secure property that sits on a point over-looking the ocean. Outside the front door you can listen and see hummingbirds on the quiet path through almond trees …see more

from $90 / night

$600 - $950 / week

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from $90 / night

43

Vacation home in St. Ann's Bay

Saint Ann Parish / St. Ann's Bay

4 6 3 nights min

  • 4 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 20 mi
  • Suitable for children age 5+
  • Ask about pets
Make the most out of your island getaway by staying at Jazzy Glen's Place in St. Ann, Jamaica. Book our vacation rental any time by calling our friendly representatives in Brooklyn, New York. Our beautiful vacation home lies along the panoramic Caribbean coast, and is …see more

from $65 / night

$420 - $945 / week

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from $65 / night

(4) Excellent 

37

St. Ann's Bay Vacation home rental

Saint Ann Parish / St. Ann's Bay

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
We are in great company and so will you. This newly built, fully furnished, 2 BR,1 BR, is available as a perch or home on a long or short term basis, today! Sleeps 4 comfortably! Neighbouring Riu Hotel, Mammee Bay and only 10 minutes from Downtown Ocho Rios, 7 minute …see more

from $90 / night

$630 / week

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from $90 / night

20

Vacation home in St. Ann's Bay

Saint Ann Parish / St. Ann's Bay

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Come share our Jamaican Dream. Fully-furnished 3-bedroom, 2-bath villa with TV/Cable/WiFi and air conditioning/ceiling fan in bedrooms and living/dining room. Kitchen is fully outfitted with stove, dishwasher, fridge, coffee maker, blender and washer/dryer. Housekeeper …see more

from $150 / night

$1,000 - $1,300 / week

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from $150 / night

11

Vacation bungalow with golf nearby in St. Ann's Bay

Saint Ann Parish / St. Ann's Bay

3 8 5 nights min

  • 3 bedrooms
  • Sleeps 8
  • 5 nights min
  • Child friendly
Located three minutes from the North-South Highway (taking you into St. Catherine and Kingston); this newly-built 3 bedroom / 3.5 bathroom gated community home is ideal away-home in St. Ann. It is 10 minutes away from the towns of Ocho Rios and Runaway Bay in each dire …see more

from $140 / night

$1,000 / week

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from $140 / night

(13) Very Good 

30

St. Ann's Bay Vacation apartment rental

Saint Ann Parish / St. Ann's Bay

1 6 3 nights min

  • 1 bedroom
  • Sleeps 6
  • 3 nights min
  • Nearest beach 0.1 mi
  • Swimming pool
  • Child friendly
This bi level apartment is perfect for a weekend getaway or a month in the jamaican sun. It features a king size foam bed up stairs in a loft style kind of room. There is another king size mattress that can be placed on the floor and is useful if you have more than 4 g …see more

from $80 / night

$350 / week

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Responds fast!
avg. 2 hours 15 minutes

from $80 / night

21

Apartment rental in St. Ann's Bay

Saint Ann Parish / St. Ann's Bay

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Private garden
CasaBamboo caters to travelers who wants an affordable vacation rental, but who wants the best, a home away from home. The apartment is located in the Greenwich Acres community, 10 minutes away from Ocho Rios and all major tourist attractions. We offer 3 bedrooms, (Que …see more

from $40 / night

$280 / week

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from $40 / night