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

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36 Vacation rentals

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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from $120 / 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 $145 / night

$1015 / week

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from $145 / night

(1) Excellent 

62

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

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
An awesome view of the beautiful Caribbean Sea from sitting on the porch in addition to all the comfort of a tastefully decorated home at a lower cost than most hotels in Ocho Rios, Jamaica. Available for your comfort is a master bedroom that has a king size bed with …see more

from $145 / night

$950 / week

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from $145 / 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

(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 $130 / night

$910 / week

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from $130 / 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
  • Suitable for children age 5+
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

$1260 / 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

30

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

Saint Ann Parish / St. Ann's Bay

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
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 $100 / night

$700 / week

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from $100 / 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

(15) Excellent 

Certificate of Excellence

63

St. Ann's Bay Vacation home rental

Saint Ann Parish / St. Ann's Bay

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
Gorgeous and affordable two bedroom property that can also be rented as a one bedroom property. The perfect getaway, we welcome families, groups of friends and all like-minded to our Oasis that is located in a private, quiet and very secure gated community which is situ …see more

Certificate of Excellence

from $110 / night

$770 - $980 / week

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from $110 / night

(4) Very Good 

38

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 $145 / night

$1015 / week

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from $145 / night

(10) Excellent 

Certificate of Excellence

29

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 13 mi
  • Swimming pool
Kreations Cozy 3 bedroom Villa is nestled away in the lush, scenic gated community of Richmond Estates, St. Ann. Just 20 minutes from Ocho Rios and 45 minutes from Donald Sangster International Airport. This eco-friendly community of Richmond offers 24 hours security, …see more

Certificate of Excellence

from $109 / night

$750 - $1320 / week

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from $109 / 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 $90 / night

$448 - $2061 / week

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from $90 / 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. Ever wanted to sleep under the stars but stay inside on a comfy bed? the upstairs ceiling is painted to look like you are outside. It features a king size foam bed up stairs in a l …see more

from $80 / night

$350 / week

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from $80 / 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 $75 / night

$400 - $950 / week

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from $75 / night

(3) Excellent 

60

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
  • 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

from $110 / night

$770 - $1630 / week

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from $110 / 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

18

Vacation chalet 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 6 mi
  • Ask about children
  • Ask about pets
FREE: Shuttle Service. Teresinajamaica. A unique eco-lodge chalet located in a rustic country side setting. We offer you a natural and realistic living at home Jamaican experience. Teresina is a unique eco-lodge chalet located inside the foot hills of the S …see more

from $175 / night

$1295 / week

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from $175 / 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

28

Vacation cottage in St. Ann's Bay

Saint Ann Parish / St. Ann's Bay

4 10 1 night min

  • 4 bedrooms
  • Sleeps 10
  • 1 night min
  • Child friendly
  • Ask about pets
  • Private garden
Here at Liberty Hill Comfort Inn Suites our goal is that our guest have total control of there stay weather its business or vacation. We take pride in your comfort being we are a family owned business. Liberty Hill Comfort Inn Suites is located near Ocho Rios one of Ja …see more

from $50 / night

$350 / week

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from $50 / night

(3) Excellent 

73

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
  • 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 $140 / night

$980 / week

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from $140 / 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 $100 / night

$945 / week

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from $100 / night

(1) Excellent 

23

Vacation home rental

Saint Ann Parish / St. Ann's Bay

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden
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 $55 / night

$360 / week

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from $55 / night

(2) Very Good 

32

St. Ann's Bay Vacation villa rental

Saint Ann Parish / St. Ann's Bay

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • 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 $155 / night

$1085 / week

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from $155 / night

28

St. Ann's Bay Vacation villa rental

Saint Ann Parish / St. Ann's Bay

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 0.8 mi
  • Swimming pool
  • Ask about children
Three bedroom villa situated in Richmond Estate, Priory, North Coast. one hour from montego bay airport, 15 minutes drive from Ocho Rios. Beautiful gated community, 24 hours security. The villa has fully functioning kitchen, two bathrooms one of which is en suite …see more

from $180 / night

$1200 / week

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from $180 / night

5

Vacation home accommodation

Saint Ann Parish / St. Ann's Bay

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 6 mi
  • Child friendly
Three bedroom beach house in cool and casual Portland, Jamaica, Everything IRIE! Walk out of bed into sea and sun. Enjoy the company of friends and family in a tranquil atmosphere. Easy commute to eco-tourism attractions and authentic Jamaican food spots. Enjoy our seas …see more

from $280 / night

$1960 / week

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from $280 / night

18

St. Ann's Bay Vacation villa 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
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 $90 / night

$620 - $1040 / week

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from $90 / night

(4) Excellent 

37

St. Ann's Bay Vacation home 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
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 $100 / night

$700 / week

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from $100 / night

12

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 $60 / night

$420 / week

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from $60 / night

16

St. Ann's Bay Vacation home rental

Saint Ann Parish / St. Ann's Bay

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
Guests love this very large new 3 bedroom and 2 1/2 bathroom vacation home in the beautiful North Coast of Jamaica! My place is close to some of the world's best beaches, great views, tourist attractions, diving, snorkeling, art and culture, restaurants and bars, and v …see more

from $89 / night

$623 / week

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from $89 / night

5

Vacation apartment in St. Ann's Bay

Saint Ann Parish / St. Ann's Bay

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Private garden
HOME AWAY FROM HOME IS IN THE COOL HILLS OF WINDSOR HEIGHTS, APPROXIMATELY FIVE MINUTES DRIVE AWAY FROM THE TOWN AREA ST. ANN'S BAY AND APPROXIMATELY EIGHT MINUTES DRIVE AWAY FROM THE BEACH. IT TAKES ONLY FIFTEEN MINUTES DRIVE TO ENJOY THE BEAUTIFUL DUNN'S RIVER FALLS. …see more

from $80 / night

$560 / week

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from $80 / 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

9

Vacation cottage in St. Ann's Bay

Saint Ann Parish / St. Ann's Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 3 mi
  • Swimming pool
  • Air conditioning
The Dollhouse cottage is located in a quiet corner of the historic Willows Estate.This beautiful cottage was once the childhood playhouse of the owners daughter. The whimsical gingerbread decoration and bright tropical colors echo of those happy times. This beautiful co …see more

from $195 / night

$2500 / week

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from $195 / night

13

Townhouse rental in St. Ann's Bay

Saint Ann Parish / St. Ann's Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 3 mi
  • Child friendly
  • Air conditioning
This jewel of a treehouse is part of the beautiful willows estate. Nestled in the lush tropical forest there are exceptional views of the rolling lawn and sea as well as the surrounding forest. The traditional spacious design has walls of windows and French doors that o …see more

from $195 / night

$2500 / week

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from $195 / night

26

Villa rental in St. Ann's Bay

Saint Ann Parish / St. Ann's Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 3 mi
  • Swimming pool
  • Child friendly
The Willows c1840 is one of the finest remaining examples of the traditional Jamaican country house. This architectural gem exhibits all the charming features of these colorful wooden houses. The beautiful grounds of the willows are part of the private estate on 50 acre …see more

from $485 / night

$7000 / week

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from $485 / night

1