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St. Ann's Bay Holiday Rentals with Pools

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    Travellers to St. Ann's Bay are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    25 Matching Rentals in St. Ann's BayView all 45 rentals
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    Sea Shell Villa   Ocean View1 / 68
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Garden Villa Ocho Rios St.Ann1 / 55
    (5)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Oasis at The Palms - Richmond - Ocho Rios - St.Ann1 / 49
    (16)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Kreations Cozy Villa- Stay for 6 Get 7th Night Free*1 / 29
    (10)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Ocean Views
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Housekeeping Included
    • Waterfront
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 July 2016
    Stayed at Kreations Cozy Villa twice..Andrea is the best host ever..Definitely will be staying there again..Home away home..
    Reviewed 24 July 2016
    My family and I consider this Kreations Cozy Villas our second home. Year after year we return this wonderful community were are treated like extended family. The community is...
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    About this property
    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, with modern amenities and...
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    St. Ann's Bay, Saint Ann Parish ST ANN
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Private Garden
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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, business travelers, and...
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    St. Ann's Bay, Saint Ann Parish 876
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 BD VILLA /HOUSEKEEPER/AIRPORT TRANSFER RETURNS1 / 29
    (7)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • DVD Player
    • Satellite TV
    • Patio
    • Housekeeping Included
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 March 2017
    Perfect Safe location , very clean home . House keeper made the most amazing food and driver really went out of his way to make my 1st trip to jamicia amazing ! Pool and gym on...
    Reviewed 25 April 2014
    My family and I came in from New York, and could not have picked a better place to stay. Everything was nice, neat, clean and cool. This 3 bedroom house in a quiet gated...
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    About this property
    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 * Chukka Cove* Green Grotto...
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    St. Ann's Bay, Saint Ann Parish ST ANN
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    COZY Coolshade Villa1 / 38
    (4)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Children's Pool
    • Washer
    • Waterfront
    • Mountain Views
    • Grill
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 December 2016
    This was a great experience. Greeted by Mr. Keith. House was amazing. Updated appliance and felt very much like home away from home. The AC was an absolute A+ , Will stay here...
    Reviewed 11 July 2016
    Mr. Keith and his staff went over and beyond to make us feel comfortable. Very professional,clean,polite,and helpful. Our family will be doing business with Mr. Keith in the...
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    About this property
    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--This is primarily a self-serve...
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    St. Ann's Bay, Saint Ann Parish 876
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Villa 99 at the Palms1 / 32
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Garden
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 March 2017
    Place was nice. Keith was very friendly and helpful. Missing a few things that should be there for it being a place where you are doing your own cooking. But we let Keith know...
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    About this property
    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--This is primarily a self-serve...
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    Location Information
    St. Ann's Bay, Saint Ann Parish 00000
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Haven Villa @ Richmond1 / 61
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Washer
    • Satellite TV
    • Mountain Views
    • Children's Pool
    • Wi-Fi
    • Ocean Views
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 November 2015
    I stayed 5 days with my spouse and friends. The house is beautiful and very clean. It is exactly as pictured if not better. The housekeeper (sorry forgot her name!) was very...
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    About this property
    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 an ensuite bathroom, the...
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    Location Information
    St. Ann's Bay, Saint Ann Parish 0310
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Satellite TV
    • Housekeeping Included
    • DVD Player
    • Wi-Fi
    • Washer
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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. Dining area and sitting...
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    Location Information
    St. Ann's Bay, Saint Ann Parish JAMAICA
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Gorgeous, Private and Secure Country Club Home #21 / 26
    (6)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Satellite TV
    • Secure Parking
    • Private Garden
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 April 2017
    The villa was new and updated. We first had the 4 bedroom but there were some issues that I don't believe was the fault of the owner. There were some services that were not...
    Reviewed 22 April 2017
    The guest house was very beautiful and family oriented. Great location and great amenities would definitely book again.
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    About this property
    This is a replica of our original home, with a few additions. This home, as our original home, has its own private en-suite bathroom in the master bedroom, that is furnished fully with a queen sized bed and a walk in closet. The second bedroom, slightly different from our original home has its own...
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    St. Ann's Bay, Saint Ann Parish JAMAICA
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 7
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    Drax Hall Country Club, Ocho Rios.1 / 36
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Patio
    • Mountain Views
    • Satellite TV
    • Ocean Views
    • Washer
    • Children's Pool
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 March 2017
    This place is BEAUTIFUL and it has New York weather A/C... fully furnished bathroom and kitchen the pictures don't lie! What you see doesn't do this place justice you have to...
    Reviewed 9 January 2017
    This place is just perfect!!! So after not spending Christmas in Jamaica for over 20 years...spent 4 nights with husband and daughter and it was amazing. This home was...
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    About this property
    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 minutes from Dunn's River Falls,...
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    St. Ann's Bay, Saint Ann Parish 00000
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    salem apartment1 / 29
    (13)Very good
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Satellite TV
    • Balcony
    • Terrace
    • Parking
    • Washer
    • Ocean Views
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 February 2016
    We stayed for only one week but this is a perfect place to sit back and relax and do your own thing. Jaclyn has everything a person needs to make your stay enjoyable. When we...
    Reviewed 16 September 2015
    Absolutely loved the Villa. It was mid sized and had everything that you could possibly need. Would absolutely return here and I will!!
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    About this property
    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 loft style kind of room. Above...
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    St. Ann's Bay, Saint Ann Parish 99999
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Nadz Chalet1 / 24
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Secure Parking
    • DVD Player
    • Wi-Fi
    • Balcony
    • Washer
    • Ocean Views
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 July 2015
    Greatly landscaped property,clean great size rooms & safe. We received a nice fruit basket as a welcome gift! The only things I didn't like was the owner had her personal...
    Reviewed 7 May 2014
    Nadz Chalet, is in an excellent location on the grounds, the owner was accommodating and she provided the extra touch with some fruits to welcome us upon arrival. The unit had...
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    About this property
    Enjoy your holidays in the tropical paradise of Jamaica<BR><BR>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 have ceiling fans. The...
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    St. Ann's Bay, Saint Ann Parish 1000
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Satellite TV
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Private Garden
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 acess to pool, gym and community...
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    St. Ann's Bay, Saint Ann Parish JAMAICA
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sunset Beach Studio1 / 18
    (1)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Waterfront
    • Mountain Views
    • Porch
    • Secure Parking
    • Housekeeping Included
    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 January 2015
    My wife and I rented this unit for 4 days. This is not a 5-star hotel, but if you really want to know how the locals live this is perfect. If you are looking for a clean place...
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    About this property
    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 has all the essentials; air...
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    St. Ann's Bay, Saint Ann Parish
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 cottage is both charming and...
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    Location Information
    St. Ann's Bay, Saint Ann Parish NONE
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 7 Bathrooms, Sleeps 2 Quick View
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    • Satellite TV
    • DVD Player
    • Patio
    • Washer
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 family run and we treat you like...
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    Location Information
    St. Ann's Bay, Saint Ann Parish 0000
    Condo/Apartment - 1 Bedroom, 7 Bathrooms, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    • Private Garden
    • Shared Outdoor Pool (Unheated)
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 amenities you can imagine. There...
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    Location Information
    St. Ann's Bay, Saint Ann Parish ST ANN
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Porch
    • Waterfront
    • Secure Parking
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wonderful Vacation Villa Pool Outdoor Grill Area Kitchenette Near to tourist attractions Quiet Air Conditioning Babysitting Available
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    Location Information
    St. Ann's Bay, Saint Ann Parish 876
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
    • Housekeeping Included
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    St. Ann's Bay, Saint Ann Parish
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Satellite TV
    • Private Garden
    • Air Conditioning
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 acres directly above the town of...
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    St. Ann's Bay, Saint Ann Parish
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Patio
    • Washer
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    St. Ann's Bay, Saint Ann Parish
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Children's Pool
    • Wi-Fi
    • Air Conditioning
    • Private Garden
    • Satellite TV
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 comfortable setting in a private gated...
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    Location Information
    St. Ann's Bay, Saint Ann Parish JAMAICA
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Garden
    • Wi-Fi
    • Air Conditioning
    • Children's Pool
    • Satellite TV
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 Park Gardens & Waterfall and...
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    Location Information
    St. Ann's Bay, Saint Ann Parish 00000
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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