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Holiday Rentals with Pools in Portland Parish

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    ₹ 33,309 Average
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    Travellers to Portland Parish are booking March dates now. Secure your holiday home today, and have the perfect trip.
    23 Matching Rentals in Portland ParishView all 91 rentals
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    All Nations Guesthouse - Superior Double Bedroom, Jacuzzi tub, Pool & Gym area1 / 35
    (3)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Mountain Views
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Ocean Views
    • Hot Tub
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 June 2017
    The location is wonderful - within easy reach of Port Antonio town. Surrounded by beautiful lush greenery, with a view of the sea from the terrace where you can eat breakfast...
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    About this property
    All Nations Guesthouse is suitable for all type of travelers visiting Jamaica. Our villa is 3 floors, the top floor is reserved for the luxury rooms with pvt terrace, the middle floor for the common spaces as kitchen and living room, and at the first floor 2 double room with Jacuzzi. All Nations Is...
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    Port Antonio, Portland Parish JMBPD15
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Iya Ites Jamaica1 / 48
    (3)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Internet Access
    • Housekeeping Included
    • Patio
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 November 2017
    One of my friends booked this place through Airbnb and it's beautiful. The chef made us dinner and breakfast and it was amazingly good. The best view you can get if staying in...
    Reviewed 6 April 2017
    My friends and I found the perfect place to rest our heads while fishing the just-concluded Port Antonio Spring Tournament. Beautiful, cool and well appointed rooms, the best...
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    About this property
    We are a small Guest House Overlooking the entire town of Port Antonio, the Harbours, piers, Navy Island(once owned by Errol Flynn) , Mountains and surrounding areas. Very peaceful, romantic surroundings with the feel of home away from home. We have a total of 4 bedrooms, each room sleeps 2, with...
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    Port Antonio, Portland Parish JAMAICA
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Shotover Gardens Estate - cottage with pool1 / 14
    (5)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Porch
    • Mountain Views
    • Parking
    • Private Outdoor Pool (Heated)
    • Shared Garden
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 June 2016
    Shotover is a wonderful place to be if your looking for peace and quite. I enjoyed the nice pool and the cottage. There was one dog on the property that was good nature and...
    Reviewed 13 October 2015
    My first time in Port Antonio and the stayed at Shot Over which sat on top of a mountain so peacefull and beautifull lots of fruit trees. It's a mountain drive but once you get...
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    About this property
    Shotover Gardens Estate offers a one bedroom cottage. The cottage is set in 6 acres of forests, lawns, gardens and pool. It is 1000 feet up in the hills outside Port Antonio, Jamaica, It is a 20 minute drive from downtown Port Antonio. The property is secure and very private, giving guests the...
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    Port Antonio, Portland Parish 00
    Cabin Holiday Rental - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Washer
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Patio
    • Mountain Views
    • Air Conditioning
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    All Nations Guesthouse is suitable for all type of travelers visiting Jamaica. Our villa is 3 floors, the top floor is reserved for the luxury rooms with pvt terrace, the middle floor for the common spaces as kitchen and living room, and at the first floor 2 double room with Jacuzzi. All Nations Is...
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    Port Antonio, Portland Parish JMBPD15
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Birdie ‘ill Villa1 / 7
    (4)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Waterfront
    • Washer
    • Cable/satellite TV
    • Internet Access
    • Balcony
    • Private Outdoor Pool (Heated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 January 2017
    Everything about this Villa is breath takingly amazing. It's a private Oasis. The view of the Ocean from the house is a Dream. Very Lush and floral hiking trail. Lovely Pool and...
    Reviewed 2 January 2017
    This is a great place for multiple people to stay (3 bedrooms) if you're looking for quasi seclusion and don't mind driving (or being driven) on the incredibly terrible roads in...
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    About this property
    Built by the Woolworth family in the early 60′s, Birdie ‘ill Villa is described as Jamaican Colonial Architecture with a French flair. Birdie ‘ill Villa formerly named Pixie Hill, is located on 5 acres of lush gardens and pathways overlooking the ocean. The likes of Vogue, German Bunte, Town &...
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    Location Information
    Port Antonio, Portland Parish JMBPD15
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Tranquility Villa~Port Antonio1 / 11
    (33)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Balcony
    • Ocean Views
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 March 2017
    I can't begin to say enough about our stay at Tranquility Villa. It surpassed all our expectations and then some!If you are looking for a five-star hotel with all the...
    Reviewed 19 March 2017
    spectacular view and tranquility is the perfect word to describe this villa. Dennis and Bev are the best host we have had over the years travelling. ask them to cook some jerk...
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    About this property
    Your Jamaican Home Away from Home ~ Lounge pool side, gaze out at the ocean from your living room or front porch ... watch the colors change over the Blue Mountains from your bedroom balcony - Nestled 1/4 mile up Richmond Hill overlooking Port Antonio & its magnificent harbor 'Tranquility' is...
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    Location Information
    Port Antonio, Portland Parish WI
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Private Outdoor Pool (Heated)
    • Washer
    • Internet Access
    • Parking
    • Mountain Views
    • Shared Garden
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bolt Hole Villa is located in Port Antonio on a one acre estate overlooking the spectacular Caribbean Sea. With its beautiful breathtaking ocean front view, you can escape all your cares and unwind in the peaceful and tranquil atmosphere. The villa is of Jamaican Colonial architecture, uniquely...
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    Location Information
    Port Antonio, Portland Parish JMBPD15
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Spicy Hill Villa, 5 Bedroom, Port Antonio, Jamaica1 / 30
    (17)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    • Washer
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Hot Tub
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 August 2017
    This villa was everything right with a vacation. We got there late on our first day. Denny, Keith, and Karen were there to greet us and show us around the property. There...
    Reviewed 18 March 2016
    A genuine 5 star loaction and accommodation.It was so comfortable,clean and spacious with fabulous grounds,a lovely swimming pool and cool games room.Only a short walk to...
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    About this property
    Spicy Hill Villa, one of Jamaica's best-kept secrets. In a secluded tropical setting surround yourself in luxury. Spend romantic candle lit moments dining around the pool or watch the sunrise on the bay.  Spicy Hill Villa is a Jamaica Tourist Board approved Villa, this achievment sets us apart from...
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    Location Information
    Port Antonio, Portland Parish SAN SAN
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Shotover Gardens Estate - cabin with pool1 / 15
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Secure Parking
    • Wi-Fi
    • Shared Garden
    • Terrace
    • Porch
    • Mountain Views
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 January 2015
    First let me start by saying how peaceful and out if the way shot over gardens is. The road leading up to the gate is rough but well worth it just for the amazing views. The...
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    About this property
    Shotover Gardens Estate offers a one bedroom studio cabin The cabin is set in 6 acres of forests, lawns, gardens and pool. It is 1000 feet up in the hills outside Port Antonio, Jamaica, It is a 20 minute drive from downtown Port Antonio. The property is secure and very private, giving guests the...
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    Location Information
    Port Antonio, Portland Parish 00
    Cabin Holiday Rental - 1 Bedroom, 1 Bathroom, Sleeps 2
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    OCEAN VIEW LUXURY 5 ACRE STAFFED ESTATE1 / 15
    (4)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Patio
    • Private Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Hot Tub
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 July 2017
    Port Antonio is an area of outstanding natural beauty, friendly, relaxed locals and vibrant market place, great beaches all around and a special mention Frenchmans Cove which...
    Reviewed 13 June 2014
    Staying at the villa was truly a unique experience. The staff was amazingly friendly and attentive and made our stay a memorable one.The location of the villa was very private...
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    About this property
    PRIVATE 5 ACRE LUXURY STAFFED ESTATE WITH BEAUTIFUL OCEAN AND MOUNTAIN VIEWS- CONSISTING OF 4 BEDROOMS, 4 BATHROOMS ,OPEN AIR CONCEPT, GORGEOUS COURTYARD WITH JACCUZI, SWIMMING POOL FREE WIFI, OVERSEAS CALLS . 20% OFF LIMITED TIME - JUNE, JULY. AUG, SEPT, OCT.. Port Antonio (San San estate)...
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    Location Information
    Port Antonio, Portland Parish 1111111
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Luxe Modern Six-bedroom Cocosan Villa, Access to Geejam Hotel & Vintage Cars1 / 15
    (1)Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Sauna
    • Air Conditioning
    • Ocean Views
    • Mountain Views
    • Cable/satellite TV
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 March 2017
    This Villa is Spectacular !Modern and luxuriously spacious !It's such an interesting place.We enjoyed our time seeing Cocosan!The views are spectacular !Gym well...
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    About this property
    The next-level six-bedroom Cocosan Villa sits 200 meters above sea level with stunning views over Portland’s coastline, featuring a private spa, gym, lap pool and heated plunge pool. The design reinterprets the use of local materials in order to create a tropical contemporary atmosphere. Many of...
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    Location Information
    Port Antonio, Portland Parish 00000
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    Shotover Gardens Estate-Villa with Pool1 / 20
    (13)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Washer
    • Mountain Views
    • Grill
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 April 2016
    the place is a complete standstill of peace. Excellent for the enlightened minds.. a positive vibration, a magical venue, the energy there is pure light, an extremely romantic...
    Reviewed 16 March 2014
    I am getting ready for another Jamaica trip and will be returning to Shotover Gardens. I just realized I did not do a review from the last stay. I always stay in the cottage. It...
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    About this property
    Shotover Gardens Estate offers a three bedroom villa ( 3 day minimum) The villa is set in 6 acres of forests, lawns, gardens and pool. It is 1000 feet up in the hills outside Port Antonio, Jamaica, It is a 20 minute drive from downtown Port Antonio. The property is secure and very private,...
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    Location Information
    Port Antonio, Portland Parish 000
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Waterfront
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Mountain Views
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Soothing sounds of nature complement your walks through aromatic fruit and vegetable gardens. Mystical waterfalls, refreshing springs, abundant rivers meet you at every turn and offer you a chance to renew and reset. Various packages are offered at this resort including a 22 Day Transformation...
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    Location Information
    Port Antonio, Portland Parish W I
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 4
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    Luxe 4-Bedroom Panorama Villa/Access to Geejam Hotel and a Fleet of Vintage Cars1 / 12
    (2)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Mountain Views
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Housekeeping Included
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 April 2017
    This Villa is perfection!Sprawling one floor, the most wonderful layout The carefully placed windows, the exotic views, hard to compare Add the Vintage cars, it's hard to...
    Reviewed 2 April 2017
    Located at the top of the hill overlooking the beautiful blue/green ocean waters, this 4 bedroom villa is the creme de la creme of properties. Complete privacy with it's own...
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    About this property
    More than an island retreat, the four-bedroom Panorama Villa, once frequented by Audrey Hepburn, is a contemporary residence set on an acre of naturally landscaped gardens that offer stunning views of the Caribbean Sea, Portland’s Coastline, and the enchanting silhouette of the Blue Mountains....
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    Location Information
    Port Antonio, Portland Parish 00000
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bedroom 1 - 1 king; 2 people Bedroom 2 - 2 double (put together as king); 2 people Bedroom 3 - 2 double (put together as king); 2 people Bedroom 4 - 2 queen , loft area has two singles.; 4 people   Cottage: Master (upstairs) King bed; 2 people Downstairs two singles; 2 people The entire...
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    Location Information
    Port Antonio, Portland Parish JMBPD05
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Norse Hill villa in Jamaica, Port Antonio, For Vacationers looking for a unspoiled beauty and away from the tourist hub, perfect hideaway, very private and a true get away to Jamaica's most beautiful parish. It is a 2 hour drive from the airport, so only people who know this gem will return to the...
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    Location Information
    Port Antonio, Portland Parish JMBPD05
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Patio
    • Air Conditioning
    • Hot Tub
    • Mountain Views
    • Washer
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    All Nations Guesthouse is suitable for all type of travelers visiting Jamaica. Our villa is 3 floors, the top floor is reserved for the luxury rooms with pvt terrace, the middle floor for the common spaces as kitchen and living room, and at the first floor 2 double room with Jacuzzi. All Nations Is...
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    Location Information
    Port Antonio, Portland Parish JMBPD15
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Housekeeping Included
    • Parking
    • Wi-Fi
    • Balcony
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Specially designed for small families or group of friends, guests can enjoy the comforts of home. The villa has its own private area to the pool. The apartment has a kitchen, patio, wifi, maid service, 3 bathrooms, and the breathtaking views. We are ideally located 5 miles east of the quaint and...
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    Drapers, Portland Parish 00000
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Parking
    • Air Conditioning
    • Patio
    • Housekeeping Included
    • Wi-Fi
    • Balcony
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa B is a spacious one bedroom villa. View of the pool and the Caribbean sea. The villa balcony is most ideal for the glorious sunset gazing. Equipped with wifi, daily maid service, balcony with outside seating area & private pool entrance. ROOM AMENITIES Sea view Garden Pool view & sea View...
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    Location Information
    Drapers, Portland Parish 0000
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Patio
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Hot Tub
    • Internet Access
    • Ocean Views
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    All Nations Guesthouse is suitable for all type of travelers visiting Jamaica. Our villa is 3 floors, the top floor is reserved for the luxury rooms with pvt terrace, the middle floor for the common spaces as kitchen and living room, and at the first floor 2 double room with Jacuzzi. All Nations Is...
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    Location Information
    Port Antonio, Portland Parish JMBPD15
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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