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Portland Parish Holiday Rentals with Pools

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    Travellers to Portland Parish are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    22 Matching Rentals in Portland ParishView all 78 rentals
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    Birdie ‘ill Villa1 / 7
    (4)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Tranquility Villa - Port Antonio & Blue Mountains1 / 66
    (33)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    CHATEAU EN EXOTICAN RENOWNED PRIVATE ESTATE . GRADS, HONEYMOON SUMMER DISCOUNT*1 / 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 7 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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    Iya Ites Jamaica1 / 48
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Parking
    • Internet Access
    • Housekeeping Included
    • Patio
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed 29 March 2016
    We stayed at this property for 3 weeks in late December through mid January. Iya Ites was under renovations during the time of our stay, but it did not effect our enjoyment of...
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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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    Location Information
    Port Antonio, Portland Parish JAMAICA
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Waterfront
    • Housekeeping Included
    • Mountain Views
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • 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, daily maid service, 3 bathrooms, and the breathtaking views. ROOM AMENITIES Sea view Toaster, Stovetop,...
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    Location Information
    Port Antonio, Portland Parish 00000
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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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 15 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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    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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    Location Information
    Port Antonio, Portland Parish JMBPD15
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Crystal Cove villa in Jamaica, Port Antonio, For Vacationers looking for a unspoiled beauty and away from the tourist hub, perfect hideaway, very private 3 bedrooms, 3 bathrooms Housekeeper/cook, handyman, house maid Air conditioning, ceiling fans in all bedrooms Cable TV, DVD, CD player Kayak,...
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    Location Information
    Port Antonio, Portland Parish
    Holiday Rental House - 3 Bedrooms, 3 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
    • 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 2 weeks ago
    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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    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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    Shotover Gardens Estate - cottage with pool1 / 14
    (5)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • 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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    Location Information
    Port Antonio, Portland Parish 00
    Cabin Holiday Rental - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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    Avalon Blue Lagoon, Port Antonio. Jamaica Villas 3BR1 / 26
    (1)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Grill
    • Washer
    • DVD Player
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 June 2017
    My mom, sister & myself and our children spent 4 relaxing & visually invigorating days @ Avalon. The closest of the villas to Blue Lagoon-200 ft oasis w/ natural...
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    About this property
    Brand new luxury villa on the Blue Lagoon in Jamaica! Avalon is located on famous Blue Lagoon, famous for is beauty, waterfront edge villas and crystalline blue waters! Avalon is one of the newest additions to the list of private luxury villas and the nearest to the famous Blue Lagoon. This villa...
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    Location Information
    Port Antonio, Portland Parish
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Satellite TV
    • Patio
    • Private Outdoor Pool (Unheated)
    • Porch
    • Waterfront
    • Air Conditioning
    • DVD Player
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    San Bar villa is located in Jamaica's world-renowned Port Antonio. This luxurious 6 bedroom villa sleeps a total of 8 adults and 6 children. Relax in exotic comfort & style. Sun tan on the beautiful deck, dine in our gorgeous dining room, or on the balcony. Swim in our plunging pool or snorkel in...
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    Location Information
    Port Antonio, Portland Parish
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    All Nations Guesthouse - Superior Double Bedroom, Jacuzzi tub, Pool & Gym area1 / 35
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • 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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    Location Information
    Port Antonio, Portland Parish JMBPD15
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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    Amenities & Details
    • Sauna
    • Air Conditioning
    • Ocean Views
    • Mountain Views
    • Satellite TV
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 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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    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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    Amenities & Details
    • Mountain Views
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • DVD Player
    • 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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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • 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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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Satellite TV
    • Grill
    • Air Conditioning
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on the famous Blue Lagoon, an exquisite 5-bedroom waterfront villa Sea Star Sea Star Villa is one of the most amazing luxury villas Jamaica nestled between the sparkling Caribbean Sea in Port Antonio and the lush foliage of Portland. The latest addition to the exceedingly luxurious villas...
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    Location Information
    Portland Parish, Jamaica
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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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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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Private Garden
    • Secure Parking
    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This pied-à-terre apartment is ideal for couples or friends wanting to decompress and indulge in the good life, relaxing and enjoying the awesome view of the Caribbean sea and the bay, without having to share their space with any other. The apartment is within Heaven Villa and once it is occupied,...
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    Location Information
    Port Antonio, Portland Parish 00100
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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