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Holiday Rentals with Pools in Boston Bay

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    Don't let other travellers get your favourite Boston Bay area holiday rental. You're so close to securing your perfect getaway. Book today.
    20 Matching Rentals in the Boston Bay AreaView all 95 rentals
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    The following rentals are within 15 kilometres of Boston Bay.
    Drapers
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Spicy Hill Villa, 5 Bedroom, Port Antonio, Jamaica1 / 30
    (18)Excellent
    Port Antonio
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Tranquility Villa - Port Antonio & Blue Mountains1 / 33
    (35)Excellent
    Port Antonio
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Mamiti Blue - San San, Port Antonio 5 Bedrooms1 / 15
    (1)Excellent
    Port Antonio
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Waterfront
    • Cable/satellite TV
    • Porch
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Mountain Views
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 July 2016
    The service was exceptional which must be said upfront because it's not easy to find great service. The house is beautiful and located in the middle of paradise with both the...
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    About this property
    Mamiti Blue Mamiti Blue is a beautiful and luxurious villa located in San San, Port Antonio, just steps away from the world-famous Blue Lagoon. Mamiti Blue was completely refurbished in 2011.The villa has four air-conditioned bedrooms, four and a half bathrooms, a spacious family room upstairs,...
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    Location Information
    Port Antonio, Portland Parish 00000
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Birdie ‘ill Villa1 / 7
    (4)Excellent
    Port Antonio
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • 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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    Port Antonio  Luxurious 4 bedrooms Private Estate Pool Beach  Jacuzzi Free Wi Fi1 / 15
    (4)Excellent
    Port Antonio
    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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    All Nations Guesthouse - Superior Double Bedroom, Jacuzzi tub, Pool & Gym area1 / 35
    (3)Very good
    Port Antonio
    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 10 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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    Port Antonio
    4 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Waterfront
    • Mountain Views
    • Shared Outdoor Pool (Unheated)
    • Private Garden
    • Grill
    • 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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    Port Antonio
    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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    Port Antonio
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Cable/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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    Shotover Gardens Estate - cabin with pool1 / 15
    (1)Excellent
    Port Antonio
    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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    Shotover Gardens Estate - cottage with pool1 / 14
    (5)Very good
    Port Antonio
    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 14 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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    Luxe Modern Six-bedroom Cocosan Villa, Access to Geejam Hotel1 / 15
    (1)Excellent
    Port Antonio
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • 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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    Drapers
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • 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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    Shotover Gardens Estate-Villa with Pool1 / 20
    (13)Very good
    Port Antonio
    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 10 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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    Luxe 4-Bedroom Panorama Villa/Access to Geejam Hotel1 / 12
    (4)Excellent
    Port Antonio
    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
    • Cable/satellite TV
    • Housekeeping Included
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 May 2018
    Panorama villa is absolutely beautiful! It's situated at the top of the hill, end of the road so you have an amazing view of Port Antonio overlooking the water. The villa itself...
    Reviewed 3 April 2018
    I had the most amazing time at the Panorama, the view is breathtaking , the most amazing 4 bedroom villa , staff on call 24 hours to cater to your needs , they are friendly and...
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    About this property
    More than an island retreat, the four-bedroom Panorama Villa, once frequented by Audrey Hepburn, is a renovated 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...
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    Location Information
    Port Antonio, Portland Parish 00000
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    Port Antonio
    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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    Drapers
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Air Conditioning
    • Washer
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Grill
    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
    Drapers, Portland Parish
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Port Antonio
    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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    Port Antonio
    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...
    View all property information
    Location Information
    Port Antonio, Portland Parish JMBPD15
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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