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Smoking Allowed Holiday Rentals in Montego Bay

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    Travellers to Montego Bay are booking January dates now. Secure your holiday rental today, and have the perfect trip.
    78 Matching Rentals in Montego BayView all 571 rentals
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Private villa, breathtaking views, pool, wi-fi, AC, full staff, sleeps 10-121 / 30
    (3)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Bungalow1 / 38
    (1)Average
    2 Bedrooms, 1 Bathroom, Sleeps 1 Quick View
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    Sea View Villa Montego Bay1 / 28
    (1)Excellent
    18 Bedrooms, 22 Bathrooms, Sleeps 36 Quick View
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    • Cable/satellite TV
    • Ocean Views
    • Internet Access
    • Waterfront
    • Hot Tub
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sea View Heights Villa Montego Bay, is a lovely private home surrounded by real authentic Jamaican homes, and luscious countryside. The villa is tastefully decorated in colorful recreational fabrics, satellite TV, VCR, Stereo and comfortable furniture inside and out. The spacious bedrooms are...
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    Montego Bay, Saint James Parish JMDEH20
    Holiday Rental House - 18 Bedrooms, 22 Bathrooms, Sleeps 36
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Private Garden
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Unavailable until March 01/2016. The property is safe and secure in a huge family centric community 2 minutes away from the community center where you will find the communities beloved Jerk stop, grocery shops, hardware and a police post which allows you the peace of mind to witness the everyday...
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    Rose Hall, Montego Bay PO BOX 1
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Mountain Views
    • Air Conditioning
    • Waterfront
    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    It doesn't get better than this! The 'Hip Strip' is the center of Montego Bay where all the action is. 14th Floor Corner Apartment with an absolutely breathtaking view of the #1 beach in Jamaica, less than 5 mins from airport and near to everything! The Space One bedroom and a separate living...
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    Montego Bay, Saint James Parish
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Secure Parking
    • Private Outdoor Pool (Unheated)
    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3 month old, modern accommodation is located 15 minutes on the outskirts of resort town Montego Bay. We are located next to the world renowned Tryall Golf Course & Resort. It’s nestled in a safe and developed area! We are 5 minutes walk from private beach- 2 minutes walk from Pachies Seafood...
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    Montego Bay, Saint James Parish 10056
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Terrace
    • Mountain Views
    • Patio
    • Washer
    • Housekeeping Included
    • Balcony
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Palmer’s Luxury Retreat is an elegant private home which is situated in Iron Shore, Montego Bay. It has a breath taking view of the beautiful Island and the Caribbean Sea. The House offers 7500 square feet of comfortable spacious living space with 4 bedrooms including a master bedroom. All rooms...
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    Rose Hall, Montego Bay 87666
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Luxurious British Colonial Estate on 17 acres with Organic Farm & Fabulous Staff1 / 34
    (27)Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    • Mountain Views
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hammerstein Highland House is a spectacular estate on 17 acres on the hillside in Montego Bay, Jamaica. Oscar Hammerstein wrote 'The Sound of Music' from the terrace, overlooking the beautiful hillside. The home is very private and located about 5 minutes from the beach and 20 minutes from the...
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    Montego Bay, Saint James Parish WEST INDIES
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Patio
    • Terrace
    • Balcony
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    Pet friendly
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    Smoking allowed
    About this property
    Spacious and gorgeous 3 bedrooms , 3 bathrooms villa located on Sunset Drive, Montego Bay, Secrets hotel is just across the street. Guests will be given a free access card to Secrets hotel, where they can enjoy the beach and restaurant. This villa is also close to other restaurants and...
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    Montego Bay, Saint James Parish 0000
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    3 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Balcony
    • Terrace
    • Ocean Views
    • Mountain Views
    • Parking
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Coastal chic meets laid-back comfort in Villa 7. Newly renovated, this villa boasts a main house, guesthouse and sparkling pool situated on a beautifully terraced tropical landscape. Tucked into the hillside for privacy, expect magnificent views of the bay from each room on the upper level - with...
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    Hopewell, Montego Bay 11111
    Holiday Rental House - 3 Bedrooms, 6 Bathrooms, Sleeps 8
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    Seaview Chateau1 / 29
    (29)Excellent
    9 Bedrooms, 9 Bathrooms, Sleeps 24 Quick View
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    • Cable/satellite TV
    • Washer
    • Hot Tub
    • Mountain Views
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    9 bed room french style villa. With great view, sleeps 18 to 24 comfortable master bed room king size bed with built in jacuzzi , 2 other rooms with king size bed and 6 rooms with 2 full size bed, each room has its own bath room a large kitchen and dining area, a laundry room,a power room, a...
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    Montego Bay, Saint James Parish JAMAICA
    Holiday Rental House - 9 Bedrooms, 9 Bathrooms, Sleeps 24
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    6 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Private Garden
    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    VACATION CALCIUM VILLA is the most spectacular views you would see in Montego Bay and is located close the the town center close to everything! It is located in a nice residential street very quiet is design specifically with you in mind. All rooms are outfitted with beds, ceiling fans storage...
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    Hopewell, Montego Bay 00000
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 14
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    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Terrace
    • Balcony
    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4 Brothers Paradise Villa promises to give a memorable and comfortable experience to all our guest We cater for corporate functions, wedding reception, room rentals, Parties, Retreats, Restaurant & Bar, We also help to make your visit enjoyable by offering tours to various attractions in Jamaica....
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    Rose Hall, Montego Bay 0000
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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    Serene Room 31 / 10
    (1)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Private Garden
    • Air Conditioning
    • Terrace
    • Wi-Fi
    • Secure Parking
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Serene Room 3 is a very private room on the 2nd floor at the front of the house, guests have complete privacy. For the guest's convenience, the room is furnished with a mini fridge and microwave. Serene Rooms are located in a safe neighbourhood within the hotel district of Montego Bay; less than...
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    Rose Hall, Montego Bay JAMAICA
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • Private Garden
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Montego West Village is a gated community conveniently located just 10 minutes from the Sangster International Airport, and 5 minutes away from the fair view shopping complex. Solid all-concrete structure, cement roofing and solar water heating. The development will feature a Community Center,...
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    Montego Bay, Saint James Parish 876
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Secure Parking
    • Patio
    • Cable/satellite TV
    • Private Garden
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the hotel district, less than 10 minutes drive from Montego Bay town center and the 'Hip Strip', the place for much fun in the sun - beach, shopping, great food and more. We are in a quiet, safe neighbourhood about 8 minutes from Sangster Int'l Airport and public transport is readily...
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    Ironshore, Montego Bay JAMAICA
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Parking
    • Air Conditioning
    • Wi-Fi
    • Private Garden
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Apartment is located close to the City of Montego Bay and many restaurants, beaches, movie theater, shopping area and the Airport. Guest will have full access to two bathrooms, two bedrooms with 3 beds, living, dining and kitchen area and a patio. The apartment is fully air-conditioned and...
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    Montego Bay, Saint James Parish ST JAMES
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Mountain Views
    • Parking
    • Air Conditioning
    • Patio
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Shores Holiday home is located next to Hip Strip, Bellefield Great House & Gardens and Fort Montego. Guests will take advantage of airport transfer and ironing service on the premises. Within 900 meters from the venue, Juici Patties and Sand at Doctors Cave Beach serve a wide selection of...
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    Montego Bay, Saint James Parish PO 2
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a beautiful spot on Bogue Hill that overlooks the entire city of Montego Bay. Spacious outdoor decks and a pool will always keep you cool. The inside is entirely modern and luxurious. The bedrooms have private baths and remote controlled air-conditioning. You may not even notice that...
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    Montego Bay, Saint James Parish NONE
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Spa 165 Retreat located in Ironshore, Montego Bay, 5 minutes away from the Sangster's International Airport and local amenities. We host 3 comfortable rooms featuring distinctive décor, including a TV, air conditioning and one bathroom. Spa 165 Retreat also boasts a shared lounge and...
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    Ironshore, Montego Bay JAMAICA
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Washer
    • Ocean Views
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sleeps - 1-10 Spring/Summer Special at Drambuie Estate! Book Now For Travel Anytime From July 1-December 14, 2016 and Receive A Special Rental Rate! * Stay 7 Nights, Pay for 5! Drambuie Estate is offering 2 Free Nights when you book the 5 Bedroom Weekly Rate...Book 7 Nights, Get 2 Nights Free!...
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    Montego Bay, Saint James Parish
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Garden
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The house can look scary from outside as it is under construction but inside there is everything what you need: spacious and clean room with comfortable bed, clean bathroom, small brand-new fridge, wi-fi. If needed, the owner - Rasta will serve you Jamaican breakfast or dinner. There is a beautiful...
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    Rose Hall, Montego Bay JMCJS13
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Private Garden
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Need a place to stay Montego bay, look no further, this is the place for You! Located in a newly built gated community and ideally located in the city, less than 5 mins from Fairview shopping mall, 10 mins away from the airport and the famous Doctors cave beach. THIS IS THE PLACE FOR YOU! COME AND...
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    Montego Bay, Saint James Parish 00000
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Secure Parking
    • Shared Outdoor Pool (Unheated)
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The property is nestled in the hills of Montego Bay over looking the City. Living is easy in this impressive, spacious cottage with fabulous views and romantic StepAway access. The open floor plan encompasses a spacious bedrooms with plenty of room for study, sleep and storage, one luxurious...
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    Montego Bay, Saint James Parish 00000
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Nickel's Garden Villas1 / 33
    (2)Terrible
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Housekeeping Included
    • Terrace
    • Washer
    • Mountain Views
    • Patio
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This property is the best value you will get anywhere. One price and you get two bedrooms. Nestled in a gated community surrounded by the lush hills of Jamaica. This property is located 4 miles from the beach and all that Montego Bay has to offer. This will be your home away from home. Two...
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    Montego Bay, Saint James Parish 00000
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We are a family living close to the airport and a big shopping plaza (a type of mall). We will treat you as another member of our family. We know it's nice to have a family when you're traveling and we want to treat our guest as such. We do offer picked up services for a fee from the airport, but...
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    Montego Bay, Saint James Parish
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    7 Bedrooms, 7 Bathrooms, Sleeps 19 Quick View
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    • Washer
    • Mountain Views
    • Housekeeping Included
    • Air Conditioning
    • Ocean Views
    • Wi-Fi
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located 10 min from the Airport, Beaches and the Hip strip & 2 min from Shoping mall. Jamaica rose is a cozy villa overlooking the prestine caribbean sea. Villa has 7 bedrooms all with bathroom ensuite, and can accommodate up to 20 people. We have transportation, and a chef avilable for additional...
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    Ironshore, Montego Bay 00000
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 19
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