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Vacation Rentals nearby Hip Strip

Gloucester Avenue, Montego Bay, Jamaica
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    Travellers to Montego Bay are booking January dates now. Secure your vacation rental today, and have the perfect trip.
    All 941 Rentals in Montego Bay
    Beautiful ocean views, Montego Bay Studio near Doctors Cave Beach and Hip Strip1 / 11
    (24)Very good
    0.4 kilometres from Hip Strip
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Gorgeous Oceanview Condo Montego Bay Jamaica1 / 26
    (5)Excellent
    0.4 kilometres from Hip Strip
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Hospitality Expert NCH: Private Pool/Beach/Chef1 / 57
    (1)Terrible
    0.2 kilometres from Hip Strip
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Ocean Front Montego Bay Club Apartments1 / 38
    (11)Very good
    0.4 kilometres from Hip Strip
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    • Mountain Views
    • Washer
    • Waterfront
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 10, 2023
    Location location location is all I have to say. Everything you need at a very short walking distance, food, beach, entertainment, etc.The view of the beach was beautiful and...
    Reviewed May 14, 2018
    This Was My First Time Traveling Out Of The US And I Was Also Traveling Alone, Karl Made Me Feel Very Comfortable Throughout The Whole Process He Was Responding Quick And...
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    About this property
    Newly renovated, open-floor, light-filled Studio apartment with a fully equipped kitchen and washer in a safe and secure building with a large balcony and stunning view. Be advised that this is a privately owned condo, not a hotel. The building itself is over 50 years old and rundown paint job -...
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    Montego Bay, Saint James Parish
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Ocean Front 2 Bed/2.5 Bath Suite Hip Strip Beach1 / 34
    (4)Very good
    0.5 kilometres from Hip Strip
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Wi-Fi
    • Ocean Views
    • Mountain Views
    • Waterfront
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 18, 2017
    Karl's place was phenomenal and exceeded any expectations we could have had about our stay in Jamaica. Right in the heart of the Hip Strip and all of the happenings of Mobay. Be...
    Reviewed June 26, 2017
    Great location, right across the street from Dr. Caves Beach and plenty of shopping. Condo was very clean. When we arrived A.C. wasn't working and it was extremely hot and...
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    About this property
    Welcome to Montego Bay Club Apartments, one of Jamaica’s most exclusive Hip Strip safe and secure buildings. Wake up and pull away your curtains to a breathtaking view of the Caribbean Sea whilst you relax and unwind in your renovated open light-filled 2-bedroom apartment with a large balcony!...
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    Montego Bay, Saint James Parish
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 7
    Cozy Montego Bay Studio Apartment Jamaica1 / 33
    (7)Very good
    0.4 kilometres from Hip Strip
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Balcony
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Cable/satellite TV
    • Parking
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 21, 2017
    This is a great little studio located in the heart of Hip Strip. There are many restaurants within walking distance. The owner has a great handbook which gives many...
    Reviewed February 25, 2015
    This was a very nice studio condo with an excellent view of the ocean and the street from the balcony. The internet worked as well as the airconditioning which was a great plus...
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    About this property
    **Check out my gorgeous 2-bedroom condo too!** http://www.flipkey.com/montego-bay-condo-rentals/p684603/ ******************************************** Great garden view studio apartment with 1 bath, fully equipped kitchen and king-size bed. Located directly across from Doctors Cave Beach. Perfect...
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    Montego Bay, Saint James Parish
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Ocean Front Modern Luxury Condo Montego Bay Club1 / 25
    (3)Excellent
    0.4 kilometres from Hip Strip
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Ocean Views
    • Mountain Views
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 19, 2017
    We really enjoyed our stay! Karl was very welcoming and accommodating. The apartment was clean and safe. Most places within walking distance. Great view of the beach. Got great...
    Reviewed November 1, 2015
    What a great place! Spotless, brand new, comfortable, clean, close to beaches, restaurants, shopping, big screen TV, high speed Internet, excellent communication with our host...
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    About this property
    Newly renovated, open-floor, light-filled Studio apartment with a fully equipped kitchen and washer in a safe and secure building with a large balcony and stunning view. Be advised that this is a privately owned condo, not a hotel. The building itself is over 50 years old and rundown paint job -...
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    Location Information
    Montego Bay, Saint James Parish
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Mobay Club Studio Hip Strip, Beach Pool Nightlife1 / 56
    (3)Excellent
    0.4 kilometres from Hip Strip
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Secure Parking
    • Patio
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 12, 2017
    Karl is amazing & and excellent at what he does. He is so informative with tours and makes them all fun from start to finish!! The condo has a beautiful view, in a great...
    Reviewed November 15, 2015
    Karl was our perfect welcome to Jamaica! Picked us up from the airport and looked after us throughout the stay, and even took us to a bargain of a car rental place to carry on...
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    About this property
    Newly renovated, open-floor, light-filled Studio apartment with a fully equipped kitchen and washer in a safe and secure building with a large balcony. Be advised that this is a privately owned condo, not a hotel. The building itself is over 50 years old and rundown paint job - sorry, nothing we...
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    Location Information
    Montego Bay, Saint James Parish
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    5.3 kilometres from Hip Strip
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Montego Bay, Saint James Parish
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Almond Hill Villa Jamaica - Luxury 4 Bedroom Villa in Montego Bay w/private pool1 / 24
    (6)Excellent
    9.0 kilometres from Hip Strip
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Location Information
    Hopewell, Montego Bay
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    GD Rooftop Lounge ocean view, salt water pool with mountain view, 1bdrm1 / 23
    (3)Excellent
    4.1 kilometres from Hip Strip
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Montego Bay, Saint James Parish
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    3.4 kilometres from Hip Strip
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Balcony
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Montego Bay, Saint James Parish
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
    4.0 kilometres from Hip Strip
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    Smoking allowed
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    Montego Bay, Saint James Parish
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    0.4 kilometres from Hip Strip
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Waterfront
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Montego Bay, Saint James Parish
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    4.5 kilometres from Hip Strip
    5 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    Montego Bay, Saint James Parish
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 8
    5.3 kilometres from Hip Strip
    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Montego Bay, Saint James Parish
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 8
    3.4 kilometres from Hip Strip
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Montego Bay, Saint James Parish
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Palm Breeze House - Gated Community - Hip strip - Free Beach Access - Airport1 / 43
    (2)Average
    0.5 kilometres from Hip Strip
    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Private Garden
    • Cable/satellite TV
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 18, 2019
    Nice new apartment! It was well appointed with nice furniture and amenities. It is a short walk to the beach and restaurants. The development is new and has a nice feel to it...
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    About this property
    This beautiful Palm breeze Smart House is located in the exclusive GATED community of Chatham Palms! An upscale gated community. Complex was built in 2018. Located next to the world famous Sandals resort and a few minutes walk away from Sangster International Airport, Doctors Cave Beach Club,...
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    Montego Bay, Saint James Parish
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 7
    A Distinguished Beach Cottage in Montego Bay1 / 12
    (7)Excellent
    0.3 kilometres from Hip Strip
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Garden
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 15, 2018
    Chatham Cottage had all the amenities i needed. Amazing location - a five minute drive from Sangster International Airport. Only a five minute walk to Doctors Cave Beach...
    Reviewed October 11, 2018
    Perfect location! We were so close to the beach, shopping, and nightlife. Beautiful and spacious house! It has an incredible back garden and veranda for relaxing.We ended up...
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    About this property
    Treat yourself to a divine escape that is just steps away from the beach! Conveniently located near Sangster International Airport(MBJ), you are walking distance to Doctors Cave Beach, tennis courts, and Montego Bay's Hip Strip. Bars, cafes, restaurants, and shopping are all within your reach! You...
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    Montego Bay, Saint James Parish
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Palm Breeze Cottage -GATED COMMUNITY, Pool, Beach Access, HipStrip, NEAR AIRPORT1 / 28
    (1)Very good
    0.1 kilometres from Hip Strip
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Children's Pool
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    Pet friendly
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    Reviewed July 20, 2019
    This is a lovely clean room with a two foot area that contains a small fridge, microwave, toaster and a washing up sink area. There is no cooker, pots or pans so you will not be...
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    About this property
    This beautiful Palm breeze Cottage is located in the exclusive community of Chatham Palms! Chatham Palms is next to the world famous Sandals resort in Montego Bay Hip Strip which is a few minutes walk away from Sangster International Airport, Montego Bay Hip Strip, Doctors Cave Beach Club,...
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    Montego Bay, Saint James Parish
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    0.4 kilometres from Hip Strip
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Terrace
    • Cable/satellite TV
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The large, sunny condo is located on the 12th floor of an elevator building on the'Hip Strip'within walking distance to all major attractions and restaurants. The large balcony overlooks Doctors Cave Beach. There is a full kitchen,fully equipped with all necessary utensils . A full bath, also...
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    Montego Bay, Saint James Parish
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    0.5 kilometres from Hip Strip
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Cozy Beach retreat apartment nestled on a hill, panoramic view of the ocean kissing the sky. 5 min from airport, 10-minute walk to DR. Cave Beach, Hip Strip, Restaurants, nightlife, Usain Bolts Tracks & Records Sports bar, Margaritaville and Summit Police station. Queen size beds in both rooms....
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    Montego Bay, Saint James Parish
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Play, Relax, Beach across the street, Hip Strip a few steps away. No car needed.1 / 30
    (5)Excellent
    0.0 kilometres from Hip Strip
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Montego Bay, Saint James Parish
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    PENTHOUSE VIEW AND FLATS VACATION HOME (#1)1 / 23
    (1)Excellent
    4.1 kilometres from Hip Strip
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
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    Montego Bay, Saint James Parish
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Luxury Beach Front Condo1 / 21
    (25)Very good
    10.4 kilometres from Hip Strip
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Hot Tub
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    Pet friendly
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    Montego Bay, Saint James Parish
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Marlin On The Bay - Montego Bay1 / 30
    (3)Very good
    3.4 kilometres from Hip Strip
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
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    • Shared Outdoor Pool (Unheated)
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    Montego Bay, Saint James Parish
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Luxury Mountainside Mansion - Montego Bay Jamaica!1 / 20
    (2)Very good
    3.7 kilometres from Hip Strip
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Montego Bay, Saint James Parish
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Quiet relaxing mountainous get away!1 / 30
    (1)Excellent
    4.3 kilometres from Hip Strip
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Montego Bay, Saint James Parish
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    4.4 kilometres from Hip Strip
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Grill
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    Pet friendly
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    Montego Bay, Saint James Parish
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
    Penthouse Apartment With Magnificent Sea Views. Minutes from the beach.1 / 30
    (2)Excellent
    10.9 kilometres from Hip Strip
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Hopewell, Montego Bay
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Beautiful Luxury Oceanfront Property Montego Bay Property1 / 25
    (64)Excellent
    3.5 kilometres from Hip Strip
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Terrace
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    Pet friendly
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    Montego Bay, Saint James Parish
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Two Bedroom Apartment in Rose Hall with Hot Water, Wifi and Cable1 / 19
    (4)Very good
    15.7 kilometres from Hip Strip
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Rose Hall, Montego Bay
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    "Sought-After" Luxurious Private Residence - Special Rates1 / 14
    (28)Excellent
    10.5 kilometres from Hip Strip
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Terrace
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    Montego Bay, Saint James Parish
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    YD Rooftop Lounge ocean view salt water pool with mountain view large 2bdrm1 / 21
    (2)Very good
    4.1 kilometres from Hip Strip
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Montego Bay, Saint James Parish
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    White Horses Beach Studio at The  Montego Bay Club1 / 30
    (5)Average
    1.1 kilometres from Hip Strip
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Montego Bay, Saint James Parish
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    A private and luxurious home away from home1 / 30
    (21)Very good
    9.4 kilometres from Hip Strip
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    Montego Bay, Saint James Parish
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
    House by the sea with a small sandy beach, fantastic view1 / 30
    (86)Excellent
    7.3 kilometres from Hip Strip
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Ironshore, Montego Bay
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    *MAY SPECIAL* 5 BDR BEACHFRONT VILLA INFINITY POOL STUNNING VIEWS CHEF BUTLER1 / 30
    (56)Excellent
    4.2 kilometres from Hip Strip
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Montego Bay, Saint James Parish
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    Amazing Montego Bay Country Club Rental, exceptional views, perfectly priced!1 / 29
    (16)Very good
    1.2 kilometres from Hip Strip
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Montego Bay, Saint James Parish
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    LUXURY MODERN VILLA 180 VIEWS POOL, FREE BEACH/GOLF FIVE STAR RESORT MEMBERSHIP1 / 30
    (10)Excellent
    8.8 kilometres from Hip Strip
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Reviewed June 26, 2022
    I have stayed here twice. The quality of the villa and its service was consistently excellent. The villa is gorgeous. The staff is excellent. The chef is talented. The...
    Reviewed June 18, 2022
    Exceptional and professional staff. Great location. Awesome view of the Caribbean Sea. Centrally located. Great vibe. Exceptional in all categories. Chef was extraordinary.
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    Montego Bay, Saint James Parish
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
    PRIVATE VACATION RENTAL PROPERTY I1 / 24
    (1)Excellent
    5.0 kilometres from Hip Strip
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Montego Bay, Saint James Parish
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    "Idle Time on the Bay". Visually Charming and newly refurbished apartment1 / 30
    (14)Excellent
    3.4 kilometres from Hip Strip
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Sauna
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    Montego Bay, Saint James Parish
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    8.1 kilometres from Hip Strip
    8 Bedrooms, 7 Bathrooms, Sleeps 20 Quick View
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    Montego Bay, Saint James Parish
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 20
    3.6 kilometres from Hip Strip
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Montego Bay, Saint James Parish
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Caribbean Sea Dreams 2 Bedroom townhome, 2 pools, 24 hour security.1 / 22
    (21)Excellent
    2.8 kilometres from Hip Strip
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Montego Bay, Saint James Parish
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Come on down! �  Car not needed! Beach across the street! Next to the Hip Strip1 / 30
    (4)Excellent
    0.0 kilometres from Hip Strip
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Montego Bay, Saint James Parish
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
    0.5 kilometres from Hip Strip
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    About this property
    S/V Desdemona is a fully refurbished 28-foot yacht moored at Doctor's Cave Beach in the heart of Montego Bay's Hip Strip, just minutes from the airport. The vessel comfortably sleeps three (3) people and is equipped with a double bed (sleeps 2) & a single bed (sleeps 1), private 1/2 bathroom with...
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    Montego Bay, Saint James Parish
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    5.3 kilometres from Hip Strip
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Montego Bay, Saint James Parish
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    5.7 kilometres from Hip Strip
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Montego Bay, Saint James Parish
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    4.0 kilometres from Hip Strip
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Montego Bay, Saint James Parish
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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