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Holiday Rentals with Pools in Sandy Bay

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    Travellers to Sandy Bay are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    22 Matching Rentals in Sandy BayView all 38 rentals
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Newly refurbished and spectacular Premier villa!! 5 bedrooms, 5 bathrooms. Tryall Resort Membership. Spectacular ocean views, 3 minutes golf cart ride to the beach! for this villa. Pineapple House is a premier villa located in the exclusive Tryall Club overlooking the ruins of the historic sugar...
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    Sandy Bay, Hanover Parish
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    5 Bedrooms, 7 Bathrooms, Sleeps 10 Quick View
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    7 bedrooms, 7 bathrooms, spectacular sea views!!! 4 minutes golf cart ride to the beach Hummingbird House, is the newly refurbished Premier villa with 7 luxury bedrooms! Hummingbird House is one of the finest villas located within the world renowned Tryall Club estate. Located on four acres of...
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    Sandy Bay, Hanover Parish
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 10
    Ocean View 3 bd/ 3 ba! Pool ! Walk 2 beach!1 / 39
    (3)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Reviewed 5 days ago
    Thank you so much Damian for your hospitality. It was such a wonderful experience staying at your spacious Villa. It was great waking up with that breathtaking view of the ocean...
    Reviewed 6 days ago
    Villa located Sandy Bay. Town nice quiet and safe! We walked the neighborhood and we felt very safe! Neighbors were super nice and host was very responsive when any minor issues...
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    About this property
    We are a 2 Villa Complex and this is our Villa B where 2 of 3 Rooms have premium ocean View! The space is 1900 sq ft! We have gorgeous open floor plan space, where you’ll find, living room, dinning room and kitchen flowing into each other ! All bedrooms are upstairs with views! We have great...
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    Sandy Bay, Hanover Parish 13
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Wi-Fi
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    • Shared Outdoor Pool (Unheated)
    • Private Garden
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    About this property
    We are 2 unit Complex! I unit Garden View the 2nd Ocean View. We’ve hosted over 100 guest between both Villas in our 14 months of opening our doors to travelers local and abroad. We are located next to the world renowned Tryall Golf Course & Resort. It’s nestled in a safe and developed area! We...
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    Sandy Bay, Hanover Parish 13
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Deluxe 2 bedroom Suite with its own private swimming pool.Own kitchen, living room, dining room and extra large bedrooms. Poinciana Great House Suite is a deluxe 2 bedroom at Tryall Club. It is the only 2 bedroom at the Great House Suites to have its own private swimming pool! - Tryall Club's...
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    Sandy Bay, Hanover Parish
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Wonderful 4 bedroom villa, with lots of gardens and grassy areas - 2 bedrooms in main house + 2 bedroom villa with views to the pool. Great for families sharing! Tryall Resort Membership. Avalon Villa, previously known as Riverlot Gardens, is a newly-renovated Jamaica villa in the Montego Bay...
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    Sandy Bay, Hanover Parish
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    About this property
    7 bedrooms, 7 bathrooms, spectacular sea views!!! 4 minutes golf cart ride to the beach. Hummingbird House, is the newly refurbished Premier villa with 7 luxury bedrooms! Hummingbird House is one of the finest villas located within the world renowned Tryall Club estate. Located on four acres of...
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    Sandy Bay, Hanover Parish
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Anticipation Villa in Tryall Club is one of the newest and most contemporary villas in Jamaica. The fabulous luxury villa Jamaica is rated premier class, the highest rating in Tryall Club and is located within the club's gated community. Being positioned directly over the golf course, it offers...
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    Sandy Bay, Hanover Parish
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    About this property
    Walk to the beach in a few minutes!!!Tryall Resort Membership. This villa can be rented as a 4 , 5 or 8 bedroom villa! Retreat Villa in Montego Bay is one of the most charming and gracious Jamaica villas located within the renowned Tryall Club Resort. Being situated near the 18th fairway of the...
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    Sandy Bay, Hanover Parish
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    About this property
    Walk to the beach in a few minutes!!!Tryall Resort Membership. This villa can be rented as a 4 , 5 or 8 bedroom villa! Retreat Villa in Montego Bay is one of the most charming and gracious Jamaica villas located within the renowned Tryall Club Resort. Being situated near the 18th fairway of the...
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    Sandy Bay, Hanover Parish
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Renting 5 bedrooms of this luxury 6 bedroom villa - Sea Glass Villa is one of Tryall's newest luxury deluxe editions located in the picturesque Montego Bay. The brand new Tryall villa is a glamorous mansion with Tryall club facilities for all guests.The very luxurious interiors and magnificent...
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    Sandy Bay, Hanover Parish
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sea Glass Villa is one of Tryall's newest luxury deluxe editions located in the picturesque Montego Bay. The brand new Tryall villa is a glamorous mansion with Tryall club facilities for all guests.The very luxurious interiors and magnificent views offered by this villa rental in Jamaica are...
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    Sandy Bay, Hanover Parish
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
    6 Bedrooms, 9 Bathrooms, Sleeps 12 Quick View
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    Smoking allowed
    About this property
    One of the most spectacular luxury villas in Jamaica! 15,000 sq ft. of luxury! Contemporary and spacious, a villa with WOW FACTOR! Elegant with first class service. You will be impressed! *9 bedrooms, 9 bathrooms (can be rented as a 6,7,8 or 9 br) * Large wrap-around verandah * Alfresco dining...
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    Sandy Bay, Hanover Parish
    Holiday Rental House - 6 Bedrooms, 9 Bathrooms, Sleeps 12
    5 Bedrooms, 8 Bathrooms, Sleeps 10 Quick View
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    Smoking allowed
    About this property
    Haystack Villa is one of the newest villas within the celebrated and exclusive Tryall Club estate. The highest rated premier villa in Tryall Club, the gorgeous and very welcoming Haystack Villa provides an unmatched vacation experience in elegance and serenity. Brilliant views of the Caribbean Sea...
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    Sandy Bay, Hanover Parish
    Holiday Rental House - 5 Bedrooms, 8 Bathrooms, Sleeps 10
    6 Bedrooms, 8 Bathrooms, Sleeps 12 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Haystack Villa is one of the newest villas within the celebrated and exclusive Tryall Club estate. The highest rated premier villa in Tryall Club, the gorgeous and very welcoming Haystack Villa provides an unmatched vacation experience in elegance and serenity. Brilliant views of the Caribbean Sea...
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    Sandy Bay, Hanover Parish
    Holiday Rental House - 6 Bedrooms, 8 Bathrooms, Sleeps 12
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a single Room within a complex! Big spacious room with TV, bathroom, Queen bed, balcony and pool access! Room doesn’t come with Kitchen access! Located close to the beach( 5 minute walk) and Top notch Seafood Restaurant right on the beach across the street! There are additional...
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    Sandy Bay, Hanover Parish 13
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Stunning 6 bedroom, Premier rated villa - Brand New Villa! 10,000 aquare ft of Luxurious Living...the finest in Caribbean living, combining Jamaica's rich architectural tradition with today's modern amenities and service. The newest member to the Tryall Club; Harmony Hill is a private oasis...
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    Sandy Bay, Hanover Parish
    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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    4 bedroom villa - BEACHFRONT! Fully staffed villa, secure gated resort - exclusive membership facilities! Sunrise Villa is a fabulous waterfront Jamaica villa located within the renowned Tryall Club Resort. The emerald green fairways of the golf club are just across the lane from the villa. The...
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    Sandy Bay, Hanover Parish
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • DVD Player
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    Stunning 7 bedroom, Premier rated villa - Brand New Villa! Luxurious Living...the finest in Caribbean living, combining Jamaica's rich architectural tradition with today's modern amenities and service. AMENITIES Designed and built with no compromise, Dragon Fly reflects the ultimate in...
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    Sandy Bay, Hanover Parish
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 14
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