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Vacation Rentals near Doctor's Cave Beach

Gloucester Ave, Montego Bay, Jamaica, Montego Bay, Jamaica
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    Travelers to Montego Bay are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    All 59 Rentals in Montego Bay
    Beautiful  4 bedrooms/4 bathrooms Villa in a very quiet area of Coral Gardens.1 / 12
    (1)Excellent
    10.3 miles from Doctor's Cave Beach
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    10.0 miles from Doctor's Cave Beach
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    3.4 miles from Doctor's Cave Beach
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    6.9 miles from Doctor's Cave Beach
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Montego Bay, Saint James Parish
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Otaheiti House, beautiful, 2 bedrooms , oceanview built for your peace of mind.1 / 35
    (4)Excellent
    8.3 miles from Doctor's Cave Beach
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Montego Bay, Saint James Parish
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    7.9 miles from Doctor's Cave Beach
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Montego Bay, Saint James Parish
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 10
    13.6 miles from Doctor's Cave Beach
    7 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    Hopewell, Montego Bay
    Rental Home - 7 Bedrooms, 7 Bathrooms, Sleeps 14
    9.8 miles from Doctor's Cave Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Montego Bay, Saint James Parish
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    11.8 miles from Doctor's Cave Beach
    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
    6.4 miles from Doctor's Cave Beach
    5 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    Montego Bay, Saint James Parish
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 8
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    8.6 miles from Doctor's Cave Beach
    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
    10.2 miles from Doctor's Cave Beach
    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
    8.0 miles from Doctor's Cave Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Montego Bay, Saint James Parish
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Royal Westmoreland - Cherry Red1 / 12
    (1)Excellent
    3.4 miles from Doctor's Cave Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Reviewed August 14, 2018
    My party of 8 had an amazing time staying at this villa. Every step of the way from reservation, to our stay was handled with class and excellence. I have to say that the...
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    About this property
    Cherry Red at 20 Sugar Cane Ridge is a well-appointed, modern Caribbean villa, nestled in the exclusive Royal Westmoreland Golf Resort in Barbados. This elegant tri-level holiday home features 4 comfortable and tastefully decorated bedrooms. The master bedroom and second bedroom both open on to the...
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    Saint James Parish, Jamaica
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Rooftop Lounge ocean view salt water pool with mountain view large 2bdrm *LHVYD1 / 22
    (1)Very good
    6.8 miles from Doctor's Cave Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Montego Bay, Saint James Parish
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Luxurious villa, private beach, ocean views, infinity pool, fully staffed1 / 28
    (39)Excellent
    7.7 miles from Doctor's Cave Beach
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
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    Montego Bay, Saint James Parish
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 10
    Penthouse Apartment With Magnificent Sea Views. Minutes from the beach.1 / 50
    (5)Excellent
    10.7 miles from Doctor's Cave Beach
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Hopewell, Montego Bay
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Looking for peace & quiet?  Come & enjoy Blue Mountain Coffee on the back patio!1 / 20
    (4)Excellent
    9.3 miles from Doctor's Cave Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Montego Bay, Saint James Parish
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 9
    Marlin On The Bay - Montego Bay1 / 41
    (3)Very good
    7.9 miles from Doctor's Cave Beach
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Montego Bay, Saint James Parish
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Luxury Beach Front Condo1 / 21
    (17)Very good
    11.7 miles from Doctor's Cave Beach
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Montego Bay, Saint James Parish
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    12.7 miles from Doctor's Cave Beach
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Hopewell, Montego Bay
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    12.7 miles from Doctor's Cave Beach
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Hopewell, Montego Bay
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Caribbean Sea Dreams 2 Bedroom townhome, 2 pools, 24 hour security.1 / 26
    (20)Excellent
    8.2 miles from Doctor's Cave Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Montego Bay, Saint James Parish
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Hip Strip, Doctor's Cave Beach, Margaritaville, free beach across the street etc1 / 21
    (5)Very good
    9.3 miles from Doctor's Cave Beach
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Montego Bay, Saint James Parish
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
    LUXURY 5 BDR BEACHFRONT VILLA POOL BAY VIEWS CHEF BUTLER  *XMAS/NY SPECIALS*1 / 36
    (35)Excellent
    7.7 miles from Doctor's Cave Beach
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Montego Bay, Saint James Parish
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    Beach front 5 bdrm Villa W/ large private pool, gym/tennis in gated community1 / 35
    (65)Excellent
    7.5 miles from Doctor's Cave Beach
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Montego Bay, Saint James Parish
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 10
    Retreat Villa Luxury villa1 / 11
    (2)Excellent
    12.8 miles from Doctor's Cave Beach
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
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    Hopewell, Montego Bay
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    LUXURY MODERN VILLA,180 VIEWS, POOL, FREE BEACH/GOLF MEMBERSHIP, XMAS/NY SPECIAL1 / 46
    (8)Excellent
    11.0 miles from Doctor's Cave Beach
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Montego Bay, Saint James Parish
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 10
    Luxury Oceanfront Townhouse - Montego Bay Jamaica!1 / 21
    (2)Very good
    7.1 miles from Doctor's Cave Beach
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Montego Bay, Saint James Parish
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    3.7 miles from Doctor's Cave Beach
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Ocean Views
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    About this property
    What is the best thing about vacationing in the beautiful Island of Jamaica? The opportunity to explore with great people and to build relationships that last forever. We would love to share this opportunity and our home with you! Our home is set on a cool, quiet hillside on our 5 acre property,...
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    Montego Bay, Saint James Parish
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    6.0 miles from Doctor's Cave Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Montego Bay, Saint James Parish
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Impressive Studio With Captivating Ocean View Overlooking Doctors Cave Beach1 / 24
    (27)Very good
    9.0 miles from Doctor's Cave Beach
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Montego Bay, Saint James Parish
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    A Distinguished Getaway Just Steps Away From the Beach and Hip Strip1 / 26
    (25)Excellent
    9.3 miles from Doctor's Cave Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Montego Bay, Saint James Parish
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Mobay La Palms, Your Oasis1 / 31
    (1)Excellent
    9.2 miles from Doctor's Cave Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Montego Bay, Saint James Parish
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    11.0 miles from Doctor's Cave Beach
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Montego Bay, Saint James Parish
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    9.0 miles from Doctor's Cave Beach
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Montego Bay, Saint James Parish
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
    Pimento Hill - Luxury Staffed Villa with Round Hill Membership1 / 50
    (92)Excellent
    8.6 miles from Doctor's Cave Beach
    6 Bedrooms, 7 Bathrooms, Sleeps 17 Quick View
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    Montego Bay, Saint James Parish
    Rental Home - 6 Bedrooms, 7 Bathrooms, Sleeps 17
    8.0 miles from Doctor's Cave Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Montego Bay, Saint James Parish
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    11.6 miles from Doctor's Cave Beach
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Rose Hall, Montego Bay
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    11.2 miles from Doctor's Cave Beach
    6 Bedrooms, 8 Bathrooms, Sleeps 12 Quick View
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    Montego Bay, Saint James Parish
    Rental Home - 6 Bedrooms, 8 Bathrooms, Sleeps 12
    10.4 miles from Doctor's Cave Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Montego Bay, Saint James Parish
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 9
    Luxury Fully Staffed 4 Bedroom Ocean View Villa with Infinity Pool1 / 40
    (11)Excellent
    9.2 miles from Doctor's Cave Beach
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Montego Bay, Saint James Parish
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    6.9 miles from Doctor's Cave Beach
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
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    • Air Conditioning
    • Parking
    • Patio
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Montego Bay, Saint James Parish
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    10.5 miles from Doctor's Cave Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Internet Access
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Montego Bay, Saint James Parish
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    6.0 miles from Doctor's Cave Beach
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Location Information
    Montego Bay, Saint James Parish
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
    12.6 miles from Doctor's Cave Beach
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Housekeeping Included
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    Pet friendly
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    Location Information
    Hopewell, Montego Bay
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    The nexus of Peace and Beauty. Beautiful Oceanview 2bedroom  Suites Townhouse1 / 30
    (1)Excellent
    8.3 miles from Doctor's Cave Beach
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Balcony
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Montego Bay, Saint James Parish
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Allamanda Villa - fully staffed - ROUND HILL membership - van & driver - nanny1 / 45
    (21)Excellent
    9.1 miles from Doctor's Cave Beach
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
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    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 2, 2021
    My extended family of 9, including 2 young children and my handicap sister-in-law, made Allamanda our home away from home for 7 wonderful days. To say we all absolutely loved...
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    Montego Bay, Saint James Parish
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    Glory * Montego Bay, St James1 / 40
    (1)Excellent
    9.0 miles from Doctor's Cave Beach
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Balcony
    • Housekeeping Included
    • Private Outdoor Pool (Unheated)
    • Washer
    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Montego Bay, Saint James Parish
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Beautiful Beachfront Villa in a Gated Community, Private Pool/Bar, Fully Staffed1 / 39
    (68)Excellent
    7.5 miles from Doctor's Cave Beach
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Patio
    • Private Outdoor Pool (Unheated)
    • Washer
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Montego Bay, Saint James Parish
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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