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Kent Island Vacation Rentals

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    C$747 Average
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    Travellers to Kent Island are booking April dates now. Secure your vacation rental today, and have the perfect trip.
    All 10 Rentals in Kent Island
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    KI Golf House-A PAR for the Course & Mile to Beach1 / 17
    (5)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Love Point Waterfront1 / 19
    (14)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets)1 / 21
    (3)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Washer
    • Cable/satellite TV
    • Waterfront
    • Air Conditioning
    • Patio
    • Ocean Views
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Picture yourself sipping morning coffee on the deck watching the charter boats get ready for the big stripers, as the dawn breaks over another perfect day. A modern day home with expansive Captains Quarters and Master Bath overlooking the Chesapeake Bay perfect for the fisherman yet classy enough...
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    Location Information
    Stevensville, Kent Island 21666
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 12
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Parking
    • Patio
    • Wi-Fi
    • Private Garden
    • Grill
    • Air Conditioning
    • Waterfront
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located across the bay from Annapolis (just 1.5 miles from the bridge), this is a convenient, quiet, and beautiful alternative to a hotel. Near to the Chesapeake Bay Beach Club, shopping, parks and Matapeake/Terrapin Beaches. Convenient to Annapolis, Baltimore, DC, Easton and St. Michaels....
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    Location Information
    Stevensville, Kent Island 21666
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Ocean Views
    • Waterfront
    • Hot Tub
    • Washer
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Space Newly updated features make this property relaxing and highly desirable! Breathtaking views of the Chester River where it meets the mouth of the Chesapeake Bay on Maryland's Eastern Shore. Beautiful cathedral ceilings with a stone stacked fireplace. This is an entertainers delight or a...
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    Location Information
    Stevensville, Kent Island 21666
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 10
    Beautiful Kent Island 4BR, Perfect Location, Close to Chesapeake Bay Beach Club!1 / 12
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 24, 2019
    This home is sparkling clean home and flawless. Ten of us stayed there for a wedding and it was even better than we hoped for. Enough room indoors AND outdoors for us to hang...
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    About this property
    Enjoy all that Kent island has to offer--golfing, fishing, crabbing and the laid back island life!! Beautifully remodeled 4 Bedroom house in a great community close to Rt 50 and mins from the Bay Bridge!! Whether you are on Maryland's picturesque Eastern shore for its beaches & water activities...
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    Location Information
    Chester, Kent Island 21619
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come to our beautiful vacation home and enjoy the scenic view while having fun on the water. Love Point Bay Vacation Home is at the mouth of the Chester River, where it connects to the Chesapeake Bay on Maryland's Eastern Shore. You will feel right at home, yet free of your everyday stress. Leave...
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    Location Information
    Stevensville, Kent Island 21666
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Huge Stevensville House Overlooking Eastern Shore!1 / 26
    (1)Excellent
    3 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Grill
    • Washer
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 10, 2016
    From the moment you ride up the driveway you already know you are in for a wonderful experience. From the cathedral ceilings to the beautiful decor this home welcomes you. The...
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    About this property
    Have the ultimate Maryland getaway by staying at this remarkable Stevensville vacation rental home, surrounded by approximately 20 breathtaking acres of open space with picturesque Eastern Shore views. Whether you're in the mood for a relaxing escape in the great outdoors or a vacation filled with...
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    Location Information
    Stevensville, Kent Island 21666
    Holiday Rental House - 3 Bedrooms, 5 Bathrooms, Sleeps 10
    KENT ISLAND-OCEAN VIEW Home for rent  -4 bedrooms EASTERN SHORE sleeps 10-121 / 29
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    other traveller has booked this property
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    Amenities & Details
    • Grill
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    • Patio
    • Wi-Fi
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 23, 2018
    The location was easy to get to, and the house was beautiful. Rosie was very responsive and answered all my questions promptly. I rented the house for myself and my...
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    About this property
    Beautiful 3000 SF house in Kent Island MD. House has a 3 bedroom 2 baths, (nite there is a mistake on the number of rooms, there are only 3 rooms available) family and living room, separate dinning area and a large pool room. The house is surrounded by beautiful pine trees and the fence covers the...
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    Location Information
    Kent Island, Maryland 21619
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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