We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Homes in Kent Island

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    $815 Average
    |||
    |||
    $0$2,000+
    Suitability
    More filters
    Travellers to Kent Island are booking April dates now. Secure your holiday rental today, and have the perfect trip.
    All 11 Rentals in Kent Island
    Sort by:
    Default
    DOLCE VIDA AT Kent Island- 4 bedrooms House for rent-SLEEPS 10-121 / 30
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    KI Golf House-A PAR for the Course & Mile to Beach1 / 17
    (5)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets)1 / 21
    (3)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Patio
    • Cable/satellite TV
    • Waterfront
    • Wi-Fi
    • Washer
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 January 2016
    We have stayed in this home several times and will return in July. It is a wonderful house with a private master suite at one end, two bedrooms with a 2nd bath at the other.The...
    Reviewed 29 July 2013
    First I would like to say thanks, to Harry, and Scott. They were the best host, I've encountered. They have a property, they can be proud of. The house was just excellent...
    See all reviews
    About this property
    Waterfront Rancher on 3 acres, centrally located between Washington DC, St. Michaels, Annapolis, and Baltimore. 4 Bed/2 Bath home with central air sleeps 8. This home has been in our family for over 50 years and is a special place. Over the years there have been many updates to the home. The...
    View all property information
    Location Information
    Chester, Kent Island 21619
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Love Point Waterfront1 / 19
    (14)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Porch
    • Waterfront
    • Washer
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 July 2018
    Had a nice family weekend enjoying the view of the Bay, the outside deck, big yard, and the dock. Great house if you are going to be outside all weekend. Inside was a bit...
    Reviewed 23 August 2017
    So impressed with Love Point - allowed all of us to relax and enjoy the wonderful property and view! Easy to get to - and convenient to many wonderful places to enjoy the great...
    See all reviews
    About this property
    Located on the Eastern shore of Maryland, Kent Island is a small area 13 miles long and 5 miles wide. The Bay Bridge spans the Cheasapeake bay from the Western shore to Kent Island. We are 4.5 miles north of the bridge in a charming dead end, waterfront community of single family homes called...
    View all property information
    Location Information
    Kent Island, Maryland 21666
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 12
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Stevensville, Kent Island 21666
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Luxury vacation condominum with private beach1 / 35
    (15)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Hot Tub
    • Waterfront
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Secure Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 June 2018
    This condo is spectacular very clean great location on the water. Convenient to restaurants, bike walk trails and outlets! Best decision we ever made to rent this condo...
    Reviewed 7 November 2017
    A great family-friendly condo with a lovely porch view and access to the bay. Our stay was for a wedding at the Chesapeake Beach Bay Club and this location was great. Ying, the...
    See all reviews
    About this property
    Swan Cove Condominiums at Kent Narrows(#49064) with private beach and views of the Chesapeake bay! - Brand new luxury condominium with 3000 sq ft, 4 bedrooms, 3 ½ bathrooms, one large family room with open kitchen, one large sunny living room and dinning area. There are 2 king size bed, 2 queen...
    View all property information
    Location Information
    Chester, Kent Island 21619
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Make Enquiry
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    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....
    View all property information
    Location Information
    Stevensville, Kent Island 21666
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Stevensville, Kent Island 21666
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 12
    Make Enquiry
    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
    Check in Check out
    Show Prices
    Payment Protection
    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 23 August 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...
    See all reviews
    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...
    View all property information
    Location Information
    Kent Island, Maryland 21619
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    Save time - get the best Kent Island rentals sent straight to your email!
    Get the List
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    View all property information
    Location Information
    Chester, Kent Island 21619
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    Make Enquiry
    List your property
    Owner log in