Kent Island, Maryland Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Kent Island, Maryland on RentalSaver.com!

Kent Island Rentals

From $303 per night (USD)
VRBO
Relax on Kent Island in 3 Bedroom Home w/Waterview
Bedrooms:
2
Bathrooms:
3
Sleeps:
11
Enjoy your vacation in this Stylish 3 Bedroom Home with a view of the Chesapeake Bay from living room and kitchen! Perfe ...
From $303 per night (USD)
VRBO
From $168 per night (USD)
VRBO
Second Floor Bed and Bath in Stevensville, MD
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Second floor bed and bath with private entrance, dedicated HVAC, and balcony overlooking the backyard, located in Chesap ...
From $168 per night (USD)
VRBO
From $522 per night (USD)
VRBO
Waterfront on Kent Island
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
Chesapeake Bay Waterfront home on Kent Island! Enjoy year round big sky and water views from the comfort of the screened ...
From $522 per night (USD)
VRBO
From $922 per night (USD)
Expedia
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Beautiful waterfront home with resort-like atmosphere just one hour from DC and Baltimore. Includes fastest high speed ...
From $922 per night (USD)
Expedia
From $333 per night (USD)
VRBO
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Bedrooms:
2
Bathrooms:
3
Sleeps:
14
Enjoy your vacation in this Stylish Coastal-Country 3+ Bedroom Home with 3 acres of outdoor living! Perfect for Families ...
From $333 per night (USD)
VRBO
From $1920 per night (USD)
Expedia
Kent Island Waterfront | Game Room | Pool | Outdoor Dining | Stunning View
Bedrooms:
5
Bathrooms:
7
Sleeps:
16
Experience spectacular sweeping views of the Chesapeake Bay Bridge from this fully renovated, well-appointed 7-bedroom, ...
From $1920 per night (USD)
Expedia
From $555 per night (USD)
VRBO
Luxurious Waterfront Kent Island Home 30 miles from Annapolis
Bedrooms:
4
Bathrooms:
4
Sleeps:
6
Enjoy this beautiful contemporary home in a gated, waterfront community for a perfect getaway! This is a rare find! This ...
From $555 per night (USD)
VRBO
From $547 per night (USD)
Expedia
The Private Pool is OPEN with Bay Views & Steps from The Kentmorr Beach Bar and Grill
Bedrooms:
3
Bathrooms:
3
Sleeps:
11
Kent Island Chesapeake Bay Cottage with Private Pool & Sunset Views Welcome to your dreamy poolside getaway! This charm ...
From $547 per night (USD)
Expedia
From $156 per night (USD)
VRBO
Perfect getaway, waterfront townhouse on Chesepeake Bay, Kent Island, Maryland
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Newly renovated 2 story, 3 bedroom, 2.5 bath located on beautiful Thompson Creek, Kent Island, Chesapeake Bay. Spectacu ...
From $156 per night (USD)
VRBO
From $325 per night (USD)
Expedia
New! Stylish downtown home w/awesome outdoor area!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Tastefully updated 3 bedroom home with everything you need to enjoy Kent Island! All new furniture and bedding! Home is ...
From $325 per night (USD)
Expedia
From $654 per night (USD)
VRBO
Charming 3 Bedroom 3 Bath Beach Front Property
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This home is situated next to Kent Point Marina at the Southern most tip of Kent Island. If you enjoy crabbing, fishing ...
From $654 per night (USD)
VRBO
From $444 per night (USD)
Expedia
Island Life! Kent Island Waterfront with Pool-Bring your boat!
Bedrooms:
2
Bathrooms:
3
Sleeps:
12
Beautiful 2 story secluded private waterfront retreat with shared pool and hot tub access. Bring your boat and tie up t ...
From $444 per night (USD)
Expedia
From $1086 per night (USD)
VRBO
Chesapeake Bay Waterfront ARTectural Home
Bedrooms:
4
Bathrooms:
3
Sleeps:
10
Welcome to this most relaxing home for your getaway. Perfect for vacations, retreats, meetings, anything that you can i ...
From $1086 per night (USD)
VRBO
From $191 per night (USD)
Expedia
Cass-Away Luxury Houseboat
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Kent Narrows Rentals welcomes you aboard Cass-Away. A 640sqft luxury getaway in the Kent Narrows. Fully equipped with a ...
From $191 per night (USD)
Expedia
From $856 per night (USD)
VRBO
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
Kent Island Beach House LLC Welcome to the original Kent Island Beach House offering comfortable water view accommodatio ...
From $856 per night (USD)
VRBO
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Expedia
4 KING Bedrooms on the Waterfront- FREE Kent Island Sunsets- Near Wedding Venues
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Are you looking for a holiday by the bay, a small reunion, a family vacation, a getaway, a golf outing, a fishing trip, ...
Click For Pricing
Expedia
From $550 per night (USD)
VRBO
Circa 1700 Chesapeake Colonial home on the National Register.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Over 3000sf. Fully stocked, (just remodeled) kitchen, study, formal dining room, large living room, full bath, all down ...
From $550 per night (USD)
VRBO
From $1474 per night (USD)
Expedia
DOLCE VIDA -KENT ISLAND HOME WITH POOL AND OCEAN VIEW-sleeps 8-10-PETS ALLOWED.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Weekend or weekly getaway in this 3000 SF house located in Kent Island MD, surrounded by the beautiful waters of the Che ...
From $1474 per night (USD)
Expedia
From $562 per night (USD)
VRBO
Love Point Waterfront Home....Chesapeake Bay views....Pets OK
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Maryland’s Chesapeake Bay is an ever changing panorama of spectacular sunsets, teeming wildlife, graceful sailboats, and ...
From $562 per night (USD)
VRBO
From $901 per night (USD)
Expedia
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.
Bedrooms:
2
Bathrooms:
5
Sleeps:
14
KI Beach House II: Over 2000 sq ft 4 bedroom/2 bath home is a modern fisherman's village on the corner by the marina. ...
From $901 per night (USD)
Expedia
From $221 per night (USD)
VRBO
Serene Waterfront Apartment on Kent Island
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Located across the bay from Annapolis (just 1.5 miles from the bridge), we offer a convenient, quiet, and beautiful alte ...
From $221 per night (USD)
VRBO
From $587 per night (USD)
VRBO
Away at the Bay: New Home on the Chesapeake Bay!
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Welcome to Away at the Bay! A new build, 4 bedroom house right on the Chesapeake Bay. Very family friendly, and in walki ...
From $587 per night (USD)
VRBO
From $592 per night (USD)
VRBO
Private pier at multi-suite waterfront home on the Bay with Hot Tub (Open!)
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to this beautiful waterfront home with a private pier that sits only 50 feet back from the Chesapeake Bay. Locat ...
From $592 per night (USD)
VRBO
Click For Pricing
Expedia
Kent Island - Gorgeous Waterfront Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Beautiful waterfront property on 10 acres of land within a short drive to Annapolis and local Kent Island restaurants. ...
Click For Pricing
Expedia
From $370 per night (USD)
VRBO
Kent Island Waterfront Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Private 2 bedroom 1 bathroom waterfront cottage on the Chester River. Enjoy the solitude that this property offers, incl ...
From $370 per night (USD)
VRBO
From $804 per night (USD)
Expedia
Kent Island Luxury Waterfront
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
Get away from the city and enjoy the waterfront views from the property that is nestled down a private road. Perfect for ...
From $804 per night (USD)
Expedia
From $413 per night (USD)
VRBO
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
We always clean and disinfect the home using extra cleaning recommendations from the Centers for Disease Control and Pre ...
From $413 per night (USD)
VRBO
From $586 per night (USD)
Expedia
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Bedrooms:
3
Bathrooms:
5
Sleeps:
25
Spacious, comfortable vacation home located on Love Point, the northern tip of Kent Island, in the heart of the upper Ch ...
From $586 per night (USD)
Expedia
Click For Pricing
VRBO
Kent Island waterfront spectacular Chesapeake Bay view
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
We hope you will enjoy our newly renovated waterfront home as much as we do. Family friendly environment, bird watchi ...
Click For Pricing
VRBO
From $1323 per night (USD)
Expedia
Kent Island Waterfront | Private Dock | Pool | Outdoor Dining | Stunning View
Bedrooms:
4
Bathrooms:
6
Sleeps:
14
Experience the ultimate getaway at this gorgeous Kent Island waterfront! This 4,600 square-foot, 6-bedroom, 4.5-bathroo ...
From $1323 per night (USD)
Expedia
Click For Pricing
VRBO
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Enjoy Kent Island Time with waterfront views of Crab Alley Bay and Gorgeous Sunsets. Catch Crabs right from your pier an ...
Click For Pricing
VRBO
From $824 per night (USD)
Expedia
Three Decks overlook Marina basin and views of the Chesapeake and Eastern Bays
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Picturesque views from three decks and 3 bedrooms; additional 3 bedrooms. Walk to beach, large entertaining room with p ...
From $824 per night (USD)
Expedia
Click For Pricing
VRBO
Renovated Rancher on Kent Island near Chesapeake Bay Bridge
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Cozy yet modern rancher equipped with 3 bedrooms, 2 baths, and spacious open floor plan! Whether you’re looking to be cl ...
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VRBO
From $193 per night (USD)
Expedia
Cass-N-Reel Luxury Houseboat
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Kent Narrows Rentals Welcomes you aboard Cass-N-Reel! A 432sqft luxury getaway in the Kent Narrows. With one bedroom, on ...
From $193 per night (USD)
Expedia
From $705 per night (USD)
VRBO
Spacious multi-level waterfront home with private pier and dog-friendly at A Shore Thing
Bedrooms:
4
Bathrooms:
3
Sleeps:
9
Enjoy waterfront views of Cox Creek from this stunning custom home on Maryland’s Eastern Shore. With its private pier, e ...
From $705 per night (USD)
VRBO
Click For Pricing
Expedia
Bayou on the Bay
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This exceptional bayfront retreat boasts breathtaking views and contemporary elegance, making it an ideal escape. Situat ...
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Expedia
From $1328 per night (USD)
VRBO
Paradise on Kent Island
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
PLEASE NOTE: If you request to book this property, you will be contacted by Annapolis Accommodations to finalize your ...
From $1328 per night (USD)
VRBO
From $84 per night (USD)
Expedia
Cozy Waterfront Apartment Chester, MD
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
*We live on the property* NO SMOKING OF ANY KIND is permitted in this apartment or on the property whatsoever. The apar ...
From $84 per night (USD)
Expedia
From $524 per night (USD)
VRBO
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to our brand-new coastal cottage, a haven for your perfect getaway in a community that offers 3 different locati ...
From $524 per night (USD)
VRBO
From $502 per night (USD)
Expedia
25-50% Off~Private Beach~Hot Tub~Fire Table~
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Welcome to our Chesapeake Bay Cottage on Kent Island, Maryland! This unique 3 bed 2 bath home with luxurious amenities i ...
From $502 per night (USD)
Expedia
From $1090 per night (USD)
VRBO
Incredible home with Panoramic Chesapeake Bay view
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Experience unforgettable Chesapeake Bay living. The lighthouse views at night, the panoramic bay vistas, and the charm o ...
From $1090 per night (USD)
VRBO
From $327 per night (USD)
Expedia
Chesapeake Houseboat Getaway on Kent Island, Maryland
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Looking for a peaceful waterfront, floating experience on the Chesapeake Bay? Julia’s Arc has got you covered. Easy acce ...
From $327 per night (USD)
Expedia
From $768 per night (USD)
VRBO
Spacious 4BR Home w/waterviews! Recently updated, game room, roof top deck.
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Recently updated 4 bedroom home in a centralized, quiet, location with no shortage of amazing views of the Chesapeake Ba ...
From $768 per night (USD)
VRBO
From $534 per night (USD)
Expedia
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Recently upgraded heating, ventilation and air conditioning with new ductless system. This private coastal decorated ho ...
From $534 per night (USD)
Expedia
From $455 per night (USD)
VRBO
Waterfront Sunset Bayview: sleeps 6
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to our beautiful, completely renovated waterfront home in the heart of Kent Island! Our home has magnificent dir ...
From $455 per night (USD)
VRBO
From $1269 per night (USD)
Expedia
Kent Island Waterfront | New Construction | Pool | Hot Tub | Stunning View | Lux
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Relax and unwind at this spa-like luxury waterfront estate. Located on the Chesapeake Bay, this newly constructed vacati ...
From $1269 per night (USD)
Expedia
From $707 per night (USD)
VRBO
Caribbean HEATED POOL Home near Matapeake Beach!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Summary: This exquisite Eastern Shore residence is perfect for relaxation and a quick trip to the beach or Annapolis, bo ...
From $707 per night (USD)
VRBO
From $342 per night (USD)
VRBO
Chic 3 BR / 2 BA Cottage Near Chesapeake Bay
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Plan your getaway on the Chesapeake Bay! Blue Heron’s Landing is on beautiful Kent Island, MD. The home is a short walk ...
From $342 per night (USD)
VRBO
$Chessie Cottage-Chesapeake Bay\nGreat views from easy single floor living!$
From $716 per night (USD)
VRBO
Chessie Cottage-Chesapeake Bay\nGreat views from easy single floor living!
Bedrooms:
3
Bathrooms:
2
Sleeps:
8
Welcome to Chessie Cottage on The Bay! There is an intangible quality to a cottage coming from a unique combination of ...
From $716 per night (USD)
VRBO
From $567 per night (USD)
VRBO
Waterfront Retreat on Kent Island — Private Dock, Bay Views, Pet Friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Escape to the shores of Kent Island at this 3-bedroom home, just minutes from historic Annapolis and under 2 ho ...
From $567 per night (USD)
VRBO
From $252 per night (USD)
VRBO
Floating 2 bed 2 bath condo stunning views of the bay
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
A truly unique experience, Enjoy the stunning view of the bay and nature staying on this 40 ft yacht moored at a fishing ...
From $252 per night (USD)
VRBO
From $484 per night (USD)
VRBO
Welcome to The Blue Crab House Stevensville Maryland Eastern Shore
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome To The Blue Crab House Full of your finest eastern shore charm in Stevensville Maryland this spacious 3 bedroo ...
From $484 per night (USD)
VRBO
From $199 per night (USD)
VRBO
Room for an Island getaway
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Enjoy easy access to everything from this perfectly located room with water views off of Rt. 50 between the Chesapeake B ...
From $199 per night (USD)
VRBO
From $684 per night (USD)
Expedia
Kent Island Waterfront | Pool | Stunning View
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Relax and unwind. Located on the Chesapeake Bay, this charming vacation rental features 3 bedrooms, 2 bathrooms, and a r ...
From $684 per night (USD)
Expedia
From $318 per night (USD)
VRBO
Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Get ready to relax in this brilliant 3-bedroom coastal-country home in Stevensville. Remodeled and refurnished complete ...
From $318 per night (USD)
VRBO
From $572 per night (USD)
Expedia
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Welcome to Bay Creek Cottage! We are excited to have you as guests and hope you enjoy your vacation on Kent Island! Plea ...
From $572 per night (USD)
Expedia
From $464 per night (USD)
VRBO
One-level waterfront home with beach and stunning views all the way to the Bay Bridge
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Stunning views and your own sandy beach! Relax with the whole family as you watch the world sail by from the comfort of ...
From $464 per night (USD)
VRBO
From $458 per night (USD)
Expedia
Island Blue Getaway! Brand new charming family friendly Home on Kent Island MD
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Discover the beauty of Kent Island from this 3-bedroom house. This fantastic property offers a king bed, a queen bed, an ...
From $458 per night (USD)
Expedia
From $613 per night (USD)
VRBO
Pier Pleasure Retreat- Waterfront & Private Pier
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Pier Pleasure Retreat: Your Waterfront Oasis Welcome to Pier Pleasure Retreat, a newly renovated 4-bedroom, 4-bathroom ...
From $613 per night (USD)
VRBO
From $169 per night (USD)
Expedia
Chesapeake Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
VERY CLOSE to Island wedding venues. Cottage is a private detached 1st floor dwelling and has off street parking. Queen ...
From $169 per night (USD)
Expedia
Click For Pricing
VRBO
Beautiful Kent Island Getaway with Pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
PRIME LOCATION! This home offers 4 bedrooms 3 1/2 baths with a bonus room for all your family entertaining. You will lov ...
Click For Pricing
VRBO
From $632 per night (USD)
Expedia
NEW Spacious 5BDR house on serene Kent Island - close to all the hot spots!
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Welcome to your serene escape on the beautiful shores of Love Point in Stevensville, MD! This spacious 5-bedroom, 3.5-b ...
From $632 per night (USD)
Expedia
From $555 per night (USD)
VRBO
Waterfront House: Hot Tub, Fire Pit, & Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Summary: Escape to a stunning Waterfront Getaway on Maryland's Eastern Shore! This charming house offers breathtaking wa ...
From $555 per night (USD)
VRBO
From $634 per night (USD)
Expedia
Kent Island Comfort 4BR Home Minutes from Waterfront, Wineries & Nature Trails
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Charming Kent Island Retreat – 4 BR • 2.5 BA • Pool Table • Near the Water ""Brand New Construction"" Escape to the East ...
From $634 per night (USD)
Expedia
From $460 per night (USD)
VRBO
Crab Alley | Waterfront Home + Hot Tub + Game Room
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
BNB Breeze Presents: Crab Alley Welcome to Crab Alley, a stunning Bayfront home nestled in the serene surroundings of Ch ...
From $460 per night (USD)
VRBO
From $805 per night (USD)
Expedia
Kent Island Maryland Getaway
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Wade a Minute Chester Escape to a charming waterfront retreat located in Chester, MD, this impressive 5-bedroom, 3.5 ba ...
From $805 per night (USD)
Expedia
From $344 per night (USD)
VRBO
Waterfront condo. Completely renovated. Walk to Kent Island's best places
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Invited to a Kent Island wedding or event -- going to a boat show or Navy football game? This waterfront condo is the pe ...
From $344 per night (USD)
VRBO
From $440 per night (USD)
VRBO
Comfortable 5 Bedroom Waterfront Home on Chesapeake Bay
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
This spacious and comfortable home on the Chesapeake Bay is the perfect location for a family vacation, reunion, or acco ...
From $440 per night (USD)
VRBO

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Kent Island Rentals

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Results: 68 Rentals