Kent Island Rentals
From $542 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 $542 per night (USD)VRBO
From $1043 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 $1043 per night (USD)Expedia
From $313 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 Home with 3 acres of outdoor living! Perfect for Families & Weddings ...
From $313 per night (USD)VRBO
From $2121 per night (USD)Expedia
Kent Island Waterfront | Game Room | Pool | Outdoor Dining | Stunning View
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 16
This short-term rental has an occupancy of 16 individuals with a max. of 12 guests being 18 years or older. Experience ...
From $2121 per night (USD)Expedia
From $750 per night (USD)VRBO
Private Pool & Stunning Bay Views on Kent Island
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 11
Experience the Difference: Professionally Managed by iTrip Annapolis Kent Island Chesapeake Bay Cottage with Private Po ...
From $750 per night (USD)VRBO
From $97 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 $97 per night (USD)VRBO
From $779 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 $779 per night (USD)VRBO
From $1576 per night (USD)Expedia
Chesapeake Bay Waterfront ARTectural Home
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 10
SPECIAL RATES FOR JANUARY AND FEBRUARY 2026! CHECK CALENDAR. Welcome to this most relaxing home for your getaway. Perfe ...
From $1576 per night (USD)Expedia
From $1450 per night (USD)VRBO
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
- 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 $1450 per night (USD)VRBO
From $573 per night (USD)Expedia
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 $573 per night (USD)Expedia
From $702 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 $702 per night (USD)VRBO
From $1387 per night (USD)Expedia
Stay by MD's Chesapeake Bay! Walk to Marina, Beach Bar & Restaurant!
- 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 $1387 per night (USD)Expedia
From $245 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 $245 per night (USD)VRBO
From $528 per night (USD)Expedia
Private Pier at Multi-Suite Waterfront Home on the Bay with Hot Tub (Open!)
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Experience the Difference: Professionally Managed by iTrip Annapolis Welcome to this beautiful waterfront home with a p ...
From $528 per night (USD)Expedia
From $534 per night (USD)VRBO
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
We pride ourselves on keeping our family vacation home very neat and clean. We will meet you to check you in, give you a ...
From $534 per night (USD)VRBO
From $690 per night (USD)Expedia
240' Private Beachfront @Kent Island Love Point - Great for Families
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 23
Spacious, comfortable vacation home located on Love Point, the northern tip of Kent Island, in the heart of the upper Ch ...
From $690 per night (USD)Expedia
From $1646 per night (USD)VRBO
Kent Island Waterfront | Private Dock | Pool | Outdoor Dining | Stunning View
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
This short-term rental has an occupancy of 14 individuals with a max. of 6 guests being 18 years or older. Experience t ...
From $1646 per night (USD)VRBO
From $999 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 $999 per night (USD)Expedia
From $523 per night (USD)VRBO
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 ...
From $523 per night (USD)VRBO
From $183 per night (USD)VRBO
Cozy Waterfront Apartment Chester, MD
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
*Only accepting bookings from travel healthcare workers* *We live on the property* NO SMOKING OF ANY KIND is p ...
From $183 per night (USD)VRBO
From $602 per night (USD)VRBO
Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our coastal cottage, a haven for your perfect getaway in a community that offers 3 different locations to acc ...
From $602 per night (USD)VRBO
From $311 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 $311 per night (USD)Expedia
From $756 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 $756 per night (USD)VRBO
From $723 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 $723 per night (USD)Expedia
From $1440 per night (USD)VRBO
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 $1440 per night (USD)VRBO
From $417 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 $417 per night (USD)VRBO
From $569 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 $569 per night (USD)VRBO
From $331 per night (USD)Expedia
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 $331 per night (USD)Expedia
From $457 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 $457 per night (USD)VRBO
From $936 per night (USD)Expedia
Kent Island Waterfront | Pool | Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
New Hot Tub available late June 2026. Relax and unwind. Located on the Chesapeake Bay, this charming vacation rental fe ...
From $936 per night (USD)Expedia
From $607 per night (USD)VRBO
House on the Bay with Private Beach Access & Panoramic Bridge Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience the Difference: Professionally Managed by iTrip Annapolis Stunning views and your own sandy beach! Relax wit ...
From $607 per night (USD)VRBO
From $930 per night (USD)Expedia
Beautiful Kent Island Getaway with Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
PRIME LOCATION! MILE FROM CHEASPEAKE BEACH CLUB. This home offers 4 bedrooms 3 1/2 baths with a bonus room for all your ...
From $930 per night (USD)Expedia
From $866 per night (USD)VRBO
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 $866 per night (USD)VRBO
From $447 per night (USD)Expedia
Crab Alley | Waterfront Home + Hot Tub + Game Room
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
BNB Breeze Presents: Crab Alley Welcome to Crab Alley, a stunning Bayfront home nestled in the serene surroundings of Ch ...
From $447 per night (USD)Expedia
From $596 per night (USD)VRBO
Kent Island Getaway with Fire Pit Near Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy an easy Eastern Shore escape at this spacious Kent Island home in historic Stevensville. With approximately 1,812 ...
From $596 per night (USD)VRBO
From $393 per night (USD)VRBO
Private & Peaceful Water Views, Big Deck, Games
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Down a gravel drive, surrounded by trees, with no neighbors in sight and water views from the deck. This home ...
From $393 per night (USD)VRBO
From $643 per night (USD)VRBO
NEW KI Creek Retreat! 3BR/2bath water view, private house near KI wedding venues
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Your home away from home while you visit Stevensville/Kent Island! This 7 yr new home and BRAND NEW, as of May 2026, to ...
From $643 per night (USD)VRBO
From $1054 per night (USD)Expedia
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Stay comfortably in Stevensville at this 5-bedroom country house. Four king beds and 2 twin bed offer plenty of space fo ...
From $1054 per night (USD)Expedia
From $989 per night (USD)VRBO
*Waterfront* 5BR w/ Pool + Firepit on Kent Island!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
FEATURED IN BETHESDA MAGAZINE JULY ‘26 ISSUE ⭐THE HIGHLIGHTS • Private waterfront setting on Kent Island • Resort- ...
From $989 per night (USD)VRBO
From $746 per night (USD)Expedia
Waterfront Escape with Pool Nature Lover Paradise
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Discover the perfect blend of relaxation and adventure at our stunning waterfront home. With breathtaking water views, a ...
From $746 per night (USD)Expedia
From $897 per night (USD)VRBO
Luxury Waterfront Escape with Swim Spa, Sauna, Game Room, Beach Access, Fire Pit
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Escape to Oyster Bay Getaway- the Pearl of Kent Island invites you to Indulge in the ultimate waterfront escape. This lu ...
From $897 per night (USD)VRBO
From $270 per night (USD)VRBO
Bay House Retreat. Main House + Guesthouse. Waterfront, spacious, private dock.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Escape to the Bay House, a peaceful waterfront retreat with panoramic views and unforgettable sunsets of the Chesapeake ...
From $270 per night (USD)VRBO