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
.
Flights
Holiday Rentals
Restaurants
Things to do
Skip to main content
Discover
Trips
Review
More
GBP
Sign in
Kent Island
Hotels
Things to Do
Restaurants
Flights
Holiday Rentals
Cruises
Car Hire
Forums
Inbox
See all
Log in
to get trip updates and message other travellers.
Holiday Rentals, Villas, and Cottages in Kent Island, MD
Holiday Rentals
USA
Maryland (MD)
Holiday Rentals, Villas, and Cottages in Kent Island, MD
Search
Owner log in
Kent Island
Holiday Rentals
Destination
Check In
Check Out
Guests
2 Guests
Map
Tripadvisor Sort
Revenue impacts this sort order.
Learn more
Bedrooms
Any
Bathrooms
Any
Amenities
Air Conditioning (56)
Internet or Wifi (55)
Washer/Dryer (50)
Other outdoor space (45)
Show all
Suitability
Kid friendly (55)
Pet friendly (23)
Smoking allowed (1)
Wheelchair access (0)
Show more
Property type
Holiday Rental House (52)
Condominium/Apartment (5)
Cabin Holiday Rental (0)
Private Room (0)
Show more
Distinctive Features
Waterfront (35)
Boat Available (7)
Private Chef (0)
Private Beach (0)
Show all
Distance from
5 mi
Terrapin Nature Park
Cult Classic Brewing
Love Point Vineyards and Winery
Mark Cascia Vineyards
Chesapeake Heritage & Visitor Center
Show all
57 rentals
in Kent Island.
Island Life! Kent Island Waterfront with Pool-Bring your boat!
56
Holiday Rental House
View on map
3 bedrooms
3 bathrooms
Sleeps 12
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
240' Private Beachfront *Kent Island Love Point - Great for Large Groups
169
Holiday Rental House
View on map
5 bedrooms
4 bathrooms
Sleeps 26
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
31
Holiday Rental House
View on map
2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Relax on Kent Island in 3 Bedroom Home w/Waterview
27
Holiday Rental House
View on map
4 bedrooms
3 bathrooms
Sleeps 11
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Circa 1700 Chesapeake Colonial home on the National Register.
25
Holiday Rental House
View on map
4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Serene Waterfront Apartment on Kent Island
43
Condo/Apartment
View on map
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
17
Holiday Rental House
View on map
4 bedrooms
3 bathrooms
Sleeps 14
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Kent Island Waterfront | Game Room | Pool | Outdoor Dining | Stunning View
9
Holiday Rental House
View on map
7 bedrooms
6 bathrooms
Sleeps 16
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Waterfront home with private pier and dog-friendly at A Shore Thing
20
Holiday Rental House
View on map
4 bedrooms
4 bathrooms
Sleeps 9
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Away at the Bay: New Home on the Chesapeake Bay!
13
Holiday Rental House
View on map
4 bedrooms
5 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
25-50% Off~Private Beach~Hot Tub~Fire Table~
15
Holiday Rental House
View on map
3 bedrooms
2 bathrooms
Sleeps 7
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
11
Holiday Rental House
View on map
5 bedrooms
4 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
New! Stylish downtown home w/awesome outdoor area!
17
Holiday Rental House
View on map
3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Second Floor Bed and Bath in Stevensville, MD
22
Holiday Rental House
View on map
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Cozy Waterfront Apartment Chester, MD
Condo/Apartment
View on map
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Waterfront Getaway - View of bay from your bed
Condo/Apartment
View on map
1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Bayou on the Bay
Holiday Rental House
View on map
2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Kent Island Waterfront Cottage
7
Condo/Apartment
View on map
3 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Renovated Rancher on Kent Island near Chesapeake Bay Bridge
Holiday Rental House
View on map
3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Apartment with Lounge Stevensville, MD
Condo/Apartment
View on map
2 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
8
Holiday Rental House
View on map
2 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Perfect getaway, waterfront townhouse on Chesepeake Bay, Kent Island, Maryland
8
Holiday Rental House
View on map
3 bedrooms
3 bathrooms
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
New rates! Kent Island House with Pool and Bay Views!
10
Holiday Rental House
View on map
3 bedrooms
3 bathrooms
Sleeps 12
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Waterfront on Kent Island
18
Holiday Rental House
View on map
4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
20
Holiday Rental House
View on map
4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Kent Island - Gorgeous Waterfront Home
Holiday Rental House
View on map
4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
4 KING Bedrooms on the Waterfront- FREE Kent Island Sunsets- Near Wedding Venues
Holiday Rental House
View on map
4 bedrooms
2 bathrooms
Sleeps 9
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.
42
Holiday Rental House
View on map
5 bedrooms
2 bathrooms
Sleeps 14
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.
75
Holiday Rental House
View on map
4 bedrooms
3 bathrooms
Sleeps 14
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Beautiful Chesapeake Bay Views -pet friendly
2
Holiday Rental House
View on map
5 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Chesapeake Bay Waterfront ARTectural Home
11
Holiday Rental House
View on map
5 bedrooms
5 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Kent Island Luxury Waterfront
4
Holiday Rental House
View on map
4 bedrooms
4 bathrooms
Sleeps 14
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Kent Island Waterfront | Private Dock | Pool | Outdoor Dining | Stunning View
8
Holiday Rental House
View on map
6 bedrooms
5 bathrooms
Sleeps 14
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Kent Island Waterfront | New Construction | Pool | Hot Tub | Stunning View | Lux
5
Holiday Rental House
View on map
5 bedrooms
5 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Private pier at Waterfront Kent Island home on the Bay with Hot Tub (Open!)
6
Holiday Rental House
View on map
4 bedrooms
4 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Kent Island Waterfront | Pool | Stunning View
1
Holiday Rental House
View on map
3 bedrooms
2 bathrooms
Sleeps 7
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Floating 2 bed 2 bath condo stunning views of the bay
1
Holiday Rental House
View on map
2 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Charming 3 Bedroom 3 Bath Beach Front Property
10
Holiday Rental House
View on map
3 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Charming Waterfront home, Kent Island, Maryland!
Holiday Rental House
View on map
4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Chessie Cottage-Chesapeake Bay Great views from easy single floor living!
2
Holiday Rental House
View on map
2 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Paradise on Kent Island
2
Holiday Rental House
View on map
4 bedrooms
4 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Luxurious Waterfront Kent Island Home 30 miles from Annapolis
43
Holiday Rental House
View on map
4 bedrooms
4 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Chic 3 BR / 2 BA Cottage Near Chesapeake Bay
3
Holiday Rental House
View on map
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Caribbean HEATED POOL Home near Matapeake Beach!
Holiday Rental House
View on map
6 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Waterfront Sunset Bayview: sleeps 6
10
Holiday Rental House
View on map
3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Chesapeake Houseboat Getaway on Kent Island, Maryland
17
Holiday Rental House
View on map
2 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
One-level waterfront home with beach and views all the way to the Bay Bridge
3
Holiday Rental House
View on map
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
BEST Exposure on the Bay for SUNSETS with Pool, Dock & Spa
10
Holiday Rental House
View on map
3 bedrooms
4 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Spacious 4BR Home w/waterviews! Recently updated, game room, roof top deck.
Holiday Rental House
View on map
4 bedrooms
4 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
7
Holiday Rental House
View on map
4 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
1
2
Showing results 1-50 of 57
Frequently Asked Questions about Kent Island
Do any holiday rentals in Kent Island have a pool?
Yes, here are some popular holiday rentals in Kent Island that have a pool:
Island Life! Kent Island Waterfront with Pool-Bring your boat!
240' Private Beachfront *Kent Island Love Point - Great for Large Groups
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
See all holiday rentals with a pool in Kent Island on Tripadvisor
Do any holiday rentals in Kent Island have internet access?
Yes, here are some popular holiday rentals in Kent Island that have internet access:
Island Life! Kent Island Waterfront with Pool-Bring your boat!
240' Private Beachfront *Kent Island Love Point - Great for Large Groups
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
See all holiday rentals in Kent Island on Tripadvisor
What are the best pet friendly rentals in Kent Island?
The best pet friendly rentals in Kent Island are:
240' Private Beachfront *Kent Island Love Point - Great for Large Groups
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
Circa 1700 Chesapeake Colonial home on the National Register.
See all pet friendly holiday rentals in Kent Island on Tripadvisor
What are some great rentals in Kent Island that are kid friendly?
Some of the most popular kid friendly rentals in Kent Island are:
Island Life! Kent Island Waterfront with Pool-Bring your boat!
240' Private Beachfront *Kent Island Love Point - Great for Large Groups
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
See all kid friendly holiday rentals in Kent Island on Tripadvisor
Kent Island
Kent Island Tourism
Kent Island Hotels
Bed and Breakfast Kent Island
Kent Island Holiday Rentals
Flights to Kent Island
Kent Island Restaurants
Kent Island Attractions
Kent Island Travel Forum
Kent Island Photos
Kent Island Map
Kent Island Guide
Hotels
All Kent Island Hotels
Kent Island Hotel Deals
By Hotel Type
Business Hotels Kent Island
Romantic Hotels in Kent Island
Spa Hotels in Kent Island
Family Hotels Kent Island
Kent Island Green Hotels
By Hotel Class
5-stars Hotels in Kent Island
4-stars Hotels in Kent Island
3-stars Hotels in Kent Island
Popular Kent Island Categories
Kent Island Non-Smoking Hotels
Couples Hotels in Kent Island
Kent Island Hotels with Banquet Hall
Kent Island Hotels with a View
Hotels with Free Wifi in Kent Island
Charming Hotels in Kent Island
Kent Island Hotels with Air Conditioning
Near Airports
Hotels near (DCA) Ronald Reagan National Airport
Hotels near (IAD) Dulles Intl Airport
Hotels near (BWI) Balt.-Wash. Intl Airport
Near Colleges
Hotels near United States Naval Academy
Things to Do
Restaurants
Flights
Holiday Rentals
Travel Stories
Cruises
Car Hire
More
Tours
Add a Place
Travel Forum
Airlines
Travellers' Choice
Help Centre
Travel Stories