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Kent Island Holiday Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
57 rentals in Kent Island.
Island Life!  Kent Island Waterfront with Pool-Bring your boat!, holiday rental in Kent Island
Island Life!  Kent Island Waterfront with Pool-Bring your boat!, holiday rental in Kent Island
Island Life!  Kent Island Waterfront with Pool-Bring your boat!, holiday rental in Kent Island

Island Life! Kent Island Waterfront with Pool-Bring your boat!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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240' Private Beachfront *Kent Island Love Point - Great for Large Groups, holiday rental in Kent Island
240' Private Beachfront *Kent Island Love Point - Great for Large Groups, holiday rental in Kent Island
240' Private Beachfront *Kent Island Love Point - Great for Large Groups, holiday rental in Kent Island

240' Private Beachfront *Kent Island Love Point - Great for Large Groups

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 26
Match: Sleeps
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Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly, holiday rental in Kent Island
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly, holiday rental in Kent Island
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly, holiday rental in Kent Island

Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Relax on Kent Island in 3 Bedroom Home w/Waterview, holiday rental in Kent Island
Relax on Kent Island in 3 Bedroom Home w/Waterview, holiday rental in Kent Island
Relax on Kent Island in 3 Bedroom Home w/Waterview, holiday rental in Kent Island

Relax on Kent Island in 3 Bedroom Home w/Waterview

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Circa 1700 Chesapeake Colonial home on the National Register., holiday rental in Kent Island
Circa 1700 Chesapeake Colonial home on the National Register., holiday rental in Kent Island
Circa 1700 Chesapeake Colonial home on the National Register., holiday rental in Kent Island

Circa 1700 Chesapeake Colonial home on the National Register.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Serene Waterfront Apartment on Kent Island, holiday rental in Kent Island
Serene Waterfront Apartment on Kent Island, holiday rental in Kent Island
Serene Waterfront Apartment on Kent Island, holiday rental in Kent Island

Serene Waterfront Apartment on Kent Island

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️, holiday rental in Kent Island
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️, holiday rental in Kent Island
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️, holiday rental in Kent Island

❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Kent Island Waterfront | Game Room | Pool | Outdoor Dining | Stunning View, holiday rental in Kent Island
Kent Island Waterfront | Game Room | Pool | Outdoor Dining | Stunning View, holiday rental in Kent Island
Kent Island Waterfront | Game Room | Pool | Outdoor Dining | Stunning View, holiday rental in Kent Island

Kent Island Waterfront | Game Room | Pool | Outdoor Dining | Stunning View

Holiday Rental House
7 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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Waterfront home with private pier and dog-friendly at A Shore Thing, holiday rental in Kent Island
Waterfront home with private pier and dog-friendly at A Shore Thing, holiday rental in Kent Island
Waterfront home with private pier and dog-friendly at A Shore Thing, holiday rental in Kent Island

Waterfront home with private pier and dog-friendly at A Shore Thing

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Away at the Bay: New Home on the Chesapeake Bay!, holiday rental in Kent Island
Away at the Bay: New Home on the Chesapeake Bay!, holiday rental in Kent Island
Away at the Bay: New Home on the Chesapeake Bay!, holiday rental in Kent Island

Away at the Bay: New Home on the Chesapeake Bay!

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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25-50% Off~Private Beach~Hot Tub~Fire Table~, holiday rental in Kent Island
25-50% Off~Private Beach~Hot Tub~Fire Table~, holiday rental in Kent Island
25-50% Off~Private Beach~Hot Tub~Fire Table~, holiday rental in Kent Island

25-50% Off~Private Beach~Hot Tub~Fire Table~

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy, holiday rental in Kent Island
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy, holiday rental in Kent Island
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy, holiday rental in Kent Island

Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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New! Stylish downtown home w/awesome outdoor area!, holiday rental in Kent Island
New! Stylish downtown home w/awesome outdoor area!, holiday rental in Kent Island
New! Stylish downtown home w/awesome outdoor area!, holiday rental in Kent Island

New! Stylish downtown home w/awesome outdoor area!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Second Floor Bed and Bath in Stevensville, MD, holiday rental in Kent Island
Second Floor Bed and Bath in Stevensville, MD, holiday rental in Kent Island
Second Floor Bed and Bath in Stevensville, MD, holiday rental in Kent Island

Second Floor Bed and Bath in Stevensville, MD

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cozy Waterfront Apartment Chester, MD, holiday rental in Kent Island
Cozy Waterfront Apartment Chester, MD, holiday rental in Kent Island
Cozy Waterfront Apartment Chester, MD, holiday rental in Kent Island

Cozy Waterfront Apartment Chester, MD

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Waterfront Getaway - View of bay from your bed, holiday rental in Kent Island
Waterfront Getaway - View of bay from your bed, holiday rental in Kent Island
Waterfront Getaway - View of bay from your bed, holiday rental in Kent Island

Waterfront Getaway - View of bay from your bed

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Bayou on the Bay, holiday rental in Kent Island
Bayou on the Bay, holiday rental in Kent Island
Bayou on the Bay, holiday rental in Kent Island

Bayou on the Bay

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Kent Island Waterfront Cottage, holiday rental in Kent Island
Kent Island Waterfront Cottage, holiday rental in Kent Island
Kent Island Waterfront Cottage, holiday rental in Kent Island

Kent Island Waterfront Cottage

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Renovated Rancher on Kent Island near Chesapeake Bay Bridge, holiday rental in Kent Island
Renovated Rancher on Kent Island near Chesapeake Bay Bridge, holiday rental in Kent Island
Renovated Rancher on Kent Island near Chesapeake Bay Bridge, holiday rental in Kent Island

Renovated Rancher on Kent Island near Chesapeake Bay Bridge

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Apartment with Lounge Stevensville, MD, holiday rental in Kent Island
Apartment with Lounge Stevensville, MD, holiday rental in Kent Island
Apartment with Lounge Stevensville, MD, holiday rental in Kent Island

Apartment with Lounge Stevensville, MD

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!, holiday rental in Kent Island
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!, holiday rental in Kent Island
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!, holiday rental in Kent Island

Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Perfect getaway, waterfront townhouse on Chesepeake Bay, Kent Island, Maryland, holiday rental in Kent Island
Perfect getaway, waterfront townhouse on Chesepeake Bay, Kent Island, Maryland, holiday rental in Kent Island
Perfect getaway, waterfront townhouse on Chesepeake Bay, Kent Island, Maryland, holiday rental in Kent Island

Perfect getaway, waterfront townhouse on Chesepeake Bay, Kent Island, Maryland

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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New rates! Kent Island House with Pool and Bay Views!, holiday rental in Kent Island
New rates! Kent Island House with Pool and Bay Views!, holiday rental in Kent Island
New rates! Kent Island House with Pool and Bay Views!, holiday rental in Kent Island

New rates! Kent Island House with Pool and Bay Views!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Waterfront on Kent Island, holiday rental in Kent Island
Waterfront on Kent Island, holiday rental in Kent Island
Waterfront on Kent Island, holiday rental in Kent Island

Waterfront on Kent Island

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!, holiday rental in Kent Island
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!, holiday rental in Kent Island
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!, holiday rental in Kent Island

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Kent Island - Gorgeous Waterfront Home, holiday rental in Kent Island
Kent Island - Gorgeous Waterfront Home, holiday rental in Kent Island
Kent Island - Gorgeous Waterfront Home, holiday rental in Kent Island

Kent Island - Gorgeous Waterfront Home

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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4 KING Bedrooms on the Waterfront- FREE Kent Island Sunsets- Near Wedding Venues, holiday rental in Kent Island
4 KING Bedrooms on the Waterfront- FREE Kent Island Sunsets- Near Wedding Venues, holiday rental in Kent Island
4 KING Bedrooms on the Waterfront- FREE Kent Island Sunsets- Near Wedding Venues, holiday rental in Kent Island

4 KING Bedrooms on the Waterfront- FREE Kent Island Sunsets- Near Wedding Venues

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues., holiday rental in Kent Island
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues., holiday rental in Kent Island
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues., holiday rental in Kent Island

Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill., holiday rental in Kent Island
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill., holiday rental in Kent Island
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill., holiday rental in Kent Island

Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Beautiful Chesapeake Bay Views -pet friendly, holiday rental in Kent Island
Beautiful Chesapeake Bay Views -pet friendly, holiday rental in Kent Island
Beautiful Chesapeake Bay Views -pet friendly, holiday rental in Kent Island

Beautiful Chesapeake Bay Views -pet friendly

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Chesapeake Bay Waterfront ARTectural Home, holiday rental in Kent Island
Chesapeake Bay Waterfront ARTectural Home, holiday rental in Kent Island
Chesapeake Bay Waterfront ARTectural Home, holiday rental in Kent Island

Chesapeake Bay Waterfront ARTectural Home

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Kent Island Luxury Waterfront, holiday rental in Kent Island
Kent Island Luxury Waterfront, holiday rental in Kent Island
Kent Island Luxury Waterfront, holiday rental in Kent Island

Kent Island Luxury Waterfront

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Kent Island Waterfront | Private Dock | Pool | Outdoor Dining | Stunning View, holiday rental in Kent Island
Kent Island Waterfront | Private Dock | Pool | Outdoor Dining | Stunning View, holiday rental in Kent Island
Kent Island Waterfront | Private Dock | Pool | Outdoor Dining | Stunning View, holiday rental in Kent Island

Kent Island Waterfront | Private Dock | Pool | Outdoor Dining | Stunning View

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Kent Island Waterfront | New Construction | Pool | Hot Tub | Stunning View | Lux, holiday rental in Kent Island
Kent Island Waterfront | New Construction | Pool | Hot Tub | Stunning View | Lux, holiday rental in Kent Island
Kent Island Waterfront | New Construction | Pool | Hot Tub | Stunning View | Lux, holiday rental in Kent Island

Kent Island Waterfront | New Construction | Pool | Hot Tub | Stunning View | Lux

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Private pier at Waterfront Kent Island home on the Bay with Hot Tub (Open!), holiday rental in Kent Island
Private pier at Waterfront Kent Island home on the Bay with Hot Tub (Open!), holiday rental in Kent Island
Private pier at Waterfront Kent Island home on the Bay with Hot Tub (Open!), holiday rental in Kent Island

Private pier at Waterfront Kent Island home on the Bay with Hot Tub (Open!)

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Kent Island Waterfront | Pool | Stunning View, holiday rental in Kent Island
Kent Island Waterfront | Pool | Stunning View, holiday rental in Kent Island
Kent Island Waterfront | Pool | Stunning View, holiday rental in Kent Island

Kent Island Waterfront | Pool | Stunning View

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Floating 2 bed 2 bath condo stunning views of the bay, holiday rental in Kent Island
Floating 2 bed 2 bath condo stunning views of the bay, holiday rental in Kent Island
Floating 2 bed 2 bath condo stunning views of the bay, holiday rental in Kent Island

Floating 2 bed 2 bath condo stunning views of the bay

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming 3 Bedroom 3 Bath Beach Front Property, holiday rental in Kent Island
Charming 3 Bedroom 3 Bath Beach Front Property, holiday rental in Kent Island
Charming 3 Bedroom 3 Bath Beach Front Property, holiday rental in Kent Island

Charming 3 Bedroom 3 Bath Beach Front Property

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming Waterfront home, Kent Island, Maryland!, holiday rental in Kent Island
Charming Waterfront home, Kent Island, Maryland!, holiday rental in Kent Island
Charming Waterfront home, Kent Island, Maryland!, holiday rental in Kent Island

Charming Waterfront home, Kent Island, Maryland!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Chessie Cottage-Chesapeake Bay
Great views from easy single floor living!, holiday rental in Kent Island
Chessie Cottage-Chesapeake Bay
Great views from easy single floor living!, holiday rental in Kent Island
Chessie Cottage-Chesapeake Bay
Great views from easy single floor living!, holiday rental in Kent Island

Chessie Cottage-Chesapeake Bay Great views from easy single floor living!

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Paradise on Kent Island, holiday rental in Kent Island
Paradise on Kent Island, holiday rental in Kent Island
Paradise on Kent Island, holiday rental in Kent Island

Paradise on Kent Island

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Luxurious Waterfront Kent Island Home 30 miles from Annapolis, holiday rental in Kent Island
Luxurious Waterfront Kent Island Home 30 miles from Annapolis, holiday rental in Kent Island
Luxurious Waterfront Kent Island Home 30 miles from Annapolis, holiday rental in Kent Island

Luxurious Waterfront Kent Island Home 30 miles from Annapolis

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Chic 3 BR / 2 BA Cottage Near Chesapeake Bay, holiday rental in Kent Island
Chic 3 BR / 2 BA Cottage Near Chesapeake Bay, holiday rental in Kent Island
Chic 3 BR / 2 BA Cottage Near Chesapeake Bay, holiday rental in Kent Island

Chic 3 BR / 2 BA Cottage Near Chesapeake Bay

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Caribbean HEATED POOL Home near Matapeake Beach!, holiday rental in Kent Island
Caribbean HEATED POOL Home near Matapeake Beach!, holiday rental in Kent Island
Caribbean HEATED POOL Home near Matapeake Beach!, holiday rental in Kent Island

Caribbean HEATED POOL Home near Matapeake Beach!

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront Sunset Bayview: sleeps 6, holiday rental in Kent Island
Waterfront Sunset Bayview: sleeps 6, holiday rental in Kent Island
Waterfront Sunset Bayview: sleeps 6, holiday rental in Kent Island

Waterfront Sunset Bayview: sleeps 6

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Chesapeake Houseboat Getaway on Kent Island, Maryland, holiday rental in Kent Island
Chesapeake Houseboat Getaway on Kent Island, Maryland, holiday rental in Kent Island
Chesapeake Houseboat Getaway on Kent Island, Maryland, holiday rental in Kent Island

Chesapeake Houseboat Getaway on Kent Island, Maryland

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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One-level waterfront home with beach and views all the way to the Bay Bridge, holiday rental in Kent Island
One-level waterfront home with beach and views all the way to the Bay Bridge, holiday rental in Kent Island
One-level waterfront home with beach and views all the way to the Bay Bridge, holiday rental in Kent Island

One-level waterfront home with beach and views all the way to the Bay Bridge

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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BEST Exposure on the Bay for SUNSETS with Pool, Dock & Spa, holiday rental in Kent Island
BEST Exposure on the Bay for SUNSETS with Pool, Dock & Spa, holiday rental in Kent Island
BEST Exposure on the Bay for SUNSETS with Pool, Dock & Spa, holiday rental in Kent Island

BEST Exposure on the Bay for SUNSETS with Pool, Dock & Spa

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Spacious 4BR Home w/waterviews! Recently updated, game room, roof top deck., holiday rental in Kent Island
Spacious 4BR Home w/waterviews! Recently updated, game room, roof top deck., holiday rental in Kent Island
Spacious 4BR Home w/waterviews! Recently updated, game room, roof top deck., holiday rental in Kent Island

Spacious 4BR Home w/waterviews! Recently updated, game room, roof top deck.

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres., holiday rental in Kent Island
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres., holiday rental in Kent Island
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres., holiday rental in Kent Island

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Showing results 1-50 of 57
Frequently Asked Questions about Kent Island