Holiday Rentals in Kent Island
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59 rentals in Kent Island.
Island Life! Kent Island Waterfront with Pool-Bring your boat!
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240' Private Beachfront *Kent Island Love Point - Great for Large Groups
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Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
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Relax on Kent Island in 3 Bedroom Home w/Waterview
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Circa 1700 Chesapeake Colonial home on the National Register.
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Serene Waterfront Apartment on Kent Island
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❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
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Kent Island Waterfront | Game Room | Pool | Outdoor Dining | Stunning View
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Waterfront home with private pier and dog-friendly at A Shore Thing
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Away at the Bay: New Home on the Chesapeake Bay!
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25-50% Off~Private Beach~Hot Tub~Fire Table~
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Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
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New! Stylish downtown home w/awesome outdoor area!
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Second Floor Bed and Bath in Stevensville, MD
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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
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Bayou on the Bay
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Kent Island Waterfront Cottage
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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
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
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Perfect getaway, waterfront townhouse on Chesepeake Bay, Kent Island, Maryland
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New rates! Kent Island House with Pool and Bay Views!
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Waterfront on Kent Island
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Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
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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 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.
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Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.
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Beautiful Chesapeake Bay Views -pet friendly
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Chesapeake Bay Waterfront ARTectural Home
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Kent Island Luxury Waterfront
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Kent Island Waterfront | Private Dock | Pool | Outdoor Dining | Stunning View
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Kent Island Waterfront | Pool | Stunning View
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Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
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Waterfront King Condo
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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BEST Exposure on the Bay for SUNSETS with Pool, Dock & Spa
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One-level waterfront home with beach and views all the way to the Bay Bridge
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Charming Waterfront home, Kent Island, Maryland!
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Three Decks overlook Marina basin and views of the Chesapeake and Eastern Bays
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Caribbean HEATED POOL Home near Matapeake Beach!
Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate
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Cozy Up This Winter – Exclusive Offers Await
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Paradise on Kent Island
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Island Blue Getaway! Brand new charming family friendly Home on Kent Island MD
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Luxurious Waterfront Kent Island Home 30 miles from Annapolis
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Floating 2 bed 2 bath condo stunning views of the bay
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Chesapeake Houseboat Getaway on Kent Island, Maryland
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Private pier at Waterfront Kent Island home on the Bay with Hot Tub (Open!)
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Chessie Cottage-Chesapeake Bay Great views from easy single floor living!
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Showing results 1-50 of 59
Frequently Asked Questions about Kent Island
- 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
- 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
- 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.
- 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
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