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Vacation rentals with a kayak in Kent Island

Find and book unique kayak rentals on Airbnb

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Kent Island kayak rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

House rentals with a kayak

Top guest favorite
An 80-foot private pier extends over calm water, lined with posts and surrounded by greenery. Two personal watercraft and a yellow pedal duck are visible at the end of the dock. The tranquil scene is enhanced by a blue sky with scattered clouds.
Home in Riviera Beach
4.95 out of 5 average rating, 153 reviews

Waterfront Cheerful 5 home

Guest favorite
A serene waterfront view is presented, featuring a wooden dock extending over still water. Lush green grass fills the foreground, while trees line the opposite bank, creating a natural backdrop under a partly cloudy blue sky.
Home in Woolford
4.93 out of 5 average rating, 163 reviews

Waterfront Getaway with Dock

Top guest favorite
A waterfront home is surrounded by lush greenery, showcasing a screened porch and wooden steps leading up to the entrance. Colorful adirondack chairs are positioned by the private pier, which extends into calm waters reflecting the vibrant landscape.
Home in Annapolis
5 out of 5 average rating, 29 reviews

Annapolis waterfront, private pier with kayaks

Guest favorite
A waterfront home is depicted with a screened-in porch and a gabled roof. A wooden pier extends from the shore, leading to the water. Lush greenery surrounds the property, and stone embankments partially border the shoreline.
Home in Shady Side
4.95 out of 5 average rating, 111 reviews

Waterfront w/ Private Pier, 35 Mins to Annapolis

Guest favorite
A bright open space features large windows offering views of the lush waterfront. The wooden dining table is surrounded by chairs, while a cozy seating area includes a dark armchair and an accent chair. The kitchen area is partially visible, showcasing modern appliances.
Home in Deale
4.88 out of 5 average rating, 100 reviews

Chesapeake Paradise Lite 4-5 Br 3 Ba Vacation Home

Superhost
A scenic waterfront view is presented from a balcony, showcasing calm waters and a clear sky. Nearby, a dock is visible with several pilings emerging from the water. A spacious lawn leads to the waterfront, bordered by a fence.
Home in Stevensville
4.72 out of 5 average rating, 18 reviews

Waterfront Escape with Pool Nature Lover Paradise

Top guest favorite
A modern kitchen features a large central island with seating for four. Pendant lights hang above, illuminating the space. Stainless steel appliances and white cabinetry create a clean look, while a window provides natural light. A decorative tray sits at the center of the island.
Home in Woolford
5 out of 5 average rating, 232 reviews

Newly Renovated Modern 3 bed 2 bath Water Front

Superhost
A covered porch is shown with a hanging egg chair and a gray sectional sofa. Soft cushions are placed on the seating area. Beyond the railing, the tranquil waters of Chesapeake Bay can be seen, complemented by lush greenery and nearby homes.
Home in Annapolis
4.87 out of 5 average rating, 182 reviews

Charming Annapolis Water View Home

Cottage rentals with a kayak

Superhost
An inviting stone patio area features comfortable outdoor seating, framed by greenery. Light pours in through the open doors, leading to an interior space that includes minimalist decor and a spiral staircase. A hot tub is visible in the background, enhancing the tranquil setting.
Cottage in Annapolis
4.85 out of 5 average rating, 91 reviews

Waterfront cottage w/hot tub/ gated/ pier/ firepit

Guest favorite
A view of the sunset over Chesapeake Bay is captured from the deck, with warm hues reflecting on the water. The scene includes a grassy area leading to the shoreline and a subtle silhouette of a dock in the background.
Cottage in Deale
4.95 out of 5 average rating, 167 reviews

Chesapeake Bay Cottage

Guest favorite
A serene waterfront scene showcases a private dock extending into the water, framed by grassy areas. The horizon is painted with purple and orange hues from the setting sun, reflecting on the water's surface. Trees line the backdrop, adding to the tranquil atmosphere.
Cottage in Cambridge
4.98 out of 5 average rating, 51 reviews

Cozy Cottage on the Bay

Top guest favorite
The interior space features a well-lit open layout with wooden beams overhead. A dining table sits to the left, while a living area with a comfortable sofa and coffee table is visible. Large windows provide ample natural light, enhancing the inviting atmosphere.
Cottage in Annapolis
4.98 out of 5 average rating, 126 reviews

Weems Creek Cottage, Annapolis Waterfront

Guest favorite
A charming cottage is nestled among lush trees, featuring a spacious yard of green grass. Ample sunlight filters through the leaves, casting playful shadows. The exterior showcases a combination of windows and porch areas, offering a welcoming appearance in a serene environment.
Cottage in Pasadena
4.97 out of 5 average rating, 185 reviews

Ft. Smallwood Overlook. Waterfront with Kayaks!

Top guest favorite
A charming cottage is positioned by the water's edge, surrounded by trees and lush greenery. The structure features large windows that allow natural light to illuminate the interior. A clear blue sky is visible above, reflecting on the calm water.
Cottage in East New Market
4.96 out of 5 average rating, 69 reviews

Cottage on Cabin Creek

Guest favorite
A scenic view is presented of a grassy area leading to a calm waterway. A sailboat glides across the water, while a dock with boats is visible. Lush trees frame the scene, creating a tranquil atmosphere.
Cottage in Saint Michaels
5 out of 5 average rating, 21 reviews

Very cosy and nicely appointed Waterfront Cottage

Top guest favorite
Two kayaks in vibrant green and bright blue are positioned at the lower deck, alongside two paddle boards that rest in an organized manner. A prominent mermaid statue is displayed in the background, adding a coastal charm to the waterfront setting.
Cottage in Essex
5 out of 5 average rating, 47 reviews

The Little House of Rockaway Beach, Maryland

Cabin rentals with a kayak

Guest favorite
A wooden dock extends over calm waters, featuring two parked kayaks in vibrant colors. Sunlight filters through surrounding trees, illuminating two foldable chairs positioned on the dock, creating an inviting spot for relaxation by the water.
Cabin in Lusby
4.9 out of 5 average rating, 282 reviews

Peaceful Waterfront Retreat on The Bay

Top guest favorite
Cabin in Saint Michaels
4.99 out of 5 average rating, 115 reviews

True St. Michaels 6 Acre Waterfront w/heated pool

Guest favorite
A serene outdoor space features a fire pit surrounded by white Adirondack chairs. Lush green grass is complemented by vibrant flowers, while trees provide shade. A cabin is visible in the background, showcasing a blend of natural greenery and modern design.
Cabin in Saint Michaels
5 out of 5 average rating, 10 reviews

Serene Waterfront Retreat – Chesapeake Bay Escape

Guest favorite
The exterior of the historic cabin is showcased, featuring a dark blue facade with a white entrance door. Flowerpots flank the entrance, and landscaped gardens present vibrant floral hues. A glimpse of the dock along the river is visible in the background, framed by mature trees.
Cabin in Queenstown
4.92 out of 5 average rating, 25 reviews

Cozy Historic Cabin on the Water

Guest favorite
A wooden dock extends into a calm body of water, reflecting the blue sky and surrounding trees. The serene scene is framed by lush green foliage, enhancing the tranquil atmosphere of the creek.
Cabin in Worton
4.94 out of 5 average rating, 102 reviews

Cabin on the Creek ~ Kayaks and Fire Pit

A serene coastal scene features a sandy beach lined with gentle waves. Overhanging branches with white flowers frame the view, while a distant pier is visible along the horizon. The sky is bright blue, accented with a few small clouds.
Cabin in Port Republic
4.75 out of 5 average rating, 12 reviews

Ocean Break

Superhost
A kayaker is seen navigating calm waters, with gentle ripples surrounding the red kayak. A shoreline of trees and grass transitions into a distant view of a white house along the bank, framed by blue skies.
Cabin in Saint Michaels
4.76 out of 5 average rating, 82 reviews

Cottage #4 Chesapeake Blue down the drive way.

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