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Vacation rentals with a kayak in Orleans

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Orleans kayak rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

House rentals with a kayak

Superhost
An inviting exterior view of the home features a well-maintained façade with light gray siding. A charming window with divided panes allows natural light to illuminate the interior, while a wooden fence surrounds a landscaped area with shrubs and flowering plants.
Home in South Dennis
4.6 out of 5 average rating, 35 reviews

Comfy Family Oasis ~ Games, Backyard, BBQ

Top guest favorite
The spacious kitchen features white cabinetry and a modern layout. A central island with seating is complemented by a dining table nearby. Natural light floods the area through sliding glass doors, enhancing the welcoming ambiance.
Home in Yarmouth
4.95 out of 5 average rating, 178 reviews

Cape Cod Life is Good Rentals

Top guest favorite
The exterior of the home is shown, featuring a well-manicured lawn with stone pathways leading to the entrance. Blue shutters frame the windows, and a bright red door adds a pop of color. The serene lake is visible beyond the property.
Home in Centerville
5 out of 5 average rating, 44 reviews

Lake charm

Guest favorite
Home in Dennis Port
5 out of 5 average rating, 7 reviews

Cottage Oasis by Lake-Kayaks, Fire Pit & Huge Yard

Top guest favorite
A wooden deck extends from the house, featuring a seated area with an Adirondack chair. Expansive views of the ocean and shoreline are visible, framed by low coastal vegetation and a wooden fence. A clear sky with scattered clouds creates a serene backdrop.
Home in Plymouth
4.96 out of 5 average rating, 28 reviews

Oceanfront Home on Cape Cod Bay with Beach Access

Superhost
An aerial view of a charming single-story home surrounded by lush greenery, featuring a well-maintained lawn and a spacious driveway. The house is complemented by landscaped gardens, and nearby trees provide a natural backdrop. The community setting is lightly wooded, adding to the tranquil atmosphere.
Home in South Yarmouth
4.88 out of 5 average rating, 8 reviews

Serenity by Bass River: Your Ultimate Cape Cod

Guest favorite
The sunlit living area features vaulted ceilings and exposed wooden beams. Two cozy sofas are arranged around a central coffee table on a decorative rug. Light flows through large windows, enhancing the inviting atmosphere. A small dining table is positioned in the background for additional seating.
Home in Brewster
5 out of 5 average rating, 6 reviews

NEW! Water Views + Dog Friendly Cape Cod Retreat

Guest favorite
A spacious backyard is highlighted by a large solar-heated pool, surrounded by a stone patio with lounge chairs and umbrellas. The well-maintained house is framed by lush trees and colorful foliage, creating a peaceful outdoor retreat.
Home in Barnstable
5 out of 5 average rating, 6 reviews

CapeSearenity-Large Pool-Beach Passes-Family Fun!

Cottage rentals with a kayak

Guest favorite
A spacious wooden deck features a single folding chair, providing a comfortable spot to relax. In the background, a scenic view of the tranquil lake is visible, surrounded by green trees under a clear blue sky.
Cottage in Falmouth
4.86 out of 5 average rating, 111 reviews

Spectacular Beach- front home, includes linen

Superhost
A hammock is suspended between two trees, providing a relaxing vantage point over a calm bay. The water reflects the clear sky, while greenery frames the serene landscape. The distant shore showcases patches of sandy beach among clusters of trees.
Cottage in Wellfleet
4.71 out of 5 average rating, 17 reviews

Waterfront Cape Cottage by Wellfleet’s TOP Beaches

Top guest favorite
A well-maintained pathway leads to a serene cottage entrance, flanked by lush greenery and landscaped beds. A stone water feature creates a calming ambiance, while lounge chairs are positioned nearby for relaxation. Sunlight filters through the trees, enhancing the tranquil outdoor setting.
Cottage in North Eastham
5 out of 5 average rating, 50 reviews

Cape Cottage Escape

Superhost
The exterior of the condo duplex is showcased, featuring a shingle-style façade, a welcoming porch with a white door, and large windows. Lush greenery, including shrubs and a small tree, surrounds the entrance, enhancing the inviting appearance of the property.
Cottage in Brewster
4.85 out of 5 average rating, 13 reviews

Cottage near bay beach- 1 Bd/1Ba

Guest favorite
A circular seating area contains five Adirondack chairs in various colors, arranged around a firepit. The space is surrounded by trees, with a view of the lake visible in the background, providing a serene outdoor spot for relaxation.
Cottage in Harwich
4.88 out of 5 average rating, 33 reviews

Lakeside Waterfront House in Harwich: 4+beds, 3bth

Guest favorite
Row of charming cottages lined along a sandy beach, with white lounge chairs positioned for relaxation. The tranquil bay is visible in the foreground, while the skyline is seen in the distance, under a bright blue sky dotted with soft clouds.
Cottage in North Truro
4.98 out of 5 average rating, 94 reviews

Beachfront at Days' Cottages! Renovated, Kayaks!

Guest favorite
The cottage exterior is showcased, featuring a charming purple façade with black shutters. A landscaped yard with a gravel pathway leads to a private deck area. Surrounding greenery includes trees and shrubs, creating a tranquil outdoor setting.
Cottage in Brewster
4.94 out of 5 average rating, 16 reviews

Modern Cottage on 6 Acres -Walk to Beach and 6A!

Superhost
A serene view of the ocean at sunset is presented, with soft pink and purple hues reflecting on the calm water. A rocky jetty is visible extending into the water, leading toward the tranquil shoreline.
Cottage in Dennis Port
4.9 out of 5 average rating, 49 reviews

Ocean Front Cottage

Other vacation rentals with a kayak

Top guest favorite
Home in Sandwich
4.99 out of 5 average rating, 89 reviews

"Cape Escape" luxury home w/pool & beach access.

Guest favorite
The exterior of a traditional Cape Cod home is shown at dusk, featuring large windows that illuminate the cozy living area. Adirondack chairs are positioned on the green lawn, surrounded by bare trees. A separate structure is visible, adding to the charm of the backyard.
Home in Falmouth
4.97 out of 5 average rating, 34 reviews

Falmouth Summer Fun–Game Barn-Dog Friendly!

Top guest favorite
Home in Mashpee
5 out of 5 average rating, 20 reviews

Swan nest escape

Top guest favorite
The classic residence features a sandy-colored exterior with a peaked roof and prominent chimney. A well-maintained lawn surrounds the entrance, which includes a porch with seating. Two garages are visible, and an American flag adds a touch of character to the welcoming facade.
Home in Harwich
4.97 out of 5 average rating, 35 reviews

Large Family Home on Long Pond - Harwich

Top guest favorite
Two white Adirondack chairs are positioned on a sandy beach area by Wequaquet Lake, facing calm waters. A swan glides gracefully in the distance, surrounded by greenery. The serene landscape offers a sense of tranquility, ideal for relaxation.
Home in Barnstable
4.98 out of 5 average rating, 48 reviews

Private Lake Beach | Spectacular Views & Amenities

Guest favorite
The living room features two comfortable sofas adorned with colorful cushions, situated around a wooden coffee table on a vibrant area rug. Natural light fills the space, highlighting the dining area and fully equipped kitchen visible in the background.
Condo in Brewster
4.84 out of 5 average rating, 51 reviews

Ocean Edge: 2 bed/2 bath - Pools & Resort Access

Top guest favorite
An outdoor space featuring a fire pit surrounded by Adirondack chairs, set on a grassy area. In the background, a two-story house is visible with a staircase leading to the second floor deck, nestled among trees.
Home in South Yarmouth
5 out of 5 average rating, 16 reviews

Amazing Mid-Cape Home, 5 Bedroom, 3 Bath, A/C

Guest favorite
A bright living area features a beige sofa adorned with yellow and striped cushions. A glass coffee table sits in front, with a blue decorative bowl at the center. A large mirror and framed artwork accentuate the walls, while natural light filters through the windows.
Home in Dennis
4.94 out of 5 average rating, 82 reviews

Dennis Getaway & Chill

Quick stats about vacation rentals with a kayak in Orleans

  • Total rentals

    30 properties

  • Nightly prices starting at

    G$35,544 GYD before taxes and fees

  • Total number of reviews

    1.1K reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

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