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Vacation rentals with a kayak in Orleans

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Vacation rentals for every style

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Popular amenities for Orleans kayak rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

House rentals with a kayak

Top guest favorite
A wooden outdoor table and benches are positioned on a stone patio, overlooking a serene pond. Lush greenery lines the water's edge, and white flowers in a planter enhance the natural setting. The calm water reflects the surrounding trees and sky.
Home in West Yarmouth
5 out of 5 average rating, 317 reviews

gorgeous waterfront cottage w/4kayaks and 2 SUPs

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
4.66 out of 5 average rating, 29 reviews

Comfy Family Oasis ~ Games, Backyard, BBQ

Guest favorite
A charming Cape-style residence is surrounded by a spacious green lawn, framed by trees. The house features a sloping roof and a brick chimney, with large windows allowing plenty of natural light. A gravel driveway provides ample parking space.
Home in Wellfleet
5 out of 5 average rating, 22 reviews

The Wellfleet Beach House. Sleeps 6

Guest favorite
The exterior of the house showcases a wooden facade framed by lush greenery. A large wooden deck extends from the back, furnished with chairs, ideal for relaxation. Sunlight filters through the trees, highlighting the serene outdoor space.
Home in Yarmouth Port
4.89 out of 5 average rating, 158 reviews

* Walk to the beach - Swiss Beach House! *

Top guest favorite
Home in Sandwich
4.99 out of 5 average rating, 85 reviews

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

Guest favorite
Home in Plymouth
4.92 out of 5 average rating, 95 reviews

Waterfront New Cottage Private Beach

Guest favorite
Home in Falmouth
4.97 out of 5 average rating, 31 reviews

Falmouth Summer Fun–Game Barn-Dog Friendly!

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

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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
4.8 out of 5 average rating, 15 reviews

Waterfront Cape Cottage by Wellfleet’s TOP Beaches

Top guest favorite
The interior space features warm wood paneling with vaulted ceilings and exposed beams. A cozy living area showcases a kitchen bar with seating, while two bedrooms are visible in the background. Natural light streams in through skylights and windows, creating a bright atmosphere.
Cottage in Dennis
4.94 out of 5 average rating, 119 reviews

Compass Rose Cottage ★ Steps to Flax Pond & Trails

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, 45 reviews

Cape Cottage Escape

Superhost
A charming Cape cottage is framed by lush greenery, with sections of neatly mulched garden beds featuring flowering plants. An American flag hangs at the entrance, complemented by a stone walkway leading to the front door. The property is bathed in natural sunlight.
Cottage in Dennis Port
4.92 out of 5 average rating, 130 reviews

Cape Escape-The Perfect Getaway

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
4.83 out of 5 average rating, 12 reviews

Cottage near bay beach- 1 Bd/1Ba

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, 90 reviews

Beachfront at Days' Cottages! Renovated, Kayaks!

Guest favorite
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 (7 nt. Min. stay July&Aug)

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Other vacation rentals with a kayak

Guest favorite
A serene sandy beach stretches along a tranquil lake, with clear blue waters reflecting the sky. Fluffy white clouds drift overhead, and trees line the shoreline in the distance, creating a peaceful natural setting perfect for relaxation or outdoor activities.
Home in Mashpee
4.93 out of 5 average rating, 46 reviews

Life is Good Rentals in Mashpee

Superhost
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
4.87 out of 5 average rating, 46 reviews

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

Top guest favorite
The exterior of the modern home is visible, featuring a spacious deck with a dining table and teal chairs. Lush greenery and colorful flowers surround the area, while a light blue umbrella adds shade. A grill is positioned nearby, creating an inviting outdoor dining space.
Home in Orleans
5 out of 5 average rating, 21 reviews

Quiet, Sleeps 6, 2 Full Ba, 5 min Drive to Beach

Guest favorite
An aerial view of a coastal ranch home is presented, showcasing a large green yard bordered by trees. The house features a well-maintained exterior and a patio area with seating. Nearby properties and a paved road contribute to the serene neighborhood atmosphere.
Home in Popponesset
4.96 out of 5 average rating, 23 reviews

25 Menemsha Rd., Popponesset, pond & beach views

Top guest favorite
A modern living area features two teal sofas arranged around a circular coffee table on a soft area rug. Natural light filters in through partially draped windows, and a spiral staircase leads to an upper level. Decorative plants add a touch of greenery to the space.
Home in Plymouth
5 out of 5 average rating, 44 reviews

Private Lakefront home w bunk house and beach

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
4.86 out of 5 average rating, 29 reviews

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

Superhost
The exterior of the house showcases a wood-shingled façade and a red door, providing a contrasting accent. A spacious deck holds a set of five outdoor chairs around a small table, ideal for al fresco dining. Clear skies and scattered clouds form the backdrop.
Home in Brewster
4.78 out of 5 average rating, 37 reviews

Cape Cod Escape Pet Friendly Hot Tub Sleeps 10

Guest favorite
A bright living room features a white sofa with decorative cushions, arranged near a rustic coffee table. A cozy armchair and an ottoman are positioned nearby. Large windows allow natural light, while a fireplace adds warmth. Green plants enrich the space with a touch of nature.
Home in Barnstable
4.98 out of 5 average rating, 44 reviews

Cozy ranch with private neighborhood beach

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Quick stats about vacation rentals with a kayak in Orleans

  • Total rentals

    30 properties

  • Nightly prices starting at

    G$35,579 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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