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Vacation rentals with a kayak in Shelter 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 Shelter Island kayak rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

House rentals with a kayak

Top guest favorite
Home in North Fork
4.93 out of 5 average rating, 30 reviews

Renovated Ranch Home wPool & Beach Acces

Guest favorite
A modern kitchen equipped with wooden cabinetry features a central island topped with dark stone. The space is illuminated by pendant lights, while glass doors offer views of the pool outside. Wall decor includes woven baskets, enhancing the aesthetic of the area.
Home in The Hamptons
4.97 out of 5 average rating, 67 reviews

Renovated Southampton Shores pool, tennis, beach

Guest favorite
A wooden walkway leads down to a calm beach, with gentle waves lapping at the shore. The water reflects a clear sky and distant land. A floating object is seen in the water, enhancing the serene coastal scene.
Home in North Fork
4.88 out of 5 average rating, 16 reviews

Private Beach access along the Wine Trail

Guest favorite
A spacious wood deck surrounds a heated pool, featuring comfortable lounge chairs. Potted plants add greenery, while lush trees create a natural setting. Two umbrellas provide shade, enhancing the inviting outdoor space ideal for relaxation.
Home in The Hamptons
4.87 out of 5 average rating, 23 reviews

East Hampton 3 bedroom with pool

Guest favorite
A serene backyard is depicted, featuring a soft green lawn bordered by flourishing plants and flowers. Stone pathways meander gently through the garden, leading towards a view of the water. Trees provide shade, enhancing the natural, peaceful setting.
Home in South End
4.89 out of 5 average rating, 27 reviews

Coastal Cottage on the Water

Guest favorite
The image captures a spacious outdoor area featuring a large heated pool with a fountain and surrounding stone patio. Nearby, lounge chairs are arranged for relaxation, while a generous lawn stretches in the background, accompanied by a well-designed home nestled among trees.
Home in The Hamptons
4.76 out of 5 average rating, 136 reviews

Sprawling Hampton Estate w/ Hot Tub + Heated Pool

Top guest favorite
A spacious deck is furnished with a wooden table surrounded by six white chairs, offering ample space for relaxation. Two large umbrellas provide shade, while a view of the calm water and distant horizon can be seen in the background.
Home in Shirley
4.99 out of 5 average rating, 78 reviews

Stunning sunset charming waterfront home 4 seasons

Superhost
Home in The Hamptons
4.8 out of 5 average rating, 71 reviews

Private and tranquil Holiday retreat.

Cottage rentals with a kayak

Guest favorite
Cottage in North Fork
5 out of 5 average rating, 22 reviews

Lovely North Fork Beach Cottage (2 BR/2 bath)!

Top guest favorite
A spacious outdoor deck features a dining table accompanied by seating and an umbrella. The deck is surrounded by sand and greenery, with a grill positioned nearby. A flowering tree adds a pop of color, enhancing the outdoor space's ambiance.
Cottage in The Hamptons
5 out of 5 average rating, 28 reviews

Amagansett Beach Cottage - Short Walk to the Ocean

Superhost
A light-colored boat is anchored in calm water, surrounded by lush greenery. Reflections of the boat can be seen on the still surface, while distant homes are visible along the shoreline under a clear blue sky.
Cottage in The Hamptons
4.87 out of 5 average rating, 91 reviews

Waterfront Beach Home & Garden —AC, BBQ, Kayaks!

Top guest favorite
The image features a serene waterfront scene, highlighting a private dock that extends over the calm water. A cozy seating area is visible on the deck, surrounded by lush greenery. In the background, a spacious cottage is framed by tall trees, providing a peaceful retreat.
Cottage in North Fork
4.98 out of 5 average rating, 50 reviews

Stunning waterfront modern farmhouse with dock.

Top guest favorite
A wooden dock extends into calm waters, featuring an orange kayak secured alongside. Lush greenery surrounds the area, with a bright sun shining overhead and a charming cottage visible in the background, framed by trees.
Cottage in North Fork
5 out of 5 average rating, 26 reviews

The Bay Breeze

A glass dining table is surrounded by four rattan chairs with light blue cushions. A simple striped runner is placed across the table, complemented by a vase of white flowers. Soft light illuminates the space, with a view of the adjoining living area and doorways visible in the background.
Cottage in North Fork
4.75 out of 5 average rating, 68 reviews

Beach Cottage in Calverton

A charming red cottage is framed by lush greenery, set back from a driveway leading to the entrance. A small white bench is visible on the left side of the well-maintained lawn, with flowering plants adding a touch of color in front of the house.
Cottage in North Fork
4.68 out of 5 average rating, 205 reviews

Lovely 2 BR Beach House No. Shore

The image shows a tranquil lake reflecting a colorful sunset with streaks of orange, pink, and purple across the sky. Two kayaks are positioned along the shore, and the water’s surface appears calm, enhancing the serene ambiance.
Cottage in The Hamptons
4.76 out of 5 average rating, 25 reviews

Spectacular Water Views! Swim, kayak, nature.

Other vacation rentals with a kayak

Guest favorite
A warm wood-paneled interior features a cozy bed adorned with a white quilt and decorative pillows. A small yellow bench sits at the foot of the bed. A bathroom entrance is visible in the background, and a landscape painting hangs above a nightstand with a lamp.
Apartment in The Hamptons
5 out of 5 average rating, 25 reviews

The Vineyard Studio of the Hamptons.

Guest favorite
A spacious studio apartment is presented, featuring a large circular mirror and light-colored furnishings. Two separate sleeping areas are visible, with one prominent bed framed by bamboo-style headboards. Natural light filters in through sliding glass doors, enhancing the welcoming ambiance of the room.
Apartment in The Hamptons
5 out of 5 average rating, 57 reviews

Spacious apartment in Sag Harbor

Superhost
A bright and airy studio apartment showcases a spacious bed with accent pillows and overlooks stunning ocean views from the balcony. A modern kitchen area is equipped with essential appliances, while a round table with chairs offers a comfortable dining space.
Apartment in The Hamptons
5 out of 5 average rating, 5 reviews

White Studio Apt w/ Balcony, Tub & Ocean view!

Guest favorite
A comfortable seating area is visible, featuring a soft gray sofa adorned with pillows. A round, white table is placed in front. Light-colored wood doors with glass panels lead to another room, enhancing the sense of openness within the space.
Apartment in The Hamptons
4.89 out of 5 average rating, 27 reviews

2BR Hampton's Serenity Getaway w/Kayaks and BBQ

Guest favorite
The house features a wraparound porch with a wooden railing and steps leading to a spacious deck. Ample windows allow for natural light, and a patio umbrella provides shade over outdoor seating. Lush greenery surrounds the exterior, contributing to a serene environment.
Home in The Hamptons
5 out of 5 average rating, 62 reviews

Beach House on the Bay

Superhost
A vintage studio interior showcases warm wood paneling with a bright red backsplash. The kitchen area includes essential appliances such as a microwave and refrigerator. Counter space is available, and a small dining table is adorned with fresh flowers. A cozy sleeping area is visible in the background.
Tiny home in The Hamptons
4.72 out of 5 average rating, 112 reviews

Private Glamptons Studio at Cute Beach Cottage

Guest favorite
A charming Italianate villa is framed by verdant trees and lush grass. The exterior, painted in soft hues, features a welcoming porch with decorative columns. A path leads through the manicured lawn towards the entrance, promoting a sense of tranquility in a private setting.
Home in North Fork
4.96 out of 5 average rating, 48 reviews

The Captain's Crib

Top guest favorite
A wooden dock extends over a serene marsh area, with a red kayak resting on a launch platform at its edge. Lush greenery frames the scene, featuring tall grasses and trees, creating a peaceful natural setting during dusk.
Guesthouse in The Hamptons
5 out of 5 average rating, 32 reviews

1 Bedroom Hamptons Waterfront Cottage Rental

Quick stats about vacation rentals with a kayak in Shelter Island

  • Total rentals

    10 properties

  • Nightly prices starting at

    G$52,301 GYD before taxes and fees

  • Total number of reviews

    330 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

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