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Vacation rentals with a kayak in Shelter Island

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Shelter Island

Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

A serene waterfront view of Hashamomuck Pond is showcased, with kayaks and paddle boards arranged on a wooden rack. Lush greenery surrounds the calm water, complemented by a small garden structure nearby. Sunlight reflects off the water, creating a tranquil atmosphere.

Home in North Fork

5 out of 5 average rating, 24 reviews

Beautiful waterfront 3 bedroom home in Southold

Beautiful waterfront home with stunning views of Hashamomuck Pond, making it the perfect escape for a memorable family vacation. Enjoy beaches, wine country, farm stands, and excellent restaurants. Featuring 3 bedrooms and 2 full baths. 1st floor, master bedroom, a guest room, and a bonus room with a pull-out couch. The second floor offers an additional guest room with two queen beds. BBQ, paddle boards, kayaks, fire pit, and plenty of seating to enjoy the beauty that surrounds this home.

Home in Southampton

4.96 out of 5 average rating, 169 reviews

Waterview+Pool, FreeForDogs! Kayaks/PingPong/Bikes

*Please note for monthly stay there are NO TAXES :) ! Beachy casual feel-good home easily located at the entrance to The Hamptons. Lovely views of the Bay, Nightly Sunsets & birds! Launch our Kayaks at street's tiny beach flowing from Cold Spring Pond into Bay. Or cuddle by the fireplace and play our many available games. We provide soft sheets & towels for the showers and & beach...priding ourselves on your comfort! Our Private-Pool is heatable & plant-surrounded with Outdoor Shower.

A patio area features a circular wooden table surrounded by several chairs, shaded by a large umbrella. Lush green grass leads to a tranquil water view, framed by trees under a clear blue sky, creating a welcoming outdoor space.

Home in North Fork

4.91 out of 5 average rating, 23 reviews

Coastal Cottage on the Water

A coastal cottage on the water surrounded by vineyards and farm stands on the North Fork. Unwind in the backyard with a private view of the Goldsmith's Inlet where you can watch the sunrise, bird watch, and admire our local swans. A quick 5-minute walk to the Long Island Sound where you can sunbathe, swim, kayak, and watch the beautiful sunset. Conveniently located near Greenport, Orient, and Southold. *IMPORTANT* Kayaks and grill are only available from May 1st to October 31st.

A spacious living room features a large sectional sofa adorned with colorful cushions, offering comfort and relaxation. A sleek television is mounted on the wall, while natural light streams through wide windows, illuminating a wooden coffee table and a decorative fireplace in the corner.

4.89 out of 5 average rating, 105 reviews

Cozy home. Comfy living

The whole group will enjoy access to everything from this centrally located home. three comfy bedroom, two bathrooms, large living room, dining and kitchen. close to the beach, nature reserved, kayaking, sky diving and Tanger outlet mall, restaurant and all the fast food located nearby. long island vast array of winery and farms stand etc. Guest is expected to follow house rules. 15 mins after check out time is given after that fees will incur at nightly rate

Top guest favorite

An outdoor deck features a dining table surrounded by six chairs, positioned over the water. The scene includes a marina with boats and lush greenery. A tranquil sunset casts soft hues across the landscape, enhancing the serene environment.

Cottage in Flanders

4.9 out of 5 average rating, 39 reviews

Bayside bliss - Charming 2bdrm on the water w dock

Lovely 2 bedroom cottage located on the water with your own private dock. 2 queen beds, 1 bathroom, and full kitchen. Enjoy a swim and outdoor shower after a blissful kayak along the shores of the Peconic Bay. Easy access to the North and South Forks of Long Island, famous wine trails, Ocean Beaches, and amazing farms. 2 kayaks included in the rental. Experience the food, drink, and beautiful scenery with a short drive to all of the Hamptons.

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, 44 reviews

Stunning waterfront modern farmhouse with dock.

Relax with the whole family or a group of friends at this peaceful, waterfront cottage. Perfect spot to bring a group for a country retreat in the heart of stunning vineyards, spectacular restaurants and stunning waterscapes. Our home’s interior is beautifully appointed where you will be comfortable both inside and outside on our patio, or deck with a breathtaking waterfront view. Peaceful, relaxing and magical place in an idyllic spot.

An outdoor deck showcases a large round table surrounded by six chairs, ideal for group gatherings. A patio umbrella stands in the center, providing shade. A propane grill is positioned nearby, with lush greenery creating a natural backdrop.

Home in Shelter Island

4.9 out of 5 average rating, 115 reviews

There's a Beach Getaway!

Welcome to our family-friendly oasis just two blocks from beautiful beaches! Our house offers an open space living area, an expansive yard, fire pits, and a basement with a playroom and workout area. Enjoy our quiet neighborhood. We provide kid-friendly toys, beach gear, bicycles, and more. Sleeps six, with additional options available for larger parties. Cleaning fees for winter stays are 0$.

A view of Long Island Sound is presented, showcasing calm waters under a clear blue sky. The shoreline is lined with rocky outcrops and greenery, while a bench is positioned along the road for leisure. Gentle waves create a serene atmosphere.

Apartment in Branford

4.95 out of 5 average rating, 22 reviews

Ocean front 1 bedroom apartment

This charming apartment is across the street from LI sound and has an outdoor shower for your use. It has been completely remodeled, including appliances and is large at 1300 sq ft. This is the ideal location for 2 people to unwind and get away from it all and enjoy the beach, put your kayaks in 50’ from property or enjoy excellent restaurants and attractions along the Connecticut shore line.

A charming waterfront cottage is seen from the water, surrounded by lush trees. A spacious deck with a canopy extends outward, while two individuals enjoy the water on a paddleboard. The shoreline features a rocky edge and a grassy area leading up to the cottage.

Cottage in Branford

5 out of 5 average rating, 10 reviews

Beachfront Cottage Serene Private Beach, Kayaks

Imagine waking up at a serene waterfront cottage overlooking the Branford River, Branford Marina, Branford Point, and a bay that opens up to Long Island Sound. Imagine breakfast or just sipping your coffee on an open deck at water’s edge. Imagine a day at the beach, two supplied kayaks, and beautiful sunsets to complete the day. And all this set in the picturesque neighborhood of Pawson Park.

A purple kayak is positioned against a wooden fence surrounded by greenery. Two light blue bicycles are parked nearby, alongside a potted plant. The area is shaded by tall trees, creating a natural and relaxed vibe.

Apartment in Sag Harbor

4.69 out of 5 average rating, 55 reviews

Sag Harbor Suite by the Beach

*Private Beach Access - 7 min walk - 0.4 mi Parking in Driveway Private Entrance Outdoor Patio 1 BR Apartment with common area with sleeper sofa (2 queen beds) Kitchenette - Fridge, Toaster Oven, Coffee/Tea, Microwave Plates, Bowls, Cups, Utensils (2) Bikes available (1) Kayak available (4) Beach Chairs provided (4) Beach towels provided Games to play

A bright red kayak rests on the grass beside a pathway. The surrounding area is lush with greenery, including tall grasses and trees. A few small solar lights are positioned on the ground, reflecting a natural outdoor setting.

Guesthouse in Hampton Bays

5 out of 5 average rating, 21 reviews

2 Bedroom Hamptons Waterfront Cottage Rental

This incredible 2 Bedroom, 1 Bath 750 sq ft Cottage is steps from an inlet leading out to Peconic Bay. The cottage sleeps 4 adults comfortably. Bedroom 1 currently has 2 Twins, Bedroom 2 has a queen Bed, but 2 twins can be requested. The cottage has a private entrance and private deck with BBQ, kitchen, and living area.

Top guest favorite

A traditional New England house is set in the central village of the island, surrounded by lush green lawn. Tall trees provide shade, and the late afternoon sun creates elongated shadows across the grass, highlighting the inviting outdoor space.

Cottage in Shelter Island

4.96 out of 5 average rating, 105 reviews

3 Bedroom Cottage Gem

Traditional Shelter Island house, located in the heart of central village. This 3bedrooms/2 bathrooms house is really quiet, convenient for tennis players with courts cross the street, 4bikes to borrow. This house is close to restaurants and is close to the beach as well...

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Popular amenities for Shelter Island kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

Top guest favorite

Two paddleboards are displayed on a wooden rack in a green outdoor setting. A blue paddleboard sits atop a black kayak, surrounded by lush grass and distant trees against a clear sky.

Home in North Fork

5 out of 5 average rating, 25 reviews

Peaceful Retreat • Waterfront Access + Huge Yard

Home in Rocky Point

4.87 out of 5 average rating, 234 reviews

The Katalpa House -by the beach

A sandy beach area is depicted, featuring a simple wooden bench and a pink chair facing the calm waters of Long Island Sound. The shoreline is complemented by patches of green grass and distant boats can be seen on the horizon.

Home in Madison

5 out of 5 average rating, 17 reviews

Beach Home & Garden Paradise

Home in North Fork

5 out of 5 average rating, 17 reviews

Waterfront with private dock & bocce court

Home in Sag Harbor

4.91 out of 5 average rating, 44 reviews

Wake up to Stunning Views at a Serene Waterfront Haven

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

4.92 out of 5 average rating, 12 reviews

Private Beach access along the Wine Trail

Two blue kayaks rest on a lush green lawn, ready for use. In the background, a wooden deck and stairway lead to a house, while an orange inflatable kayak is positioned on a raised platform. Tall grasses surround the area, creating a serene outdoor space.

Home in Mastic Beach

5 out of 5 average rating, 44 reviews

Waterfront home with amazing views

A charming single-story house is set on a grassy lot surrounded by trees and shrubs. The exterior features light yellow siding and a blue door. A wooden deck with an umbrella offers a shaded outdoor space, inviting relaxation in a serene setting.

Home in Shelter Island

4.73 out of 5 average rating, 40 reviews

All Seasons Rental

Cottage rentals with a kayak

Cottage in North Fork

5 out of 5 average rating, 13 reviews

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

A sandy beach stretches along the shoreline, meeting calm blue waters under a clear sky. A wooden staircase leads down to the beach, surrounded by sparse vegetation and rocky areas. Soft clouds drift above, contributing to a serene coastal scene.

Cottage in North Fork

4.89 out of 5 average rating, 28 reviews

Pumpkins & Sunflowers! Cozy Cottage in the Fall!

Top guest favorite

A spacious living area features large windows allowing for natural light and views of the surrounding landscape. The room includes a cozy seating arrangement with a leather couch and armchairs, alongside a dining table that accommodates several guests. A wooden staircase leads to a lofted space.

Cottage in Guilford

4.99 out of 5 average rating, 97 reviews

Waterfront Joshua Cove Cottage with private beach.

Top guest favorite

An aerial view captures the cottage's proximity to the beach, with sandy shores and gentle waves visible. The surrounding area features a blend of trees and homes, enhancing the scenic coastal environment.

Cottage in Guilford

4.94 out of 5 average rating, 263 reviews

The Cottage at Indian Cove

Aerial view of a tranquil waterfront landscape featuring numerous small islands and rocky shorelines. The serene blue waters reflect sunlight, and a few scattered trees dot the land, enhancing the natural beauty of the coastal environment.

Cottage in Guilford

4.87 out of 5 average rating, 38 reviews

Your own Thimble Islands private cottage!

An outdoor pool area is surrounded by well-maintained greenery and a spacious stone deck. Lounge chairs are positioned around the pool, inviting relaxation. A pergola is visible in the background, providing a shaded space near the cottage.

Cottage in East Patchogue

4.89 out of 5 average rating, 57 reviews

Bellport Beach Estates Private Cottage with Pool

A serene view of an inlet bay beach is presented, featuring soft sandy shores leading to calm waters. A swan stands gracefully in the water, with the shoreline visible in the background, framed by trees and houses on the opposite side.

Cottage in Branford

4.96 out of 5 average rating, 46 reviews

Ret's Coastal Cottage w/Private Association beach

An orange kayak is resting against a wooden fence, with sunlight illuminating the setup. The area features a paved surface and green grass, suggesting space for outdoor activities. Nearby, a table with chairs is visible, indicating a spot for relaxation.

Cottage in East Haven

4.93 out of 5 average rating, 29 reviews

Cozy Cottage with Water Views Steps to the Sand

Quick stats about vacation rentals with a kayak in Shelter Island

Total rentals
10 properties
Nightly prices starting at
G$31,378 GYD before taxes and fees
Total number of reviews
320 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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