Vacation rentals with a kayak in Shelter Island

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Top-rated kayak rentals in Shelter Island

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Guest favorite

A deck area is presented with a grill beside colorful potted flowers. The railing offers a view of the marina, where boats are moored alongside a calm body of water, surrounded by lush greenery.

Guest suite in Old Lyme

4.94 out of 5 average rating, 17 reviews

Marina 1 bedroom apartment sleeps 4 on-water.

Take it easy at our unique, tranquil getaway located directly on the 600 acre Great Island Salt Marsh sanctuary. This 2nd flr. marina apartment is a nature lover paradise, overlooking the estuary, with access to all of the water sports offered at Black Hall Outfitters in pristine Old Lyme Kayak, SUP, relax and unwind while overlooking the Long Island Sound at the Mouth of the CT. River. Sleeps 4 comfortably, and has a spacious open floor plan. Jungkook and Jimin of BTS filmed Are U Sure TV here.

Guest favorite

A modern kitchen features white cabinetry and a marble-like backsplash. Stainless steel appliances are present, alongside a spacious island with seating. Natural light fills the room through large windows, illuminating the light wood flooring that flows into a living area in the background.

Home in East Haven

4.97 out of 5 average rating, 146 reviews

The Breakaway - a waterfront gem.

Located next to historic Lighthouse Park, this Morgan Point, California-style bungalow overlooks a lighthouse and breakwater that protect New Haven Harbor. Prepare oceanfront dinners in your modern kitchen; relax to sunrises, sunsets, & the sound of waves. A quiet beach is steps from the door for swimming and kayaking. New Haven sights, restaurants, & nightlife are only minutes away. Picturesque coastline communities, local vineyards, breweries, fall foliage, & commuter rail to NYC are nearby.

Top guest favorite

A two-story home features a light-colored exterior with traditional shutters and a welcoming front porch. The yard is neatly landscaped with greenery and flowers. A wooden deck is visible at the back, providing an inviting outdoor space.

Home in Old Saybrook

4.97 out of 5 average rating, 121 reviews

Year Round Beach House in Old Saybrook, CT.- Pets

Our Beautiful Home is Located in Saybrook Manor Association and only a short walk to the beach . We have 4 Bedrooms that can accomadate 8 people,pull out couch,2 bathrooms, a Dining Room,Kitchen, and Spacious Living room.Our Yard is fenced in for your privacy & pets.Our home comes with many ammenities such as movies,games,kayaks, Clamming &Crabbing tools,Bikes,Floats & Beach Chairs.We have a beautiful backyard to enjoy games,barbecue or just to relax & unwind.Enjoy our beautiful & quaint beach

Guest favorite

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.

Guest favorite

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.

Home in Mastic

4.88 out of 5 average rating, 102 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.

Top guest favorite

An American flag hangs from a tree, gently waving in the evening breeze. The tranquil waterfront scene is illuminated by soft pink and blue hues from the sunset reflection on the water, framed by lush greenery and outdoor seating nearby.

Cottage in Old Saybrook

5 out of 5 average rating, 99 reviews

Cozy Waterfront Retreat

Serene waterfront retreat! Direct waterfront property on Oyster River perfect for kayaking, fishing, paddle boarding or just soaking up the sun. This cozy cottage with views of stunning sunsets allows guests to relax and unwind. Minutes to local restaurants and shopping, walking/bicycling distance to the towns best beaches; close to outlets and casinos. Quaint, charming cottage with beach decor throughout.

Superhost

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$.

Guest favorite

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.

Top guest favorite

Boat in Old Lyme

5 out of 5 average rating, 63 reviews

Cozy waterfront houseboat with views on views !

This riverside houseboat is truly is a hidden gem. Enveloped by stunning views and leading out to Rocky Neck, it offers a mix of adventure and serenity. Lounge with a view, paddle board on the river, and unwind under the stars by a fire pit. This secluded retreat provides a unique blend of peaceful relaxation and outdoor activities, all set in a charming and scenic coastal town!

Guest favorite

An expansive elevated deck offers scenic views of Jordan Cove, with the calm water reflecting the clear blue sky. Surrounding areas showcase tall grasses along the shoreline, and a private dock extends into the water, emphasizing the tranquil, natural setting.

Home in Waterford

4.95 out of 5 average rating, 114 reviews

Coastal New England Waterfront Home-The Reed House

The Reed House – Waterfront Getaway in Waterford, CT Enjoy the best of both relaxation and adventure at The Reed House, located in the peaceful Pleasure Beach neighborhood of Waterford. This charming home offers breathtaking views of Jordan Cove and is just steps away from the beach, making it the ideal retreat for families, friends, or anyone looking to unwind by the water..

Guest favorite

A spacious outdoor deck is featured, showcasing a sturdy wooden table surrounded by benches. A large woven light fixture hangs above, providing a relaxed ambience. The deck is shaded by a decorative cover, with views of greenery in the background, enhancing the inviting outdoor space.

Home in Montauk

4.88 out of 5 average rating, 146 reviews

Waterfront House on Fort Pond, MTK

Spacious house right on Fort Pond with relaxed bohemian vibe. Enjoy the open kitchen, reclaimed wood beams, and hand crafted furniture. Access directly to the water from the back yard. There are two other cottages that are two bedrooms each on property as well. We do live on the property full time and enjoy making our space a safe and clean environment.