Vacation rentals with a kayak in Shelter Island

4.97 out of 5 average rating, 121 reviews

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

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

5 out of 5 average rating, 24 reviews

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

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.

4.86 out of 5 average rating, 29 reviews

A contemporary living area features a spacious, dark sectional sofa paired with a wooden coffee table. A textured area rug lies on the floor, while large windows allow natural light to illuminate the space. Artwork is displayed on the walls, enhancing the modern decor.

Apartment in Westbrook

Shoreline postmodern apartment

Brand New Construction- Everything shiny and new! Located in the heart of the marine district. This 2 bedroom apartment with pull out couch for a third bed offers postmodern styling, and a wide open floor plan. Just steps from all of the major restaurants, bars, breweries, and beaches in Westbrook ct. Brand new and high end finishes, offers easy access to 1-95, all of the local marinas, and famous gathering places such as Lenny and Joes Fish Tales, Bill's Seafood, and Westbrook Lobster co.

4.91 out of 5 average rating, 23 reviews

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

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.

4.88 out of 5 average rating, 102 reviews

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

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

4.9 out of 5 average rating, 39 reviews

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

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.

5 out of 5 average rating, 98 reviews

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

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.

4.9 out of 5 average rating, 115 reviews

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

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$.

4.95 out of 5 average rating, 22 reviews

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

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.

5 out of 5 average rating, 10 reviews

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

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.

4.69 out of 5 average rating, 55 reviews

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

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