Vacation rentals with a kayak in Shelter Island

4.97 out of 5 average rating, 146 reviews

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

The Breakaway - a waterfront gem.

AndreaRating, 5 stars1 month ago

Ray is an amazing host as is his Airbnb. My friend and I have gone there twice to get away and to write, and it is the perfect location for this. The sound right behind the house is spectacular, as is the beach entry down the street. We took many walks and collected shells and sat outside on the deck to watch the sunsets. The house is not far from New Haven so there were times we would head into town for dinner. Ray is very kind and quickly responded to us when we had questions. The home is beautiful and clean and we hope to go back there again!!

4.96 out of 5 average rating, 168 reviews

Home in Southampton

Waterview+Pool, FreeForDogs! Kayaks/PingPong/Bikes

ChristiRating, 5 stars3 days ago

We had a wonderful two day stay at Roger and Amy’s place. It was fantastic- such a beautiful, inviting home. Our kids had a blast in the heated pool- we could barely get them to come out despite it being under 60 degrees out! The kitchen was stocked with more than just kitchen basics- the spice cabinet had soo many different choices ! It was probably the most perfect AirBnb experience I’ve had and we travel plenty.

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

AndrewRating, 5 stars4 months ago

We've stayed at Mae's lovely house several times, in many different seasons, and once again it did not disappoint. Excellent fireplace, comfortable furnishings, nicely equipped kitchen, stylish bathroom. And the gorgeous view of the pond and its abundant birdlife is always a treat. We can't wait for our next visit!

4.96 out of 5 average rating, 100 reviews

A charming beach cottage stands prominently on sandy ground, showcasing a spacious deck with white railings. Clear views of the Long Island Sound are visible from the large windows. Nearby, other beach houses can be seen, contributing to the coastal atmosphere.

Home in East Haven

Cozy Beach - Direct Waterfront!

SarahRating, 5 stars4 months ago

This house is a gem! I came to stay a week in off season with my dog, Rollo. The location is breathtaking, right on the Long Island Sound. We had a great time exploring the beach, looking for all the biodiversity in the birds and sea creatures, watching the boats, and this place is relatively close to an airport so watching the planes land and take off was awsome as well. We came for privacy, and I expected the beach to be a little more private than it was due to my dog's reactivity. But the neighbors did not seem to have issues with us, and once you are close to the water, especially in low tide, the beach is pretty open for all the locals. Walking around, the locals all waved and said hello. Not too many restaurants close by, but the Lobster Shack down the road had good food! Would stay again! The deck alone was worth it!

4.98 out of 5 average rating, 44 reviews

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

Stunning waterfront modern farmhouse with dock.

PatriciaRating, 5 stars1 month ago

Returning guest, we had a wonderful weekend at Michelle's idyllic home. Plenty of space for our two families and 3 kids. The kids love having their own space in the "she shed" while the adults enjoy the lakeside views from both the yard and inside the spacious living area. The house is always immaculately clean. Beds and other furnishings are comfortable, and the house is an easy drive to everything the North Fork has to offer. We look forward to returning (again!) soon.

Guesthouse in Hampton Bays

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.

5 out of 5 average rating, 21 reviews

2 Bedroom Hamptons Waterfront Cottage Rental

BrianRating, 5 stars9 months ago

A quaint cottage that was sparkling clean. Access to the Peconic from a private dock with the available kayaks and canoes. There is a pristine built-in pool with new decking. There was a 10 minute drive to Hampton Bays town with great restaurants, grocery and shopping.

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Popular amenities for Shelter Island kayak rentals

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Pool

Free parking on premises

Air conditioning

House rentals with a kayak

5 out of 5 average rating, 33 reviews

Home in Southampton

Tranquility at the Water’s Edge

JenniferRating, 5 stars1 month ago

A beautiful, relaxing and peaceful setting and a quick and easy trip to town. Great views and house was perfect with tons of amenities and perfect to bring our dog. Host was fantastic and so responsive. An amazing stay!

4.88 out of 5 average rating, 233 reviews

Home in Rocky Point

The Katalpa House -by the beach

JessicaRating, 5 stars1 month ago

Amazing place, super accommodating, and so understanding. Experience was absolutely amazing.

5 out of 5 average rating, 16 reviews

A serene beach scene is captured at sunset, featuring soft, warm hues in the sky blending with the calm water. The sandy shore curves gently along the edge, with distant islands visible on the horizon, creating a peaceful coastal atmosphere.

Home in Sag Harbor

Beach Cottage | Steps to Water | Firepit

JuanRating, 5 stars1 week ago

We loved staying at Ann’s place. Exactly like the photos, very close to Sag Harbor and the beach. The cottage has everything you would ever need! We would love to stay again in the future.

5 out of 5 average rating, 17 reviews

Home in North Fork

Waterfront with private dock & bocce court

AlisonRating, 5 stars5 months ago

We thoroughly enjoyed our stay and would definitely book again ! Close to the many wineries and cute towns, and peaceful and comfortable to come back and relax at. We enjoyed the fire pit , the view from the dock of the changing tree colors and the flow of the kitchen. ❤️

4.84 out of 5 average rating, 31 reviews

Two kayaks are positioned under a covered area, with one green kayak prominently displayed. In the background, a serene waterfront view features lush grass and calm water, leading towards a dock and distant homes. Clear skies and light clouds are visible overhead.

Home in Hampton Bays

Waterfront Home | Chefs Kitchen | Sleeps 10

VigneshRating, 5 stars3 months ago

The place was wonderful and absolutely close to the description. lot of details are added around the house including instructions making it very easy and good experience. would definitely recommend

4.92 out of 5 average rating, 12 reviews

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

Private Beach access along the Wine Trail

RaeganRating, 5 stars1 month ago

I would highly recommend Melissa's place in Jamesport. It was a great location with room to enjoy with some family members including children. It was perfect with some toys and a big outdoor area (and a private beach!) for us all to spend some time together while visiting family in the area. Melissa was accommodating and clear in her directions and gave us a warm welcome with a greeting basket, information about the area and coffee! The location is lovely and everything about the house was fun and comfortable. Thanks!

4.73 out of 5 average rating, 40 reviews

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

All Seasons Rental

ChristianRating, 5 stars1 week ago

The house was as advertised and well appointed and comfortable. I would stay again. Our family had a very nice memorable long weekend.

4.71 out of 5 average rating, 90 reviews

A coastal view is presented with sandy access leading to the water. Flanking the path, vibrant pink flowers in large planters add color. The house features a light exterior and is set against a backdrop of blue skies dotted with white clouds.

Home in Clinton

Year-Round Waterview 4 Bds/2Bths, Sleeps 13 Linens

MaryRating, 5 stars2 days ago

This house was very good for me and my friends and we would love to go back!

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Cottage rentals with a kayak

5 out of 5 average rating, 13 reviews

Cottage in North Fork

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

ChristinaRating, 5 stars2 weeks ago

Had a great weekend at the cottage! Meredith was so great letting us check in early and was super helpful and responsive. The cottage is gorgeous and has everything you need. Loved it! Thank you!

4.89 out of 5 average rating, 28 reviews

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

Pumpkins & Sunflowers! Cozy Cottage in the Fall!

DanRating, 5 stars8 months ago

Had a nice stay here with a group of people attending a wedding a short drive away.

4.99 out of 5 average rating, 97 reviews

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

Waterfront Joshua Cove Cottage with private beach.

FrankRating, 5 stars5 months ago

We spent Thanksgiving in the beautiful Joshua cottage. This was one of the best Airb&b stays we have ever had. The hosts were wonderful- making sure we had everything we needed. The spot directly on the water is magical.

4.94 out of 5 average rating, 263 reviews

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

The Cottage at Indian Cove

RosalindRating, 5 stars1 day ago

My adult daughters and I thoroughly enjoyed our stay in this peaceful cottage! The cottage was cozy, comfortable, and just the right size for the three of us. The house and kitchen had all the essentials and we enjoyed the treats and complimentary food that Gail provided. We relaxed and strolled down to Indian Cove and Barbra Pine Memorial beaches. Overall, we had a fantastic stay and highly recommend!

4.86 out of 5 average rating, 37 reviews

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

Your own Thimble Islands private cottage!

LilianRating, 5 stars1 week ago

We had an amazing stay with Sean and Jenny. The property is perfect for a peaceful getaway from the stresses of daily life- unique location, impeccable views, spotless and well furnished house, we were able to unplug and enjoy some nice quality time. Sean is a gracious host, offered lots of local recommendations as well as details of the house that were very helpful. Was responsive for questions and easy to communicate with. Hope to be back one day!

Cottage in East Patchogue

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.

4.89 out of 5 average rating, 57 reviews

Bellport Beach Estates Private Cottage with Pool

NicoleRating, 5 stars10 months ago

The house was so peaceful and quiet. The deer were just walking around and calming to watch! The backyard is better than the pictures and would stay there again! My only issue was with the lack of privacy in the house. The doors are similar to shutters to allow airflow, but you could here everyone in all the rooms. Not a huge deal unless you have loud kids!

4.96 out of 5 average rating, 45 reviews

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

Ret's Coastal Cottage w/Private Association beach

LauraRating, 5 stars2 days ago

Thank you !! We enjoyed our stay. The home is lovely and the area was so convenient to all ! The airport is 7 minutes away. Def would stay here again. Thanks again