
Holiday rentals with a kayak in Shelter Island
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Top-rated rentals with kayak in Shelter Island
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Popular amenities for kayak rentals in Shelter Island
House rentals with a kayak

Tranquility at the Water’s Edge
This place was divine. We came for a week with our two kids (4&6) and had the easiest most laid back time. We kayaked, walked to the beach, the kids played constantly around the house as it’s right on the water but the yard is fenced off. It was so good you guys 10/10 would book again. And Jeff was the best host. So quick to respond, provide options etc. He rocks.

Beach Home & Garden Paradise
Amazing house that could not be any closer to the beach. Super well thought out house with very nice appliances and finishes. Kids and parents alike had a great time and will look forward to visiting again. A real gem!

Waterfront with private dock & bocce court
We had five adults, an 8 year old, a baby and a dog converging for some time together on the east coast, and Hattie’s house was perfect for us. Lots of room for all, lots of great spots nearby, and for the few small issues that arose, Hattie was very responsive. But honestly, it could have been a lot worse and I’d still have given it five stars for the bocce court alone.

Year Round Beach House in Old Saybrook, CT.- Pets
My family had an excellent stay. The house was clean, organized and had an abundance of supplies. The house was decorated very nice and had everything we needed for the beach. We hung outside at night on the porch. The host was extremely helpful and reached out prior to our trip with key information. It was a perfect stay.

Bright Hamptons Getaway ☀️ Pool▪︎ Beach▪︎FamilyFun
we had a quiet girls getaway to celebrate my sister getting married-upon arrival we checked out the entirety of the home…to which we were pleasantly surprised every corner we turned! exquisite home with comfortable, aesthetically pleasing furnishing and so much gorgeous natural light. the outdoor shower was a huge BONUS! heated pool had us outside moving our bodies more than we’d imagined and was such a fun way to spend time together. the living room is so cozy and a great space to have a game-night-in! i could go on and on about each detail but you should simply stay here and enjoy for yourself all this property has to offer!

Great Hammock Getaway | Beaches, Views & Hot Tub
This was our second stay at this lovely home. It was the perfect place to spend a week celebrating our 51st anniversary! The house itself is beautifully decorated, impeccably clean, and offers everything we could need for cooking, comfort, and leisure. We especially enjoyed the gas fireplace and the hot tub! We made good use of the local beach pass that was furnished for us. The two very close by beaches were well-maintained and very enjoyable. We would highly recommend this location and plan to make this our go to Airbnb when we are in this area. Irina is the perfect host! She is extremely responsive and reliable.

Waterfront House on Fort Pond, MTK
Noah was amazingly helpful for a long weekend we took with our two kids. He had a full size folding crib which made sleeping our 3 year old, easy. He keeps a beautiful, well-stocked home, which made it so convenient to cook some meals at home. The location is amazing, only a short drive to town and a priceless view of Fort Pond only steps away. Would love to stay here again.

The Captain's Crib
Joseph was a great host! Very communicative, thorough and quick to respond. The home is so charming and clean and we had such a great time visiting the area. Would love to stay there again and highly recommend.
Cottage rentals with a kayak

Lovely North Fork Beach Cottage (2 BR/2 bath)!
We very much enjoyed staying in Meredith’s place. The cottage is surrounded by trees so it feels secluded and peaceful. The cottage is elegantly decorated; there were so many nice books around which we enjoyed checking out. Meredith was so nice and responsive. We will definitely go back.

Pumpkins & Sunflowers! Cozy Cottage in the Fall!
Had a nice stay here with a group of people attending a wedding a short drive away.

Stunning waterfront modern farmhouse with dock.
Simply wonderful spot! We will try to come back! The personal touches were great. Shampoo and conditioner! Make up wipes! Plenty of toilet paper and so on. Traveling guests really appreciate those small things. Thank you!

Bellport Beach Estates Private Cottage with Pool
Had a great time despite the weather, there was so much todo. The place was cozy!

The Bay Breeze
Wonderful bay side cottage! Stayed here for a long weekend with my husband and in laws. It’s a great location!! Water views, walkable cute neighborhood, and 20 mins from some of the bigger towns (Jamesport & Greenport) Place was clean and a fully stocked kitchen made it easy to stay in and grill out.

Guest House at the Marina
We absolutely loved our stay in Clinton! The apartment was beautiful and clean with an amazing view. We tried lots of local hot spots and had a great swim at nearby Hammonasset. Communication and instructions were excellent. We look forward to returning!

Cozy Cottage with Water Views Steps to the Sand
We had a great stay! The kitchen was nicely stocked and the house was clean. Plenty of outdoor space and beds made it comfortable even for a large group!

Cozy Waterfront Retreat
Meghan's place is exactly as posted it is absolutely beautiful, cozy, comfortable and did I say beautiful? one of my favorite things to do was sit in front of the big windows and read. You have everything you can think of close, at least 4 to 6 minutes away. There are restaurants, super market and pharmacies. But if you are like me and also like to cook sometimes on vacation the kitchen was equipped with everything you need. Highly, highly recommend.
Quick stats about holiday rentals with a kayak in Shelter Island
Total rentals
10 properties
Nightly prices starting at
₹12,899 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
Destinations to explore
- The Hamptons Holiday rentals
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- Beach
- Charlestown Beach
- Fairfield Beach
- Southampton Beach
- Yale University
- Foxwoods Resort Casino
- Cooper's Beach, Southampton
- Napeague Beach
- TPC River Highlands
- Shinnecock Hills Golf Club
- Ocean Beach Park
- Walnut Public Beach
- Woodmont Beach
- Jennings Beach
- Amagansett Beach
- Groton Long Point Main Beach
- Seaside Beach
- Silver Sands Beach
- Blue Shutters Beach
- Groton Long Point South Beach
- Quotonset Beach
- Heckscher State Park
- Outer Beach at Smith Point County Park
- Ninigret Beach