
Vacation rentals with a kayak in Montauk
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Top-rated kayak rentals in Montauk
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House rentals with a kayak

Beachfront house on Long Island Sound
We loved our stay! The private beach was perfect for our kiddos - far enough away from the water that they could play independently in the sand while we sat on the beautiful deck. The kitchen had all the items we needed (we even took a virtual cooking class while there). Dmitry was super responsive and helpful. The master bedroom was a beautiful place to watch the sunrise/sunset.

House on Napeague Harbor, Amagansett
We had a wonderful stay at Harbor House. The view of Napeague Harbor is gorgeous and the sunsets are just next level spectacular. The kitchen is well equipped for cooking in and the furnishings are very comfortable. The location is great halfway between Amagansett and Montaik. We have rented so many homes over the years, but Rod’s house is by far in the most gorgeous setting. We cannot wait to return.

Beach House in Private Community on LI Sound
Bill’s place provided a wonderful location for our family of seven to spend our Thanksgiving holiday. The house was clean, uncluttered, and comfortable in every way. The kitchen had everything we could hope to find for meal preparation. The two sitting rooms provided delightful spots for reading, conversation or catching up on the television news. The upstairs bathroom was especially room and well-appointed. While it was winter when we visited, we could tell that this house would be a truly marvelous spot during the summer months as it had a great back deck and was truly only a hundred yards or so from a beach on the Long Island Sound. While it may not be the first choice of those who are on a tight budget, we recommend this home highly.

Amagansett, Waterfront retreat
My family had a wonderful time at Robert’s home. The house was clean and cozy and the view of the water was peaceful. He was super communicative and friendly and check in/out was a breeze. The house is in a great area and super close to East Hampton, Amagansett, and Montauk. Highly recommend!

Waterfront with private dock & bocce court
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. ❤️

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV
Had a wonderful time over Easter with my family and dog. The view was exquisite and the house very comfortable. Eileen was very responsive and even had hair dryers sent over. The house was very well equipped with lots of kitchen staple goods. Just be aware there is no microwave, but there is a very nice Breville toaster oven. Also, there is a large table outside for a group, but only a small table and counter seating in kitchen inside. We didn't have any issue since the weather was perfect for us to enjoy our Easter dinner outside. Overall, a beautiful home and only minutes from Greenport and wineries.

Breezy Waterfront Home With private Dock
Petra’s house is in the most beautiful spot on a small lake and a stones throw from the beach. This was our second year there and we hope to be back. The house is stocked with everything you need to feel comfortable including great bath products, kitchen, equipment, and toys and books. I never felt uncomfortable in her house. This was a wonderful family week in heaven.

Beachfront paradise- come, stay, relax!
we rented La Spiaggia in December, and while it's mostly going to be more beautiful and better in the summer (since it's a beach house) it was still perfectly fine in the winter; well insulated and with good strong heaters. speaking of the beach I can't stress enough of how close this place is to the water; I'm talking literally ten steps to the sand. I would certainly recommend the place as a great summer getaway!
Cottage rentals with a kayak

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

Salty Kisses Cottage Relax
Our stay was perfect! The home was so clean and Denise even left us a baby gate for our 1 year old. Denise was very responsive and provided great recommendations of places to eat and things to do. There is a private beach across the street but we walked about .25 miles down the street to the Silver Sands State Park beach so that our 1 year old could play in more shallow water before high tide. We would highly recommend and will be back!

The Cottage at Indian Cove
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!

Waterfront Beach Home with Fab Gardens, AC, Kayaks
We lived our stay at Carey’s place and plan to come back next year. Amazing location if you want to relax and take a few days away from the city. The house is very cozy and comfortable with a great backyard facing the water. Thanks Carey!!

Stunning waterfront modern farmhouse with dock.
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.

Cottage at the Marina
My stay at Chris and Ann’s listing was the perfect last stop on my stay in CT……beautiful, welcoming accommodations enhanced by the natural, peaceful, setting of the salt marsh and wildlife. It’s absolutely a favorite place the next time I’m visiting CT.

Your own Thimble Islands private cottage!
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!

Ret's Coastal Cottage w/Private Association beach
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
Quick stats about vacation rentals with a kayak in Montauk
Total rentals
70 properties
Nightly prices starting at
ﺩ.ﺇ735 before taxes and fees
Total number of reviews
1.5K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
50 properties have a pool
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- Beach
- Charlestown Beach
- Southampton Beach
- Easton Beach
- Foxwoods Resort Casino
- Napeague Beach
- Ocean Beach Park
- Cooper's Beach, Southampton
- Quotonset Beach
- Shinnecock Hills Golf Club
- Giants Neck Beach
- Blue Shutters Beach
- Clinton Town Beach
- Amagansett Beach
- Shennecossett Beach
- Attawan Beach
- Long Island Aquarium
- Clinton Beach
- Groton Long Point Main Beach
- The Breakers
- Shoreham Beach
- Barbara Pine Memorial Beach
- Grove Beach
- Horton Lane Beach