Vacation rentals with a kayak in Montauk

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Montauk

Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

Home in North Fork

5 out of 5 average rating, 24 reviews

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.

Top guest favorite

Home in Woodmont

4.96 out of 5 average rating, 27 reviews

Charming 3 bedroom Beach Front Cottage

The Spring is a great time to enjoy the solitude of the beach and watch as the tide ebbs and flows on warm days and cool nights. Have fun with the whole family, friends or loved ones at our beach front escape. Perfect for some fun in the sun. An amazing Sandbar at low-tide, a deck to relax on and a cozy inside are just a few of our great amenities. There is also a Kayak, Paddle-board and raft to enjoy. Feel free to use the fire-pit or fish off the beach. The opportunities are endless.

Guest favorite

Home in Southampton

4.96 out of 5 average rating, 167 reviews

POOL in APRIL! Waterview, Free For Dogs! Kayaks

*Please note for monthly stay there are NO TAXES :) ! Beachy casual feel-good home easily located at the entrance to The Hamptons. Lovely views of the Bay, Nightly Sunsets & birds! Launch our Kayaks at street's tiny beach flowing from Cold Spring Pond into Bay. Or cuddle by the fireplace and play our many available games. We provide soft sheets & towels for the showers and & beach...priding ourselves on your comfort! Our Private-Pool is heatable & plant-surrounded with Outdoor Shower.

Guest favorite

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

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

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.

Superhost

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

Apartment in Branford

4.95 out of 5 average rating, 22 reviews

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.

Guest favorite

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.

Guest favorite

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.

Superhost

Apartment in Sag Harbor

4.69 out of 5 average rating, 55 reviews

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

Superhost

Guesthouse in Hampton Bays

5 out of 5 average rating, 21 reviews

2 Bedroom Hamptons Waterfront Cottage Rental

This incredible 2 Bedroom, 1 Bath 750 sq ft Cottage is steps from an inlet leading out to Peconic Bay. The cottage sleeps 4 adults comfortably. Bedroom 1 currently has 2 Twins, Bedroom 2 has a queen Bed, but 2 twins can be requested. The cottage has a private entrance and private deck with BBQ, kitchen, and living area.

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What guests are saying

Waterfront NoFo Cottage w/ public beach access

4.94 out of 5 average rating, 31 reviews4 months ago

Andrew and Kenneth were excellent hosts. Some of the most professional, responsive and attentive I have experienced. The home is cozy, and the space is really well used and appointed. Some of the appliances are a bit quirky -- like the washer/dryer, which isn't very effective; and the stove/oven which the hosts are aware needs some repairs. The location is lovely. Be prepared to listen to the ducks on the lake. They can be loud even during the night. The outdoor shower was the icing on the cake for me. I nearly stayed longer, except I had another opportunity overseas.

Home in North Fork

What guests are saying

Amagansett, Waterfront retreat

4.93 out of 5 average rating, 14 reviews7 months ago

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!

Home in Amagansett

What guests are saying

The Sandy Shack - Coastal Escape

4.9 out of 5 average rating, 21 reviews6 days ago

As a native long islander I enjoy finding great properties I can bring my family to to take advantage of all long island has to offer. This was the DREAMIEST beach bungalow!! The bedroom with the two beds was just my favorite room especially since we visited off season. You cannot beat this location. I can't wait to book again during high season! Thanks for sharing your home with us !!

Home in North Fork

What guests are saying

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV

5 out of 5 average rating, 9 reviews3 days ago

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.

Home in North Fork

What guests are saying

Beach House on the Bay

5 out of 5 average rating, 61 reviews8 months ago

We loved this beautiful house. The views and sunsets were spectacular! The only issue we had was that we never received the entry code and when we got to the house, I had trouble getting in touch with Jim because I had no internet service. I was able to call my husband who was able to get me Jim’s number. He helped us immediately and we were able to access the home. I would highly recommend this home and would absolutely stay here again.

Home in Sag Harbor

What guests are saying

4 Bedroom Beach Bungalow

4.89 out of 5 average rating, 28 reviews6 months ago

Jennifer’s placed checked all 4 C’s with 5 plus stars! Extremely comfortable, charming, cozy and clean. We absolutely loved the enclosed porch and fire pit areas. Great getaway for my parent’s 60th wedding anniversary weekend on the NoFo. I’ve rented from lots of owners, Jennifer is by far one of the best. Great communicator and very flexible. Highly, highly recommend!!

Home in North Fork

What guests are saying

Hang by the (Chel)SEA

5 out of 5 average rating, 14 reviews4 days ago

The place is stunning. The views and being right on the beach is priceless. We stayed with two kids and a dog. Would want to buy the place that is how much we loved it! Everything is there as described and more. The piano was great for the kids! Chelsea is super helpful and nice. Finally again an AirBnB that feels like home.

Home in North Fork

What guests are saying

Stunning sunset charming waterfront home 4 seasons

4.98 out of 5 average rating, 65 reviews3 months ago

Absolutely stunning! This house has an amazing view from gigantic glass doors in the main room. Details in the house are well thought out and of great quality, including a high end coffee maker and other appliances. The place has lots of premium touches that make this experience a cut above the rest. Steven is an amazing, friendly, and communicative host. Incredible experience all around, I would definitely book here again.

Home in Shirley

What guests are saying

Incredible Beach Front Bungalow w/ Private Beach!

4.92 out of 5 average rating, 63 reviews6 months ago

This place exceeded our expectations- the listing photos do not do the views justice. Everything else was just as advertised and met or exceeded all of our needs. The entire place was spotless upon arrival, plenty of towels and kitchen wares. Easy simple requests from host for check-out too! This was a long girls weekend with my two adult daughters and we loved it so much we barely left. Our original plan was to fill the weekend with wineries, restaurants and maybe some shopping or sightseeing of the area, we planned a pretty full weekend. However, we loved the views and tranquility of the place so much we BARELY left the house. Over the weekend, we only hit a few wineries, (with great recommendations from the host by the way) then we door-dashed every meal in so we could enjoy the back patio area and the beauty and peace of the beach and views. You won’t be sorry if you book this property. Such an amazing little place, you’ll never want to leave.

Bungalow in North Fork

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