Holiday rentals with a kayak in Montauk

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Top-rated rentals with kayak in Montauk

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

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Guest favourite

Home

5 out of 5 average rating, 22 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.

Guest favourite

Home

4.95 out of 5 average rating, 22 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 September 30th.

Guest favourite

Cottage

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.

Guest favourite

Home

4.96 out of 5 average rating, 160 reviews

Waterview, DogsStayFree! Kayaks, Ping-Pong

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 favourite

Flat

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 the excellent restaurants and attractions along the Connecticut shore line.

Superhost

Home

4.9 out of 5 average rating, 115 reviews

Hay 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 favourite

Home

4.96 out of 5 average rating, 23 reviews

Southampton Lake Front Home

Kick back and relax in this calm, stylish space with a lakefront view, modern decor, and beautiful outdoor plant life. Enjoy a night out at the Tavern Bar & Grill just up the road and close out the night with a boat ride under a blanket of stars. Feed the family with the outdoor Weber Grill with views and ambiance to make you amazed that the beach is just a short drive away.

Guest favourite

Home

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

Flat

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

Home

4.86 out of 5 average rating, 43 reviews

Cedar Hot Tub, Suana, Heated Pool walk to water

Heated pool through November 1st. Kayak, swim, fish 3 mile harbor, 5 min walk to water, 1 mile to Sammy's Beach, 9min to EH village and 13min to Sag Harbor. organic bedding, best cookware, decorated with ligne roset, Roche Bobois etc. 3 bikes , 2-single sea kayaks. gunite pool. Brand new HUUM Sauna, 1200 sq ft ipe deck with cedar hot tub.

Superhost

Guest house

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.