Holiday rentals with a kayak in Napeague

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Top-rated rentals with kayak in Napeague

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

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Guest favourite

Cottage in Montauk

4.93 out of 5 average rating, 56 reviews

Montauk Modern Waterfront Cottage

Perfect Sunsets all year, this amazing 2 bedroom waterfront cottage, on bucolic Fort Pond is as close as it gets to perfection. A short walk to town, dining, Jitney & beaches. Beautifully decorated with mid century modern furniture & spectacular landscaping. Large living area, state of the art kitchen & bathroom with door to outdoor shower. A flat screen with Apple TV and WiFi. Ideal for couples, singles or a small family (1 dog per booking accepted). EH Montauk Rental #20-550 (2022-2024)

Top guest favourite

Cottage in Guilford

4.99 out of 5 average rating, 104 reviews

Waterfront Joshua Cove Cottage with private beach.

Beautiful architecturally designed 1 Bedroom + loft Cottage on Joshua Cove in Guilford. The sunsets are spectacular from your own private beach. Enjoy Fall Foliage, swimming, fishing, and some of the best Kayaking from this perfect setting. Minutes from the Guilford train station, restaurants, shopping, and historic town green. The property is just 15 minutes from New Haven, and the Yale campus. The Thimble Island cruise, and the Ct. river steam train/cruise are nearby as well.

Guest favourite

Cottage in Guilford

4.86 out of 5 average rating, 42 reviews

Your own Thimble Islands private cottage!

Escape to your own piece of private paradise! This unforgettable property encompasses 1+ acres of Narrows Island (Thimble Islands/Old Quarry Peninsula) - accessible by car via permanent land-bridge to island. Spectacular one-bedroom cottage with jaw-dropping surround oceanfront and accompanying views; modern and well-appointed. Approx 20 min to Yale, 5-10 min to town green and shops/restaurants. Indulge in sanctuary on an exclusive piece of Connecticut's most coveted shoreline.

Superhost

Home in Hampton Bays

4.84 out of 5 average rating, 107 reviews

Stunning Hamptons Waterfront Escape w/ Sunset View

Experience an unforgettable trip in the Hamptons at our waterfront haven! Savor the views from our spacious deck, complete with a Weber grill. Vaulted ceilings and large windows flood the space with natural light. We have completed renovations of 3 bathrooms, 2 kitchens, and the entire pool house over the last 18 months. Our home is <10 minutes drive to the beach, groceries, and restaurants! Note our pool and dock are open for the season and will close by mid September 2025.

Guest favourite

Home in Amagansett

4.93 out of 5 average rating, 15 reviews

Amagansett, Waterfront retreat

(4 night minimum) Perfect place for a family, couple, or friends. Close to Amagansett Village and 12 minutes to Montauk, this waterfront retreat is great for nature activities like windsurfing, kiteboarding, sailing, stand-up paddle board, hiking, biking, and much more. Located just minutes from ocean beaches and 3 minutes to the "Napeague stretch", home to the famous "Lobster Roll" a/k/a "LUNCH" and the Napeague Clam Bar restaurants. East Hampton registry RR 25-417

Top guest favourite

Home in North Fork

5 out of 5 average rating, 14 reviews

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

★ "Beautiful hidden home on the water… enjoy the North Fork summer in style." Private beachfront property with 2 homes & views of Gardiner’s bay. ☞ Bikes + kayaks + paddle boards ☞ Wrap around balcony w/ seating ☞ Fully equipped + stocked kitchen ☞ Deck w/ lounging + water views ☞ Dedicated workspace + printer ☞ Master w/ king + bathroom ☞ 55” Smart TV + Xbox ☞ Indoor gas fireplace 6 mins → DT Greenport (cafes, dining, shopping) 13 mins → Orient Beach State Park ⛱

Top guest favourite

Cottage in Guilford

4.94 out of 5 average rating, 272 reviews

The Cottage at Indian Cove

A charming original turn of the century cottage that was recently renovated. One main room plus a full bathroom and Ikea kitchen. It includes a back porch that gets a perfect amount of late afternoon sun. The cottage has electric baseboard heat for cool nights. We are located in Indian Cove beach Association with a two block walk to the beach. You are welcome to enjoy our kayaks, bikes to tour the area and a fire pit.

Top guest favourite

Villa in East Hampton

4.98 out of 5 average rating, 53 reviews

PINKWOOD PLAYHOUSE is the perfect spot for your Hamptons stay, offering elevated design and relaxed luxury with laid back beach vibes. Perfect for families or couples. This stylish and serene home features 4 bedrooms, 2.5 bathrooms, a fully equipped kitchen, soaring ceilings and an open floorplan. Bring the outdoors in with oversized windows and over 1000 square feet of deck space overlooking the gorgeous pool.

Guest favourite

Home in Montauk

5 out of 5 average rating, 31 reviews

House on Napeague Harbor, Amagansett

This family-friendly, rustic beach house was designed around the position of the setting sun and weather co-operating, most evenings guests are not disappointed. The shallow water of the Harbor is a mere 50' from the house - enjoy breakfast on the patio while cormorants and egrets cruise the harbor. Windsurfers, kite-surfers are active when the wind is up; kayakers and SUPers love the calmness of the bay.

Superhost

Home in Shelter Island

4.9 out of 5 average rating, 117 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 favourite

Home in Montauk

4.88 out of 5 average rating, 147 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 in Amagansett

5 out of 5 average rating, 3 reviews

Ocean theme Balcony-View Studio Apt w/ 1 BTH & Tub

Professionally Managed by: PMI GOLD COAST PROPERTIES Enjoy a beach vacation in this Ocean theme studio apartment just minutes from the ocean—a perfect stay in the heart of downtown. Relax on the balcony, and take a soak in the tub in the spacious bathroom. Perfect for a couple to escape and enjoy quality time together.