Vacation rentals with a kayak in Montauk

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Top-rated kayak rentals in Montauk

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Guest favorite

Rental unit in Sag Harbor

4.83 out of 5 average rating, 183 reviews

Pet friendly Apt. Plus cabin, EV charger & sauna.

Artists apartment and cabin located on quaint cul-de-sac just outside Sag Harbor Village, minutes from Long Beach, pet friendly beaches are even closer. Centrally located for easy commutes to all towns and even ocean beaches. Free bikes, surf boards, 3 stand up paddle boards and 2 canoes. Life vests for you and pets A large tick free, shaded, shaded dog run. The cabin is a separate sleeping space from the apartment and has a 2 person SAUNA recently installed. WIFI AC and heat but No bathroom!.

Guest favorite

Home in East Haven

4.96 out of 5 average rating, 128 reviews

The Breakaway - a waterfront gem.

Located next to historic Lighthouse Park, this Morgan Point, California-style bungalow overlooks a lighthouse and breakwater that protect New Haven Harbor. Prepare oceanfront dinners in your modern kitchen; relax to sunrises, sunsets, & the sound of waves. A quiet beach is steps from the door for swimming and kayaking. New Haven sights, restaurants, & nightlife are only minutes away. Picturesque coastline communities, local vineyards, breweries, fall foliage, & commuter rail to NYC are nearby.

Guest favorite

Home in Montauk

4.97 out of 5 average rating, 32 reviews

Montauk Waterfront Retreat w/2 fireplaces

Enjoy peaceful luxury in this 4 bedroom, 4 bath 3,500 sq ft home with 20-foot ceilings on 1.1 acres of Lake Montauk waterfront. Families are preferred. 4 elegant bedrooms, office with a sofa bed, 3.5 baths in the house and another full bath in the pool house. A chef's kitchen w/ Viking appliances and everything you need for entertaining. A 30x40 heated pool is available after Memorial Day. There are 3 adult and 2 child kayaks with life vests, and 4 bikes. Dogs permitted: $200 fee per dog.

Superhost

Home in Hampton Bays

4.84 out of 5 average rating, 101 reviews

Heart of the Hamptons

Peaceful 3 bedroom cottage in a quaint section of the Hamptons. Located on the south shore, closest to the ocean beaches you can get. Bay water at end of lane, ocean beach just over the Ponquogue bridge. Large backyard for games & BBQ grilling. Enclosed patio for morning coffee & evening dinners. The house is best suited for families & friends needing space & looking for simple, low key relaxation. Please click "Contact Host" if you have specific booking requests & I will look to accommodate.

Guest favorite

Home in Montauk

4.95 out of 5 average rating, 38 reviews

LUXE,Waterviews,Redesigned,Renovated&Refurnished!

**PLEASE DO NOT submit a booking request before messaging us* Modern Chic Beach Design with Chef's kitchen. Sweeping, panoramic water views, amazing sunsets from this home are breathtaking, huge heated SALTWATER pool with SLIDE. Minutes to the ocean and harbor. A 5 minute walk to very secluded bay beach in this almost zero traffic location on a cul-de-sac. Imagine relaxing on the beautiful deck enjoying a cocktail, some fresh seafood as the kids enjoy the huge heated pool with slide.

Superhost

Home in Rocky Point

4.89 out of 5 average rating, 213 reviews

The Katalpa House -by the beach

-Our beach is private, key and beach tag provided- (in brown shed) This 1000+ sf home, features a newly renovated kitchen, outdoor shower, and many quirks that come with a 90 year old home. The furnishings are eclectic and vintage. Most of the flooring is also new. The beach and bluffs are only about a 2 minute walk. The 1/4 acre lot is shared with a secondary unit as you can see in the photos which is occupied by my sister.

Guest favorite

Cottage in Guilford

4.93 out of 5 average rating, 257 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.

Guest favorite

Home in East Hampton

5 out of 5 average rating, 12 reviews

Cozy for the Fall- East Hampton Cottage

This four bedroom, three bathroom Springs home is stylish and simple with tons of outdoor space, an outdoor shower, and a quick two minute walk down to the swimming bay and Bostwick's on the Harbor which has the best sunset in the Hamptons right at the end of our street. 8 minute drive to East Hampton town, 10 minute drive to ocean beach. Walking distance to EHP Resort, S&S coffee shop, Rita's Cantina and Maidstone Park.

Superhost

Home in Shelter Island

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. Monday-Thursday stays February through June no cleaning fees!!!

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.

Guest favorite

Home in Southampton

4.95 out of 5 average rating, 149 reviews

Waterview, Dogs StayFree! Kayaks, Ping-Pong

Beachy casual feel-good home easily located entrance The Hamptons. Lovely views of Bay, sunsets & birds! Launch our Kayaks at street's tiny beach flowing from Cold Spring Pond into Bay! Our private pool is heatable and plant-surrounded. Bike less than a mile to Bay / Drive 4 miles to famous Cooper's Beach on the Atlantic!

Guest favorite

Cottage in Shelter Island

4.96 out of 5 average rating, 104 reviews

3 Bedroom Cottage Gem

Traditional Shelter Island house, located in the heart of central village. This 3bedrooms/2 bathrooms house is really quiet, convenient for tennis players with courts cross the street, 4bikes to borrow. This house is close to restaurants and is close to the beach as well...