Vacation rentals with a kayak in The Hamptons

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Top-rated kayak rentals in The Hamptons

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Guest favorite

Home in Greenport

4.92 out of 5 average rating, 121 reviews

Beautiful Cottage Home W/ Beach & Dock Access

Beautiful, spacious beach side home situated within a block of a private beach. This cozy home is walking distance to Kontokosta Winery, Island's End Golf & Country Club, Lavender By the Bay and a five minute drive to the Village of Greenport. Replete with natural light and an open backyard perfect for outdoor dining and barbecues, this home is perfect for your stay in Greenport. Netflix/Hulu/Disney+ / ESPN+ / HBO MAX. Please note, 4 Bikes/1 Paddle Board/1 Kayak & Life Jackets provided May-Sept.

Jun 6 – 13

$765 per night

Guest favorite

Apartment in Sagaponack

4.97 out of 5 average rating, 38 reviews

Hamptons elegant and comfortable apartment

Enjoy your stay in this beautifully decorated and completely private basement apartment - with all original artwork- in the center of the Hamptons with the added convenience of being close to major towns and beaches. Large bedroom with comfortable king sized bed and high quality mattress and linen. Large-screen smart TV with many channels. Closet space, well equipped kitchenette, bathroom with glass-enclosed shower. Seating area for 4 and second large-screen smart-TV with comfy oversized couch.

Dec 22 – 29

$434 per night

Guest favorite

Apartment in Sag Harbor

4.96 out of 5 average rating, 132 reviews

Hamptons Hills Escape

Located in a quiet and safe neighborhood tucked into the woods of Sag Harbor, yet just a 10-minute drive from Sag Harbor town. Down the road is "Morton's Wildlife Refuge" with a beautiful walk to a beach and where birds eat seed directly from your hand. The lovely Long Beach is 5 minutes away - day passes are available. You only have one entrance/exit to deal with, the white door at the top of the wooden stairs that are pictured. Perfect for a couple looking to cook, relax, and spin records.

Jun 30 – Jul 7

$347 per night

Guest favorite

Home in Southampton

5.0 out of 5 average rating, 17 reviews

Year Round Hamptons Waterfront

Magical year-round waterfront home with private dock, direct access to Peconic Bay & spectacular views in prime Hamptons location. Minutes to Southampton Village & Sag Harbor. Renovated & newly furnished, the house features an open concept kitchen, dining, living room & bathroom on the 1st floor. 2nd floor has 3 bedrooms /2 baths & den /office. Dine al fresco on the beautifully furnished outdoor patio with fire pit. Paddleboards & Kayaks provided & ready to launch directly from the dock.

Oct 23 – 30

$475 per night

Superhost

Home in East Hampton

5.0 out of 5 average rating, 5 reviews

Waterfront Oasis + Pool/Spa & Private Beach

Waterfront in East Hampton! This perfectly renovated 5br | 3.5ba modern home with frontage on 2 bodies of water, offers stunning views year round. Relax by the saltwater heated pool & built-in spa or cozy up by the mid-century fireplace. WALK TO OUR PRIVATE BEACH & enjoy our 7 bikes, 4 paddle-boards & 3 kayaks, or take in the sunset over the water while you prepare dinner in the fully stocked chef's kitchen. Designer furniture promotes indoor-outdoor living w/refined simplicity. Registry#24-14

Dec 12 – 19

$900 per night

Guest favorite

Home in East Hampton

5.0 out of 5 average rating, 8 reviews

Chic & Sun-Filled Modern Oasis, Heated Pool & Spa

Ideally situated between East Hampton & Sag Harbor, this stunning 5br & 4ba home is the perfect year-round escape. A gated entrance brings you inside a private 1 acre compound & up a 300ft long landscaped & lighted driveway. Greeted with sunny interiors, a modern floor plan, designer furniture & a 20x40ft sun-drenched heated saltwater pool, hot tub & roof deck, this beach house is perfect for large family gatherings and is an entertainer's dream with a fully stocked chef’s kitchen. #22-1,284

Feb 17 – 24

$940 per night

Guest favorite

Vacation home in Flanders

4.96 out of 5 average rating, 68 reviews

Amazing Waterfront Bungalow

Self Check with private entrance of this amazing waterfront studio bungalow. Hot tub is maintained and open all yr round. A true oasis with own private porch in a waterfront resort style compound. Extra large salt water hot tub overlooks waterfront, open all year round. Dock with 2 person kayak. See both sunrise & sunsets. *Central Air *kitchenette * 55 inch smart TV *electric fireplace *Oversized outdoor shower * Closeby great farm to table restaurants & vineyards * NO Pet /Child policy.

Aug 4 – 11

$587 per night

Guest favorite

Apartment in Sag Harbor

4.84 out of 5 average rating, 172 reviews

Pet friendly, artists apartment & guest cabin.

Artists apartment and cabin located on quaint cul-de-sac just outside Sag Harbor Village, minutes from Long Beach. Centrally located. Free bikes, surf boards, 3 stand up paddle boards and a large canoe. Minutes from most beaches. A shaded, fenced in dog run. The cabin is a separate sleeping space from the apartment and has a 2 person SAUNA recently installed. Used if you bring more guests or if the two primary guests require separate rooms. WIFI AC and heat but No bathroom in the cabin.

Oct 24 – 31

$441 per night

Guest favorite

Home in Oakdale

4.85 out of 5 average rating, 122 reviews

Waterfront Round House View

A unique little beach house on the south shore of long island with the most beautiful view. The house is located on a canal. Dock is available! **We have Paddle Boards, Surf Boards and 3- 2 person Kayaks onsite for you to use during your stay** You can get to the Great South Bay by paddling to the mouth of the canal. And you can get to Fire Island by hiring a Water Taxi to pick you up! The octagon house was built in the 1970s. It's recently been refreshed with all new beds & linens.

Jan 11 – 18

$507 per night

Guest favorite

Guesthouse in Southampton

4.98 out of 5 average rating, 45 reviews

Southampton Modern Barn, Private Hot Tub and Pool

This magical getaway delivers peace and relaxation. Wake up to coffee on your private deck with bucolic views. Play in your heated, saltwater pool, and relax under the stars in your hot tub (open year round). During your stay, these amenities and more will be for your personal use. Stroll to the owner’s dock on Big Fresh Pond, for paddle boarding, kayaking and sunsets. You can also drive 8 minutes to Southampton Village for shopping, restaurants, art galleries and Ocean Beaches.

Oct 5 – 12

$525 per night

Guest favorite

Home in Rocky Point

4.91 out of 5 average rating, 178 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.

Dec 3 – 10

$136 per night

Guest favorite

Home in Montauk

4.88 out of 5 average rating, 141 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.

Feb 25 – Mar 4

$799 per night