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

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

R9,537 ZAR 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.

Oct 3 – 10

R5,975 ZAR 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

R19,883 ZAR 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

Nov 10 – 17

R17,819 ZAR 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 5 – 12

R12,896 ZAR 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.

Aug 27 – Sep 3

R14,078 ZAR 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.

Sep 23 – 30

R12,590 ZAR per night

Guest favorite

Bungalow in Hampton Bays

4.95 out of 5 average rating, 38 reviews

Hamptons Beach House- Sun, Sand & Relaxation!

This beautiful Hamptons home is right on the water with your own sandy beach right in the backyard! Relax with your toes in the sand or go for a swim. Located just 4 min. from the main town, just 8 min. from the Ocean beaches and within walking distance to two of the Hamptons best waterfront restaurants. No worries about having a drink and getting home. The location and ambiance is what makes my place stand out from the rest. You are gonna love it here!

Jan 15 – 22

R11,157 ZAR per night

Guest favorite

Home in Old Lyme

4.96 out of 5 average rating, 125 reviews

Cozy Beach Cottage with short walk to the beach

Relax with the whole family with all the best New England has to offer! The Beach Barn is located in the quiet neighborhood of Hawks Nest Beach and is a quick half-mile walk to the beach in a very family friendly neighborhood. From sipping on morning coffee at the beach to watching sunset with the ocean breeze - there is plenty to do in the area during every season. All you have to do is show up ready to relax, have fun, and enjoy your stay!

Mar 18 – 25

R5,950 ZAR 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.

Nov 27 – Dec 4

R3,665 ZAR 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.

Oct 2 – 9

R12,571 ZAR per night

Guest favorite

Guesthouse in Westhampton

5.0 out of 5 average rating, 18 reviews

The “Birdy” Guest house

Take it easy at this peaceful guesthouse near Westhampton Beach village, Country Club, wine country (North folk), Moriches Bay and Westhampton Beaches. An amazing location for birding and kayaking. Ideal place for a couple looking to escape the city, attend a wedding, or explore wine country for a weekend to get some fresh air and experience nature.

Sep 12 – 19

R6,307 ZAR per night