Holiday rentals with a kayak in The Hamptons

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.

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.

Luxe Beach Cottage-Steps to Water-USGolf-Firepit

Kick back and relax in this calm, stylish beach cottage with NEW Kitchen and NEW bathroom (completed April 2026) in Sag Harbor. It is the perfect spot for a single or couple to enjoy the Hamptons beachy lifestyle. Fully appointed for your stay, just bring your bathing suit. Outside is your own patio with sitting area, dining table with umbrella, BBQ and my own tiny cottage “Bouy Cottage” is across the lawn so I (or other guests may be there in May-Sept. Beach chairs, umbrella and smiles!

3 Bedroom Beach House with Hot Tub!

Enjoy breathtaking sunset views in our spacious beach house while dining or relaxing in the hot tub. Snuggle up in front of the fireplace while watching a movie on the frame TV. Wake up in the master suite to spectacular marsh views while listening to birds from the Audubon Society. Steps to a white sand beach, heated bathroom floors, luxury bathrobes, linens, and organic mattresses. 6-bikes for exploring. A true resort-like experience with a chef's kitchen making a home away from home.

Magnificent Bayfront Retreat

Welcome to the Hamptons! The view from this home, that sits right on the water, boasts the most beautiful sunsets that need to be seen to be believed. Whether you’re spending the day in the sun on the beach (a short 5 minute walk), grilling on the deck watching the sunset over the bay, soaking in the hot tub, fishing on the private dock, or lounging on the couch watching a movie on our 75 inch TV after a day of fun in the sun, this home is a perfect getaway for you, your family, and friends!

Hamptons Beach House- Sun, Sand & Relax-Beachfront

This beautiful Hamptons beachfront home is right on Shinnecock bay 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. by car from the main town for all your shopping needs. My place is also within walking distance to one of the Hamptons best waterfront restaurants- so no worries about having a drink and getting home. The location and ambiance is what makes my place stand out from the rest. You’re gonna love it here!

Harborfront Star Walk to Harbor & Village

Leave your car parked , hang your keys, and step into the charm of Port Jefferson Village from this beautifully styled coastal retreat. Perfectly located just steps from the waterfront, placing you within easy walking distance of the marina, Harborfront Park, boutique shops, cafés, restaurants, and the ferry. Whether you’re here for a relaxing getaway, visiting Stony Brook, or exploring Long Island’s North Shore, this home offers the perfect blend of comfort, style, and location.

Private Beach Community with exceptional light

Kick back and relax in this calm, light filled home in Lionshead’s Private Beach Community. Paddle right out off your backyard. Enjoy organic garden vegetables, feed the swans. Kayac into the sunsets or sit by a gorgeous fireplace.This is a NO SMOKING , no vaping and no party home. If you are intending to travel with your dog please let us know prior to your arrival and ask for permission. We are very dog friendly but would love to know what kind of dog and will decide ASAP

Beach & Woods: Cozy Cabin, Hot tub, Peloton, Oh My

Welcome to nature's retreat, our secluded North Fork haven where 2+ acres of wild beauty and private beach access promise unparalleled relaxation. Delight in our hot tub's warmth under the stars, unwind on swings, or glide on bay waters with our kayak. With enchanting porch views, an invigorating outdoor shower, and nearby organic farms, our cabin is an idyllic escape. Experience the local charm with vineyard tours and return to a haven of comfort and adventure.

Cozy home. Comfy living

The whole group will enjoy access to everything from this centrally located home. three comfy bedroom, two bathrooms, large living room, dining and kitchen. close to the beach, nature reserved, kayaking, sky diving and Tanger outlet mall, restaurant and all the fast food located nearby. long island vast array of winery and farms stand etc. Guest is expected to follow house rules. 15 mins after check out time is given after that fees will incur at nightly rate

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.

Walk to Breakwater Beach in Heart of Wine Country

Private and peaceful cottage walking distance to Breakwater Beach and Old Mill Inn Restaurant on the water opening Spring 2025. There are two large decks to relax by the firepit and drink your wine from the local wineries. Bikes, kayak, and paddle board are stored in the barn for guests use. Easy access to the marina, fishing, fine dining, vineyards, and farm stands.