Holiday rentals with a kayak in Napeague

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)

Hang by the (Chel)SEA

Enjoy a relaxing stay with family and friends at this cozy soundview beach house. Wake up to breathtaking views of the water, where you can go right into the back yard of your very own private beach! Have a morning coffee on the front balcony of the home that overlooks the beautiful marshlands and then spend the day relaxing on the beach, or kayaking in the water! End the evening with a glass of wine on the back deck, that overlooks the water with the most spectacular sunsets!

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

Luxe 5BR Waterfront Estate | Private Pool Oasis

Welcome to your luxury 5BR Southampton waterfront retreat, designed for unforgettable group getaways, family vacations, and remote work escapes. Take in stunning water views, gather in the chef’s kitchen, enjoy movie nights in the private media room, or relax around the fire pit in the lush backyard. With outdoor dining, generous space, and top-tier amenities, this home is just minutes from Southampton beaches, vineyards, and boutique shopping.

Beach Cottage | Steps to Water| Fireplace|Firepit

Kick back and relax in this calm, stylish beach cottage 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, firepit/BBQ area, and my own tiny cottage across the lawn so I (or other guests may be there in August/September/October stays).

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$.

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.

Secluded Hamptons Cottage

This cottage has high ceilings, is bright and airy, has a wrap around deck with a great overhang for hanging out in the shade or sun. You can not see a neighbor. It has been described as “an adult tree house.” Just a fun and relaxing place to be. It is on over an acre of rustic property. Perfect for watching wildlife.

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...