Family-friendly holiday rentals in Amagansett

Private beach, fully updated house, on 2 acres.

Each the special magic that only the Hamptons offer—historic charm, a rural atmosphere, white sandy beaches and a relaxed lifestyle—while staying in this light-filled three-story cottage. Tucked away on a beautiful 2.2-acre wooded lot, this bayside oasis offers a tranquil retreat, with deer sightings, private beach access, stunning view and picture-perfect sunsets. A short drive to the beaches and town, quick trips to nearby shops, market stands, restaurants, museums and Jackson Pollack house.

Silver House: 3BR Home with Private Beach Access

Located on a half-acre property surrounded by tall oak trees, this three-bedroom, two-bathroom home is the perfect getaway. The house is part of the Clearwater Beach community with private beach access. The recently renovated kitchen and bathrooms are modern and minimal. Natural light floods the space throughout the entire house. Here is your perfect getaway from the chaos of city life The fireplace is NOT available for guest use. Early check-in and late check-out are NOT available in season

Tiny Cottage in Hither Woods, Montauk

A little cabin on our property in Hither Woods. A cozy hideaway conveniently located 12 minutes walk from Gurney's Beach Resort, 16 minute walk from public path to beach, and 6 minutes drive from Montauk town for restaurants and nightlife. Good for couples and solo adventurers, the space is private and homey, with outdoor shower and Chimenea fire pit. The main house is 65ft away, but we honor your privacy. The cottage comes with WiFi, window A/C and complimentary coffee or tea. Parking for 1 car

Casa Amagansett

*REMODELED FEB 2022* Casa Amagansett is a classic Hamptons bungalow, 3 minutes from the beach. Our 3br/2b home features a beautiful kitchen with 2 sinks, a laundry room, a truly sunny Sunroom, and gorgeous outdoor space. We are perfectly situated minutes from the beach, the Amagansett LIRR train station, grocery stores, and great shops & dining. There are four bicycles available for easy breezy access to everything nearby. Suitable for couples, families, business travelers, and friends.

The Quail’s Nest

A beautifully landscaped tranquil oasis. Newly constructed private two bedroom, one bathroom guest extension to owner occupied house. Guests share large yard and pool with owner, and have private deck and seating area. Private entry and parking. Guest's may enjoy outdoor shower and BBQ. Please note there is no kitchen, however a small fridge, Keurig coffeemaker and microwave, plates/utensils are provided. Conveniently located to beaches, shopping and local restaurants in East Hampton.

Hamptons Dream Suite

Hampton's Dream Suite- Is a guest suite in East Hampton, NY. From relaxing by the pool, to taking a day trip to Montauk, or visiting some of the best beaches in the Hamptons, the opportunities here are endless! It offers a bedroom with a Queen size Select Comfort bed, living room has two queen sofa beds and a full bathroom. It has a Kitchenette, Central AC/Heat with a 65" smart TV with surround sound and DVD, Blue ray and Xbox Games . There is also a TV and blue Ray player in the bedroom.

3 BR/Pool. Walk to Beach & Town!

Welcome to Good Tauk – a cheerful, retro-inspired 3BR, 2BA cottage tucked in the heart of Montauk and walkable to town and the beach. Thoughtfully renovated and full of personality, it’s perfect for families or longer stays. The vibe is fun, relaxed, and unmistakably Montauk. Outside, unwind in your private backyard with a pool, grill, and dining patio—ideal for lazy afternoons and sunset dinners. Just minutes from the beach, town, and everything that makes Montauk magical.

Beachglass Barn en-suite retreat prvt pool 2 baths

Beautiful, bright, spacious King suite w fireplace, two en-suite bathrooms & private separate poolside entrance. We are just minutes to beaches, boating, golf, hiking, biking, yoga and wineries. Play games, grill or cozy up fireside w a good book or movie. The space is creatively designed with a nod to natural elements and luxe comfort. Sleep your very best on our super deluxe king sized bed w/your choice of pillows. Complimentary coffee/tea/treats

The Cooper-Burke House

Many Main Street restaurants such as the American Hotel, Lulu's, Page 63, Wolffer Kitchen, Sen, Sag Pizza and Goldberg's, etc are a few minutes away. On Main Street one finds the Sag Harbor Cinema, The Bay Street Theater, Schiavoni's Market and Yoga Shanti. The house is a 12-minute walk to Haven's Beach. 1-minute around the corner from the house is Cavaniola's Wine, Cheese and Kitchen shops as well as the Sag Harbor Beverage store.

Private Cozy Cottage with Pool / Private Beach

**POOL CLOSES SEPTEMBER 30TH** **POOL opens last week of May** This is a guest house for 1 or 2 adults. Its separate from the main house. Kids are allowed but must bring own sleeping arrangements. You do NOT have to do any chores before checking out. **PETS NOT ALLOWED** I hate to do this but someone ruined it for everyone. Max Occupancy: 4 Guests can only bring 1 vehicle since there is not enough room in the driveway

Carriage House - Cottage in East Hampton Village

Darling cottage in East Hampton Village. Situated in a historic picturesque tree-canopied neighborhood. Easy stroll to Newtown Lane and Main Street shops. (1/2 mile). Classic atmosphere. Very comfortable, bright, and clean. A perfect place from which to enjoy East Hampton and the surrounding area. Fully renovated (2019).

4 BD w/ Heated Pool in E Hampton, Fully Furnished

Rent a beautiful and spacious 4 bedroom/3 bathroom property in East Hampton with a heated swimming pool in the backyard. This three level house with large kitchen, central A/C, BBQ in the backyard, and a garage is the perfect place to entertain guests or to relax and escape in East Hampton.