Family-friendly vacation rentals in Montauk

Chic + serene w/ pool~1 block to waterfront dining

Serene, chic, Hamptons oasis! 1 block to waterfront dining + 8 minutes to Main St. + beaches Enjoy your calm, zen, private home nestled in nature + peacefulness. Swim in your pool all day, spark up the firepit + BBQ under the starry sky! Curl up in the living room; cook in the Chef's kitchen + stream on the 80' TV. Enjoy a 1 block stroll to waterfront dining + cafe for coffee on the sea + dinner/drinks watching the sunset over the harbor You'll be 8 mins to Main St., beaches + so much more!

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

Montauk Private Beach Bungalow

Beautiful secluded cottage tucked away at the end of cul-de-sac and surrounded by a nature preserve. Montauk’s finest waterfront dining and bars are less than a mile. The house has a large living room with a fireplace, king bed in one and a full bed with a twin in the other, a full bath, outdoor shower hot & cold, an eat-in kitchen. There is a large very private patio with a grill, dining table and lounge area. The private beach is stunning and a 3 minute walk from the house. Pets are welcome.

Hamptons Oceanfront Oasis

Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

Montauk Waterfront Condo w/ Sunset Views

Modern 1 Bedroom Condo in gated community (Rough Riders) with sunset views from beautiful deck. The community has multiple tennis courts, pool, jacuzzi, and sauna (pool / sauna / jacuzzi only open Late May - early October). The property is great for walks along the boardwalk and many guests enjoy swimming off the pier. The unit is less than a 5 minute car / Uber ride to town and a short 5-10 minute walk to Navy Beach and Duryea's. Strong wifi in unit, Smart TV ( Netflix, etc, - no cable)

Modern Montauk retreat with wood stove by Harbor

Scandinavia meets Montauk in this sophisticated, comfy, all-season getaway with open-plan interior & large, private fenced yard. • 950 sq ft, 2 BRs (compact but comfy), 1 Ba, full high-end kitchen, W/D, A/C • Wood stove, Solo stove, patio, outdoor shower, high-end linens & furnishings/decor • Steps to LI Sound & Harbor. 3 mi to ocean/Town • Owner is in a private studio w/ own entrance in the house. No shared spaces! • Ask about dogs & flexible rental periods CLICK MORE for IMPORTANT INFO!

Oasis backyard, Pool, Gym, and Sunroom!

Oasis pool and landscaping makes it feel like your on a private island. Sunroom with smart TV over looking oasis back yard. Decks in the back yard with lounge chairs and 2 patio dining tables. Front deck with lounge chairs. Outdoor gym located in the corner of the yard. Paddle boards, boogie boards, beach chairs, and beach towels provided. Walk to EHP Resort (SiSi Restaurant), and Harbor Bistro featured on Delicious Destinations. Paddle Diva paddle board/kayak rentals also nearby.

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.

Coastline View Studio

This sun drenched studio apartment is perfect for families, couples or friends looking to get away and discover Montauk! Located in Montauk's harbor district. This unit is perfectly located to experience all that Montauk has to offer... Sit back on the balcony and enjoy a glass of wine as the sun sets perfectly over Culloden Point. A short walk to the Harbor, the Dock, Gosmans, TTs, Salivars, Sunday Funday, La Fin, Viking Fleet (fishing, Whale watching & Ferry).

Sea Roost

This private, two-cottage property contains a few of the last remaining original fisherman cottages at Hither Hills built in the 1940s. Set on a lush, private knoll - South of the Highway - Sea Roost boasts mature landscaping and is located steps to Montauk's quiet and secluded Hither Hills Beach. The property consists of a 2 bed/2 bath cottage with separate artist studio (Qn bed, kitchenette & full bath). Dogs negotiable with pet fee. IG @searoosts

2 BR apartment near ocean in Hither Hills

Relax and enjoy a peaceful stay that is a 3 block walk to one of the most beautiful ocean beaches in the Hamptons! This apartment is located in a beautiful, wooded, quiet neighborhood. Town is 1.5 miles away. This apartment has an open concept living space with a fully equipped kitchen. There are 2 cozy bedrooms and one bath with a walk in shower. We prefer families and mature adults. We supply beach towels, chairs, umbrella and beach wagon.

Recharge at our Renovated ocean front unit

Looking for a relaxing weekend to recharge on the beach? Then this newly renovated, bohemian-chic, apartment is perfect for you. Imagine waking up every morning to beautiful unobstructed ocean views and ending your night with a drink in hand watching the sunset. If you’re lucky, you might see some whales or dolphins breaching in the water right off our private beach. We would love to host you for your Montauk beach getaway.