Family-friendly vacation rentals in Montauk

4.85 out of 5 average rating, 110 reviews

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.

4.96 out of 5 average rating, 519 reviews

The interior of the cabin features a spacious bed framed by large windows that invite natural light. A small dining table is set beside a plant, and the wooden ceiling enhances the cozy ambiance. A decorative blanket adds a splash of color to the bed.

Cabin in Montauk

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

4.95 out of 5 average rating, 140 reviews

An open living area features a comfortable sectional sofa and a large area rug, with natural light streaming through multiple windows. A dining table is visible, accompanied by stools, and the kitchen area includes modern appliances and a view into the outdoor patio space.

Apartment in Montauk

Modern Montauk retreat with wood stove by Harbor

Scandinavia meets Montauk in this sophisticated, comfy, all-season getaway. • 950 sq ft, 2 BR, 1 bath, high-end kitchen, W/D, A/C • Wood stove, Solo stove, patio, outdoor shower, high-end linens, furnishings & decor, large private fenced yard • Steps to LI Sound & Harbor. 3 mi to ocean/Town • Owner is in a private space w/ own entrance in the house. No shared spaces! • Note: Nightly rates now include Airbnb guest fee • Ask about dogs & flexible rental periods CLICK "MORE" for IMPORTANT INFO!

Two wooden Adirondack chairs are positioned on a spacious sun deck, overlooking expansive views of lush greenery and the waterfront. The bright blue sky complements the serene atmosphere, creating an inviting space for relaxation and enjoyment of the natural surroundings.

5.0 out of 5 average rating, 262 reviews

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)

Superhost

A bright studio cottage features a spacious bed with light linens and a working fireplace. A round table with two white chairs sits on a soft area rug, while a blue accent chair is positioned in the corner. Soft light enters through large windows.

Bungalow in Montauk

Atlantic Whispers

Wake up to ocean vistas every morning in a charming cottage. There are stunning views of the waves, soothing ocean sounds, and a gentle sea breeze. Sip coffee on a sun-drenched porch, enjoy a sunset stroll along sandy beaches, or simply unwind with the mesmerizing horizon as your backdrop, this cottage provides the perfect blend of comfort and charm. The cottage features a cozy interior with a working fireplace, modern amenities, and large windows that showcase the stunning seaside scenery.

4.9 out of 5 average rating, 672 reviews

4.93 out of 5 average rating, 113 reviews

An outdoor seating area features a round table surrounded by four wooden chairs under a vibrant red umbrella. The grassy ground extends towards a clear view of the ocean, framed by trees and shrubs, with a gravel path leading away from the space.

Bungalow in Montauk

Montauk Beach Bungalow East Apt.

Charming, clean, private, quiet, 2 bed 1 bath ocean view apartment across from ocean beach via through dunes path. Check the surf from the living room window. Dine in or out with the moon rising over the ocean. Includes BBQ and fire pit, outside table. Private entrance, lawn, outdoor shower, storage space for bikes, etc. Perfect vacation rental. Full kitchen with stove oven, fridge, sink, coffee maker, toaster, microwave, pots pans dishes etc - monthly discounts. Small bathrm & shower

4.98 out of 5 average rating, 184 reviews

A light-filled living space is highlighted by a wall of glass, providing expansive views of the water and a natural landscape. The space includes a round coffee table on a light floor, with comfortable seating arranged to enjoy the serene outdoor scenery.

Cottage in Riverhead

Savor Ocean Sunsets at a Soothing Beachfront Haven

Newly renovated and featured as a top Airbnb by New York Magazine, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Stay on the property for swimming, beach walks, sunsets and BBQs - or venture out to enjoy all the North Fork has to offer.

The studio features a queen-sized bed adorned with a floral-patterned blanket. A comfortable sofa and armchair are positioned nearby, along with a small table. Natural light filters through a nearby door, illuminating the warm wood flooring.

4.84 out of 5 average rating, 221 reviews

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).

4.97 out of 5 average rating, 145 reviews

An inviting living area is presented, featuring a white brick fireplace as a focal point. Comfortable seating includes light-colored sofas adorned with varying throw pillows. Large windows allow natural light to fill the space, and double doors lead to the outdoor area.

Vacation home in Montauk

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.

4.88 out of 5 average rating, 233 reviews

Laid Back Bungalow btwn Surf Lodge, Beach & Town

Welcome to Casa Bungo, our laid-back, surf inspired beach bungalow in the heart of Montauk. Located on Edgemere Street, in between Surf Lodge & downtown and walking distance to the beach, our 2-bd bungalow is perfect for families or two couples. Owned by the husband and wife team behind Studio MTK, a local interior design firm, this is Montauk at its best! Follow us @studiomtk to learn more! EH Rental Registry: 26-1155

A spacious green lawn extends towards the ocean, with gentle waves visible in the distance. A multi-story building with defined balconies is situated to the left, surrounded by well-maintained bushes and trees, contributing to a serene coastal atmosphere.

4.85 out of 5 average rating, 113 reviews

Beautiful Condo on the Ocean Bluffs

Located just outside of town on Old Montauk Highway that runs along the ocean. Just a 10 minute walk to town, enjoy a private beach, beautiful grounds and stunning pool. Located at the Atlantic Bluffs Club, one of the nicest private condo facilities in Montauk, you get to enjoy the peace and tranquility of Montauk yet you’re just a short walk to the village with its restaurants, shops and nightlife.

The exterior of the beach house is presented, showcasing a dark blue façade complemented by a wooden deck. A white door is visible, flanked by two large windows that allow natural light. Surrounding greenery adds to the inviting entrance.

4.9 out of 5 average rating, 504 reviews

DITCH PLAINS SURF HOUSE

Beach house on quiet street, 200 yards to Montauk's best surfing beach, Ditch Plains. The house is a simple all white home with 2 decks, BBQ, bikes, kayak, and easy open floorplan. You can hear the ocean all day long on this hidden Montauk street. Easily walk or bike to the beach, where you find waves, food trucks in the summer & miles of sand and ocean heading west to Montauk.

Popular amenities for Montauk family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.78 out of 5 average rating, 146 reviews

The image captures a spacious outdoor area featuring a large heated pool with a fountain and surrounding stone patio. Nearby, lounge chairs are arranged for relaxation, while a generous lawn stretches in the background, accompanied by a well-designed home nestled among trees.

Home in East Hampton

Sprawling Hamptons Estate with Hot Tub & Amenities

4.95 out of 5 average rating, 101 reviews

A well-designed outdoor area features a pristine pool with colorful floats, bordered by a spacious deck. Lounge chairs, adorned in striped blue and white, provide comfortable seating under large umbrellas. The house is illuminated, showcasing a welcoming atmosphere amidst lush greenery.

Villa in East Hampton

4.96 out of 5 average rating, 189 reviews

Home in Mastic

Family Retreat with Heated Pool, Hot Tub, Sauna.

4.98 out of 5 average rating, 148 reviews

A crystal-clear swimming pool is surrounded by a landscaped garden featuring lush greenery and blooming flowers. Natural stone patio borders the pool, offering space for lounging and relaxation in a private setting nestled among trees.

Home in East Hampton

Explore the Water & Woods at a Relaxing Retreat

Superhost

An outdoor area features a rectangular pool surrounded by a wooden deck. Lounge chairs are positioned along the pool's edge, and a shaded seating area is located nearby under an umbrella. Lush trees provide privacy and a natural backdrop.

4.83 out of 5 average rating, 144 reviews

East Hampton Oasis - Pool and Hot Tub

4.99 out of 5 average rating, 113 reviews

Home in Branford

Steps to Beach • Hot Tub • Game Room • Water Views

4.95 out of 5 average rating, 212 reviews

A spacious pool area is framed by well-maintained greenery and flowering plants. Two large umbrellas provide shade over lounge chairs beside a sparkling pool, with expansive coastal views and a serene landscape of grasses and trees beyond.

Cottage in Guilford

Luxury cottage by the sea with hot tub and pool

4.97 out of 5 average rating, 164 reviews

A contemporary house exterior features a combination of wood and metal finishes, set against a backdrop of lush greenery. Large glass windows provide ample natural light, and a pathway of stepping stones leads through a manicured lawn, enhancing the inviting atmosphere.

Home in East Hampton

East Hampton (walking distance to village)

Family- and pet-friendly home rentals

4.9 out of 5 average rating, 144 reviews

Serene, chic private house near best attractions!

4.94 out of 5 average rating, 111 reviews

A portable cabana is placed on a sandy beach with a view of the ocean. Two blue beach chairs are positioned underneath the cabana, providing shade. The shoreline and gentle waves are visible in the background, framed by a clear blue sky.

Cottage in Amagansett

Amagansett Dunes Gem

A bright living area features a light grey sofa paired with two black chairs, positioned around a glass coffee table. Large windows allow natural light to fill the space, while a minimalist fireplace offers visual interest. A small desk is visible against the wall.

4.95 out of 5 average rating, 525 reviews

Silver House: 3BR Home with Private Beach Access

4.87 out of 5 average rating, 144 reviews

A serene scene features a well-kept pool surrounded by lounge chairs, reflecting the colors of the sunset. The main house and pool house are visible, each with large windows and inviting outdoor spaces. Lush greenery outlines the property, enhancing the tranquil setting.

Home in Hampton Bays

Stunning Hamptons Waterfront Escape w/ Sunset View

4.98 out of 5 average rating, 160 reviews

A heated saltwater pool is surrounded by a spacious green lawn and lounge chairs, with a tree-lined white fence in the background. The house features a charming design with large windows and a wide patio area, suitable for outdoor dining and relaxation.

Home in Hampton Bays

Stylish + Modern Cozy Cape - 5 min to beach

Luxe

4.97 out of 5 average rating, 112 reviews

East Hampton Home: Heated Pool, Gym, Fully Fenced

4.87 out of 5 average rating, 126 reviews

An outdoor dining area is located beneath a wooden pergola, surrounded by a spacious lawn. A stone patio features a table with blue metal chairs. Lush greenery is visible in the background, along with a cottage painted in muted colors, accented by vibrant flowering bushes.

Cottage in Montauk

Secluded 1Br cottage on the lake, close to Ditch

A tranquil saltwater pool area is surrounded by lush greenery, featuring four sun loungers with colorful cushions. A large blue umbrella provides shade on the paved deck, enhancing the outdoor relaxation space.

4.87 out of 5 average rating, 237 reviews

Fall-Getaway, WoodFireplace, Walk2Beach, Spotless

Family-friendly home rentals with a pool

Home in Westhampton Beach

A charming cottage exterior features wood shingles and white trim. An American flag hangs proudly from the front, while window boxes with greenery add a touch of color. The light blue front door complements the natural elements, inviting guests inside.

Luxury Hamptons Home with Heated Saltwater Pool

4.98 out of 5 average rating, 179 reviews

4.88 out of 5 average rating, 144 reviews

Apartment in Montauk

Recharge at our Renovated ocean front unit

4.91 out of 5 average rating, 267 reviews

An inviting in-ground pool is surrounded by lush greenery and vibrant trees. Sunlight reflects off the clear blue water, enhancing the serene atmosphere. Outdoor seating can be seen nearby, providing a tranquil spot to relax amidst the natural setting.

Guest suite in Springs

Private Cozy Cottage with Pool / Private Beach

Superhost

A view from the balcony overlooks the pool area, featuring a clear blue pool surrounded by lounge chairs. Colorful umbrellas provide shade for several tables, while the surrounding buildings reflect a simple, two-story design.

4.8 out of 5 average rating, 248 reviews

Montauk Royal Atlantic Beach Resort North

A modern home is set against a twilight sky, accessible via a well-lit stone pathway lined with greenery. The landscaped garden features low shrubs and ornamental grasses, while the house is designed with large windows that provide a glimpse of the inviting interior.

5.0 out of 5 average rating, 19 reviews

Modern beach getaway ocean views

5.0 out of 5 average rating, 29 reviews

Apartment in Montauk

Renovated Oceanfront Montauk Studio Retreat

5.0 out of 5 average rating, 98 reviews

Cozy Poolside 1 BR in town | Fast WiFi