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.

KitchenIndoor spacesCheck-in

4.91 out of 5 average rating, 142 reviews

Near apple/pumpkin picking ~ 8 mins to Main Street

The perfect Hamptons getaway! Near all of the best attractions. Enjoy this chic, serene home surrounded by the beauty of Hamptons nature + birds' chirping, deer sauntering. Cozy up to the wood burning fireplace, 80' TV + Chef's kitchen. Spark up the BBQ + firepit under the starry sky! Enjoy the bucolic views from every room. Here, you will be 8 minutes to Main St of East Hampton + Amagansett for endless dining + shopping options! Also 5-10 minutes to gorgeous beaches (great any time of year!).

KitchenIndoor spacesPool

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, 524 reviews

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

KitchenIndoor spacesGrill

4.95 out of 5 average rating, 139 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!

Indoor spacesKitchenCheckout

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, 260 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)

Indoor spacesFamilyGetting around

4.9 out of 5 average rating, 671 reviews

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.

KitchenIndoor spacesParking

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

FamilyKitchenLocation

The living area features two rattan chairs facing a coffee table, surrounded by vibrant wall art. A cozy sofa and plants add life to the space. Natural light streams through large windows, creating a bright and inviting atmosphere.

4.99 out of 5 average rating, 135 reviews

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.

KitchenFamilyParking

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.

4.83 out of 5 average rating, 217 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).

Indoor spacesKitchenWalkability

4.97 out of 5 average rating, 143 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.

KitchenIndoor spacesDecor

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

KitchenIndoor spacesAmenities

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.

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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

Indoor spacesKitchenGrill

4.95 out of 5 average rating, 100 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

FamilyIndoor spacesBackyard

4.97 out of 5 average rating, 102 reviews

The exterior of a modern two-story home features a sleek white facade with large windows allowing for ample natural light. A covered porch provides a welcoming entrance, alongside neatly arranged greenery and stone pathway leading to the front door.

Home in Southampton

Southampton Village Newly Built Gem

Indoor spacesFamilyCondition

4.98 out of 5 average rating, 147 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

KitchenFamilyCheckout

4.97 out of 5 average rating, 163 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)

Indoor spacesFamilyPets

4.93 out of 5 average rating, 147 reviews

A modern farmhouse is set on a spacious lot. The architecture features a blend of dark and light siding with a white chimney. A well-maintained path leads to a front porch, surrounded by landscaped greenery, enhancing the inviting curb appeal.

Home in Sound Beach

Luxury modern farmhouse with heated pool & hot tub

FamilyKitchenAccess

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

Indoor spacesKitchenAccuracy

4.95 out of 5 average rating, 211 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

Indoor spacesKitchenLong stay

Family- and pet-friendly home rentals

4.93 out of 5 average rating, 136 reviews

A serene landscape features a heated saltwater pool bordered by lush greenery. Sun loungers are positioned around the pool under umbrellas, while a wooden fence with trees creates a peaceful backdrop, enhancing the outdoor relaxation space.

Home in Mattituck

Modern farmhouse w/ pool, beach, horses and winery

KitchenFamilyHeating

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

KitchenIndoor spacesDecor

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

Indoor spacesFamilyBathroom

4.94 out of 5 average rating, 118 reviews

A spacious backyard is showcased with a large saltwater pool, featuring a floating inflatable and sun loungers arranged along the edge. The house stands in the background, framed by trees and an inviting grassy area, enclosed by a black fence.

Home in Hampton Bays

Coastal Retreat|Heated Saltwater Pool|5 MinToBeach

KitchenFamilyBackyard

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

KitchenFamilyLaundry

A spacious backyard features a heated swimming pool surrounded by a sun deck, adorned with loungers. Lush greenery and trees provide a natural backdrop to the inviting setting, while a charming house is visible in the distance.

4.89 out of 5 average rating, 133 reviews

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

FamilyIndoor spacesAir conditioning

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

FamilyKitchenAccuracy

4.87 out of 5 average rating, 141 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

KitchenFamilyDecor

Family-friendly home rentals with a pool

4.88 out of 5 average rating, 142 reviews

Apartment in Montauk

Recharge at our Renovated ocean front unit

FamilyKitchenComfort

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, 247 reviews

Montauk Royal Atlantic Beach Resort North

KitchenIndoor spacesAmenities

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.

4.98 out of 5 average rating, 175 reviews

Luxury Hamptons Home with Heated Saltwater Pool

FamilyKitchenDecor

4.91 out of 5 average rating, 266 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

FamilyKitchenDecor

4.95 out of 5 average rating, 102 reviews

A seasonal pool is framed by leafy trees, with a stone patio featuring lounge chairs for relaxation. Surrounding gardens are visible, enhancing the tranquil atmosphere of the space.

Home in Hampton Bays

Splendid private cottage

FamilyKitchenBeach

A large outdoor swimming pool is framed by a wooden deck, with two buildings positioned nearby. The house features light-colored siding and multiple sets of steps leading to the pool area, surrounded by open green space and trees in the background.

4.96 out of 5 average rating, 56 reviews

Stones throw to Montauket & Duryeas!

FamilyIndoor spacesCondition

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

Indoor spacesFamilyCondition