Family-friendly vacation rentals in Montauk

4.84 out of 5 average rating, 109 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.

Indoor spacesKitchenBathroom

4.91 out of 5 average rating, 141 reviews

Serene w/ large pool ~1 block to waterfront dining

Serene, chic Hamptons oasis! Located 1 block to waterfront dining + 8 mins to Main St. A perfect escape for any time of year! During summer, swim all day + walk 1 block to waterfront dining for dinner, drinks, coffee on the sea! During fall/winter, enjoy the firepit, indoor wood burning fireplace, 80' streaming TV + large fully stocked Chef's kitchen! The home is nestled in nature and serenity, perched back on a large piece of private property. Perfect for a serene escape to relax and unwind!

KitchenIndoor spacesTV

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, 521 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 spacesCheck-in

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)

KitchenIndoor spacesLayout

4.93 out of 5 average rating, 112 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

FamilyIndoor spacesAmenities

4.95 out of 5 average rating, 135 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 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!

FamilyIndoor spacesView

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.

4.98 out of 5 average rating, 132 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.

FamilyKitchenQuiet

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, 215 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 spacesFamilyAir conditioning

A cozy living area features a light-colored sofa adorned with blue and white throw pillows. Woven armchairs flank a wooden coffee table, while a stone fireplace adds warmth. Two large windows allow natural light to fill the space, complemented by greenery and decorative accents.

4.98 out of 5 average rating, 115 reviews

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

Indoor spacesFamilyDecor

4.97 out of 5 average rating, 139 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.

KitchenFamilyBathroom

4.88 out of 5 average rating, 141 reviews

Apartment in Montauk

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.

Indoor spacesFamilyParking

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

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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

4.91 out of 5 average rating, 201 reviews

Home in Sag Harbor

Barefoot Bliss | Quiet Family Retreat Heated Pool

Indoor spacesFamilyAccuracy

4.78 out of 5 average rating, 145 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

KitchenIndoor spacesHospitality

4.98 out of 5 average rating, 144 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

Indoor spacesKitchenSleep quality

4.96 out of 5 average rating, 184 reviews

Home in Mastic

Family Retreat with Heated Pool, Hot Tub, Sauna.

Indoor spacesFamilyCondition

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.

4.84 out of 5 average rating, 142 reviews

East Hampton Oasis - Pool and Hot Tub

KitchenIndoor spacesCheckout

4.96 out of 5 average rating, 109 reviews

A vibrant pool scene is captured, featuring a colorful unicorn float positioned on the water. Lush hydrangea blooms frame the area in shades of pink, complementing the surrounding greenery and the wooden fence that provides privacy.

Apartment in Southampton

Swimming pool w/Hot tub Fire Pit Coffee Bar

FamilyIndoor spacesValue

4.95 out of 5 average rating, 210 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

KitchenIndoor spacesComfort

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 spacesFamilyParking

Family- and pet-friendly home rentals

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 spacesHeating

4.91 out of 5 average rating, 330 reviews

A tranquil bedroom features a queen size bed with crisp white bedding and a tufted gray headboard. Natural light enters from a large window, highlighting the hardwood floor. A piece of coastal artwork is displayed above the bed, and bedside tables with lamps provide additional lighting.

Cottage in Montauk

Atlantic Echoes

Indoor spacesKitchenAccuracy

4.93 out of 5 average rating, 134 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

Indoor spacesFamilyBeach

A serene sunset is captured over the bay, with warm hues reflecting on the water's surface. Silhouettes of wooden posts emerge from the calm waves, creating a tranquil atmosphere. The horizon showcases a mix of colors as the day transitions to evening.

4.95 out of 5 average rating, 266 reviews

Private beach, fully updated house, on 2 acres.

KitchenFamilyDecor

A spacious backyard is highlighted by a blue in-ground pool surrounded by lounge chairs. Red umbrellas provide shade, while a tall wooden fence adds privacy. Lush green grass complements the natural setting, and a rustic home is visible in the background among the trees.

4.93 out of 5 average rating, 138 reviews

Private & Pristine with Pool and Kid’s Playard

Indoor spacesKitchenLayout

4.98 out of 5 average rating, 182 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

FamilyIndoor spacesCheckout

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

KitchenFamilySleep quality

A modern home is set on a spacious green lawn, featuring a combination of wood and metal siding. Large windows allow natural light to fill the interior. A stone pathway leads to the entrance, framed by lush landscaping and trees, enhancing the outdoor tranquility.

4.89 out of 5 average rating, 117 reviews

Modern East Hampton Home w/ Heated Saltwater Pool

KitchenFamilyAccuracy

Family-friendly home rentals with a pool

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, 112 reviews

Beautiful Condo on the Ocean Bluffs

FamilyKitchenLong stay

4.91 out of 5 average rating, 265 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

KitchenFamilyWifi

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, 246 reviews

Montauk Royal Atlantic Beach Resort North

Indoor spacesFamilyPool

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, 173 reviews

Luxury Hamptons Home with Heated Saltwater Pool

KitchenFamilyAmenities

5.0 out of 5 average rating, 24 reviews

Apartment in Montauk

Renovated Oceanfront Montauk Studio Retreat

Indoor spacesFamilyHospitality

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, 54 reviews

Stones throw to Montauket & Duryeas!

KitchenIndoor spacesCleanliness

5.0 out of 5 average rating, 95 reviews

Montauk Poolside Suite, Steps to Beach

KitchenIndoor spacesBeach