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Family-friendly holiday rentals in Lake Montauk

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Top-rated family-friendly rentals in Lake Montauk

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Guest favourite
Home in Montauk

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 spacesValue

4.84 out of 5 average rating, 109 reviews
Guest favourite
Home in Springs

Serene + private ~ 1 block to waterfront dining

Enjoy zen living at this serene, chic, Hamptons oasis! Ideally located 1 block to waterfront dining, 8 minutes to beaches + 9 minutes to Main St! Relax poolside w/ tons of greenery + nature views. Spark up the BBQ + firepit under the starry sky. Listen to the crickets + spot a deer on the property. Curl up to the wood burning fireplace, cook in your Chef's kitchen + stream on your 80' TV Enjoy coffee on the sea + dinner w the best sunsets just 1 block away. A perfect escape + place to unwind!

FamilyIndoor spacesComfort

4.91 out of 5 average rating, 141 reviews
Top Guest favourite
A balcony view captures a serene beachfront scene at sunset, with gentle waves lapping at the sandy shore. A detailed metal chair is positioned on the deck, providing a quiet spot to enjoy the tranquil waters and cloudy sky.
Home in Niantic

Beachfront Paradise

Beautiful beachfront home available weekly in season third week of June through Labor Day) and nightly (2 night min.) off season. Step out the door and into the sand. Sit on the porch and watch sailboat races from Niantic Bay Yacht Club just steps away. Close to downtown Niantic with restaurants, shops, etc. 18 miles from Mohegan Sun Casino. Attractions within 1/2 hour: Beautiful Mystic, CT, several vineyards, Harkness State Park, Eugene O'Neill Theatre, U.S. Coast Guard Academy, golf courses.

Indoor spacesKitchenTV

4.97 out of 5 average rating, 226 reviews
Top Guest favourite
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.
Condo in Montauk

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 spacesKitchenWalkability

5.0 out of 5 average rating, 260 reviews
Top Guest favourite
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

A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.

Indoor spacesKitchenAccuracy

4.93 out of 5 average rating, 134 reviews
Top Guest favourite
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

KitchenIndoor spacesAmenities

4.93 out of 5 average rating, 112 reviews
Top Guest favourite
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!

KitchenFamilyBarbecue

4.95 out of 5 average rating, 136 reviews
Top Guest favourite
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.
Home in Montauk

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.

Indoor spacesFamilyCondition

4.98 out of 5 average rating, 132 reviews
Guest favourite
Adirondack chairs are arranged on a grassy area overlooking a serene lake, with a bright orange kayak positioned nearby. A vibrant sunset casts a warm glow across the water, and delicate grasses frame the scene, enhancing the tranquil setting.
Apartment in Montauk

Duffy's on Lake Montauk

Recently renovated in soft blues and whites, these sleek units offer a full kitchen, washer/dryer, living area and large deck steps from Lake Montauk. Paddle boards, kayaks and beach chairs available in warmer months. All units have Bose players and Roku. The units sit at a 90 degree angle to the lake with partial lake views from the deck. The lake and beachfront are a 1 minute walk from the unit. RENTAL PRICES ALREADY INCLUDE SUFFOLK COUNTY SALES AND OCCUPANCY TAXES.

Indoor spacesFamilyLayout

4.97 out of 5 average rating, 139 reviews
Guest favourite
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.
Condo in Montauk

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).

KitchenFamilyWalkability

4.83 out of 5 average rating, 215 reviews
Top Guest favourite
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.
Holiday 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.

FamilyKitchenParks

4.97 out of 5 average rating, 139 reviews
Guest favourite
Home in Montauk

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

Indoor spacesFamilyGetting around

4.88 out of 5 average rating, 233 reviews

Popular amenities for Lake Montauk family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Guest favourite
Home in Sag Harbor

Barefoot Bliss | Quiet Family Retreat Heated Pool

Indoor spacesFamilyBeach

4.91 out of 5 average rating, 202 reviews
Guest favourite
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 spacesKitchenCondition

4.78 out of 5 average rating, 145 reviews
Top Guest favourite
The farmhouse, constructed in 1856, is showcased with its classic white exterior and black accents. Large windows allow natural light to fill the space, while lush greenery surrounds the property. A pebble pathway leads to the entrance, enhancing the inviting atmosphere.
Home in Old Lyme

Modern Farmhouse with Hot Tub in Old Lyme, CT

Indoor spacesKitchenNearby

4.97 out of 5 average rating, 229 reviews
Top Guest favourite
An aerial view showcases a traditional New England-style home with a distinct green roof. A private pool with steps is situated on a spacious deck, surrounded by lounge chairs and tropical plants. Scenic outdoor areas for relaxation and recreation are visible on the property.
Home in Stonington

Perfect New England Getaway has a pool/ hot tub

Indoor spacesFamilyAccuracy

4.97 out of 5 average rating, 262 reviews
Top Guest favourite
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 spacesKitchenPool

4.98 out of 5 average rating, 144 reviews
Guest favourite
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 spacesHot tub

4.96 out of 5 average rating, 109 reviews
Top Guest favourite
Guest suite in Stonington

Morgan Suite - spacious | hot tub | water views!

FamilyIndoor spacesQuiet

4.98 out of 5 average rating, 396 reviews
Guest favourite
The image features a serene lake scene with a wooden dock extending out over the water. Two white chairs are positioned on the dock, facing the calm water, while an American flag waves nearby. Lush green trees frame the lake, creating a peaceful atmosphere.
Cottage in Ledyard

Lakeside cottage with beautiful views up the lake!

FamilyKitchenGetting around

4.92 out of 5 average rating, 298 reviews

Family- and pet-friendly home rentals

Superhost
A serene beach view captures gentle waves lapping at the shore under a soft light. The smooth sand stretches into the distance, with subtle textures and footprints creating a sense of tranquility. A distant silhouette of a bird can be seen against the sky.
Cottage in Montauk

Montauk Oceanview

Indoor spacesKitchenView

4.9 out of 5 average rating, 660 reviews
Top Guest favourite
An open living area features a light wood floor and a spacious sofa, complemented by a round dining table. A compact kitchenette with stainless steel finishes includes a mini fridge. Natural light enters through sliding glass doors leading to a patio, creating a bright atmosphere.
Guest suite in Montauk

Montauk Guest Suite

KitchenIndoor spacesQuiet

4.93 out of 5 average rating, 169 reviews
Guest favourite
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.
Home in Springs

Silver House: 3BR Home with Private Beach Access

KitchenFamilyHiking

4.95 out of 5 average rating, 523 reviews
Top Guest favourite
Home in Charlestown

2 Acre Lakefront Getaway (Sauna/Firepit/Kayaks)

FamilyIndoor spacesLocation

4.99 out of 5 average rating, 104 reviews
Top Guest favourite
An inviting living space is characterized by high post and beam cathedral ceilings, with a floor-to-ceiling fieldstone fireplace as a focal point. Cozy seating is arranged around a central coffee table, with warm lighting provided by string lights. The area reflects a blend of rustic charm and modern comfort.
Cabin in Westerly

Sunny Days, Starry Nights | 10 Min to Beaches

Indoor spacesKitchenValue

5.0 out of 5 average rating, 175 reviews
Top Guest favourite
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.
Home in Springs

Private beach, fully updated house, on 2 acres.

KitchenIndoor spacesBackyard

4.95 out of 5 average rating, 266 reviews
Top Guest favourite
An enclosed outdoor living space features a wooden deck overlooking a heated pool. Furnished with a large round table and comfortable seating, natural light floods through the screens, creating an airy atmosphere. Elegant trees and lounge chairs visible outside enhance the serene environment.
Home in Bridgehampton

Amazing Home close to Everything -

FamilyIndoor spacesWi-Fi

4.94 out of 5 average rating, 334 reviews
Top Guest favourite
Home in Stonington

Historic Home and Cottage with Seaport View

FamilyIndoor spacesTV

4.98 out of 5 average rating, 439 reviews

Family-friendly home rentals with a pool

Guest favourite
Apartment in Montauk

Recharge at our Renovated ocean front unit

FamilyKitchenNearby

4.88 out of 5 average rating, 141 reviews
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.
Condo in Montauk

Montauk Royal Atlantic Beach Resort North

Indoor spacesFamilyHospitality

4.8 out of 5 average rating, 246 reviews
Guest favourite
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.
Home in Springs

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

KitchenIndoor spacesCheck-in

4.89 out of 5 average rating, 133 reviews
Top Guest favourite
Home in Stonington

FREE Private Indoor Heated Pool - Mystic Home

FamilyIndoor spacesNearby

4.99 out of 5 average rating, 145 reviews
Superhost
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.
Home in Springs

Modern East Hampton Home w/ Heated Saltwater Pool

Indoor spacesFamilyGetting around

4.89 out of 5 average rating, 117 reviews
Top Guest favourite
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.
Condo in Montauk

Beautiful Condo on the Ocean Bluffs

Indoor spacesFamilyAccess

4.85 out of 5 average rating, 113 reviews
Guest favourite
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.
Home in Springs

HeatedPool, Walk2Beach, Yard4Pup, Spotless, GasBBQ

KitchenIndoor spacesComfort

4.88 out of 5 average rating, 236 reviews
Guest favourite
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.
Home in Montauk

Stones throw to Montauket & Duryeas!

KitchenFamilyHiking

4.96 out of 5 average rating, 54 reviews

Destinations to explore