Family-friendly vacation rentals in Water Mill

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Water Mill

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Superhost

A spacious backyard is depicted, featuring a deck with comfortable seating, a glass table, and blue and white accents. Nearby, a swing set and a hammock are visible beneath leafy trees, while additional seating circled around a central area invites relaxation.

Home in Hampton Bays

4.88 out of 5 average rating, 226 reviews

Nautical Cottage Near Beach, Wineries, Golf, Shops

Coastal themed cottage located in the center of The Hamptons. Super Hosts! Great WiFi. Bright & comfortable space! Cowfish/Canoe Place Inn closeby! Near WINERIES, BEACHES, GOLF, WATERFRONT RESTAURANTS, & SHOPPING. 4 bedroom areas 2 full baths & outdoor shower. Spacious backyard w/ fire pit & deck w/ string lights. Lot's to do each season for couples, friends, coworkers & families. Everything you need & want in a Hampton's home. Large screen TVs/Roku, Foosball. Access to loft bedroom by ladder.

Top guest favorite

Two colorful sailboats glide across the water, their vibrant sails displaying shades of orange, yellow, and blue. In the background, a green tree line is visible along the shore, suggesting a natural setting.

Home in Milford

4.94 out of 5 average rating, 137 reviews

#2 Milford Beach (across street) Charles Isle 2BR

Welcome to your perfect Milford beachfront escape! This beautifully furnished 2-bedroom, 1-bath 2nd floor unit sits directly across from the beach, with beautiful water views. Just 100 yards from Silver Sands State Park, you’ll have easy access to its beaches, nature trails, and famous boardwalk. This unit offers beach gear, private yard for sunset dining, and proximity to Milford’s lively downtown. Whether here for a romantic getaway or family retreat, this spot offers relaxation or adventure!

Superhost

A spacious living area features a large sectional sofa adorned with decorative pillows, complementing a dining area with a round table and four chairs. Bright overhead lights illuminate the space, which includes a modern kitchen visible in the background.

Guesthouse in Milford

4.92 out of 5 average rating, 205 reviews

Chic Coastal Retreat: Modern Apt Steps from Beach

Enjoy our freshly renovated 2-bedroom apartment with a private entrance, kitchen, and in-unit washer/dryer all just a stone's throw from the beach. At Silver Sands State Park, take in views of Charles Island, accessible via a sandbar at low tide. Explore scenic bike trails or stroll the picturesque boardwalk. Perfect for families and group get togethers. Beach amenities are provided, including kayaks, and enjoy a private backyard where you can fire up the BBQ and fire pit. No pets, please.

Superhost

Cabin in Shirley

4.87 out of 5 average rating, 153 reviews

A-Frame cabin with private beach & epic sunsets

Just a 1.5 hour drive from NYC, this home is the perfect beach getaway spot, with a few steps from the deck to the private beach with its beautiful view across the Great South Bay. Remote work with stunning water views through the wall of windows & in cold weather light a fire while sunlight floods the living space. Two queen bedrooms & bunk bed room sleeps 6 guests, great for families or a small gathering of friends. 5 min drive to ocean beach with great swimming & surfing at Smith Point.

Guest favorite

A large, fenced-in backyard features a wooden playground with a slide and climbing structure, surrounded by lush greenery. Soft grass covers the ground, creating a safe play area for children. Mature trees provide natural shade in this private outdoor space.

Home in East Hampton

4.93 out of 5 average rating, 109 reviews

Private & Pristine with Pool and Kid’s Playard

INSTANT BOOK/ dates are current. Private and Pristine 3 bed / 2 bath home in the heart of East Hampton set on 1.3 acres. Home features a chef's kitchen, in-ground gated pool, and pure privacy and relaxation. Close proximity to East Hampton Village (5 mins) and East Hampton, Amangansett and Bay Beaches (7mins), Montauk (20 mins), Sag Harbor (15 mins). Kids adore the huge playground! Entire property fenced-in to ensure the safety of kids! Heated Pool open: Memorial Day - Sept 30.

Guest favorite

An outdoor dining area is visible, featuring a glass-top table surrounded by six chairs beneath a large umbrella. A grill sits nearby, with a view of the water and lush greenery in the background, creating a relaxing setting for meals and gatherings.

Bungalow in Hampton Bays

4.98 out of 5 average rating, 110 reviews

Hamptons Waterfront- Relax & Getaway!

My place is right on the water with your own sandy beach. A quick walk to the restaurant and dining. No worries about having a drink and getting home. You’ll love my place because of the location and the ambiance. My place is good for couples, solo adventurers, business travelers, and families (with kids). Conveniently located just minutes from the center of town for all your shopping needs; grocery store, Starbucks, 7-11, rite-aid, bagel cafe, pizzaria, farmers market and more.

Top guest favorite

The entryway features a light-colored door with a glass panel, allowing natural light to enter. A decorative compass wall sign reading 'Aqua Vista Greenport' is displayed nearby, adding a nautical touch to the welcoming atmosphere.

Home in North Fork

4.98 out of 5 average rating, 214 reviews

Aqua Vista

Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

Guest favorite

The front exterior of the home is framed by lush greenery and a flower-lined pathway made of stone. Two trees add natural shade, while a charming yellow door welcomes guests. A fenced yard and gravel accents enhance the inviting entrance.

Home in North Fork

4.94 out of 5 average rating, 108 reviews

Maritime Village Getaway with Backyard

Well located Greenport 3 bedroom, 2 bath home. Historic renovated private home with modern furnishings and updated appliances and finishings. Patio and yard with outdoor shower, fire pit, and yard. Central AC and heat. Properly licensed as a rental with Greenport Village and Suffolk County. I now add the airbnb fees and local and state taxes onto the listing. If you have questions about this please reach out. Not sure how transparent the fee structure is for guests.

Guest favorite

The open kitchen area features a light color palette with horizontal stripes on the walls. A doorway leads to a garden, inviting natural light. A natural fiber rug lines the floor, and a comfortable seating arrangement is visible to the left.

Guest suite in Montauk

4.94 out of 5 average rating, 124 reviews

Cozy guesthouse in an English style Tudor house

Light and airy, lots of blue and white (think Ralph Lauren) cozy and country feeling cottage in an English tudor house. The perfect place for a relaxing stay in Montauk. Reminiscent of an English county cottage with all its charm and imperfections. Its the perfect spot for a BBQ and relaxing outside with the sounds of birds chirping and the leaves rustling. 20 min walk to town, 25 min walk to the beach. I hope you'll enjoy your stay :)

Superhost

Lush green trees line the water's edge, reflecting shades of gold and green onto the calm surface. The tranquil scene is accentuated by the gentle ripples, creating a harmonious blend of nature and serenity.

Guesthouse in Shelter Island

4.96 out of 5 average rating, 115 reviews

Waterfront carriage house studio

Access to endless pool/spa, private beach around corner, breathtaking views, access for kayak, sup etc on property, playful friendly dog, easy access to all including sunset beach, beautiful breeze, private location, 46 foot classic powerboat available for charter at discounted rate w/ rental

Guest favorite

A private entrance features a white door set against a backdrop of textured wooden siding. Colorful purple irises bloom along the stone pathway, complemented by lush greenery, contributing to the inviting exterior of the studio apartment.

Apartment in Southampton

4.87 out of 5 average rating, 126 reviews

Southampton Village Studio

Location, Location, Location!!!! New renovated stand along Studio Apartment in the heart of Southampton Village. Private with lots of light, Cable TV and living room area. Located in wonderful Southampton Village location, only 1 mile to village shops and 2 miles Coopers Beach. Wi-Fi

Top guest favorite

A traditional New England-style house features a front porch supported by white columns. Two white chairs and a small table are arranged on the porch, complemented by a dark front door. Large windows allow natural light to fill the space, surrounded by green landscaped areas.

Cottage in Shelter Island

4.96 out of 5 average rating, 105 reviews

3 Bedroom Cottage Gem

Traditional Shelter Island house, located in the heart of central village. This 3bedrooms/2 bathrooms house is really quiet, convenient for tennis players with courts cross the street, 4bikes to borrow. This house is close to restaurants and is close to the beach as well...

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What guests are saying

Private pool/walk to beach; farms/vineyards abound

4.98 out of 5 average rating, 43 reviews7 months ago

Staying at Amy's place was perfect for my friends and I while we're out on the North Fork for a wedding. Amy was very responsive with any questions we had. We were all very comfortable in the main living area as well as our bedrooms. The house was conveniently located to the wedding venue and my friends were also very happy that it was located near some pickleball courts. Thank you Amy for a wonderful stay.

Home in North Fork

What guests are saying

The Greenport Bungalow

4.97 out of 5 average rating, 254 reviews4 weeks ago

This is an AMAZING Airbnb. High quality blankets, towels, ornamental details throughout the space. Comfortable beds. Beautiful ambient lighting. Large backyard with a fire pit. The neighborhood is quiet, beautiful houses, surrounded by water, with lovey little shores and nooks to walk to. My 4 year old had toys to play with and a little potty that all came with the home. I will DEFINITELY stay again. My family and I loved this place.

Home in North Fork

What guests are saying

Waterfront Beach Cottage

4.88 out of 5 average rating, 147 reviews7 months ago

Allyson’s home was in a beautiful location. We loved the uniqueness of the home. We came for a music festival and were surprised to find out it was a neighborhood porch festival. The neighbors let us know and invited us to join in the fun - as they had 3 bands playing on Saturday. It was so much fun and gave us a glimpse of the welcoming neighborhood. Now we want to come back next year for PorchFest!

Cottage in Woodmont

What guests are saying

Waterfront Home with Private Beach

4.95 out of 5 average rating, 60 reviews3 months ago

Brandon's place was dreamy for our two families with young kiddos -- cozy and quiet winter beach vibes, very atmospheric and peaceful and relaxing. We built a fire in the fireplace, watched movies, enjoyed the sunrise and sunset, and walked along the rocky shore. Would recommend, even in the dead of winter.

Home in Montauk

What guests are saying

GREENPORT RETREAT- PRIVATE 2 BR APT w/ PRIV BEACH

4.92 out of 5 average rating, 155 reviews7 months ago

We had a wonderful stay at George’s. The unit is exactly as described, don’t be deterred by the adherence to the house, it’s completely private. It’s at a great location for north fork explorations and the amount of towels was outstanding!

Guest suite in North Fork

What guests are saying

Cozy Farmhouse Retreat in North Fork, NY

4.91 out of 5 average rating, 104 reviews3 weeks ago

This was a great find! I booked this Airbnb for myself and 4 other girls and there was plenty of room and space for us to hangout, sleep, and get ready. Walkable to town. Extremely clean and had all the amenities you would need for a short weekend getaway. Marianne and Steven were very responsive whenever I had a question. I would totally book this Airbnb again!

Home in North Fork

What guests are saying

walk to bay, woods cottage

5 out of 5 average rating, 31 reviews6 months ago

We had the most wonderful and peaceful fall weekend at Brooke’s cozy cottage to celebrate our anniversary, and it was truly unforgettable! The cottage itself is beautifully decorated and felt like a warm home away from home. Brooke went above and beyond to make our stay special, leaving us complimentary champagne and wine to kick off our celebration. The location was perfect for enjoying the crisp fall air and stunning foliage, providing the peaceful retreat we were hoping for. We can’t recommend this place enough and will definitely be back for another stay!

Cottage in Hampton Bays

What guests are saying

Spectacular Waterfront Home on Private Sandy Beach

4.94 out of 5 average rating, 52 reviews8 months ago

My 4 year old son and I had a wonderful stay! The house is comfortable, clean and has a well equipped kitchen for cooking. We enjoyed going to the private beach where beach chairs, life vests, toys, an umbrella, etc. are provided. There is an outdoor shower conveniently located under the house, along with a swing that my son had so much fun with. The neighborhood was quiet, seemed safe and the neighbors were friendly. Heather was welcoming and very responsive. Thank you!

Home in East Haven

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