Family-friendly vacation rentals in Water Mill

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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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Guest favorite

A welcoming living area features a comfortable sofa adorned with coral-patterned pillows. A rustic coffee table sits at the center, surrounded by natural light from large windows. A view of the open space and kitchen area can be seen in the background.

Home in Sag Harbor

4.97 out of 5 average rating, 149 reviews

Relax into Coastal Life at a Sun-Drenched Sag Harbor Home

Take a bike ride to Havens Beach and feel the sand in your toes. Walk to explore the shops, restaurants and bars on the quaint Main Street of Sag Harbor. Repair to your sun drenched home away from home to enjoy a relaxed meal alfresco on the deck. Unwind under the umbrellas on the expansive deck surveying the private fenced in backyard. Take in all the amenities of a newly renovated home situated in the Hampton - recent updates include a furnished basement, ping pong table, smart TVs and sound system. Extra touches include beach towels, beach chairs, bikes, cooler, games and more. This beautifully renovated 3 BR, 2 Bath home is situated on a quiet street, with a fenced half acre yard. It is located less than a mile to the shops, bars and restaurants of Main Street and the Hampton Jitney stop with service to NYC. The open floor plan boasts an abundance of natural light with 4 skylights and large windows to bring the outdoors in. Brand new appliances, custom kitchen cabinets, large center island with bar stools are perfect for hosting friends & family. Central AC/forced air heating controlled by the Nest ensure your complete comfort. The master BR features a king bed and ensuite Bath with custom tile shower. The guest BRs have a queen bed and full bed respectively and share the hall bathroom with tub/shower. The large deck runs the length of the home and is perfect for al fresco dining & entertaining. Totally furnished with everything you need to enjoy yourself from the second you enter the home! We have four brand new adult bikes, helmets and locks for your enjoyment. Explore the village, bike to the beach or get some exercise while you're here. If you prefer to stay in, you'll find a games console / DVD player in the front room with a good selection of games and movies. Additionally, we provide 4 beach chairs, beach towels and a small cooler for your use. Enjoy! Guests have access to the entire house, backyard, deck, garage and driveway parking. We can be reached via cell or email and are very responsive. We will also have a friend who is local to the area who will be able to assist with any issues. Sag Harbor is the coolest, most authentic town in the Hamptons. Home to household names, the town retains its small-town charm and rustic maritime vibe. Browse the artsy, eclectic stores and strike up conversations in the coffee shops and local bars. Sag Harbor is a quaint, walkable town on the wharf with great restaurants and bars. The house is located less than a mile's walk into the main street. Beaches are accessible via bike or car. The Jitney stop from Manhattan is located on Main Street less than a mile from the house. There are taxis in the area available via phone for pick up. We provide four adult bikes, helmets and locks for your use.

Top guest favorite

A classic two-story house with a wooden exterior is framed by neatly trimmed greenery. The front porch features a white gate, inviting guests. Views of the water and trees are visible in the background, suggesting a serene location.

Apartment in Sag Harbor

4.93 out of 5 average rating, 149 reviews

Whaling Captain Pierson's Apartment TOO

Whaling Captain Pierson's Apartment TOO is at a waterfront property. An apartment in one of the contributing homes which define Sag Harbor as a historic village. The house is a 7 minutes’ walk from the center of historic Sag Harbor Village. It is the only house and apartment offering a vast, picturesque, panoramic view of beautiful Sag Harbor Cove from Main Street as well as spectacular sunsets. (See my other listings of Whaling Captain Pierson's Apartment and Whaling Captain Pierson's Cottage)

Superhost

A cozy lounge area is furnished with a generous sofa and two white chairs, surrounded by bookshelves filled with various books. A coffee table sits at the center, and a cast iron fireplace is present, enhancing the inviting atmosphere. Natural light fills the room through large windows.

Guesthouse in Sag Harbor

4.86 out of 5 average rating, 106 reviews

Charming 2BR Cottage, Walk to Town

Beech Tree Cottage is a charming 2-bedroom, 1-bath cottage conveniently located in the peaceful historic district of Sag Harbor, NY. It is a 5-minute walk along the waterfront to Main Street and the center of the village. PLEASE NOTE: We have a 1 MONTH MINIMUM stay for bookings in July and August, and 1 WEEK for June until May 15. Thereafter, we accept requests for short stays subject to availability. Please review our booking and cancellation policy and house rules before making a request.

Guest favorite

A cozy living space features a brown leather sofa and a white coffee table on a geometric patterned rug. A large window allows natural light to fill the room, showcasing a wall-mounted fish decor and colorful accents. A decorative plant sits on the table.

Guesthouse in Southampton

4.95 out of 5 average rating, 440 reviews

Tiny Home in Prime Spot in Southampton Village

Located in the heart of Southampton Village, this intimate, centrally-located cottage is the perfect getaway! Nestled in an easily accessible, safe, and well-lit neighborhood, it is ideal for those with or without a vehicle. Only a 5 min. walk from the train station and a 5 min. walk to town, which includes premier shopping and restaurants. Enjoy nearby wineries, museums, and pristine, top-ranked beaches. Be close to everything Southampton has to offer while enjoying absolute peace and quiet!

Guest favorite

A swimming pool with clear blue water is surrounded by a spacious deck. Lounge chairs with striped cushions are arranged for relaxation. Colorful umbrellas provide shade over outdoor sofas, and lush greenery in the background enhances the serene environment.

Home in East Hampton

4.93 out of 5 average rating, 151 reviews

Large heated pool, games room, near private beach

Contemporary 4-bed + 4 1/2 bath home sitting on a park-like acre of gardens. Swim in the large pool (opens 04/25 and closes mid-October (there's an additional charge for heating - see below), relax in a hammock or bbq on the deck. Play ping-pong, darts, pool or take a 15 min walk to private bay beach to swim and paddle board. Or drive 15mins to the Atlantic beaches and visit picturesque Sag Harbor, Montauk. Reduced cleaning fee for small groups. RentReg RR-25-399 Local taxes included

Top guest favorite

A blue door is framed by two large pots of vibrant yellow and purple flowers, enhancing the entrance of a cozy cottage. Natural light highlights the door and nearby window, which features an air conditioning unit. Decorative lattice adds privacy to the space.

Apartment in Hampton Bays

4.96 out of 5 average rating, 382 reviews

Private & Cozy Cottage with short walk to beach!

Walking distance to Bay Beach & Rumba, & short drive to town & ocean. Quiet neighborhood, great for couples, King bed upstairs, bit of a steep staircase, so may not be suited for anyone with mobility challenges. Kayaks, paddle-boards, available to enjoy. Dog friendly with fenced in patio and doggy door. Private outdoor patio, with charcoal grill. A/C & Heat for year-round enjoyment. Easy to get in/out from the city. Close drive to visit Westhampton and Southampton Main Streets.

Top guest favorite

A cozy living area features a brown sectional sofa adorned with patterned throw pillows. A black coffee table sits on a striped area rug, providing a neutral contrast to the light hardwood flooring. Natural light filters through multiple windows, enhancing the welcoming ambiance.

Home in North Fork

4.94 out of 5 average rating, 185 reviews

Harbor Heights

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).

Superhost

The living area is characterized by high vaulted ceilings and large windows allowing natural light. A sofa with light cushions is centered around a wooden coffee table on a neutral rug. A decorative fireplace is framed with a modern mantle, adding warmth to the space.

Home in Southampton

4.83 out of 5 average rating, 210 reviews

Chic Southampton Retreat – Near Beaches & Village

Chic & cozy Hamptons retreat just minutes from Southampton Village and beaches! Enjoy a private backyard with sundeck, hot tub, fire pit, outdoor shower, and indoor fireplace. Next door to world-famous Shinnecock Hills Golf Club and 15 mins to Poxabogue public course. Close to Wölffer Estate, Duck Walk, and Channing Daughters wineries. Walk the nearby Scallop Pond Preserve or Elizabeth Morton Wildlife Refuge. Perfect year-round getaway!

Guest favorite

A serene view of calm water featuring kayakers enjoying a sunny day. The distant shoreline is dotted with houses, creating a relaxed coastal atmosphere. Clear blue skies reflect on the water, enhancing the peaceful scene.

Home in Southampton

4.96 out of 5 average rating, 169 reviews

Waterview+Pool, FreeForDogs! Kayaks/PingPong/Bikes

Beachy casual feel-good home easily located at the entrance to The Hamptons. Lovely views of the Bay, Nightly Sunsets & birds! Launch our Kayaks at street's tiny beach flowing from Cold Spring Pond into Bay. Or cuddle by the fireplace and play our many available games. We provide soft sheets & towels for the showers and & beach...priding ourselves on your comfort! Our Private-Pool is heatable & plant-surrounded with Outdoor Shower.

Guest favorite

The exterior of a two-story home is visible, featuring large glass windows that promote natural light. A spacious wooden deck hosts a dining area with a white umbrella. Lush green grass and trees surround the area, creating a serene outdoor setting.

Home in Water Mill

4.91 out of 5 average rating, 102 reviews

Elegant Modern Artist's Residence

This simple and serene home is set against a farm preserve, exposed to beautiful light and views and biking distance to the beach. Very relaxing - a terrific, creative space for a couple or small group. A large vegetable garden is maintained on the property and is available for guests to harvest as they like. Fresh salad greens, herbs, vegetables for you to enjoy!

Guest favorite

The exterior of a historic Tudor home is shown, featuring a blend of brick and wood accents. A winding driveway leads to the entrance, surrounded by lush greenery and a decorative black fence. Trees provide shade, enhancing the serene outdoor setting.

Guest suite in North Fork

4.88 out of 5 average rating, 663 reviews

Walk to Vineyards, Beaches, Farms & Town

Private bungalow with a separate entrance in a historical tudor home. Spacious bedroom with king-sized bed, kitchenette and bathroom. Two bikes, cable TV, internet, AC, beach towels, parking, snacks, coffee and water all provided. Walking distance to the beach, restaurants, shops, vineyards, grocery, farms and fish market. Jitney stop is one block away!

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

4.88 out of 5 average rating, 128 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