Family-friendly holiday rentals in Wading River

Find and book unique family-friendly homes on Airbnb

Quick stats about holiday rentals that are family-friendly in Wading River

Total holiday rentals
Explore 30 holiday rentals in Wading River
Nightly prices starting at
Wading River holiday rentals start at $509 NZD per night before taxes and fees
Verified guest reviews
Over 1,090 verified reviews to help you choose
Pet-friendly accommodation
Find 20 rentals that welcome pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wi-Fi availability
30 of Wading River holiday rentals include Wi-Fi access
Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Wading River rentals
4.9 Average rating
Wading River stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated family-friendly rentals in Wading River

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

1 of 1 pages1 / 1

Guest favourite

A shoreline is depicted with a mixture of smooth, round pebbles covering the sand. Gentle waves are seen rolling onto the beach, and a colorful sunset fills the sky, casting reflections over the water's surface.

Cabin in Rocky Point

Little, cozy place near beach for a couple.

It's quiet and cozy here. The yard is completely fenced with tall living shrubs, flowers, and trees. There's a gas grill, a fire pit, and a place to dine under an umbrella in the garden. I rent out a separate half of the house to guests: one bedroom, a small kitchen combined with a hallway. Peace and quiet reign here. You won't be disturbed. Sometimes I go into my half of the house, but very rarely. There are no other guests on the property, just you. I don't charge extra for pets. Parking free.

Indoor spacesFamilyView

4.88 out of 5 average rating, 592 reviews

Superhost

Apartment in Ridge

Spacious 1Bedroom Apartment By Wineries & Beaches

Relax and unwind in this private, spacious 1-bedroom apartment designed for comfort, convenience, and a peaceful stay. Whether you’re here for a weekend getaway, visiting the North Fork wineries, or need a quiet place to work remotely, this space has everything you need. Enjoy fully private apartment with its own entrance and yard - giving you uninterrupted freedom. Comfortable bedroom, cozy living area & full kitchen Relax in or after a day exploring nearby beaches, wineries, and attractions.

FamilyIndoor spacesAmenities

4.76 out of 5 average rating, 196 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.

KitchenFamilyWi-Fi

4.93 out of 5 average rating, 134 reviews

Guest favourite

A bright yellow door with a window covered by blinds is framed by gray shingles. Two exterior lamps are mounted on either side, and a small porch area features a decorative mat in front of the door.

Guest suite in North Fork

Beachy En Suite /Gateway to The North Fork

Adorable,quiet,clean, w private entrance, private bedroom and bathroom,breakfast nook and patio.We are located in a beach front town dubbed“Gateway to the North Fork”.Walking/driving directions to local beaches,15minute walk to our community beach,Wildwood StPk(.6mi away).Niks deli nearby.Minutes by car to wineries,breweries,farm stands,EastWind,TangerOutlets15min away,35min to Hamptons,Greenport!Hosts live in adjoining house.NoTV but Wifi is good so bring your device for entertainment.

Indoor spacesKitchenCleanliness

4.91 out of 5 average rating, 309 reviews

Top Guest favourite

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

Newly renovated and featured as a top Airbnb by New York Magazine, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Stay on the property for swimming, beach walks, sunsets and BBQs - or venture out to enjoy all the North Fork has to offer.

FamilyIndoor spacesBathroom

4.98 out of 5 average rating, 182 reviews

Guest favourite

Home in Mastic

Family Retreat with Heated Pool, Hot Tub, Sauna.

🛏 6 Bedrooms, 9 beds & 3 Full Baths 🏊‍♂️ Heated Pool & Relaxing Hot Tub 4-person Sauna 🏀 Half Basketball Court & 🏐 Volleyball Area 🏌️‍♂️ Private Golf Putting Green 🔥 Cozy Firepit & Outdoor Lounge Area 🛝 Swing Set & Kid-Friendly Yard 🍽 Fully Stocked Kitchen & Spacious Dining 🌐 High-Speed Wi-Fi & Smart TVs 10 min to Smith Point Beach & Boardwalk 15–20 min to Long Island Wine Country Nearby hiking at Wertheim Wildlife Refuge Short drive to Tanger Outlets & restaurants

KitchenIndoor spacesLocation

4.96 out of 5 average rating, 184 reviews

Top Guest favourite

A cozy living area features a sectional sofa and two armchairs arranged around a glass-top coffee table. A rug provides a soft touch to the wood flooring. The kitchenette, equipped with modern appliances, is visible in the background, alongside large windows that invite natural light.

Guesthouse in Wading River

North Country Cottage

Located near Long Island's beautiful beaches, vineyards, and wedding venues, this cozy cottage in the woods provides a quiet and comfortable place to stay while visiting! A spacious patio extends the living area, adding space to enjoy the outdoors in front of the fire pit or outdoor dining table. This property is located behind the owners' home and uses a shared driveway. While the owner is close by to address any issues during your stay, your space allows for total privacy.

FamilyIndoor spacesView

4.99 out of 5 average rating, 128 reviews

Top Guest favourite

A cozy living area is presented, featuring a full-size couch and love seat in soft brown fabric. A round black coffee table sits at the center, complemented by a patterned area rug. Natural light enters through a skylight and glass doors, creating a warm ambiance.

Apartment in Shirley

Welcome to Bill & Debbies AirBnb

Welcome to our AirBNB. We hope you will enjoy your stay in your private apartment. You will appreciate the off street parking & private entrance. We are only a short drive away from Long Island’s North Fork Vineyards, Skydiving, Smith Point County Beach, Fire Island and much, much more. We are also only 2.5 miles from Brookhaven National Laboratory. Only a short drive from a huge selection of stores & restaurants. We are in easy walking distance to a deli and 7/11.

FamilyIndoor spacesCheckout

4.99 out of 5 average rating, 107 reviews

Guest favourite

A modern kitchen is showcased, featuring a large center island with four wooden bar stools. Stainless steel appliances and white cabinetry are complemented by granite countertops. Natural light filters in through a window above the sink, illuminating the inviting space.

Home in North Fork

Modern Farmhouse Retreat North Fork Wine Country

Escape to this modern farmhouse retreat in North Fork Wine Country. Enjoy a luxurious stay with a fully stocked kitchen, cozy fireplace, Spacious bedrooms, and spa-inspired bathrooms. Relax in peaceful surroundings close to farms, beaches, pumpkin & apple picking, Tanger Outlets, Splish Splash Water Park, and top wineries. Outdoor dining, private fire pit, scenic views, and nearby hiking trails make it perfect for families, couples, or friends.

Indoor spacesKitchenCheckout

4.95 out of 5 average rating, 152 reviews

Guest favourite

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

*Pool is now open until late October This beautiful modern farmhouse is located on a one-acre lot and features a custom designed open-concept living space with vaulted ceilings that opens directly into a pool area. Hidden behind a bookshelf, you'll find a gorgeous game room with a piano and a pool table that can be easily converted into a ping pong table or working space. Please note that we do not allow weddings and events at this time.

KitchenFamilyWalkability

4.92 out of 5 average rating, 145 reviews

Guest favourite

A spacious lawn is surrounded by mature trees, providing shade and greenery. A vintage home is visible, with outdoor seating and a grill setup nearby. Gravel paths lead through the property, inviting exploration of the shared outdoor space.

Home in Rocky Point

The Katalpa House -by the beach

-Our beach is private, key and beach tag provided- (in brown shed) This 1000+ sf home, features a newly renovated kitchen, outdoor shower, and many quirks that come with a 90 year old home. The furnishings are eclectic and vintage. Most of the flooring is also new. The beach and bluffs are only about a 2 minute walk. The 1/4 acre lot is shared with a secondary unit as you can see in the photos which is occupied by my sister.

FamilyKitchenView

4.88 out of 5 average rating, 291 reviews

Top Guest favourite

A sandy pathway illuminated by soft lights leads toward a tranquil beach at dusk. Tall grass borders the path, and the horizon showcases a gentle gradient of colors as the sun sets over the calm water.

Home in Miller Place

Ocean House

Rare opportunity to rent your own 100’ Private Beach Front Oasis and enjoy all four seasons! This one-of-a-kind gem on a full sandy acre is only 60 miles from NYC. Brand new chef's kitchen w. Viking appliances. Living room w. wall of glass showcasing the breathtaking views of the Sound. The home also has a hot sauna & in sauna shower. Port Jefferson ferry (5mins away) connects you to New England. Our prices are not negotiable.

KitchenFamilyLayout

4.96 out of 5 average rating, 114 reviews