Family-friendly vacation rentals in Darien

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Darien

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

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Guest favorite

The living area features a neutral color palette with a contemporary couch and a low coffee table. A bar-style dining area with high stools is visible, complemented by a 42-inch Roku TV mounted on the wall. Natural light enters through a window, enhancing the inviting ambiance.

Apartment in Norwalk

4.91 out of 5 average rating, 323 reviews

The Seasons Luxe Pad 1 Bedroom | Center of Norwalk

The Space Private one bedroom apartment with a modern decor offers everything you need for a short or long term stay. Space includes a separate living/dining area and New York City inspired artwork. Bedroom offers a Queen Sized bed, desk, 40 inch Roku Smart TV & plenty of closet space. The Location Half mile from I-95 & near Merritt Parkway, South Norwalk train station, South Norwalk downtown and a half mile away from the Norwalk Hospital. Minutes away from shopping centers and grocery stores.

Top guest favorite

A spacious living area features a dark sofa and a patterned armchair, offering comfortable seating. A wooden Murphy bed is folded against the wall, while a small table with a lamp and decorative flowers adds to the inviting ambiance. Large windows provide natural light.

Guest suite in Fairfield

4.94 out of 5 average rating, 418 reviews

Private Studio Apartment; Kitchen; Fully Furnished

This 625 sqft fully furnished studio apartment has its own private entrance and sleeps 2-3 with a queen bed and Murphy bed. Other than outside, there is no contact with other people (hosts, other guests, etc) possible unless the guest allows such. The unit consists of a living room, dining space (breakfast basics provided), kitchen, full bathroom/laundry. Walk to Fairfield U; an easy train ride to NYC. (Need the Murphy bed? PLEASE do not wait until just before checkin to let us know that!)

Top guest favorite

A serene pool area features a clear blue in-ground pool surrounded by lounge chairs with red cushions. A vibrant hibiscus flower adds a splash of color, and a slide is visible for added fun. The area is enclosed for safety.

Home in Monroe

4.97 out of 5 average rating, 200 reviews

Garden Level Suite with Beautiful Pool

Enjoy complete privacy and 900+ square feet of living space in the ground floor suite/apartment of our home. Complete with its own private entrance and personal garage - our ground floor suite is your own private domain. There is one king bed, one queen bed, and a comfy sectional couch. Enjoy a small kitchenette for simple cooking inside, and an alfresco BBQ for bigger cooking. There is plenty of living space inside and out! A new washer/dryer unit will take care of all the pool towels used!

Top guest favorite

A spacious bedroom features a cozy bed with decorative pillows and a light-colored blanket. Two bedside lamps illuminate wooden nightstands on either side. A small desk and chair sit against the wall, providing a work area, while angled ceilings create a unique architectural detail.

Guest suite in Huntington Station

4.9 out of 5 average rating, 110 reviews

Spacious Huntington Suite- Private and Central

The guest suite is private, spacious and will accommodate those looking to spend time in the area . The guest suite is attached to the main house by locked French doors . There are no shared spaces . You’ll love my place because it is close to public transportation (LIRR- HUNTINGTON STATION) as well as the Paramount Theater ,Huntington Village and all Huntington has to offer. Those in town for weddings and events in the Woodbury/Syosset area will find this is a great place to tip off from .

Superhost

Sailboats glide across a calm blue sea, with distant shorelines visible under a clear sky. The tranquil waters reflect shades of blue, creating a serene nautical setting that accentuates the beauty of the surrounding landscape.

Home in Shippan Point

4.94 out of 5 average rating, 115 reviews

OCEAN COAST LUXURY BEACH HOUSE/45 min to NYC

Large 4 bdr newer colonial house/w fully-equipped spacious kitchen & huge spa-like bathroom/w Jacuzzi. Just across the road from the beach, 5 min drive to NYC train & downtown Stamford. 10 min drive to Greenwich. 45 min commute to NYC. Popular/w MALS guests. 1bdr and 1 full bthr are on the 1st floor. Everything is new in the house. Spacious bedrooms, private parking. Ocean Coast Beach House is across our other listing - Nautical Fairytale Beach House. Larger groups could book both houses.

Top guest favorite

A serene view of the Hudson River at sunset, featuring vibrant orange and yellow hues reflected on the calm water. Silhouettes of trees outline the scene, creating a peaceful atmosphere with the distant hills visible against the colorful sky.

Apartment in Ossining

4.96 out of 5 average rating, 434 reviews

Hudson River Peaceful Getaway, Explore from here

Self Check-In/Private Entrance. House trained Dogs and declawed Cats are Welcome (No additional pet fee). Driveway Parking for two cars. Peaceful, private flat on the Hudson River. Train to NYC (Scarborough Station) 10 min walk through historic neighborhood. Arcadian Mall (Grocery Store, Starbucks, etc) 7 min walk. Lots to explore in the area. Panoramic Rivers views from inside and out. Two televisions. Coffee/Condiments/Cooking Essentials provided. $25 cleaning with or without pets.

Guest favorite

A wooden porch is visible, featuring two black chairs and an orange table. Potted flowers add color on either side, with a stone pathway leading into the surrounding greenery. The gray siding of the building complements the outdoor seating area.

Apartment in Redding

4.94 out of 5 average rating, 482 reviews

Huckleberry Quarters, the Cozy Redding Retreat.

Time to book your summer getaway to the Huckleberry Quarters, a beautifully renovated studio apartment with full bathroom in a secluded, 1918 farm house. A nature lover's retreat within hiking distance of the Saugatuck reservoir and the Centennial Watershed Forest. Private entrance with all the amenities; internet, access to laundry. A peaceful country getaway to enjoy this summer, a writer or artist's retreat. Easy access to Merritt Parkway, trains, local eateries, parks.

Top guest favorite

A bright sunroom features a round table surrounded by two white metal chairs with blue cushions. Large windows allow natural light to fill the space, showcasing a coastal view. Straw hats are hung on the walls, adding a touch of seaside charm.

Cottage in Fairfield

4.97 out of 5 average rating, 119 reviews

Charming Fairfield Beach 3BR Cottage By The Sea

Charming Beach Cottage – Steps from Private Beach! Welcome to our newly renovated seaside retreat—a perfect getaway for families, couples, or anyone looking to relax by the shore. Nestled just steps from a private beach (right across the street!), our charming cottage offers the ideal balance of coastal tranquility and convenient access to town. Whether you enjoy walking, biking, swimming, fishing, kayaking, or simply napping in a shady hammock, this is the place for you.

Guest favorite

The Solar Cabin is nestled among lush greenery, featuring a rustic wooden exterior with a metal roof. Large windows allow natural light to fill the space, while a stone pathway leads to the entrance. Surrounding foliage enhances the cabin's secluded ambience.

Cabin in Newtown

4.9 out of 5 average rating, 115 reviews

Sticks and Stones Farm - The Solar Cabin

Sticks and Stones Farm offers a rustic glamping experience! When you stay with us you'll get the adventure and fun of camping (no electricity, outdoor showers etc.) while still getting to lay your head on a soft pillow in a bed. You can treat your stay here as a chance to go inward or enjoy interacting with the different programs and events going on! If you want to be up to date on events or ask about weekday checkins you can message us directly.

Top guest favorite

A bright sitting room features a cozy sofa adorned with colorful pillows. A wooden sideboard stands against the wall, while a small side table holds reading materials. Natural light filters in through two windows, illuminating the room's warm, wooden flooring and vibrant area rug.

Guesthouse in South Salem

4.94 out of 5 average rating, 283 reviews

1795 colonial w private 2 bd rm, 1 bth,LR,Kit apt

A unique private and quiet 2 bedroom (1 double bed, two single full beds) totally self contained apt,with sitting room, bathroom ,mud room and full eat in kitchen, in Shaker Hollow, a classic 1795 colonial.Stone patio overlooking 3 1/2 acres of garden and a meadow along with a large fire pit.

Top guest favorite

An open concept living area features cathedral ceilings with wooden beams, providing a spacious ambiance. A comfortable seating arrangement is positioned towards a wall-mounted television, with natural light filtering through curtains. A dining table is visible alongside a well-furnished sideboard.

Guest suite in Lake Ronkonkoma

4.99 out of 5 average rating, 269 reviews

Private New Apartment

Open concept living. Cathedral ceilings. 1 Bedroom, Full Bath. Private parking. Patio. 5 minutes from train, 15 minutes to MacArthur Airport. Close to Stony Brook, South shore ocean beaches, and the north shore of Long Island. Perfect if you are planning on heading out east to the wineries!

Guest favorite

A bright living area features large windows that allow natural light to illuminate two stylish chairs and a dark sofa. A round glass coffee table sits atop a textured rug, and a small potted plant adds a touch of greenery to the space.

Home in Croton-on-Hudson

4.96 out of 5 average rating, 186 reviews

The Carriage House: Vacation Home & Retreat

Tucked away in the foothills of the lower Hudson Valley, the Carriage House offers a mountain retreat just outside the city. The meticulously designed arts-and-crafts cabin sits on a hillside in the rivertown of Croton-on-Hudson, NY, and is perfect for a quiet getaway or active retreat.