Family-friendly vacation rentals in New Canaan

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in New Canaan

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

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Guest favorite

Home in Milford

4.94 out of 5 average rating, 136 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!

Guest favorite

Cottage in Guilford

4.93 out of 5 average rating, 265 reviews

Charm + location. Walk to beach, town, & harbor.

We are sharing our "happy place". Cozy, family-friendly cottage has everything you need to enjoy a lovely vacation in a quintessential New England town. Ideally located between Guilford's famous green, gorgeous harbor and town beach, easily walk everywhere. High-season/weekend rate reflected in general view--check for actual. Recommended for groups of up to 4 (5 if with kids). Second bedroom (king) is open to living area-we provide a folding screen for door area and curtain for “passthrough”.

Superhost

Cottage in Branford

4.86 out of 5 average rating, 222 reviews

Cozy Home In Short Beach Community

A cozy home in a beach community which is in a central location with easy access to many outdoor activities(private beach access) & local restaurants. The location is also 5 minutes from the Branford Train Station, Stony Creek Brewery, Branford's town center. New Haven the home of Yale University, Yale Hospital and other colleges in the New Haven area are a short drive The house is across the street from Farm River. across the street in opposite direction is a short walk to Johnsons beach.

Superhost

Guesthouse in Milford

4.92 out of 5 average rating, 204 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

4.86 out of 5 average rating, 143 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

Apartment in Clinton Hill

4.98 out of 5 average rating, 111 reviews

Family brownstone with backyard

Located in Clinton Hill, a historic Brooklyn neighborhood, with lots of wonderful restaurants, cafes, and markets, our home is a quintessential brownstone. It was built in 1860 and freshly renovated in a way that preserved all of its old charm. The space available is the master bedroom with an en suite bathroom in the owners duplex. The apartment is loved by parents and kids all over the neighborhood, especially the backyard. The subway is just a block away. Discounts for monthly rentals.

Superhost

Home in New Milford

4.88 out of 5 average rating, 188 reviews

Renovated, one level home in an excellent location

Guests are sure to enjoy a memorable time in this beautiful fully furnished 3 bedrooms and 2 bathroom house. The house has been recently renovated to maximize comfort and overall experience. Excellent location close to major stores, restaurants and at walking distance to Candlewood Lake and Candlewood Lake Point private beach. Highlights: Free WIFI, Roku TV with Youtube TV, towels & beach towels, bed linens, and a beautiful deck with dining table, propane grill, and patio furniture.

Guest favorite

Home in New Fairfield

4.92 out of 5 average rating, 111 reviews

Beautiful Lakefront Retreat with Private Dock

Relax on the lake at this beautiful, one of a kind 3 bedroom, 2.5 bath DIRECT waterfront home in a private community on peaceful Squantz Pond, adjacent to Candlewood Lake. Enjoy spectacular views across the lake of unspoiled Pootatuck State Forest from the deck or screened in porch. Swim, fish, or just relax on the private dock. Kayak and paddleboard rental nearby. The home is central air-conditioned with a fully equipped kitchen. Our special place is waiting for you!

Guest favorite

Cabin in North Fork

4.86 out of 5 average rating, 100 reviews

Beach & Forest: Cozy Cabin, Hot Tub, Peloton

Welcome to nature's retreat, our secluded North Fork haven where 2+ acres of wild beauty and private beach access promise unparalleled relaxation. Delight in our hot tub's warmth under the stars, unwind on swings, or glide on bay waters with our kayak. With enchanting porch views, an invigorating outdoor shower, and nearby organic farms, our cabin is an idyllic escape. Experience the local charm with vineyard tours and return to a haven of comfort and adventure.

Superhost

Home in Beacon

4.89 out of 5 average rating, 180 reviews

Warm and worderful craftsman style comfort

Our home is in a quiet, family neighborhood, and just a short walk to Beacon's Main Street with all its' cafes, restaurants, specialty shops, galleries and antiquing. This fully renovated Cape Cod style home is perfect for families or groups and has a very large, private, fenced in yard and beautiful garden. Cable TV and WiFi complete your Hudson River experience.

Guest favorite

Apartment in Carmel

4.87 out of 5 average rating, 293 reviews

Private space, with yard

A little bit country with a modern twist, the space provides comfortable sleeping for up to five guests with a queen bed, queen sofa, and an extra twin mattress (if requested). Has many kitchen amenities. You will have a private yard (table, chairs, and grill) plus 5 peaceful acres and short hiking trails to explore. Pet friendly for additional fee.

Guest favorite

Home in Beacon

4.95 out of 5 average rating, 129 reviews

Family weekend getaway

Two bedroom home located in Beacon. Mt. Views from living room and dining room windows. Close to mt. and Main st. Children welcome. Baby items available pack n play, bouncy seat, swing. Bear Mt and West Point within driving range. Extra charge for pets $100.00. Four adults or families up to 6.