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Family-friendly holiday rentals in Southbury

Find and book unique family-friendly homes on Airbnb

Quick stats about holiday rentals that are family-friendly in Southbury

  • Total holiday rentals

    Explore 20 holiday rentals in Southbury

  • Nightly prices starting at

    Southbury holiday rentals start at $255 NZD per night before taxes and fees

  • Verified guest reviews

    Over 780 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Southbury holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Southbury rentals

  • 4.9 Average rating

    Southbury stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated family-friendly rentals in Southbury

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

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Top Guest favourite
A newly renovated barn features a dark exterior with large windows on both levels. A gravel patio area is surrounded by low shrubs, providing a space with a table and chairs for outdoor dining. Lush green trees frame the serene setting.
Barn in Roxbury

Luxury Rural Barn

Renovated luxury barn on a quiet rural road yet close to all the attractions of Southern Litchfield County. The light-filled barn has two large patio doors into a substantial living and entertaining area with a large sectional sofa-bed, a dining table for 10 and adjacent kitchen area with an island. There is a downstairs washroom. A large light-filled upstairs sleeping area has a king-size bed and a bathroom with shower. Outside is a patio dining area and parking is in the dedicated driveway.

5.0 out of 5 average rating, 110 reviews
Top Guest favourite
The historic home features a two-story structure with white siding and black shutters. A covered porch is highlighted at the front, surrounded by lush greenery and blooming flowers, set against a clear blue sky. A grassy lawn offers open space in the foreground.
Guest suite in Watertown

Private King suite w/ separate entry-Walk to Taft!

Enjoy Litchfield County, CT! This renovated 1-bedroom guest suite in an 1859 historic home has a private entrance off a dedicated covered porch. Enter through the private stairway into the bedroom with a King size bed and comfortable foam mattress. French doors open into a living room with a pullout full size sofa bed and a Nespresso coffee maker. The renovated bath has marble floors and a glass door shower. Free parking for up to two cars in the drive and directly across the street from Taft.

4.98 out of 5 average rating, 102 reviews
Top Guest favourite
Vibrant orange tulips bloom in the foreground, contrasting with lush green foliage. A sign for Studio Holtquist is visible in the background, alongside colorful artistic sculptures standing amidst a bed of pink flowers. The scene is set against a backdrop of trees, indicative of a serene environment.
Home in Woodbury

Your Perfectly Wonderful Woodbury Sanctuary!

Just 90 minutes from NYC, this Getaway is Perfect! Antiques, photographs, & sculptures fill this rambling, light-filled 2 story 4 bedroom 2.5 bath historic district home on Connecticut's Antique Trail. All 2,800 sq. ft of my home is at your disposal and 2 minutes from popular restaurants and diners. Your Host lives in the attached Artist Studio with its own access and parking. Stay here and you may agree with Reader’s Digest magazine that "Woodbury is Connecticut's Most Charming Small Town."

4.99 out of 5 average rating, 147 reviews
Guest favourite
A cozy living room features a stone fireplace with a mounted television above. Natural light enters through a large window, accented by sheer curtains. A plush rug covers the floor, surrounded by a sectional sofa and a chair, offering a comfortable gathering space.
Home in Waterbury

Come and enjoy the BURY's of CT!

Welcome to your home away from home! Nestled in a charming, safe, and quiet neighborhood, our cozy retreat offers the perfect blend of comfort and convenience. You'll love the tree-lined streets and peaceful atmosphere—a perfect place to relax after a day of exploring. Whether you're here for business or leisure, our home provides a warm and welcoming space in a delightfully cute corner of town. Enjoy all that CT has to offer from the rolling hills of Litchfield to the waters of the sound.

4.95 out of 5 average rating, 105 reviews
Top Guest favourite
Apartment in Southbury

Cozy Apartment Centrally Located in Southbury

Keep it simple at this peaceful and centrally-located apartment. Recently renovated with all the essential amenities to make your stay just like home. Wi-Fi, washer, dryer, cooktop, fridge, oven, microwave, toaster, TV and Keurig are ready to make your stay pleasant. An outdoor porch is available for dining in warmer months. It includes one new queen bed plus sofa bed for one adult or two kids. Located just minutes from shopping and dining in downtown Southbury with easy access to i84

4.97 out of 5 average rating, 110 reviews
Top Guest favourite
Home in Newtown

Comfortable home away from home- near everything

Price includes Airbnb fees. Cozy, pet-friendly cottage in a peaceful setting just 70 miles from NYC and minutes from I-84 (Exit 8 or 9). This clean & comfortable retreat features 3 bedrooms (2 queens, 1 full), and pull-out couch. Portable A/C's in summer, and fireplace for cozy nights. The greenhouse adds plenty of natural light, the yard is perfect for kids, the front deck is great for morning coffee, and the gas grill great for cooking out. High-speed WiFi and 3 smart TVs.

4.99 out of 5 average rating, 147 reviews
Top Guest favourite
A timber-style cottage is surrounded by landscaping featuring stones and low shrubs. A spacious deck with white railings leads to a welcoming entrance. Light-colored siding and multiple windows enhance the two-story structure, set against a backdrop of trees and open land.
Home in Southbury

The Cottage at Cedar Spring Farm

Welcome to The Cottage at Cedar Spring Farm, a one bedroom, one bath cottage located on a 16 acre working Christmas tree farm bordered by 155 acres of protected land trust with marked hiking trails. Conveniently located to I-84, shopping, local farms, wineries, breweries, restaurants, and Heritage Village. Please note that we allow pets (dogs only) and have a limit of two. **Access to the 2nd floor bedroom is a steep and open staircase** (see interior photo listed under Laundry)

4.98 out of 5 average rating, 175 reviews
Top Guest favourite
A spacious deck features a round table surrounded by four cushioned chairs, covered by a large red umbrella. Lush greenery and landscaped gardens are visible in the background, creating a serene outdoor setting.
Cottage in Seymour

3 Acre Forest, 2 King Beds, Fireplace, BBQ & more

🛏️2 king, 2 twin, BBQ, fireplace, firepit, 1550 sqft entire house 🅿️🛜 Tucked away at the end of a quiet street, set on 3+ acres of lush wooded land, our home is the perfect blend of seclusion and convenience. With a forest as your backyard and RT34 one min away, you can easily balance your desire for nature and adventure with the need for easy travel and commuting, take a short hike into a forest (trails minutes away) and/or relax under the stars around a fire pit.

4.97 out of 5 average rating, 143 reviews
Guest favourite
A rustic cabin is nestled among tall trees, showcasing a stone chimney and wooden exterior. Warm-colored windows invite natural light, while a gravel path leads to the entrance. Surrounding lush greenery enhances the cabin's secluded setting.
Cabin in Sherman

The Cove Cabin

An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, two SUP, and two two-person kayaks are available for use from May 1 to November 1.

4.96 out of 5 average rating, 458 reviews
Guest favourite
A spacious deck is furnished with several striped lounge chairs surrounding a central table. Soft glow lights are suspended overhead, illuminating the area. A panoramic view of the lake and vibrant sunset colors create a serene setting for relaxation and social gatherings.
Home in Brookfield

Sleeps 18 LAKE VIEWS! Perfect for large group!

*We only book to 25 or older PERFECT SPOT TO BRING YOUR BOAT! This home sleeps up to 18 people + is perfect for large groups, wedding parties or team retreats. You’ll love the sunset views, large living room and kitchen for entertaining and hanging out, pool table, dart board and large yard for games. There’s even a spot to bring your own boat or jet ski and room to park your trailer! IG stay_at_the_lake

4.93 out of 5 average rating, 140 reviews
Guest favourite
A studio space is highlighted by a colorful patterned bedspread covering a spacious bed. A comfortable gray sectional sofa offers seating, and a coffee table sits in front. A kitchen area with modern appliances is visible in the background, enhancing the functionality of the space.
Apartment in Southbury

Suite Hill Studio

A private entrance to your studio located at the top of a hill. Surrounded by trees. Tranquility can be found. We are located near the Antique trail of Southbury. Its a 25 min ride to Danbury or 20 min ride to Waterbury. Just under 2 hours to NYC. And a little over 2 hours to Boston. We can provide a daily clean at an additional cost. There are grocery stores, TJ. Maxx and Starbucks within minutes.

4.85 out of 5 average rating, 122 reviews
Top Guest favourite
Home in Redding

Retreat with Heated Pool, 1 Mile to NYC Train

The pool is open for the 2026 season. Escape to a stunning 4-BR home on 2 acres in Redding, CT (#1 Small Town). Just 90 mins from NYC, this luxurious retreat comfortably fits 8 guests. Enjoy hotel-style amenities, a heated saltwater pool, and a gourmet kitchen. Breathe in fresh country air in a peaceful, park-like setting. Perfect for families, offering a blend of modern comfort and outdoor living.

4.99 out of 5 average rating, 104 reviews

Popular amenities for Southbury family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top Guest favourite
A spacious deck features a traditional wood-burning hot tub, reflecting the surrounding trees and sky. Nearby, a dining set provides a place to enjoy meals outdoors, surrounded by the natural beauty and serenity of the cabin's setting.
Cabin in New Milford

Stylish & Scenic Escape: Chef's Kitchen ~ Hot Tub

5.0 out of 5 average rating, 112 reviews
Top Guest favourite
A sunlit enclosed sunroom features a curved sectional sofa adorned with decorative pillows and a central wooden table. Large windows invite natural light, offering views of the backyard. A rocking chair and potted plant add a cozy touch to the inviting space.
Home in Dover Plains

Hillside Grove

4.96 out of 5 average rating, 100 reviews
Top Guest favourite
The entrance showcases a wooden door with a rustic design and a blue frame. A yellow flower arrangement hangs from the door, welcoming guests. The space beyond is an open-concept living area with natural light filtering through sheer curtains, revealing a sectional sofa and wood ceiling beams.
Cottage in Bethlehem

Cozy Cottage |Quintessential CT | Pet Friendly

4.99 out of 5 average rating, 170 reviews
Guest favourite
The charming cottage, with its white siding and red door accents, is set amidst lush greenery. A well-maintained yard features grass and flowering plants, while a stone wall frames the scene, adding to the property's rustic appeal.
Cottage in Litchfield

Litchfield-Hot Tub-Shops & Eats-Vineyards-Hikes

4.87 out of 5 average rating, 411 reviews
Guest favourite
A winding stone path leads to a rustic stone chimney of the cabin, surrounded by autumn foliage. Small lanterns line the path, casting soft light against the backdrop of trees and textured wooden siding.
Cabin in New Milford

Creekside Cabin with Wood Fired Hot Tub & Firepit

4.95 out of 5 average rating, 239 reviews
Guest favourite
A charming red barn-style house is framed by a vibrant field of wildflowers. Various hues of blue, red, and white blossoms create a colorful foreground, while lush greenery surrounds the property, contributing to a serene natural setting.
Barn in Katonah

Magic Red Barn with Heated Salt Pool (opened now)

4.96 out of 5 average rating, 145 reviews
Top Guest favourite
A stone archway leads to a red barn-style house, framed by greenery and a variety of plants. The pathway is paved with stones, providing a natural ambiance. Small bistro tables and chairs are visible through the arch, creating a welcoming outdoor seating area.
Farm stay in Kent

(°) The Wandering Peacock (°)

4.88 out of 5 average rating, 370 reviews
Top Guest favourite
Campervan/RV in Wassaic

Glamp in a 1970s Airstream | Hot Tub | NYC Train

4.99 out of 5 average rating, 100 reviews

Family- and pet-friendly home rentals

Guest favourite
A modern kitchen area is featured with white cabinetry and gray countertops. Natural light enters through two windows, highlighting a sink, microwave, and a compact refrigerator. A coffee maker is situated on a counter, providing convenient amenities for guests.
Guest suite in Newtown

Light and airy, pet friendly rental in Newtown

4.93 out of 5 average rating, 128 reviews
Top Guest favourite
A rustic farmhouse exterior showcases a wooden façade with red double doors and a welcoming balcony adorned with potted flowers. The balcony is accessed by wooden steps, leading to a charming outdoor seating area. Seasonal foliage decorates the surrounding landscape.
Farm stay in West Simsbury

Flamig Farm Staycation

4.96 out of 5 average rating, 555 reviews
Top Guest favourite
A warm wooden interior is featured, with wall art depicting horses and rural scenes. A rustic wooden table is positioned near the window, and a candle sits at its center. A potted plant adds a touch of greenery beside a cozy armchair.
Farm stay in Redding

Charming Historic Cottage in the Redwoods

4.98 out of 5 average rating, 102 reviews
Top Guest favourite
Apartment in Holmes

Top Side

5.0 out of 5 average rating, 143 reviews
Superhost
A rustic cabin with green log siding is surrounded by tall trees. The front porch features two black chairs, and a storage trunk adds a practical touch. A decorative star and wall clock enhance the inviting exterior, while a garden area complements the natural setting.
Bungalow in Trumbull

Cozy, romantic cabin by the lake.

4.82 out of 5 average rating, 260 reviews
Guest favourite
The exterior of a charming three-bedroom house is displayed, featuring a sloped roof and neatly trimmed bushes. A large tree provides shade in the front yard, while a stone pathway leads to the entrance. Side decorations include a swing and tree remnants.
Home in Bristol

Cozy Family Home - Kid & Pet Friendly

4.92 out of 5 average rating, 237 reviews
Top Guest favourite
Cabin in Cornwall

Beautiful country house in Cornwall CT.

4.98 out of 5 average rating, 104 reviews
Guest favourite
Home in New Milford

The Getaway: Beautiful Waterfront - New Milford CT

4.9 out of 5 average rating, 143 reviews

Family-friendly home rentals with a pool

Top Guest favourite
An aerial view showcases the antique farm property set within a spacious landscape. Surrounding areas feature a mix of treed land and open fields. The main house, along with additional structures and a large yard, is visible alongside winding roads, emphasizing the rural setting.
Barn in Bethel

Escape to a Restored New England Antique Milk Barn

4.98 out of 5 average rating, 266 reviews
Top Guest favourite
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.
Guest suite in Monroe

Garden Level Suite with Beautiful Pool

4.97 out of 5 average rating, 214 reviews
Top Guest favourite
A large farmhouse is depicted in the background, featuring a broad balcony and distinctive architectural details. Sunflowers are prominently featured in the foreground, with bright yellow petals and green leaves, surrounded by lush grass and trees providing a serene atmosphere.
Barn in Bloomfield

Farm Stay with Horses & Pool | Mountaintop Views

4.97 out of 5 average rating, 139 reviews
Top Guest favourite
A serene outdoor space features a heated saltwater pool surrounded by a spacious lawn. Sun loungers are positioned near an umbrella for shade, with lush greenery and a wooden fence creating a tranquil backdrop.
Home in Pound Ridge

Peaceful Light-Filled Guesthouse salt pool/sauna

5.0 out of 5 average rating, 187 reviews
Guest favourite
A serene view of the pool is presented, framed by lush greenery and vibrant plant life. The clear water reflects the sky, while distant hills and a pond are visible at the horizon, creating a peaceful outdoor retreat.
Home in Litchfield

Stunning Views, Bucolic Bliss in 1790s Farmhouse

4.93 out of 5 average rating, 212 reviews
Guest favourite
A spacious bedroom is presented with a comfortable bed, layered in plush white linens and accented with dark pillows. A wooden dresser sits in front of a large window, allowing natural light to fill the room, while art decorates the walls.
Apartment in New Haven

King 1BR W/ Parking, Pool & Gym

4.97 out of 5 average rating, 117 reviews
Superhost
A swim spa with dual zones is shown, featuring illuminated blue and red lights. The adjacent outdoor area includes a large screen displaying a sports event. Steam rises from the hot tub, creating a relaxing ambiance in the evening setting.
Home in Hamden

Sleeping Giant Stay/Swim Spa w/Tread/Tonal/Peleton

4.88 out of 5 average rating, 129 reviews
Top Guest favourite
Apartment in Milford

The Pond Mill Retreat w/ 2 Bdrms & Pool

4.98 out of 5 average rating, 162 reviews

When is the best time to visit Southbury?

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Avg. price$366 NZD$339 NZD$424 NZD$424 NZD$424 NZD$458 NZD$424 NZD$424 NZD$424 NZD$424 NZD$438 NZD$424 NZD
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