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Family-friendly vacation rentals in Orangeville

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Orangeville

  • Total vacation rentals

    Explore 20 vacation rentals in Orangeville

  • Nightly prices starting at

    Orangeville vacation rentals start at G$12,552 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,890 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Orangeville vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Orangeville rentals

  • 4.7 Average rating

    Orangeville stays receive an average rating of 4.7 out of 5 from guests

Top-rated family-friendly rentals in Orangeville

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

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Top guest favorite
An outdoor pool area features a surrounding deck with wooden steps leading up to it. Bright blue water reflects the sky, and vibrant green grass borders the patio. Two red Adirondack chairs are placed nearby, complemented by lush trees and a distant green landscape.
Guesthouse in Orangeville

Sunny Pines Farm Studio Tennis Court/Bruce Trail

Perfect for a getaway in the country. A bright, spacious, open-concept designer studio featuring beautiful rolling-hill vistas, queen bed, 3-piece bathroom, dedicated bbq, heat/AC plus a wood burning stove, wet bar with a Nespresso machine, deluxe counter-top oven & bar fridge and all new tennis court, laundry available upon request. Mono Cliffs, Boyne Valley, Hockley Valley Nature Reserve Prov. Parks & Mansfield Recreation Centre are minutes away. Ideal hiking, cycling, snowshoeing and xcsking.

FamilyIndoor spacesLong stay

4.96 out of 5 average rating, 404 reviews
Top guest favorite
A private wooden deck is shown with an umbrella-covered table and four chairs, surrounded by lush greenery. Windows on the building's façade allow natural light, while potted plants add a touch of color, enhancing the outdoor space for relaxation.
Apartment in Horning's Mills

Beautiful Riverside Country Apartment

Bright, warm and newly renovated, this 900sqft apartment, a private floor of a charming country home with separate entrance and garden patio, awaits you in Melancthon. SmartHDTV, Wifi, tranquil surroundings, and the Bruce Trail. Close to Shelburne, Mansfield, Creemore, Pine River Institue and many excellent restaurants (The Globe and Mrs Mitchels). Only 40 minutes to the Scandinave Spa, Collingwood, Blue Mountain, Wasaga Beach. Golf Courses are close by. A perfect retreat just north of Toronto.

Indoor spacesFamilyOutdoor spaces

4.96 out of 5 average rating, 347 reviews
Guest favorite
A sleek bathroom features a modern vanity with a vessel sink and polished faucet. Clean white tiles adorn the walls, complemented by a spacious walk-in shower. Minimalist accents include a framed decorative piece and neatly arranged white towels on shelves.
Apartment in Orangeville

A bright & modern urban studio

Come & unwind...in comfort. "The Snug" is a 740 square foot studio-style unit, that is bright & modern. You will be on the basement level of the main house, with a completely separate entrance. Nice kitchen & Sleek 3 pc bathroom(with rainfall shower head and heated floors). The queen bed, with luxury-firm mattress, has built in storage for all your needs. Reliable wifi so you can work at home! A short hop from Toronto, Dufferin County has all you need for a relaxing getaway! Come & See :)

KitchenIndoor spacesTV

4.94 out of 5 average rating, 102 reviews
Guest favorite
The kitchen features modern appliances, including a stainless steel refrigerator, oven, and microwave, arranged around a warm, wooden countertop. White cabinetry complements the neutral walls, while a sleek sink is positioned near the countertop, enhancing functionality in the space.
Condo in Orangeville

Modern Private Suite | Full Kitchen, Self Check-In

Welcome to our fully renovated 700 sq ft, lower-level suite, complete with a full kitchen. Basement suite is accessed through a shared front foyer, private locked door and self check-in via keypad. A 2 min walk to the hospital, and a short drive to arenas and downtown. Ideal for medical stays, hockey families, and anyone looking for quiet. Parking for one car on the driveway (free street parking May-October). Our 5-day cancellation policy ensures your dates are held exclusively for you.

KitchenFamilyParks

4.84 out of 5 average rating, 109 reviews
Top guest favorite
Place to stay in Grand Valley

Tamarack Trails Wilderness Cabin

Welcome to Tamarack Trails, your peaceful escape nestled in a quiet forest. This luxury cabin offers the perfect blend of comfort and nature, surrounded by 40 acres of unspoiled wilderness. Drift off to sleep in a cozy queen-sized bed and wake to the sound of song sparrows. Soak in a relaxing tub as you gaze out floor-to-ceiling windows. Enjoy breakfast on your private deck. Spend your days wandering private trails with stunning scenery or snowshoe through snow-draped white pines in winter.

Indoor spacesFamilyHospitality

4.98 out of 5 average rating, 98 reviews
Top guest favorite
An open concept living area showcases large panel doors that fully open to the outdoor deck. Inside, a comfortable seating arrangement is visible, along with a cozy area rug and a neutral color palette. Natural light floods the space, enhancing the connection to nature.
Cottage in Mono

Hockley Riverside Cottage • Loft and Bunkie

Needing an unforgettable escape? This cozy cottage is nestled in nature along the Nottawasaga river and has large panel doors that fully open for picture worthy views & peaceful sounds of the river. A new incredible outdoor fire-pit with hanging egg chairs. A cozy indoor wood burning fireplace along with a comfy pull out couch that has a projector above for the best movie nights. Heated floors if you aren't interested in maintaining a fire, fully equipped kitchen, Wi-fi, AC and washer/dryer.

Indoor spacesKitchenHospitality

4.95 out of 5 average rating, 167 reviews
Top guest favorite
A charming two-story cabin is nestled among lush greenery, with a pathway leading to the entrance. Tall trees and well-maintained hedges surround the home, creating a sense of privacy. Soft sunlight illuminates the cabin, enhancing its rustic appeal.
Cabin in Mono

The Trails Retreat (Private Cabin)

Beautifully renovated 2-story private hilltop cabin for romantic getaway, family stay or friends' retreat, experience a taste of the country together. Backed by forest and trails and set away from our family home, minutes to the Bruce Trail, Hockley Ski & Golf Resort, Mansfield Ski Club and charming Orangeville. Enjoy total guest privacy & spectacular sunrises. Guests are welcome to share our heated pool in season:) Add a playful Yoga/Functional Movement class or chef's dinner to your stay!

KitchenFamilyShared spaces

4.95 out of 5 average rating, 356 reviews
Superhost
An aerial view captures the waterfront trailer set against lush greenery, with a private deck featuring seating arrangements. Nearby, two kayaks await by the water, and a fire pit is surrounded by logs. The tranquil lake reflects the surrounding foliage.
Tiny home in Action

Lakefront 1 bedroom tiny home

Reconnect with nature at this unforgettable escape. Enjoy a wonderful stay in our lovely waterfront trailer located on Breezes Trailer park. It is a private quiet trailer park with 15 acres of nature and private access to Fairy Lake (Acton). Trailer is suitable for couple or small family. It is suited to people looking to relax and enjoy the scenery, explore the lake on kayak, exercise and explore on water bikes, fishing in the lake, enjoy some outdoor movies or campfire or under the stars.

KitchenFamilyBiking

4.85 out of 5 average rating, 159 reviews
Top guest favorite
A modern living area is presented with two light grey sofas facing a glass coffee table, which rests on a decorative rug featuring shades of blue and neutral tones. Natural light enters through two windows, highlighting the stylish wall decor.
Apartment in Shelburne

L&S Comfy Suite

Beautiful inviting space for families as well as individuals. Brand New Fully renovated area with lots of amenities for the whole family. 2 Great size bedroom with queen size beds. Jack And Jill full washroom with an amazing shower that boast body jets. Comes with all the bells and whistles. Open concept with Living room, Dining room, Full Kitchen, Washer and Dryer, free parking, work area ideal for remote work, and lots more…. NO UNREGISTERED GUESTS ARE ALLOWED AS PER HOUSE RULES.

Indoor spacesKitchenBreakfast

4.93 out of 5 average rating, 172 reviews
Top guest favorite
This inviting bedroom features a spacious bed adorned with soft linens and a textured throw. A large armoire stands alongside, complemented by decorative plants and soft lighting. Natural light is welcomed through an adjacent glass door leading to a private entrance.
Guest suite in Orangeville

Headwaters Retreat - Private Hot Tub & Fireplace

Escape to our modern and rustic Queen Suite, with private hot tub right at your door. Relax by the pool, or unwind by the fireplace & enjoy Netflix & Amazon TV. This cozy retreat features a private entrance, ensuite bathroom, and a second bedroom with twin beds. Steps from scenic hiking trails, minutes from the town center, your stay is ideal for outdoor adventures, wine tours, weddings, work trips or a quiet escape away. Book now for your ultimate getaway in comfort and nature!

Indoor spacesFamilyAir conditioning

4.92 out of 5 average rating, 896 reviews
Top guest favorite
A spacious living area features a blue sofa with a light throw, positioned beside a circular coffee table. Wall art adorns the white walls, and natural light filters through a decorative window. A white cabinet and a small plant complete the cozy atmosphere.
Loft in Orangeville

Hockley Haven

Kick back and relax in this calm, stylish space. Cozy 1 bedroom carriage house loft (appx 650 sq ft) above detached 3 bay garage in serene country setting on 5 acres of pine and cedar with a river running thru it. Pullout couch can accommodate 2 additional people. Walk across the road to Pollinator Garden & Island Lake Trails. 6 min drive to Hockley Valley Resort and Adamo Estate Winery, as well as beautiful downtown Orangeville boasting fabulous restaurants and quaint shops.

FamilyKitchenCleanliness

4.98 out of 5 average rating, 189 reviews
Top guest favorite
A cozy living area features a light-colored sofa with decorative cushions, a coffee table, and a wall-mounted television. A slim electric fireplace is situated beneath the TV. To the rear, a fully equipped kitchen can be seen, enhancing the space's functionality.
Guest suite in Orangeville

Garden Studio Orangeville

🌿 Country-Soul, Town-Heart Haven: Walk to Cafes, Mins to Premium Spas & PGA Golf. A newly renovated 1 bdrm walkout apartment located in our home in downtown Orangeville. Steps to Theatre Orangeville, Orangeville farmers market, and Jazz & Blues Festival. Enjoy evenings on your own patio in a private backyard overlooking the garden. Enjoy walks on the Island lake Conservation Park.. Dine at any of the many fine restaurants or cook at meal in your own fully equipped kitchen.

KitchenIndoor spacesAir conditioning

5.0 out of 5 average rating, 203 reviews

Popular amenities for Orangeville family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top guest favorite
A modern living area features a large, dark sectional sofa adorned with blue and orange cushions. A floral area rug adds a splash of color beneath the furniture. Natural light enters through two windows, and a mirror reflects the space, enhancing the open feel.
Home in Orangeville

HotTub & Private Suite - Casa Facciolo

Indoor spacesKitchenQuiet

4.97 out of 5 average rating, 195 reviews
Guest favorite
The exterior of the house features a combination of stone and wooden siding, with a pronounced roofline. A welcoming pathway leads to a spacious front deck, surrounded by manicured greenery and landscaping. Large windows and a colorful door enhance the inviting appearance.
Home in Alton

Cozy Fall Escape | HotTub + Fire Pit + River

Indoor spacesKitchenSleep quality

4.96 out of 5 average rating, 135 reviews
Top guest favorite
A cozy sitting area is presented with a blue checkered sofa and a striped armchair, adorned with nautical-themed cushions. Light is provided by two lamps on either side, illuminating the artwork and rustic wooden beams above.
Guesthouse in Erin

The Captain's Cottage at Willow Pond

KitchenFamilyWalkability

4.96 out of 5 average rating, 154 reviews
Superhost
An inviting outdoor space features a wooden pergola with string lights, surrounding a dining table and seating area. A private hot tub is positioned nearby, with lush greenery and vibrant flower arrangements enhancing the serene environment.
Cabin in Erin

Erin Cabin & Bunkie. Your fall colour experience!

Indoor spacesFamilyAmenities

4.9 out of 5 average rating, 554 reviews
Top guest favorite
Cottage in Georgina

Lakefront | Private Dock, Sandy Beach & Hot Tub

Indoor spacesKitchenAccess

4.91 out of 5 average rating, 304 reviews
Top guest favorite
Dome in Utopia

Glamping Dome Riverview Utopia

KitchenIndoor spacesValue

4.96 out of 5 average rating, 208 reviews
Guest favorite
A covered patio area features a hot tub alongside a glass-topped table with comfortable seating. The peaceful lakeside view showcases expansive green space and a row of chairs positioned along the shore, framed by trees lining the property.
Cottage in Georgina

Sunset Shores Lakehouse- Hot Tub, Wet Bar & Games

KitchenFamilyLayout

4.96 out of 5 average rating, 106 reviews
Top guest favorite
A spacious building is seen with a large deck overlooking a tranquil pond. A canoe rests on the grassy bank, with a stone waterfall nearby. Bright seating areas are arranged on the porch, surrounded by lush greenery and well-maintained landscaping.
Farm stay in Fergus

Waterpark Acres

FamilyKitchenHot tub

4.96 out of 5 average rating, 336 reviews

Family- and pet-friendly home rentals

Top guest favorite
A brightly lit living area features a red sofa adorned with decorative pillows. A wooden coffee table sits on a light rug, while large windows allow natural light to flood in, offering views of the surrounding greenery.
Home in Grand Valley

House on the bank of river

KitchenFamilyAmenities

4.78 out of 5 average rating, 102 reviews
Top guest favorite
A charming stone house is set against a backdrop of lush greenery. The facade features large windows and a welcoming porch. A well-kept lawn leads to the entrance, offering a serene view of the surrounding trees.
Cabin in Arthur

The Stone Heron

FamilyKitchenBackyard

4.99 out of 5 average rating, 434 reviews
Guest favorite
The rustic beach house is surrounded by greenery, featuring wooden siding and a welcoming porch. A separate structure is visible nearby, both enhancing the tranquil setting. The clear blue sky adds to the serene atmosphere of the property.
Cabin in Erin

Rustic Cabin on Private Pond

KitchenIndoor spacesSkiing

4.95 out of 5 average rating, 180 reviews
Top guest favorite
A serene winter scene captures a snowy landscape framed by tall evergreen trees. A clear blue sky contrasts with the bright white snow covering the ground and adjacent areas. The pathway leads towards a structure partly obscured by the snow-laden trees, suggesting a peaceful retreat.
Guest suite in Orangeville

Your Peaceful Santuary in Nature

KitchenFamilyHiking

4.96 out of 5 average rating, 189 reviews
Guest favorite
A winding path is framed by tall trees, leading to a rustic cabin nestled among the forest. Lush greenery flanks the path, creating a serene and secluded ambiance, inviting exploration into the natural surroundings.
Tiny home in Mono

Whispering Pines Cabin in Woodland Acres

KitchenFamilyHospitality

4.91 out of 5 average rating, 175 reviews
Top guest favorite
Cabin in Guelph/Eramosa

Fern Hill Cabin

KitchenIndoor spacesCondition

4.99 out of 5 average rating, 114 reviews
Guest favorite
Home in Caledon

Studio Apartment

KitchenIndoor spacesAccess

4.86 out of 5 average rating, 285 reviews
Top guest favorite
Guesthouse in Breslau

House on the Hill

KitchenFamilyNearby

4.97 out of 5 average rating, 228 reviews

Family-friendly home rentals with a pool

Top guest favorite
Vibrant autumn foliage displays shades of yellow and orange surrounding a geodesic dome. A pathway of stone steps leads through a lawn covered in colorful leaves, creating a serene outdoor setting amidst lush greenery.
Dome in Bradford West Gwillimbury

Four season glamping dome under the stars

FamilyKitchenHeating

4.97 out of 5 average rating, 507 reviews
Top guest favorite
A welcoming porch features a blue exterior with white trim, adorned by potted plants and lush greenery. Rocking chairs are positioned on the porch, providing a comfortable space to relax. The pathway is lined with stones, leading from the driveway to the entrance.
Apartment in Ariss

Rural Retreat, near to Elora

FamilyKitchenBreakfast

4.95 out of 5 average rating, 217 reviews
Superhost
A serene backyard is highlighted by a clear swimming pool surrounded by natural stone coping. Comfortable seating arrangements with dark wicker chairs and a sleek table are positioned nearby, offering a relaxing spot. Lush greenery frames the area, providing a peaceful atmosphere.
Guesthouse in Mississauga

“CasaDeLeon”- Modern and cozy Lakeview guesthouse

Indoor spacesKitchenPool

4.89 out of 5 average rating, 116 reviews
Guest favorite
Camper/RV in Lisle

Givi’s Cozy Camper: Warm & Welcoming

KitchenFamilyGetting around

4.92 out of 5 average rating, 131 reviews
Top guest favorite
A stone fireplace is set into a rustic wall made of various sized natural stones, providing a textured and earthy backdrop. A flat-screen TV is mounted above, and a wooden cabinet is positioned to the left, adding warmth to the living space.
Apartment in Caledon

Separate apartment with pool, on golf course.

Indoor spacesKitchenOutdoor spaces

4.95 out of 5 average rating, 109 reviews
Top guest favorite
Home in Erin Mills

Luxurious 2 bdr suite near SQ1, UTM, parking/pool

Indoor spacesFamilyDecor

4.96 out of 5 average rating, 123 reviews
Top guest favorite
A backyard seating area is viewed, featuring a dark outdoor sectional couch with a black coffee table placed on a striped rug. Surrounding the heated saltwater pool are lounge chairs and lush greenery, creating a serene outdoor space.
Guesthouse in Brampton

Bright and Airy Guest Suite with Pool

Indoor spacesFamilyComfort

5.0 out of 5 average rating, 127 reviews
Guest favorite
A modern condominium building is showcased from a street view, highlighting two tall, sleek towers with an expansive glass façade. The ground level features a multi-story section with large windows and contemporary architectural elements, set against a clear blue sky.
Condo in Mississauga

Beautiful & Cozy 2Bed 2Bath Condo Steps to Square1

FamilyIndoor spacesAir conditioning

4.9 out of 5 average rating, 170 reviews

When is the best time to visit Orangeville?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$19,665 GYDG$23,012 GYDG$24,267 GYDG$25,522 GYDG$20,711 GYDG$20,083 GYDG$28,242 GYDG$26,778 GYDG$22,594 GYDG$22,803 GYDG$21,757 GYDG$25,732 GYD
Avg. temp-7°C-6°C-1°C6°C12°C17°C20°C19°C15°C9°C3°C-3°C

Destinations to explore