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Family-friendly holiday rentals in Orangeville

Find and book unique family-friendly homes on Airbnb

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

  • Total holiday rentals

    Explore 20 holiday rentals in Orangeville

  • Nightly prices starting at

    Orangeville holiday rentals start at $101 NZD 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 holiday 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 favourite
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.

KitchenFamilyLong stay

4.96 out of 5 average rating, 404 reviews
Top Guest favourite
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

Whether you are looking for a romantic getaway for two, a solo remote work week in solitude surrounded by nature, or a family adventure, this 4-season geodesic dome is just the right place. Explore picturesque trails of Scanlon Creek Conservation Area, enjoy inground pool in summer, experience breathtaking sunsets over the farm fields, the starry skies by the bonfire, mesmerizing dance of fireflies in June, and let the frogs and crickets lull you to sleep in the place where time stands still...

FamilyIndoor spacesComfort

4.97 out of 5 average rating, 499 reviews
Top Guest favourite
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.

FamilyIndoor spacesLaundry

4.96 out of 5 average rating, 345 reviews
Guest favourite
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.

FamilyKitchenNearby

4.84 out of 5 average rating, 104 reviews
Guest favourite
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 :)

Indoor spacesKitchenWi-Fi

4.94 out of 5 average rating, 102 reviews
Top Guest favourite
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.

FamilyKitchenTV

4.95 out of 5 average rating, 163 reviews
Top Guest favourite
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!

FamilyIndoor spacesCleanliness

4.95 out of 5 average rating, 353 reviews
Top Guest favourite
A private detached apartment is visible nestled among tall trees and lush greenery. The wooden exterior of the structure blends harmoniously with the natural surroundings. A pathway leads towards the entrance, framed by a vibrant landscape of ferns and colorful shrubs.
Guest suite in Caledon

Casa Caledon-Secluded Suite Surrounded by Nature

Take it easy at this unique and tranquil getaway, nestled on 3 acres of peaceful countryside Close to the Cheltenham Badlands, Forks of the Credit, Terra Cotta and Bruce Trail, plus golf, restaurants, bakeries and farm-fresh produce ❤️Every season is special 🌿 Enjoy lush forests, the pond and fire pit in spring & summer 🍁Spectacular fall colours and beautiful walks ❄️Peaceful winter wonderland with access to local winter sports A perfect place to slow down and reconnect with nature

KitchenIndoor spacesHiking

4.98 out of 5 average rating, 160 reviews
Top Guest favourite
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.

FamilyKitchenValue

4.93 out of 5 average rating, 166 reviews
Top Guest favourite
Guest suite in Orangeville

Private Hot Tub & Pool - Headwaters Retreat

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!

KitchenIndoor spacesHot tub

4.92 out of 5 average rating, 890 reviews
Top Guest favourite
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.

FamilyKitchenAccess

4.98 out of 5 average rating, 186 reviews
Top Guest favourite
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.

FamilyKitchenQuiet

5.0 out of 5 average rating, 202 reviews

Popular amenities for Orangeville family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Guest favourite
The exterior of a two-story house showcases a blend of stone and dark wood siding, with a spacious deck accessible from the upper floor. Lush green grass and neatly arranged flower beds surround the home, while a gray sky sets a calm backdrop.
Home in Alton

Cozy Country Spring Getaway | HotTub + Fire Pit

Indoor spacesKitchenDecor

4.96 out of 5 average rating, 130 reviews
Top Guest favourite
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

Hot Tub & Private Suite - Casa Facciolo

FamilyKitchenLocation

4.97 out of 5 average rating, 192 reviews
Guest favourite
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

Cabin stay and play! 10 mins to Canadian Open!

KitchenFamilyComfort

4.9 out of 5 average rating, 546 reviews
Top Guest favourite
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

FamilyKitchenSkiing

4.96 out of 5 average rating, 153 reviews
Top Guest favourite
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

KitchenIndoor spacesCondition

4.96 out of 5 average rating, 332 reviews
Top Guest favourite
Dome in Utopia

Glamping Dome Riverview Utopia

Indoor spacesFamilyBarbecue

4.96 out of 5 average rating, 204 reviews
Guest favourite
A luxury tent is set amongst lush greenery, featuring a wooden deck with Muskoka chairs and a private hot tub. A hammock is visible to one side, with a picnic table positioned nearby, all surrounded by trees and natural landscaping.
Farm stay in Elora-Salem

Luxury Glamping on Elora Sunflower Farm -Sunflower

KitchenFamilyAccess

4.94 out of 5 average rating, 231 reviews
Top Guest favourite
The exterior of a modern home is highlighted at sunset, showcasing large windows that reflect warm interior lighting. A spacious backyard features green grass, a dining area under a gazebo, and a hot tub on the deck, creating an inviting outdoor space.
Home in Barrie

Waterfront Home, City/Sunset View & Steps to Beach

KitchenFamilyView

4.97 out of 5 average rating, 158 reviews

Family- and pet-friendly home rentals

Top Guest favourite
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

FamilyKitchenAccuracy

4.99 out of 5 average rating, 429 reviews
Guest favourite
The historic log cabin from the 1850s is surrounded by lush greenery. A covered porch with wooden beams invites relaxation, while hanging flower baskets add subtle color. The peaked roof and wooden siding emphasize the cabin's rustic charm in a serene forest setting.
Cabin in Erin

1850 Settler's Cabin in Private Forest

FamilyKitchenLocation

4.95 out of 5 average rating, 202 reviews
Top Guest favourite
Cabin in Guelph/Eramosa

Fern Hill Cabin

FamilyKitchenOutdoor spaces

4.99 out of 5 average rating, 109 reviews
Top Guest favourite
A log cabin exterior showcases a blend of rustic charm and natural surroundings. The structure features various window styles, allowing light to enter, while green grass and garden elements enhance the peaceful ambiance. Surrounding trees create a serene and private setting.
Cabin in Holstein

Kettle Creek Cabin

KitchenFamilyComfort

4.99 out of 5 average rating, 154 reviews
Guest favourite
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

FamilyKitchenSleep quality

4.91 out of 5 average rating, 174 reviews
Top Guest favourite
A spacious dining area features a large wooden table surrounded by black chairs. A clock with a white face is mounted on the wall, and natural light fills the room through large windows. A view into the living area is visible in the background.
Home in Bond Head

3BR Spacious Home - KING BED

KitchenFamilyPets

4.97 out of 5 average rating, 113 reviews
Guest favourite
Home in Caledon

Studio Apartment

Indoor spacesFamilyCheck-in

4.86 out of 5 average rating, 273 reviews
Top Guest favourite
An open concept living area features rustic wood beams and sliding barn doors. Comfortable wicker chairs are paired with a wooden coffee table, while a cozy sofa adds to the inviting space. The modern kitchen is visible in the background, creating a seamless flow.
Guesthouse in Mansfield

Brookside Cottage - Charming Rural Getaway Mulmur

KitchenFamilyQuiet

4.99 out of 5 average rating, 122 reviews

Family-friendly home rentals with a pool

Top Guest favourite
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.

FamilyKitchenSleep quality

4.95 out of 5 average rating, 109 reviews
Superhost
The indoor swimming pool area features a tiled pool surrounded by natural light from large skylights. Two colorful floats are positioned on the water surface, and glass doors provide a view of the outdoors, enhancing the open and airy feel of the space.
Villa in Toronto

Toronto Vacation | ➊ The One Toronto Villa

Indoor spacesFamilyBarbecue

4.92 out of 5 average rating, 217 reviews
Top Guest favourite
Guesthouse in Breslau

House on the Hill

Indoor spacesFamilyRiver

4.97 out of 5 average rating, 225 reviews
Guest favourite
Campervan/RV in Lisle

Givi’s Cozy Camper: Warm & Welcoming

Indoor spacesFamilyTV

4.93 out of 5 average rating, 120 reviews
Top Guest favourite
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

Indoor spacesFamilyHot tub

4.95 out of 5 average rating, 213 reviews
Superhost
A spacious living room is highlighted by tall wooden ceilings and large windows that invite ample natural light. Two comfortable sofas face each other over a coffee table, with a patterned area rug underfoot. A small fireplace and colorful stained glass add character to the warm design.
Barn in Milton

Five Star Hayloft Suite

KitchenFamilyBackyard

4.87 out of 5 average rating, 111 reviews
Superhost
The entrance features double doors in a dark finish, adorned with elegant seasonal wreaths. Flanking the doors are decorative wall art pieces. A small bistro table with two chairs is positioned on a stone patio, complemented by potted snake plants and decorative pumpkins.
Home in Barrie

Luxurious 4BDRM-King Bed-Barrie-near Snow Resorts

FamilyIndoor spacesAccuracy

4.89 out of 5 average rating, 140 reviews
Guest favourite
Guesthouse in Orangeville

Ballo - GuestHouse

PoolComfortCleanliness

4.89 out of 5 average rating, 9 reviews

When is the best time to visit Orangeville?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$159 NZD$186 NZD$196 NZD$206 NZD$167 NZD$162 NZD$228 NZD$216 NZD$182 NZD$184 NZD$176 NZD$208 NZD
Avg. temp-7°C-6°C-1°C6°C12°C17°C20°C19°C15°C9°C3°C-3°C

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