Family-friendly vacation rentals in Orangeville

Find and book unique family-friendly homes on Airbnb

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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Guest favorite

Guesthouse in Orangeville

4.95 out of 5 average rating, 310 reviews

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.

Aug 19 – 26

R2,761 ZAR per night

Guest favorite

Tiny home in Mono

4.94 out of 5 average rating, 152 reviews

Tiny home Soaring Heart Wellness Spa

A clean, bright space with high ceilings, privacy, and charm overlooking our Herbal Tea Garden. You can hike the Bruce Trail, relax by our pond or cycle through the Dufferin County Forest. Relax in the hot tub, book a massage, or enjoy a campfire under the stars. Check services online: Soaring Heart Wellness Inside is a bed, kitchenette, writing desk and sitting area. Outdoor is barbecue , firepit, and attached outhouse. Short walk to indoor bath Great local food and restaurants close by.

May 9 – 16

R1,135 ZAR per night

Guest favorite

Chalet in Priceville

4.91 out of 5 average rating, 448 reviews

ReLive Hilltop Chalet w/brand-new hottub, sunrises

Relive Retreat's Hilltop Chalet is a 700 sq ft open concept rustic cabin w/high ceilings, full-length windows, spring water, private + new hot tub, fireplace, BBQ, wrap around deck w/views, hiking trails + more. Perfect for couples, friends or families looking to relax & rejuvenate in nature. If peace is what you are looking for this is it! Occassionally dog friendly so please inquire first. This is a private 72 acre retreat. We live here with our 2 dogs, currently hosting 2 yurts and 2 cabins.

Aug 24 – 31

R3,050 ZAR per night

Guest favorite

Apartment in Horning's Mills

4.96 out of 5 average rating, 255 reviews

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 next to the Bruce Trail. Close to Shelburne, Mansfield, Creemore, and many excellent restaurants (like The Globe and Mrs Mitchels). Only 40 minutes to the Scandinave Spa, Collingwood, Blue Mountain, and Wasaga Beach. Golf Courses are close by. A perfect retreat just north of Toronto.

Oct 31 – Nov 7

R1,498 ZAR per night

Guest favorite

Guest suite in Orangeville

4.92 out of 5 average rating, 656 reviews

Private Hot Tub - Headwaters Retreat

Escape to our cozy and rustic queen suite with a modern touch. Private entrance & hot tub steps from your door, overlooking our peaceful conservation area. Spacious fireplace in main suite with en-suite bathroom, Apple TV, Netflix, and second bedroom with two twin beds. Steps from the hiking trails and just minutes from the town center. Perfect for outdoor adventures, art gallery visits, wine tours, weddings, sporting events, work trips or just a quiet getaway. Your getaway awaits!

Dec 8 – 15

R1,411 ZAR per night

Guest favorite

Guest suite in Holland Centre

4.97 out of 5 average rating, 193 reviews

Dragonfly Hollow bnb

Nature lovers, Come experience the natural beauty of the Grey-Bruce region. Our home is in a very quite natural setting surrounded by trees. In summer explore the many lakes, beach or waterfalls . Hike the Bruce trail, or one of many others; good for ATVing, Scenic Motorcycle Routes. Fall is especially beautiful, the hills and valleys fill with vibrant colours. In winter, enjoy cross-country, downhill skiing, snowboarding, skidooing. Blue Mountain only a Scenic 40 mins away.

Jan 11 – 18

R1,572 ZAR per night

Guest favorite

Guesthouse in Guelph

4.9 out of 5 average rating, 499 reviews

Beautiful Studio Cottage ~Urban Retreat ~Fast WiFi

Experience an independent, private, sparkling clean studio close to downtown Guelph with full amenities. Located in a gorgeous tree-filled 200 ft backyard, this cozy urban cottage has a comfortable double bed with new mattress, gas fireplace, fully stocked kitchen, separate shower, 2-piece washroom, sleeping loft, and private back deck.Located in the heart of the Junction Village intentional community, guests can connect with others, or have a private retreat experience.

Aug 29 – Sep 5

R2,241 ZAR per night

Guest favorite

Cabin in Mono

4.94 out of 5 average rating, 272 reviews

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 and yoga studio, minutes to the Bruce Trail, Hockley Ski & Resort, and Mansfield Ski Club, enjoy total guest privacy & spectacular sunrises. Guests are welcome to share our heated pool in season:) Chef's creations and Private yoga and group classes available

Jul 23 – 30

R3,150 ZAR per night

Guest favorite

Cabin in Wallenstein

4.91 out of 5 average rating, 225 reviews

Rustic private getaway with Jacuzzi tub

Walnut Hill Cabin is a beautiful cabin located near the historic village of St. Jacobs. We invite you to come relax in our oasis, we love our place and are happy to share our cabin with you! Kitchenette and continental breakfast is included. Great for business travel. Come, relax and refresh while watching squirrels and birds play A great couples weekend getaway! We thoroughly clean after every visit. When you book you get the whole cabin to yourself!

Jan 26 – Feb 2

R1,999 ZAR per night

Guest favorite

Apartment in Innisfil

4.99 out of 5 average rating, 495 reviews

Cozy One bedroom Apartment by the Lake

A clean and inviting upper level one-bedroom apartment across the street from beautiful Lake Simcoe & Innisfil Beach Park! A short walk to all amenities in town, (Tim's, LCBO, Pizza, Nofrills, Canadian Tire & More) just 20 minutes to Barrie and 50 minutes to Toronto. This apartment is perfect for a summer weekends to the beach. Also ideal for ice fishing in winter. You have your own private outdoor space with a BBQ and plenty of parking for car & boat.

May 21 – 28

R1,427 ZAR per night

Guest favorite

Farm stay in Fergus

4.95 out of 5 average rating, 216 reviews

Waterpark Acres

Waterpark Acres offers a unique country experience to relax with spectacular views from the balcony. You have complete privacy in this separate building. No other rooms are rented out while you are here. See farm animals ( horses, llama's, dogs, sheep, pheasants and other birds. Also some out of the ordinary animals including kangaroos, lemurs, kinkajou's, parrots etc. ) Please note : WEDDING EVENTS are not hosted on this property

Sep 11 – 18

R4,014 ZAR per night

Guest favorite

Guest suite in Mono

4.9 out of 5 average rating, 155 reviews

Dew Drop Inn

Welcome to your temporary home away from home! Separate apartment within our home (930 square feet). Separate entrance with large foyer. Two bedrooms, 1 with a queen bed and kitchen, the other with a queen bed, futon and T.V. (sitting area). Three piece bathroom with step-in shower. Tons of parking. Hardwood floors throughout. Spectacular views and 2 firepits to use. Please see pictures. No pets allowed.

Apr 7 – 14

R1,342 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Orangeville family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Guest favorite

Cottage in Kimberley

4.87 out of 5 average rating, 307 reviews

A Cozy Country Retreat *Indoor Hot Tub* Ski* Wi-Fi

Aug 14 – 21

R10,508 ZAR per night

Superhost

Condo in Toronto

4.81 out of 5 average rating, 302 reviews

Spacious Downtown (midtown) 2bed 2 bath free parki

May 6 – 13

R3,461 ZAR per night

Guest favorite

Home in Kimberley

4.88 out of 5 average rating, 176 reviews

Heart of Kimberley - with views and a hot tub

May 13 – 20

R5,327 ZAR per night

Guest favorite

Bungalow in Innisfil

4.82 out of 5 average rating, 272 reviews

Lake Simcoe-3bdr,hot tub,sauna,swim,play,hike

Apr 9 – 16

R2,386 ZAR per night

Guest favorite

Apartment in Toronto

4.91 out of 5 average rating, 257 reviews

Honey House in the Beach

Jan 2 – 9

R1,572 ZAR per night

Guest favorite

Condo in Toronto

4.89 out of 5 average rating, 273 reviews

CENTRAL DOWNTOWN LUXURY APT STEPS TO CN TOWER/LAKE

Sep 29 – Oct 6

R8,130 ZAR per night

Guest favorite

Condo in Toronto

4.97 out of 5 average rating, 291 reviews

Beautiful Condo + CN Tower View + Free Parking

Oct 22 – 29

R11,975 ZAR per night

Superhost

Condo in Toronto

4.84 out of 5 average rating, 121 reviews

Modern 1 Bdrm Suite Downtown District - Lake View

May 11 – 18

R3,664 ZAR per night

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Family- and pet-friendly home rentals

Guest favorite

Barn in Eugenia

4.98 out of 5 average rating, 165 reviews

Blue Barn Bed n Bale / Blue Mountain

Feb 4 – 11

R3,161 ZAR per night

Guest favorite

Tiny home in Schomberg

4.99 out of 5 average rating, 190 reviews

SNAKE CABIN(rustic, 'off-the-grid')

Nov 11 – 18

R2,964 ZAR per night

Superhost

Condo in Innisfil

4.95 out of 5 average rating, 183 reviews

Designer Condo with beautiful harbour view.

Nov 7 – 14

R2,779 ZAR per night

Guest favorite

Guest suite in King City

4.98 out of 5 average rating, 177 reviews

Spacious guest apartment on beautiful greenspace

Feb 24 – Mar 3

R2,551 ZAR per night

Guest favorite

Bungalow in Elora

4.98 out of 5 average rating, 228 reviews

Studio Downtown Elora

Sep 11 – 18

R3,904 ZAR per night

Guest favorite

Cottage in Flesherton

4.94 out of 5 average rating, 122 reviews

Cottage Get-Away on the Lake

Nov 27 – Dec 4

R6,032 ZAR per night

Superhost

Apartment in Milton

4.71 out of 5 average rating, 143 reviews

Studio Apt in Milton Dorset Park

Dec 29 – Jan 5

R1,530 ZAR per night

Guest favorite

Home in Grey Highlands

4.96 out of 5 average rating, 126 reviews

Newly Renovated! Charming Beaver Valley Farmhouse

May 5 – 12

R4,248 ZAR per night

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Family-friendly home rentals with a pool

Guest favorite

Home in Cambridge

4.91 out of 5 average rating, 238 reviews

Spacious Bungalow Guest House

Dec 4 – 11

R3,013 ZAR per night

Guest favorite

Guest suite in Mississauga

4.92 out of 5 average rating, 132 reviews

Full apt on Upper floor near HWY - S Mississauga

May 1 – 8

R1,606 ZAR per night

Guest favorite

Home in Toronto

4.91 out of 5 average rating, 264 reviews

King West Victorian Studio Gem

Jul 16 – 23

R3,190 ZAR per night

Guest favorite

Guest suite in Oakville

4.85 out of 5 average rating, 176 reviews

LL*1 BR Suite*Wi-fi*Parking*Near Lake

Sep 22 – 29

R1,927 ZAR per night

Guest favorite

Condo in Toronto

4.97 out of 5 average rating, 217 reviews

Chic, High-Rise Apartment with CN Tower Views

May 8 – 15

R4,559 ZAR per night

Guest favorite

Apartment in Toronto

4.79 out of 5 average rating, 141 reviews

Stunning Condo @ the Heart of Toronto (w/ Parking)

May 7 – 14

R3,713 ZAR per night

Superhost

Condo in Toronto

4.86 out of 5 average rating, 178 reviews

Best View in Downtown 5 Star Luxury 1+1 w/office

May 14 – 19

R3,812 ZAR per night

Guest favorite

Condo in Innisfil

4.84 out of 5 average rating, 171 reviews

Marina view at Friday Harbor 2bdm/2bth Pool option

Aug 28 – Sep 4

R3,992 ZAR per night

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

Total rentals
20 properties
Local attractions
Island Lake Conservation Area, Metro, and Walmart Orangeville Supercentre
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
20 properties include access to wifi
Total number of reviews
1.1K reviews
Nightly prices starting at
R1,129 ZAR before taxes and fees

Family-friendly vacation rentals in Orangeville

Top-rated family-friendly rentals in Orangeville

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Orangeville family-friendly rentals

Family-friendly home rentals with a hot tub

Cottage in Kimberley

Condo in Toronto

Home in Kimberley

Bungalow in Innisfil

Apartment in Toronto

Condo in Toronto

Condo in Toronto

Condo in Toronto

Family- and pet-friendly home rentals

Barn in Eugenia

Tiny home in Schomberg

Condo in Innisfil

Guest suite in King City

Bungalow in Elora

Cottage in Flesherton

Apartment in Milton

Home in Grey Highlands

Family-friendly home rentals with a pool

Home in Cambridge

Guest suite in Mississauga

Home in Toronto

Guest suite in Oakville

Condo in Toronto

Apartment in Toronto

Condo in Toronto

Condo in Innisfil

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

Total rentals

Local attractions

Popular amenities

Wifi availability

Total number of reviews

Nightly prices starting at

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