Family-friendly holiday rentals in Orangeville

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Orangeville

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Guest favourite

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.

19 – 26 Aug

$1,750 AUD total

Guest favourite

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.

9 – 16 May

$669 AUD total

Guest favourite

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.

24 – 31 Aug

$2,033 AUD total

Guest favourite

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.

31 Oct – 7 Nov

$1,006 AUD total

Guest favourite

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!

8 – 15 Dec

$950 AUD total

Guest favourite

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.

11 – 18 Jan

$997 AUD total

Guest favourite

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.

29 Aug – 5 Sept

$1,537 AUD total

Guest favourite

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

23 – 30 July

$2,040 AUD total

Guest favourite

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!

26 Jan – 2 Feb

$1,305 AUD total

Guest favourite

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.

21 – 28 May

$942 AUD total

Guest favourite

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

11 – 18 Sept

$2,385 AUD total

Guest favourite

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.

7 – 14 Apr

$876 AUD total

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Orangeville family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Guest favourite

Cottage in Kimberley

4.87 out of 5 average rating, 307 reviews

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

14 – 21 Aug

$6,258 AUD total

Superhost

Condo in Toronto

4.81 out of 5 average rating, 302 reviews

Spacious Downtown (midtown) 2bed 2 bath free parki

6 – 13 May

$2,434 AUD total

Guest favourite

Home in Kimberley

4.88 out of 5 average rating, 176 reviews

Heart of Kimberley - with views and a hot tub

13 – 20 May

$3,625 AUD total

Guest favourite

Bungalow in Innisfil

4.82 out of 5 average rating, 272 reviews

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

9 – 16 Apr

$1,470 AUD total

Guest favourite

Apartment in Toronto

4.91 out of 5 average rating, 257 reviews

Honey House in the Beach

2 – 9 Jan

$1,044 AUD total

Guest favourite

Condo in Toronto

4.89 out of 5 average rating, 273 reviews

CENTRAL DOWNTOWN LUXURY APT STEPS TO CN TOWER/LAKE

29 Sept – 6 Oct

$5,559 AUD total

Guest favourite

Condo in Toronto

4.97 out of 5 average rating, 291 reviews

Beautiful Condo + CN Tower View + Free Parking

22 – 29 Oct

$8,077 AUD total

Superhost

Condo in Toronto

4.84 out of 5 average rating, 121 reviews

Modern 1 Bdrm Suite Downtown District - Lake View

11 – 18 May

$2,575 AUD total

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Family- and pet-friendly home rentals

Guest favourite

Barn in Eugenia

4.98 out of 5 average rating, 165 reviews

Blue Barn Bed n Bale / Blue Mountain

4 – 11 Feb

$2,078 AUD total

Guest favourite

Tiny home in Schomberg

4.99 out of 5 average rating, 190 reviews

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

11 – 18 Nov

$1,687 AUD total

Superhost

Condo in Innisfil

4.95 out of 5 average rating, 183 reviews

Designer Condo with beautiful harbour view.

7 – 14 Nov

$1,693 AUD total

Guest favourite

Guest suite in King City

4.98 out of 5 average rating, 177 reviews

Spacious guest apartment on beautiful greenspace

24 Feb – 3 Mar

$1,689 AUD total

Guest favourite

Bungalow in Elora

4.98 out of 5 average rating, 228 reviews

Studio Downtown Elora

11 – 18 Sept

$2,537 AUD total

Guest favourite

Cottage in Flesherton

4.94 out of 5 average rating, 122 reviews

Cottage Get-Away on the Lake

27 Nov – 4 Dec

$3,972 AUD total

Superhost

Apartment in Milton

4.71 out of 5 average rating, 143 reviews

Studio Apt in Milton Dorset Park

29 Dec – 5 Jan

$1,020 AUD total

Guest favourite

Home in Grey Highlands

4.96 out of 5 average rating, 126 reviews

Newly Renovated! Charming Beaver Valley Farmhouse

5 – 12 May

$2,911 AUD total

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Family-friendly home rentals with a pool

Guest favourite

Home in Cambridge

4.91 out of 5 average rating, 238 reviews

Spacious Bungalow Guest House

4 – 11 Dec

$2,079 AUD total

Guest favourite

Guest suite in Mississauga

4.92 out of 5 average rating, 132 reviews

Full apt on Upper floor near HWY - S Mississauga

1 – 8 May

$1,197 AUD total

Guest favourite

Home in Toronto

4.91 out of 5 average rating, 264 reviews

King West Victorian Studio Gem

16 – 23 July

$2,058 AUD total

Guest favourite

Guest suite in Oakville

4.85 out of 5 average rating, 176 reviews

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

22 – 29 Sept

$1,359 AUD total

Guest favourite

Condo in Toronto

4.97 out of 5 average rating, 217 reviews

Chic, High-Rise Apartment with CN Tower Views

8 – 15 May

$3,111 AUD total

Guest favourite

Apartment in Toronto

4.79 out of 5 average rating, 141 reviews

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

7 – 14 May

$2,588 AUD total

Superhost

Condo in Toronto

4.86 out of 5 average rating, 178 reviews

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

14 – 19 May

$1,748 AUD total

Guest favourite

Condo in Innisfil

4.84 out of 5 average rating, 171 reviews

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

28 Aug – 4 Sept

$2,667 AUD total

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Quick stats about holiday 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, Wi-Fi and Pool
Wi-Fi availability
20 properties include access to Wi-Fi
Total number of reviews
1.1K reviews
Nightly prices starting at
$92 AUD before taxes and fees

Family-friendly holiday rentals in Orangeville

Top-rated family-friendly rentals in Orangeville

Holiday 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 holiday rentals that are family-friendly in Orangeville

Total rentals

Local attractions

Popular amenities

Wi-Fi availability

Total number of reviews

Nightly prices starting at

Destinations to explore