Family-friendly vacation rentals in Simcoe County

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Simcoe County

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.

Jun 8 – 15

ﺩ.ﺇ522 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 24 – 31

ﺩ.ﺇ219 per night

Guest favorite

Barn in Eugenia

4.98 out of 5 average rating, 165 reviews

Blue Barn Bed n Bale / Blue Mountain

2 q. beds A relaxing farm stay on a working farm with or without your horses. Bright clean bunkie built in 2016 in our 160 year old barn. The space is new, cozy and offers a chance to spend hours of time with your horses or ours. Nothing like having coffee with your horses in the morning. We back on to 30,000 acres of trailed crown land and the Kolapore Trails lending itself to horseback riding, hiking, snow shoeing, atving, mountain biking. Check out the beautiful sunset behind the barn.

Nov 2 – 9

ﺩ.ﺇ627 per night

Guest favorite

Loft in Midland

4.92 out of 5 average rating, 244 reviews

Perch by the Bay - Downtown Midland / Private Loft

Luxury, Comfort & Georgian Bay Style. This first class rental, "Perch By The Bay", is located in Downtown Midland. Walk everywhere, park your car (free) & enjoy what Midland has to offer. Midland's boat harbour, is only minutes by foot. Live our lifestyle, enjoy our many festivals, professional theatre, artisans, culinary cuisine, etc! It's "sister" AirBnB is "Nest By The Bay" private loft at the rear of the building. 2 night min. preferred, 1 night by request. Not suitable for ages under 6

Jul 15 – 22

ﺩ.ﺇ573 per night

Guest favorite

Apartment in Wasaga Beach

4.95 out of 5 average rating, 357 reviews

2 bedroom beachfront apartment

Lovely suite with its own 3 piece bathroom, living room with flat screen TV and kitchenette. Has its own deck, barbecue and entranceway overlooking the sandy shores of Georgian Bay. Steps to go swimming, kayaking or a sunset stroll. Parking available. No pets. Between June 30th - September 1st the apartment can only be rented by the week (check in & check out on Saturdays only). Outside of these dates, we are happy to host visitors with a minimum 1 night stay, check in/out any day of the week.

Dec 21 – 28

ﺩ.ﺇ515 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.

Dec 2 – 9

ﺩ.ﺇ297 per night

Guest favorite

Guest suite in Collingwood

4.92 out of 5 average rating, 1009 reviews

Tiny Home Tranquility

Tiny Home Tranquility! Located just 15 minutes from Blue Mountain Ski Resort and Wasaga Beach. Walking distance to Collingwood downtown core and Georgian Bay . A custom built tiny home with all the amenities needed for a perfect getaway. This clean, bright and cozy tiny home is private and is attached to the main house with a breezeway to comply with the town bylaws. The Tiny Home has a separate entrance and private back patio giving guests total privacy. Absolutely no pets due to allergies.

Nov 12 – 19

ﺩ.ﺇ458 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

Friday Harbour is a brand new all season resort just 1 hour and 15 minutes from Toronto. A perfect getaway without the long drive. Airbnb guests can now purchase a pass for the beach club pool! This Airbnb is an eight hundred square foot condo all newly furnished with king bed in master bedroom with ensuite bathroom, Queen bed in guest bedroom. Enjoy 65” Samsung Smart TV or sitting on the huge deck overlooking the marina and island homes. Board walk to beach, this place is amazing!

Dec 16 – 23

ﺩ.ﺇ355 per night

Guest favorite

Guest suite in Collingwood

4.8 out of 5 average rating, 168 reviews

Pretty, private and clean

Steps from Georgian Bay and 15 minute drive to ski hills, this completely private, small bedroom is totally separate from the main house with a private entrance. Although the room is small, it has its own 3-peice ensuite bathroom with in-floor heating (helpful on cold winter mornings), and privately controlled heating & air conditioning. Equipped with TV, mini fridge, coffee maker, kettle and microwave. Conveniently located on a quiet lane between Collingwood and Wasaga Beach.

Jan 23 – 30

ﺩ.ﺇ274 per night

Guest favorite

Cabin in Mono

4.94 out of 5 average rating, 273 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

Dec 3 – 10

ﺩ.ﺇ624 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

ﺩ.ﺇ283 per night

Guest favorite

Guesthouse in Schomberg

4.93 out of 5 average rating, 344 reviews

Country Cabin for Long and Short Stays Queen bed

Our Country Cabin get-away is perfect for those looking to get out of the city and back to nature for a short or extended stay! Enjoy a little winter getaway and share our paradise in the countryside and be part of it all. You’ll love our location, full kitchen, access to camp fire pit, propane bbq, wifi internet, 40" Smart TV, three piece bathroom, laundry facilities and more.

May 15 – 22

ﺩ.ﺇ400 per night