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.

0 of 0 items showing

1 of 3 pages

Guest favorite

Guesthouse in Mansfield

4.99 out of 5 average rating, 103 reviews

Brookside Cottage - Charming Rural Getaway Mulmur

Our cozy guest house, situated in the Headwaters region, has it all! Close to hiking,golfing,biking,skiing. XCski/snowshoe from your door! Big skies for astronomers and astrophotography! We offer 32 acres of forest and fields for walking and taking in the magnificent views. The area boasts fine restaurants, boutiques, markets and artisans. Minutes to Mono Cliffs, Boyne, Mansfield Ski Club and easy driving to Blue Mountain and Wasaga Beach. Ideal for couples, solo adventurers or a small family.

Guest favorite

Rental unit in Wasaga Beach

4.95 out of 5 average rating, 381 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.

Guest favorite

Rental unit in Horning's Mills

4.96 out of 5 average rating, 272 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.

Guest favorite

Bungalow in Wasaga Beach

4.92 out of 5 average rating, 112 reviews

Nice Wasaga Cottage

We welcome well traveled guests over the age of 25 and families. Perfect for 4 people. Large 2 bedroom, 4 season cottage with big living room and eat-in kitchen; in a desirable area of Wasaga Beach Area 4. Renovated kitchen and bathroom. WiFi, gas furnace, and central air conditioning. 1 block to beach area, park, and bike path. 1 block to Nottawasaga river and boat launch. 25 min to Blue Mountain Village. Hiking, Golfing, and Skiing all nearby. 1 extra guest allowed for an additional fee.

Guest favorite

Loft in Midland

4.89 out of 5 average rating, 322 reviews

Nest By The Bay - Downtown Midland / Private Loft

Luxury, Comfort & Style. This one-of-a-kind rental, "Nest By The Bay", is located in Downtown Midland. Walk everywhere, park your car & enjoy what Midland has to offer. Midland Harbour is only minutes by foot. Live our lifestyle, enjoy our many festivals, professional theatre, artisans, culinary cuisine, seasonal events & so much more! See our other listing "Perch By The Bay", also at this same location. 2 nights min. preferred, 1 night by request. Listing not suitable for ages under 6.

Guest favorite

Guest suite in Collingwood

4.92 out of 5 average rating, 1,073 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. The Tiny Home has a separate entrance and private back patio giving guests lots of privacy. For the ultimate relaxation experience, you can add access to the sauna and cold plunge as an optional upgrade to your stay. Absolutely no pets due to allergies.

Guest favorite

Condo in Innisfil

4.94 out of 5 average rating, 202 reviews

Designer Condo with beautiful harbour view.

Unique top floor. Rare views where every room overlooks the harbour. Professionally designed with new stylish furnishings. Ideal for those who like a little sophistication while spending time at the lake. Enjoy going out to eat every night or make a meal and curl up and relax in the beautiful living room, or a combination of both! Friday Harbour is a resort with beautiful walking trails, cafes, and restaurants, and a perfect get-away that celebrates the seasons with exiting activities.

Guest favorite

Bungalow in Innisfil

4.82 out of 5 average rating, 278 reviews

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

NEW!!: seasonal or monthly rental available, contact me directly to get the exact pricing, thank you Our cottage is about a 800 m from the beach at family friendly Innisfil Beach Park! The kitchen is modern and bright with lots of room for lounging inside the cottage or entertaining outside in the large yard with a fire pit. Our cottage is ideal for couples and families. It is beautifully furnished. There is a BBQ, patio furniture & firepit, smart TV with Roku and Chromecast.

Guest favorite

Cabin in Mono

4.95 out of 5 average rating, 291 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, 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:) Private yoga and group classes available

Guest favorite

Guesthouse in Schomberg

4.93 out of 5 average rating, 396 reviews

Country Cabin for Long and Short Stays King 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.

Guest favorite

Cottage in Lafontaine

4.82 out of 5 average rating, 224 reviews

Beach house (with pool open May-Oct)

Georgian Bay Beach club. Cute cottage perfect for families, couples, or anyone wanting to relax! 2 bedrooms, 1 bathroom, furnished, pool and private beach on the shores of beautiful Georgian Bay! Cottage is part of a 12 cottage community that shares the pool and beach area. Always super clean, professionally cleaned after every guest! Note: pool is closed October to mid May.

Guest favorite

Guest suite in Orangeville

4.97 out of 5 average rating, 155 reviews

Your very own peaceful santuary in nature

Tranquil space to go walking through the 20 acres of forest with trails, lots of wildlife, and beautiful bright stars at night for stargazers. You can have a coffee in the morning on the patio set in front of the suite and have a drink on one of the hills in comfortable muskoka chairs up on a hill of the property and watch the sunset or sunrise if you are an early bird.