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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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Home in Barrie

4.81 out of 5 average rating, 231 reviews

Entire House w/Games Room-by Beach/Downtown Barrie

Entire, completely private, cozy 3-bedroom house: • Full kitchen w/ coffee maker, microwave • 3 beds, 1 sofabed, 1 foldable cot • 1 full bathroom & 1.5 bathroom • Bed linen/towels • Fast wifi • TV w/ netflix (living room & main bedroom) • Games room w/ pool table, darts, table soccer • Long driveway • Fenced backyard w/ charcoal bbq, yard table, swing set • 2-5 min to restaurants/shops • 5 min to downtown Barrie • 5 min to Centennial Beach • 15 min to Innisfil • 20 mins to Horseshoe Resort

Guesthouse in Orangeville

4.95 out of 5 average rating, 344 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.

Loft in Midland

4.93 out of 5 average rating, 282 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

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.

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.

Rental unit in Horning's Mills

4.96 out of 5 average rating, 271 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.

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 suite in Collingwood

4.92 out of 5 average rating, 1,064 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.

Chalet in Gravenhurst

4.93 out of 5 average rating, 216 reviews

Log Cabin on the Lake Bed and Breakfast

Log Cabin on the Lake Bed and Breakfast We provide a 1st morning continental breakfast A Lakefront getaway for couples with an amazing view. Experience tiny home living in a custom built Log Cabin. Landscaping provides privacy for all parties (owner next door) we have parking for a boat , with 2 launches within 5 min. One into Morrison Lake the other into the Trent Severn . cross country skiing, ice fishing, water skiing swimming boating. Ready to escape, our Log Cabin could be it.

Cabin in Mono

4.94 out of 5 average rating, 289 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:) Chef's creations and Private yoga and group classes available

Guesthouse in Schomberg

4.93 out of 5 average rating, 390 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.

Cottage in Lafontaine

4.82 out of 5 average rating, 222 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.

Vacation rentals for every style

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Kick off your hiking boots at these rustic lodgings

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Luxurious estates for the ultimate escape

Popular amenities for Simcoe County family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Cottage in Gravenhurst

4.83 out of 5 average rating, 166 reviews

Trenanthia "Cahoots" Cottage: HotTub,Sauna,GamesRm

Cottage in Tiny

4.86 out of 5 average rating, 219 reviews

PrivateBeach@ThunderBeach100 acres Georgian Bay

Chalet in The Blue Mountains

4.8 out of 5 average rating, 183 reviews

Chalet At Blue - Private chalet with hot tub

Bungalow in Innisfil

4.82 out of 5 average rating, 278 reviews

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

Cabin in The Blue Mountains

4.9 out of 5 average rating, 345 reviews

🍺"Margaritaville" Big Space, Lots of fun+Hot Tub

Loft in The Blue Mountains

4.74 out of 5 average rating, 472 reviews

Cozy Blue Mountain Retreat @!@Spring Rates@!@

Cottage in Port Severn

4.94 out of 5 average rating, 135 reviews

Muskoka Cottage on warm lake - 3 BR/2 BR/Hottub

Chalet in Coldwater

4.95 out of 5 average rating, 431 reviews

OakRidge Retreat-HOT TUB 100s of acres WIFI

Family- and pet-friendly home rentals

Cottage in Wasaga Beach

4.97 out of 5 average rating, 73 reviews

Wasaga on the Water with Loads of Amenities

Cottage in Gravenhurst

4.96 out of 5 average rating, 56 reviews

Stunning Log Cottage on an Island in Muskoka

Cottage in Washago

4.94 out of 5 average rating, 53 reviews

Stunning Waterfront w/Hot Tub - Nature's Cottage

Guest suite in East Gwillimbury

4.86 out of 5 average rating, 21 reviews

Waterfront Tranquil Retreat Just North of Toronto

Cabin in Tiny

4.96 out of 5 average rating, 70 reviews

The Beach House Licence#: STRTT-2024-028

Townhouse in The Blue Mountains

4.94 out of 5 average rating, 95 reviews

BLUE MOUNTAIN LUX 3 BED AT VILLAGE chalet

Chalet in The Blue Mountains

4.83 out of 5 average rating, 161 reviews

Octagon Chalet firepit, sauna, close to theVillage

Home in Sebright

5 out of 5 average rating, 35 reviews

All Season Waterfront Retreat with Pool & Hot Tub

Family-friendly home rentals with a pool

Townhouse in The Blue Mountains

4.9 out of 5 average rating, 141 reviews

The Snowbridge Lookout on Monterra Golf Course

Chalet in The Blue Mountains

4.85 out of 5 average rating, 722 reviews

Blue Mountain / Collingwood Hill Side Condo

Townhouse in The Blue Mountains

4.96 out of 5 average rating, 101 reviews

Luxury Vacation Home at Blue Mountain Village

Townhouse in The Blue Mountains

4.94 out of 5 average rating, 470 reviews

3BR Sierra Scandi Chic - Closest to Village

Condo in The Blue Mountains

4.86 out of 5 average rating, 138 reviews

Large, luxury, upper floor condo, steps to Village

Condo in The Blue Mountains

4.95 out of 5 average rating, 797 reviews

Stunning Mountain Views- WalkTo Blue, Pool, HotTub

Townhouse in The Blue Mountains

4.89 out of 5 average rating, 167 reviews

Private condo getaway at base of Blue Mountain

Townhouse in The Blue Mountains

4.96 out of 5 average rating, 313 reviews

Walk to Village, Pool, Renovated 3 bdrm, patio/BBQ

Destinations to explore