
Kid-friendly vacation rentals in Grey Highlands
Find and book unique kid-friendly rentals on Airbnb
Top-rated kid-friendly rentals in Grey Highlands
Guests agree: these kid-friendly rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Grey Highlands kid-friendly rentals
Kid-friendly house rentals

Cheerful 4-Bedroom home.
I stayed at Steven's place with my family for a month. You have the whole house to yourself except the basement, where another tenant lives. The house was very clean and organized and just as shown in the pictures. Steven had the house stocked up with every amenity you could ask for. He was friendly and welcoming and was always responsive for any issue that popped up. After a night of heavy snow, I woke up the next morning expecting to shovel the driveway and entrance, but lo and behold, the whole area was already salted and cleaned! The house is located in a safe residential area so it's quiet and great for families. I will definitely look up this listing again in the future. Thanks for your hospitality, Steven.

20 min from Blue Mountain -Relax & Enjoy Winter
Such a great place to stay after skiing at Blue Mountain! Definitely recommend.

Modern Cozy and Specious cottage
Very nice place. Newly built, lots of space.

1 Cozy and Spacious 4BR, 4WR, New Home in Caledon
had a great time with family at this place

Movie Theme| Hot Tub | Pool Table |Karaoke |Arcade
We had a fantastic stay at Rohit’s place over the long weekend! The house is packed with so many activities for both kids and adults that there was never a dull moment. Every corner of the house has been thoughtfully utilized with games, amenities, and entertainment — no matter where you are, there’s always something fun to do! We stayed for two nights and honestly wished we had more time to enjoy everything. The basement with the pool table, video games, and karaoke was a highlight — definitely plan your time well so you can experience it all! The home is clean, exactly as shown in the pictures, and Rohit was an absolute pleasure to interact with. He was friendly, responsive, and very accommodating to any requests we had, always making sure we were comfortable. Highly recommend this place for anyone looking for a fun, relaxing stay with plenty to keep everyone entertained. Thanks again, Rohit!

Modern Home with Pool & Jacuzzi [no cleaning fee]
We had a wonderful stay at Angie's house. The place is amazing—clean, bright, and welcoming. The host is incredibly sociable, friendly, positive, helpful, and proactive. Overall, we had a fantastic time, and I just want to say thank you!

Theniceday - Family Friendly House
Great location. Amy was a wonderful host and she made sure we were well

Happy Valley Ski Golf Spa Relax
We had a wonderful stay! The listing has everything you need and more. It’s quiet and clean and feels like you are in a cozy hotel. Loved our stay and will definitely come back! Highly recommend!
Family-friendly apartment rentals

Nice basement apartment
The room was very nice and the host was very accommodating in finding a way for my large truck to stay at the property. Maybe a half hour walk to the mall in a very nice neighborhood

Stylish Private Suite
Really enjoyed Blake’s house, so cute!! Blake was easy to communicate with. Would definitely stay there again.

Sunrise and Bayview with Kayaks & Bikes
Fantastic stay from start to finish everything was perfect

New Cosy and Clean apartment with private entrance
We had a great stay at Terry’s place, it was exactly as described and the location worked well for us. There were some drinks in the fridge and some snacks left on the counter which we thought was a nice touch, also the bed was very comfortable. Terry provided clear instructions for us and was a pleasure to communicate with. We would definitely return if we are ever in the area again.

Beautiful Walkout Suite with Separate Entrance
It was a wonderful experience! Maryam was an outstanding host, always quick to respond and went above and beyond to ensure we had everything we needed. Highly recommend to anyone looking for a cozy and clean place to stay. Thank you, Maryam for an unforgettable stay!

East Side Serenity Apartment
The apartment exceeded our expectation. It was very clean, and even nicer than the photos. It was a very easy place to stay, we had everything we needed, thanks to Donna. We would highly recommend this Airbnb and Donna as a host.

Lovely 1-Bedroom rental unit in Markham
Great location and friendly, responsive host. Thanks for the hospitality.

Executive residential place with NETFLIX
Very clean and comfortable. My daughter and I went for a mini vacation. Some time spent at events and some time spent relaxing at the house, watching movies! As mentioned in the ad, it is a basement apartment with a couple living upstairs so normal amount of noise is heard through floors but not disruptive. Very comfy beds and blankets. Will definitely stay again!
Family-friendly condo rentals

Lovely 3 Bedroom Condo with Stunning View and Pool
We have a wonderful time at Sabine's place, which was an ideal space in every way. It was beautiful, well laid out, and had everything we needed. Sabine was very responsive and accommodating. We would gladly go back when we are next at Blue Mountain.

2BR Getaway at Friday Harbour All Season Resort
Brilliant location for the harbour everything in walkable distance, clean and well stocked kitchen . Responsive host would recommend.

Large, luxury, upper floor condo, steps to Village
Excellent place by a fantastic host. The place was clean, well located and has everything you would need such as kitchen utensils, games + TV, and plenty of clean quality towels. Ulana and Amir were also very friendly and responsive. We enjoyed our stay a lot.

Stylish & Spacious 2 Bdrm/2 bths/2 balc Condo Loft
Rosa’s was exactly as advertised. It was lovely and quiet and perfect for our trip to collingwood with our dog. We would definitely stay again!

Stylish getaway condo, resort living
very clean place, has everything you need for a great getaway. Ron is an amazing, always available host!

Friday Harbor Upscale 1Bed+Sofabed+Pool Option
Kevin was a responsive and friendly host, and his place is clean and comfortable and very close to Friday Harbour. We loved the balcony for breakfast and coffee, and the condo itself was full of friendly folks. We can't wait to go back sometime!

Beautiful Condo, 2 Bedrooms and a Den in a Resort!
Shahed's place at Friday Harbour is beautiful and well appointed. He gave very clear instructions for entry and parking, including photos. The condo was clean and had all the amenities needed, even extra charging cables for devices! The space was comfortable and uncluttered. Shahed was great at communicating and always responded quickly to any questions. Friday Harbour has activities and restaurants available on weekends in the winter and is a fun engaging place by the harbour in the spring, summer and early fall. We were there in the early part of the week in February so the harbourfront was quiet but still nice for a stroll. We spent time in both Barrie (20 minutes away) and Orillia (about 50 minutes away).

2 Bedroom, 2 Level Condo on Blue Mountain!
It was the best location in the village, and it was quiet and the sound of the stream was friendly. If you are skiing during the ski season, it would be very convenient because the bottom of the slope and the entrance to the building are in contact. The interior was clean and well-organized. Thanks, Richard.
Quick stats about vacation rentals that are kid-friendly in Grey Highlands
Total rentals
320 properties
Nightly prices starting at
$55 CAD before taxes and fees
Total number of reviews
28K reviews
Family-friendly rentals
260 properties are a good fit for families
Pet-friendly rentals
130 properties allow pets
Rentals with a pool
120 properties have a pool
Destinations to explore
- Grand River Vacation rentals
- Brampton Vacation rentals
- London Vacation rentals
- Muskoka Lakes Vacation rentals
- Vaughan Vacation rentals
- Markham Vacation rentals
- Georgian Bay Vacation rentals
- Kitchener Vacation rentals
- Waterloo Vacation rentals
- Mississauga Vacation rentals
- Greater Toronto and Hamilton Area Vacation rentals
- Greater Toronto Area Vacation rentals
- Family-friendly rentals Grey Highlands
- Rentals with beach access Grey Highlands
- Rentals with a firepit Grey Highlands
- Rentals with a washer and dryer Grey Highlands
- Chalet rentals Grey Highlands
- Townhouse rentals Grey Highlands
- Rentals with pools Grey Highlands
- Beachfront rentals Grey Highlands
- House rentals Grey Highlands
- Condo rentals Grey Highlands
- Rentals with a patio Grey Highlands
- Rentals with a sauna Grey Highlands
- Cottage rentals Grey Highlands
- Pet-friendly rentals Grey Highlands
- Rentals with a kayak Grey Highlands
- Cabin rentals Grey Highlands
- Waterfront rentals Grey Highlands
- Fitness-friendly rentals Grey Highlands
- Rentals with a fireplace Grey Highlands
- Rentals with lake access Grey Highlands
- Rentals with an EV charger Grey Highlands
- Ski-in/ski-out rentals Grey Highlands
- Apartment rentals Grey Highlands
- Rentals with breakfast Grey Highlands
- Rentals with a hot tub Grey Highlands
- Rentals with outdoor seating Grey Highlands
- Loft rentals Grey Highlands
- Bed and breakfasts Grey Highlands
- Private suite rentals Grey Highlands
- Kid-friendly rentals Grey County
- Kid-friendly rentals Ontario
- Kid-friendly rentals Canada
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Blue Mountain Village
- Horseshoe Resort
- Mount St. Louis Moonstone
- TPC Toronto at Osprey Valley
- Snow Valley Ski Resort
- Osler Bluff Ski Club
- Beaver Valley Ski Club
- Hockley Valley Resort - Golf, Spa and Ski
- Devil's Glen Country Club
- Cobble Beach Golf Resort Community
- Legacy Ridge Golf Club
- Alpine Ski Club
- National Pines Golf Club
- Inglis Falls
- The Georgian Peaks Club
- The Georgian Bay Club
- Toronto Ski Club
- The Pulpit Club
- Caledon Country Club
- Shanty Bay Golf Club
- The Club At Bond Head
- Craigleith Ski Club
- Mad River Golf Club
- Mansfield Ski Club