Family-friendly vacation rentals in Grey Highlands
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Grey Highlands
Guests agree: these family-friendly homes 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 family-friendly rentals
Family-friendly home rentals with a hot tub
Cottage in Kimberley
4.87 out of 5 average rating, 307 reviewsA Cozy Country Retreat *Indoor Hot Tub* Ski* Wi-Fi
Aug 1 – 8
Cottage in Meaford
4.91 out of 5 average rating, 219 reviewsBirch Meadow Acres
Jul 4 – 11
Tiny home in Mono
4.94 out of 5 average rating, 152 reviewsTiny home Soaring Heart Wellness Spa
May 24 – 31
Home in Collingwood
4.98 out of 5 average rating, 119 reviewsHome Away From Home!
Dec 6 – 13
Farm stay in Fergus
4.95 out of 5 average rating, 216 reviewsWaterpark Acres
Jul 26 – Aug 2
Chalet in The Blue Mountains
4.99 out of 5 average rating, 138 reviewsWalk to Village at Blue - Grand
Sep 16 – 23
Chalet in The Blue Mountains
4.96 out of 5 average rating, 149 reviewsEntire Rustic Chalet - Hot Tub, Sauna, Large Yard!
Nov 9 – 16
Chalet in The Blue Mountains
4.79 out of 5 average rating, 176 reviewsChalet At Blue - Private chalet with hot tub
Nov 15 – 22
Family- and pet-friendly home rentals
Guesthouse in Schomberg
4.93 out of 5 average rating, 344 reviewsCountry Cabin for Long and Short Stays Queen bed
May 15 – 22
Farm stay in Meaford
4.88 out of 5 average rating, 192 reviewsThe SEED lodge: A Rural Retreat & Gathering Place
Mar 4 – 11
Home in Durham
4.9 out of 5 average rating, 155 reviewsHeron's Perch
Dec 25 – Jan 1
Townhouse in The Blue Mountains
4.9 out of 5 average rating, 124 reviewsThe Snowbridge Lookout on Monterra Golf Course
Jul 20 – 27
Tiny home in Schomberg
4.99 out of 5 average rating, 191 reviewsSNAKE CABIN(rustic, 'off-the-grid')
Jan 22 – 29
Home in Penetanguishene
4.98 out of 5 average rating, 150 reviewsLafontaine Beach Paradise
Dec 26 – Jan 2
Home in Barrie
4.81 out of 5 average rating, 208 reviewsEntire Private House+Games Room-by Downtown/Skiing
Apr 8 – 15
Cottage in Lafontaine
4.8 out of 5 average rating, 196 reviewsBeach house (with pool open May-Oct)
Oct 25 – Nov 1
Family-friendly home rentals with a pool
Home in Kimberley
4.88 out of 5 average rating, 176 reviewsHeart of Kimberley - with views and a hot tub
May 13 – 20
Chalet in The Blue Mountains
4.85 out of 5 average rating, 675 reviewsBlue Mountain / Collingwood Hill Side Condo
Oct 7 – 14
Condo in The Blue Mountains
4.77 out of 5 average rating, 229 reviewsSki-in/Ski-out Cozy studio at North Creek Resort
Jun 9 – 16
Townhouse in The Blue Mountains
4.94 out of 5 average rating, 443 reviewsSierra Lane - Closest to Village - Fully Equipped
Jun 10 – 17
Cabin in Mono
4.94 out of 5 average rating, 273 reviewsThe Trails Retreat (Private Cabin)
Dec 3 – 10
Guest suite in Orangeville
4.92 out of 5 average rating, 656 reviewsPrivate HotTub - Headwaters Retreat
Dec 8 – 15
Condo in The Blue Mountains
4.95 out of 5 average rating, 714 reviewsBlue Mountain Village| Stunning Mountain Views
Aug 27 – Sep 3
Townhouse in The Blue Mountains
4.96 out of 5 average rating, 296 reviewsWalk to Village, Fully Renovated 3 bdrm, patio/BBQ
May 28 – Jun 4
Quick stats about vacation rentals that are family-friendly in Grey Highlands
Total rentals
1.1K properties
Rentals with dedicated workspaces
560 properties have a dedicated workspace
Rentals with a pool
330 properties have a pool
Pet-friendly rentals
460 properties allow pets
Total number of reviews
46K reviews
Nightly prices starting at
$40 before taxes and fees
Destinations to explore
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