Family-friendly vacation rentals in Grey Highlands

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Grey Highlands family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Cottage in Kimberley
4.86 out of 5 average rating, 338 reviews

A Cozy Country Retreat *Indoor Hot Tub* Ski* Wi-Fi

AustinRating, 5 stars1 month ago
Thank you for the wonderful stay! Our group loved our stay! Would highly recommend.
Superhost
An outdoor hot tub is situated by a scenic lakeside, surrounded by trees and greenery. Four individuals are enjoying the warm water, with arms raised playfully. The tranquil lake and blue sky create a serene backdrop.
Cottage in Gravenhurst
4.82 out of 5 average rating, 181 reviews

Trenanthia "Cahoots" Cottage: HotTub,Sauna,GamesRm

IcaroRating, 5 stars1 week ago
Christine & Rebecca were very kind and always provided quick and useful answers to all our questions. 5 stars landlord The house is super big, organized and has so many amenities to entertain yourself, no matter how is the weather outside. Would definitely consider to return in a near future for a gateway with my friends.
Superhost
The exterior of the chalet is framed by lush trees adorned with vibrant autumn leaves. A well-maintained lawn is visible, featuring a picnic table and chairs, offering a serene outdoor setting. Sunlight gently illuminates the scene, enhancing the tranquil atmosphere of the surroundings.
Chalet in The Blue Mountains
4.8 out of 5 average rating, 193 reviews

Chalet At Blue - Private chalet with hot tub

JamieRating, 5 stars1 month ago
Great communication with Shawn from start to finish, the home was what we expected and equipped with almost everything we needed. Lots of parking available, great spaces for groups to hang out, easy to host team meals. We were there for a ski trip and got pounded with snow, burying all sidewalks and making the walk to villages and chairlifts more difficult - but doable.
Guest favorite
Bungalow in Innisfil
4.82 out of 5 average rating, 279 reviews

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

StephanieRating, 5 stars4 months ago
Nice home in a quiet and safe feeling neighbourhood. Easy to find and access. Big back yard for kids and dog (although not fully fenced, which was fine as we brought our own leash). We arrived from out of province (via flying) and were surprised to find the beds already made with the necessary linens (we had packed our own via suitcase as per the ad details). But we appreciated the kind gesture had we somehow failed to bring our own! The kitchen is updated (so different from pictures) but still has all the appliances and cooking items a family would need for their stay. Lots of stores (grocery, banks, restaurants, Canadian Tire etc) are within a 10 min drive or less, making “going into town” to grab stuff a breeze. Plus having access to a hot tub, sauna and BBQ are a very nice treat :) We had a very comfortable stay and appreciated Tamila’s prompt responses for any questions we had. Would happily stay again!
Guest favorite
A room featuring a foosball table and hardwood flooring is illuminated by natural light from a nearby window. The window is framed by dark curtains, and a wooden door leads to another area of the home. Vintage woodwork and a decorative mirror add character.
Home in Kimberley
4.88 out of 5 average rating, 197 reviews

Heart of Kimberley - with views and a hot tub

TeresaRating, 5 stars1 month ago
Thanks for a great stay!
Superhost
The living room features two brown leather sofas, complemented by warm wood detailing and a large window. Light enters through decorative glass and a view of the outdoors is visible. Decorative elements include subtle throw pillows and a small wall hanging.
Home in Owen Sound
4.93 out of 5 average rating, 117 reviews

Century Home in downtown Owen Sound - Hot Tub

KevinRating, 5 stars4 months ago
Excellent place to stay. Very clean. Very accommodating.
Guest favorite
A spacious dining area features a large wooden table with bench seating under an arched ceiling. Large windows allow for natural light, highlighting the rustic stone accents and wooden beams. A cozy seating area is visible in the background, enhancing the inviting feel of the space.
Chalet in The Blue Mountains
4.88 out of 5 average rating, 104 reviews

Rustic Spanish Chalet inthe Heart of Nature/hottub

AnneRating, 5 stars1 month ago
We booked this home for a family and friends cottage weekend and the place was exactly as described. It is a beautiful home very close to the slopes with lots of things to do (billiards, board games, hot tub, TV, BBQ). The host was very kind and responsive and was very flexible with out checkout time, which was very nice. Our group of 11 people all had a great weekend and we would definitely book this place again :)
Guest favorite
A rustic cabin sits among lush greenery, featuring a wrap-around deck and large windows that invite natural light. The structure blends into the landscape, providing a serene escape surrounded by trees and open spaces.
Chalet in Priceville
4.91 out of 5 average rating, 469 reviews

ReLive Hilltop Chalet w/brand-new hottub, sunrises

AndrewRating, 5 stars1 month ago
We had a great stay in this cabin on a GORGEOUS wooded property. Awesome to watch the snow fall against the old pines. I took my dog on the snowshoe trails. Very cozy and it was great to get out of the city.

Family- and pet-friendly home rentals

Superhost
Bungalow in Orillia
4.87 out of 5 average rating, 242 reviews

Luxury, Waterfront, 4 bdrm Bungalow in Sth Muskoka

AutumnRating, 5 stars4 weeks ago
Even with a series of unfortunate weather events the stay was great! Do and family are responsive and kind and the place was fantastic! We will be back!
Guest favorite
Guesthouse in Schomberg
4.93 out of 5 average rating, 421 reviews

Country Cabin Escape | King Bed | Pet Friendly

JazmineRating, 5 stars1 week ago
one of my all time favorite places I've stayed. there was nothing even remotely sub par about the location or accomodations. beautiful and quiet. great communication and easy check-in and out. 10/10 fabulous
Superhost
A cozy mezzanine area is highlighted by wooden ceilings and natural light from three large windows. Two bean bags provide comfortable seating, while a small plant adds a touch of greenery. Decorative frames hang on the walls, complementing the inviting atmosphere.
Farm stay in Meaford
4.87 out of 5 average rating, 203 reviews

The SEED lodge: A Rural Retreat & Gathering Place

Jessica Rating, 5 stars3 months ago
Awesome place for our friend group to get together (families with kids ages 3-11) Tons of cooking spices, bowls, plates, mugs. Sauna is a nice touch and so is the fire pit. Large property for the kids to run around. I wasn't sure about the single beds but they were very comfortable. Nice bathroom/shower set up. Perfect for a large group. Would go back!
Superhost
The kitchen is equipped with modern appliances, including a stove, microwave, and fridge. White cabinetry complements the sleek gray countertops, while a window provides natural light. A minimalist design is achieved with a stylish pendant light hanging above the sink area.
Home in Barrie
4.81 out of 5 average rating, 255 reviews

Entire House w/ Games Room- by Beaches & Downtown

DavidRating, 5 stars3 weeks ago
Great place, will stay again
Guest favorite
Home in Richmond Hill
4.89 out of 5 average rating, 152 reviews

Luxury 5 beds, 6 Baths custom home

FarhanRating, 5 stars2 weeks ago
Jay’s place was great for our family. Big space, lots of rooms, nice big kitchen. Bring more towels if you’re a big group. One of the showers was leaking to the floor below (Jay was really responsive to get this fixed, which he said he’d do after our visit). Kitchen is huge and definite plus if you’re with a big group, was a nice place to gather each morning and make breakfast together! Well stocked, though missing a basic frying pan. If you have elderly family, the stairs are a bit difficult to navigate. And lots of sharp edges around if you have little kids. Overall worked out well for our multi generation family trip!
Top guest favorite
A rural landscape features a gravel driveway leading to a spacious barn-style cabin, surrounded by tall evergreen trees. A road sign indicating a speed limit of 60 km/h is visible at the edge of the road, showcasing a tranquil countryside setting.
Tiny home in Schomberg
4.99 out of 5 average rating, 204 reviews

SNAKE CABIN(rustic, 'off-the-grid')

MattRating, 5 stars1 month ago
Exactly as advertised - Beautiful property, cozy and comfortable off-grid cabin and super friendly hosts. Would absolutely come back and recommend to a friend!
Guest favorite
A serene lakeside view is presented as the sun sets, casting vibrant orange and pink hues across the sky and reflecting on the water. A small dock is visible, with several red Adirondack chairs arranged on the grassy area, inviting relaxation.
Cottage in Flesherton
4.94 out of 5 average rating, 138 reviews

All-Season Cottage on the Lake

JudithRating, 5 stars2 months ago
Great place in a beautiful location! Perfect for our two families to get together and enjoy the outdoors in winter. The kitchen is well-supplied and it’s great to have towels and sheets provided. Carrie is friendly, flexible and well organized. Thanks so much!
Top guest favorite
An inviting outdoor space features a cozy fire pit surrounded by gravel and wooden seating. Soft lighting from above highlights the stone wall and enhances the serene atmosphere. The area provides a perfect spot for relaxation and outdoor gatherings.
Barn in Eugenia
4.98 out of 5 average rating, 179 reviews

Blue Barn Bed n Bale / Blue Mountain

AnneRating, 5 stars6 months ago
We really enjoyed our stay in Kim’s spacious barn, with friendly horses and great views right outside the front door. We have loved exploring the area over the years and this is one of our more unique experiences.

Family-friendly home rentals with a pool

Guest favorite
A modern living area features high vaulted ceilings and large windows allowing natural light to illuminate the space. A comfortable sofa, adorned with pillows, is positioned around a glass coffee table. Scenic views of the outdoors can be seen through the glass doors.
Townhouse in The Blue Mountains
4.9 out of 5 average rating, 151 reviews

The Snowbridge Lookout on Monterra Golf Course

WendyRating, 5 stars1 month ago
Beautiful condo, very clean, the most comfortable beds. Only downside is there is no bathtub We will return forsure
Top guest favorite
A backyard area features a wooden deck with a hot tub and an adjacent pool. Colorful hanging flower baskets add vibrancy, while cozy seating on the upper balcony invites relaxation. Lush greenery complements the stone-paved patio and the well-maintained lawn.
Guest suite in Orangeville
4.92 out of 5 average rating, 753 reviews

HotTub & Cozy Getaway - Headwaters Retreat

JosephRating, 5 stars1 week ago
Had a great stay! The place was clean, comfortable, and exactly as described. The host was friendly and responsive. Would definitely recommend!
Guest favorite
The bathroom features a glass-enclosed shower and a spacious vanity with a single sink. A large mirror reflects the ample lighting from above. Neutral colors and tile flooring create a clean, modern aesthetic, while an open doorway leads to the neighboring bedroom area.
Townhouse in The Blue Mountains
4.96 out of 5 average rating, 104 reviews

Luxury Vacation Home at Blue Mountain Village

RachelRating, 5 stars2 months ago
This was a beautiful place with great views, only a 5 minute walk away from the village. It was clean with an organized bathroom and kitchen amenities. We weren’t missing anything. There was a nice fireplace with a lot of board games. Super cozy, and a great place to take photos. You also had access to a shared hot tub. Sometimes other people got rowdy at the hot tub, but that is to be expected. Overall this is a great place for families or get togethers for skiers and people that like great restaurants and social events. Thanks, Adam!
Top guest favorite
A clear swimming pool is surrounded by a concrete patio. A small shed is visible in the background, accompanied by green plants and a watering can. Lounge chairs are placed along the edge of the pool, creating a welcoming outdoor space.
Guest suite in Orangeville
4.98 out of 5 average rating, 160 reviews

Your Peaceful Santuary in Nature

JillRating, 5 stars2 months ago
Would highly recommend! A very spacious spot with lots of activities and lovely surroundings. The place is very cozy with the wood burning stove and plethora of candles. Annette was very pleasant, responsive and accommodating! We had a great time playing with her dogs in the snow. We will be back!
Guest favorite
A spacious outdoor deck is furnished with a modern seating area and a dining table, surrounded by lush greenery. A sculptural horse figure stands nearby, while a scenic view of open fields and a distant structure completes the tranquil country setting.
Guesthouse in Orangeville
4.95 out of 5 average rating, 351 reviews

Sunny Pines Farm Studio Tennis Court/Bruce Trail

AlexRating, 5 stars3 weeks ago
What a gorgeous place to get away from the city for a few days. The comfortable studio has everything you'd need during your stay. The fields are great for walking (especially if you have a dog), and there are all kinds of magnificent hiking trails nearby. My arrival coincided with a massive ice storm and Vince and Miranda were in touch every step of the way, keeping me updated on conditions and options. They were a pleasure to deal with. I look forward to returning next time I need a taste of the country.
Superhost
A lush green lawn is dotted with trees, providing a natural setting for relaxation. The structure features a brick exterior, and a large patio area is seen with seating and an umbrella. In the background, the in-ground pool is partially visible, surrounded by a privacy fence.
Home in Chatsworth
4.89 out of 5 average rating, 145 reviews

Stonehaven - large country retreat, with pool*

TawnyaRating, 5 stars1 month ago
We struggled to find a place for our group of 17 and Stonehaven was an amazing find! The beds were comfortable, we loved being able to have meals all together in one spot, and there was lots of space for people to do different activities inside since it was winter. Outside, we enjoyed tobogganing, snowshoeing and cross country skiing on the property. Steve was quick to communicate and provided clear instructions and maps. We were already talking about going back so we can enjoy the property in the summer! Thank you for a memorable and fun weekend!
Guest favorite
An outdoor tennis court is showcased, featuring well-maintained surfaces and a clear view of surrounding trees and hills. Nets are positioned at each end, and the space is designed for recreational play. The distant buildings suggest the proximity of amenities.
Condo in Blue Mountains
4.92 out of 5 average rating, 339 reviews

2 Bedroom, 2 Level Condo on Blue Mountain!

JamesRating, 5 stars3 days ago
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.
Guest favorite
A cozy living area is seen with a plush gray sofa, complemented by two light gray armchairs. A simple coffee table sits in the center, with wall art featuring soft, neutral tones above. Bright light fills the space from nearby windows, enhancing the open layout.
Chalet in Blue Mountain
4.8 out of 5 average rating, 362 reviews

Cozy Sleep 10 ,Hot Tub & BBQ, Steps to Blue Mtn

AlisonRating, 5 stars3 months ago
A lovely stay in Blue Mountain with my family for new years! Greg was extremely communicative and was always quick to respond with any inquiries. The location is walking distance to the village and the neighbourhood had the most friendliest people. We felt right at home and Greg's place had all the right amenities for our family's needs. We will definitely come back here for our next stay in Blue!

Quick stats about vacation rentals that are family-friendly in Grey Highlands

  • Total rentals

    1K properties

  • Nightly prices starting at

    ﺩ.ﺇ147 before taxes and fees

  • Total number of reviews

    53K reviews

  • Pet-friendly rentals

    450 properties allow pets

  • Rentals with a pool

    340 properties have a pool

  • Rentals with dedicated workspaces

    600 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. Canada
  3. Ontario
  4. Grey County
  5. Grey Highlands
  6. Family-friendly rentals