Family-friendly vacation rentals in Midland

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Midland family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
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.
Top guest favourite
Cabin in Port Carling
4.92 out of 5 average rating, 113 reviews

Icicle Valley

Mahri LatifiRating, 5 stars4 months ago
Jason had a beautiful home that we were grateful to spend our Christmas holidays at. When there was an issue with electronics that we needed help with, not only did he respond rapidly but also came in person to help rectify the issue. A beautiful home and a wonderful host. :)
Superhost
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 favourite
Chalet in The Blue Mountains
4.9 out of 5 average rating, 79 reviews

Stylish Log Chalet w/ Hot tub Minutes to Village

Lindsay AnnRating, 5 stars4 weeks ago
A MUST STAY!! Arriving late at night, outdoor lights greeted us & looked like the Idealic atmosphere for a fun weekend. Private & peaceful. We were delighted to find rustic charm, but with modern finishes and amenities. Tamara was so kind to check that we arrived ok & left me a sweet birthday message. We absolutely loved the upstairs bathroom with heated floors, stunning tub, & shower. The kitchen was a dream to cook in, everything you could imagine needing was provided, including ample cocktail glasses. The hot tub was quite big, 5 of us fit in there. The bedrooms were quaint & beds comfy. We just happen to be there during a massive ice storm. However, the cottage was the perfect - lots of wool blankets, the wood burning fire place heat up the cabin quickly & gas stove. Tamara was extremely helpful assisting us by locating safety supplies & great advice on how to ride out the storm. Her kindness & generosity turned our weekend to be one of the best memories, we will revisit for years
Guest favourite
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 favourite
Cottage in Port Severn
4.94 out of 5 average rating, 137 reviews

Muskoka Cottage on warm lake - 4 BR/2 BR/Hottub

RachelRating, 5 stars5 months ago
This beautiful cottage has room for the entire family to enjoy while still having enough rooms or outdoor spaces for family members to enjoy their own quiet time as well. The lake is beautiful and we look forward to going back in the summer!
Superhost
Cottage in MacTier
4.9 out of 5 average rating, 103 reviews

Baysong Cottage, Hot Tub and Sauna on Georgian Bay

MaryRating, 5 stars3 months ago
A great retreat for a New Year’s nest. Loved the hot tub in the snow - and the bunkie! Very relaxing, comfortable. You should organize your food supply carefully though as it would take about 2 hours (40 min to Foodland, 40 min back and 20 min shopping). We were fine as we had brought lots of food with us. Also, the walls between the two bedrooms are very thin, so if you have a snorer….Otherwise, a wonderful property!!
Guest favourite
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 :)

Family- and pet-friendly home rentals

Top guest favourite
Apartment in Horning's Mills
4.95 out of 5 average rating, 286 reviews

Beautiful Riverside Country Apartment

JordanRating, 5 stars2 months ago
Excellent place to stay for the night, very well priced, easy to find and was very clean and clutter free. Had easy access to internet and tv without issues. Wendy was very responsive and accommodating.
Guest favourite
Townhouse in The Blue Mountains
4.92 out of 5 average rating, 109 reviews

BLUE MOUNTAIN LUX 3 BED AT VILLAGE chalet

NancyRating, 5 stars1 month ago
This place was a home away from home which was close to the hill we could walk with skis. The fireplace was clean and easy yo use. Great family getaway with lots of room to gather. Love it would book again.
Guest favourite
Chalet in The Blue Mountains
4.83 out of 5 average rating, 171 reviews

Octagon Chalet firepit, sauna, close to theVillage

MayaRating, 5 stars1 month ago
We had a great stay at Vivian's place! The chalet was very clean, exactly as described, and fit our group of 13 comfortably. We especially liked the big dining table that was great for meals and games together, and that the kitchen/living room area was on a separate floor from all the bedrooms as this made it easy to accommodate different schedules within the group. One thing to note is that the kitchen didn't have some cooking items like tin foil, cooking oil, and a baking sheet, so be sure to bring those if you'll need them. There was coffee however which we really appreciated! Vivian was very responsive to all messages and sent clear instructions for the space. Definitely recommend for a big group trip, would book again!
Superhost
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 favourite
Home in Gravenhurst
4.83 out of 5 average rating, 321 reviews

Beautiful 6 BEDROOM Muskoka Cottage

MaryRating, 5 stars2 months ago
Fred’s house was great! The house’s open concept was large enough for all of us (6 adults) to hang out in through the cold winter days without feeling crowded. The fireplace added lovely ambience and warmth. The six bedrooms ensured we all had our own space, which was a nice treat for our girls’ weekend. The master bedroom with ensuite was particularly spacious. The whole house was nicely decorated, and overall was a cozy and welcoming place. We didn’t use the sunroom, as is unfortunately smelled of smoke. Fred was a very responsive host. He quickly answered any questions. We had a lovely stay here, and wouldn’t hesitate to fully recommend it.
Top guest favourite
Chalet in Gravenhurst
4.93 out of 5 average rating, 230 reviews

Log Cabin on the Lake Bed and Breakfast

StephanieRating, 5 stars1 month ago
Stephen's place is just as described. Private cabin with everything you need to bbq and stay warm. The views were beautiful and the sauna was a great amenity. Would recommend staying here!
Guest favourite
Cottage in Innisfil
4.83 out of 5 average rating, 218 reviews

Private lakefront cozy 3B1B 1hr from the city

JessicaRating, 5 stars1 week ago
Great value, nice waterfront property at the end of the road. Beautiful sunrise and nice to watch the ducks all day. Boat launch just down the road. Zoey was a great host! Thank you!
Top guest favourite
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

Superhost
Chalet in The Blue Mountains
4.84 out of 5 average rating, 773 reviews

Blue Mountain / Collingwood Hill Side Condo

Aikon NikkiRating, 5 stars3 weeks ago
The host was very clear on instructions and the place was spotless. Great location and space for two people Unfortunately, with the heavy rain, there seems to be a hole on the sliding door of the balcony that let water in enough to pool on the floors and got our stuff wet. The host said it will be fixed
Guest favourite
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
Guest favourite
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!
Guest favourite
Home in Sebright
5 out of 5 average rating, 35 reviews

All Season Waterfront Retreat with Pool & Hot Tub

AaronRating, 5 stars8 months ago
Gary & Mina were excellent hosts. They greeted us for check in and where very accommodating. Any questions we had were quickly answered via the AirBNB app. The house was full of character and had lots of things to do indoors and outdoors. The kitchen was well stocked with supplies, utensils and kitchen wares. There was a washer/dryer centrally located which was great for towels and the Weber BBQ was in top notch condition. Water toys well maintained (2 kayaks, 1 paddle board, 1 canoe and 1 paddle boat). Pool and hot tub worked great, which was a must for our cottage getaway.
Guest favourite
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.
Guest favourite
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 favourite
Bungalow in Lafontaine Beach
4.9 out of 5 average rating, 50 reviews

Sweet Memories of Georgian Bay

FionaRating, 5 stars7 months ago
Idyllic gem on Georgian bay. Perfect for a small family getaway by the lake. The resort pool is a big plus for the kids. Beautiful surroundings and stunning sunsets. Jefferson is a great host. Very friendly and responsive. He kindly accommodated our request.
Guest favourite
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 Midland

  • Total rentals

    140 properties

  • Nightly prices starting at

    $55 CAD before taxes and fees

  • Total number of reviews

    5.5K reviews

  • Pet-friendly rentals

    70 properties allow pets

  • Rentals with a pool

    20 properties have a pool

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. Canada
  3. Ontario
  4. Simcoe County
  5. Midland
  6. Family-friendly rentals