Kid-friendly holiday rentals in Midland

Find and book unique family-friendly rentals on Airbnb

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Popular amenities for Midland family-friendly rentals

Kid-friendly house rentals

Guest favourite
Home in Gravenhurst
5 out of 5 average rating, 8 reviews

Osku Inn 4 Bedrooms 6 beds 3 bath family friendly

EvaRating, 5 stars1 month ago
We used this airbnb for our crew to stay at while they worked in the area. It had everything they needed to feel at home, away from home! The host was always quick to respond and quick to help. I would recommend staying here!
Guest favourite
Home in Wasaga Beach
4.89 out of 5 average rating, 109 reviews

20 min from Blue Mountain -Relax & Enjoy Winter

TawnyaRating, 5 stars1 month ago
Such a great place to stay after skiing at Blue Mountain! Definitely recommend.
Superhost
Home in Wasaga Beach
5 out of 5 average rating, 6 reviews

Modern Cozy and Specious cottage

JudyRating, 5 stars3 months ago
Very nice place. Newly built, lots of space.
Guest favourite
Home in Kirkfield
4.93 out of 5 average rating, 30 reviews

The Hickey Hide-Away

VivianRating, 5 stars8 months ago
Brett was an awesome host. Was always super responsive and helpful. His cottage was such a relaxing time for my family and I. The backyard was very private and great for my dog to run around in. We enjoyed fishing, canoeing, and using the fire pit!
Superhost
Home in Barrie
4.87 out of 5 average rating, 101 reviews

Entire House, Private/Clean 5bdr 6 Beds/Sleeps 12

BenRating, 5 stars1 week ago
We had a good experience. A+ for the host. Check-in was easy. The home was clean and well stocked / furnished. Location is good. There is some traffic noise from the highway but it didn't disturb our sleep. I've stayed in hotel's that are much louder. I wish the mattresses were a little softer but at the same time I feel we got a good value. We wouldn't hesitate to stay here again.
Top guest favourite
Home in Innisfil
5 out of 5 average rating, 27 reviews

Simcoe Retreat

KellyRating, 5 stars1 week ago
From the moment I opened the door I was in love with Alison's place! It was bright, warm and welcoming (not to mentioned beautifully decorated). There were too many amenities to mention and so many thoughtful touches. Alison was an excellent host, allowing me to check in early and always responding in a timely manner. Alison's place has definitely raised the bar for me when it comes to Airbnb stays. I would 100% recommend Alison....you will not be disappointed!
Top guest favourite
Home in Port McNicoll
5 out of 5 average rating, 19 reviews

Steps From Ice Fishing and Snowmobile Trails!

EmilyRating, 5 stars1 month ago
The cottage is so cozy and clean. The space had everything we needed for a weekend getaway with our dogs. The neighborhood is great and so close to the beach which would be a great perk in the summer.
Superhost
Home in Orillia
4.83 out of 5 average rating, 252 reviews

Waterfront Cottage Over-the-Water view w fast Wifi

ChandniRating, 5 stars1 month ago
amazing location on the waterfront. So relaxing to be away from the city. was great for travelling with kids. thank you for letting us stay

Family-friendly apartment rentals

Top guest favourite
Flat in Horning's Mills
4.95 out of 5 average rating, 288 reviews

Beautiful Riverside Country Apartment

MelissaRating, 5 stars2 days ago
I enjoyed a peaceful 2 weeks at this beautiful Airbnb! The setting is surreal surrounded by nature and a river! I had everything I needed and I enjoyed a few nights with a cozy fire in the wood stove. The bed and couches were very comfortable. The No Frills in Shelburne was a great grocery store nearby. Wendy was always very responsive and helpful. As clearly noted in the description, there is no cell service but not a big deal as there is wifi. I hope to be back again one day! A true gem!
Guest favourite
Flat in Barrie
4.92 out of 5 average rating, 91 reviews

Renovated Basement Apartment!

FabiolaRating, 5 stars1 month ago
We had a fantastic stay at Nick’s place! The space was clean, comfortable, and exactly as described. The location was great, and the host provided excellent recommendations that made our trip even better. Communication was easy, and check-in/check-out was seamless. Would definitely stay here again—highly recommend!
Top guest favourite
Flat in Collingwood
4.95 out of 5 average rating, 21 reviews

Stylish Private Suite

FranRating, 5 stars4 weeks ago
Really enjoyed Blake’s house, so cute!! Blake was easy to communicate with. Would definitely stay there again.
Top guest favourite
Flat in Port Perry
4.97 out of 5 average rating, 170 reviews

Modern Lakefront Apartment

MuinRating, 5 stars4 months ago
Doreen and Derek were excellent hosts. They were warm, friendly and receptive. The place was clean, nicely furnished and the kitchen had all necessary amenities. The neighbourhood was quiet and beautiful. We would like to visit the place again if the opportunity arises.
Guest favourite
Flat in Windfields
4.95 out of 5 average rating, 127 reviews

Family Friendly | Cozy | HOT TUB | Near UOIT

MichaelRating, 5 stars1 week ago
I had a wonderful stay at Sahiya and Gibran's place! From the moment I arrived, they made me feel right at home. The space was clean, cozy, and well-equipped, offering everything I needed for a comfortable stay. They were incredibly responsive and helpful, always ready to assist with any questions. I highly recommend their place for anyone looking for a welcoming and peaceful stay. Thank you, Sahiya and Gibran, for being such great host! I will surely visit again.
Guest favourite
Flat in Holland Landing
4.95 out of 5 average rating, 20 reviews

New Cosy and Clean apartment with private entrance

PeterRating, 5 stars2 months ago
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.
Guest favourite
Flat in Barrie
4.86 out of 5 average rating, 350 reviews

Executive residential place with NETFLIX

KarianneRating, 5 stars2 months ago
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!
Guest favourite
Flat in Oak Ridges
4.9 out of 5 average rating, 111 reviews

Large Walk-out private apartment w/ parking

JanesseRating, 5 stars3 days ago
A great place at a very reasonable price

Family-friendly apartment rentals

Guest favourite
Apartment in The Blue Mountains
4.98 out of 5 average rating, 151 reviews

Lovely 3 Bedroom Condo with Stunning View and Pool

SusanRating, 5 stars1 month ago
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.
Superhost
Apartment in Innisfil
4.87 out of 5 average rating, 222 reviews

2BR Getaway at Friday Harbour All Season Resort

JohnRating, 5 stars3 weeks ago
Brilliant location for the harbour everything in walkable distance, clean and well stocked kitchen . Responsive host would recommend.
Guest favourite
Apartment in The Blue Mountains
4.85 out of 5 average rating, 141 reviews

Large, luxury, upper floor condo, steps to Village

MatthewRating, 5 stars4 months ago
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.
Superhost
Apartment in The Blue Mountains
4.86 out of 5 average rating, 245 reviews

Stylish & Spacious 2 Bdrm/2 bths/2 balc Condo Loft

JillRating, 5 stars2 weeks ago
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!
Top guest favourite
Apartment in Innisfil
4.97 out of 5 average rating, 164 reviews

Stylish getaway condo, resort living

DanielleRating, 5 stars2 months ago
very clean place, has everything you need for a great getaway. Ron is an amazing, always available host!
Guest favourite
Apartment in Innisfil
4.89 out of 5 average rating, 139 reviews

Friday Harbor Upscale 1Bed+Sofabed+Pool Option

DaveRating, 5 stars7 months ago
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!
Superhost
Apartment in Innisfil
4.91 out of 5 average rating, 140 reviews

Beautiful Condo, 2 Bedrooms and a Den in a Resort!

LoriRating, 5 stars2 months ago
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).
Guest favourite
Apartment in Blue Mountains
4.92 out of 5 average rating, 340 reviews

2 Bedroom, 2 Level Condo on Blue Mountain!

JamesRating, 5 stars1 week 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.

Quick stats about holiday rentals that are kid-friendly in Midland

  • Total rentals

    50 properties

  • Nightly prices starting at

    £30 before taxes and fees

  • Total number of reviews

    2.1K reviews

  • Family-friendly rentals

    50 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with a pool

    10 properties have a pool

Destinations to explore

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