
Kid-friendly holiday rentals in Midland
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Top-rated family-friendly rentals in Midland
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Popular amenities for Midland family-friendly rentals
Kid-friendly house rentals

Waterfront Muskoka guest suite near Casino Rama
Lisa was such an amazing host. At first, she helped us change the date of the booking very easily. After check-in, she stopped by to make sure we have everything we need. She brought a mosquito spray for my mom. The location is absolutely beautiful. Totally recommend staying at her place.

Cozy Cottage with Private Beach Access
My family and I recently stayed at Magdalena‘s. The cottage was clean and Magdalena was very friendly and accommodating. There’s beach access and a little playground for children. We enjoyed our stay.

Luxury Cottage - The Lookout. Next to Balm Beach
Great spot to rent...Beautiful space. Host were very friendly and had prompt communication. Perfect type of place to get away. Would have been better if the weather was nicer. I expect we will rent here again in the future.

Luxury Guest House with Private Hot Tub and Trails
We had a lovely stay. The place was even nicer than we expected. This is the best air bnb we’ve ever had. It was really private and really clean, which was exactly what we were looking for. They provided so many little things which just added to the overall experience. Its the small things that go a long way. The place was really open concept and just really well furnished. Gave a fantastic vibe. The hot stub was clean, private and lovely. You wont be disappointed whatsoever here. Thank you for being a fantastic host Rebecca.

100% Private 1-Bdrm+Fireplace. Quiet+comfortable.
Great location in downtown Collingwood everything is very close the neighborhood itself is very quiet. Kerin was very helpful with everything great place for a weekend getaway

Steps From the Beach and Hiking Trails!
Best mom and daughter getaway for a three day weekend! Lovely accommodations, cozy, clean and comfy beds. Great location close to drive to great shopping and restaurants in Midland. Nearby beach area 2 mins away and beautiful. Highly recommend this spot, good value.

Bright basement apt with private entrance, Barrie
We had an incredible stay at this immaculate suite. From the moment we arrived, it was clear that every detail had been thoughtfully considered—from plush blankets and cozy robes to a curated selection of toiletries, candles, and a fully stocked coffee and tea station. It truly felt like we were staying in a boutique resort or luxurious cabin. The suite is very spacious and located in a quiet, peaceful neighborhood, yet it’s surprisingly convenient—just minutes to the beach and downtown Barrie. We loved how easy it was to explore the area, and there were tons of great food options nearby to suit every craving. The beds and linens were ultra comfortable, making it hard to get up in the morning! Everything about the space was inviting, warm, and relaxing. Highly recommend for anyone looking for a serene escape with top-tier comfort and thoughtful touches.

Spacious Barrie Basement with Separate Entrance
Great to stay for a Wedding weekend. Close enough to get to both Innisfuil and Midhurst! -LM & DM
Family-friendly apartment rentals

2 bedroom beachfront apartment
A fabulous beach front location, within steps of a sandy and shallow waterfront. Tess and Jeff are great hosts and extremely helpful. The accommodation is super cosy and much bigger than expected. It had everything we needed and more! The kitchenette may be small but it is well stocked and we didn’t have any issues with cooking. The BBQ is a gas one and very good. We enjoyed eating outside on the large sized deck. Even though it’s shared with the owners, the privacy screen was ample. The beach was pretty quiet and made for a relaxing stay. We sadly didn’t get to witness any sunsets since it was a little cloudy, but you can see how amazing it would be! Thank you Tess and Jeff for your kind hospitality.

Luxury 1 Bedroom Apt In The *HEART* Of Orilla
My stay at Carley’s place was amazing ! Her place is stunning , incredible attention to detail , comfortable and peaceful. Great location , short walk into the downtown offerings. I highly recommend anyone to stay at Carley’s place if you’re in the area , you will only be left very impressed ! Thank you for hosting my short visit Toby

The Upper Deck
Cathy was an exceptional host! The accommodations were so beautiful, so much love and hard work put in to making it a cozy place to stay. Bed was huge and comfy. Cinnamon buns were delicious. Hot tub was relaxing and private. We want to come back and try one of her other suites.

The Muskoka River Chalet - The King's Den
A friend and I decided to head north for a quick night away. Taurean’s “King’s Den” apartment was the perfect choice! A gorgeous accommodation, filled with special little extras and attention to detail! We enjoyed our stay and will be back!

Cozy getaway for two with hot tub!
We absolutely loved our stay at Chantal and Sylvain’s place! From the moment we walked in, we were very impressed by this clean, cozy, and beautifully-furnished home-away-from-home. Our hosts thought of everything, and were friendly, responsive and helpful. Their place is complete with everything you could need for a comfortable stay, in addition to some additional thoughtful, special touches. We had fun playing some of the many available board games, and found it so peaceful to sit in their quiet backyard, surrounded by trees. We LOVED lounging in the beautiful hot tub. Next time we’re in Coldwater, we would definitely stay at Chantal and Sylvain’s place again! Highly recommend!

Modern Condo at Friday harbour/Pet Friendly
We had a great stay! The place was spotless, the check-in process was super easy, and the location was perfect—just a short walk to the harbour. The host was very responsive and made sure everything went smoothly. We would definitely stay here again!

Quite in Nature
This Air B&B is great for a get away it's exactly as posted would definitely stay again.

Welcome to waterfront paradise on Georgian Bay
We had a fantastic weekend staying at Gerard’s place! It was just as described from the pics and Gerard provided very clear instructions which made checking in seamless. The place was very clean, spacious, and right on the water! There was also a ton of things to do including kayaking, stand up paddle boarding, board games, a gym with weights as well as a fully stocked kitchen. We had a great time and would definitely come back again in the future!
Family-friendly apartment rentals

Bright MCM 2 Bedroom Walk Up with Private Deck/BBQ
I rented unit for my parents and they absolutely loved their stay! The place was clean, nicely decorated, and had everything they needed for a comfortable visit. The host was incredibly welcoming and responsive, making check-in was nice and easy. The location was perfect—quiet, yet close to everything. Would definitely stay here again and highly recommend to anyone visiting the area!

Cozy 1-Bedroom Romantic Retreat with full Kitchen
Loved our stay here!! Can't say enough positive things about our vacation here. Kitchen was fully stocked, clean bathroom and rooms, easy check in and check out and excellent cooling system as it was a hot few days. Amenities were great and welcoming for families, environment was peaceful and we also loved how the balcony backed onto trees and nature. Would 100% stay here again in the future. Thank you!

Cozy Studio Mountainside stay in Blue Mountains
Absolutely Wonderful Stay! I had an amazing stay at John and Kristi’s condo! From the moment I arrived, everything was spotless, cozy, and thoughtfully equipped with everything one could possibly need for a comfortable stay. The attention to detail made it feel like a home away from home. The pool and hot tub area were a real bonus—clean, relaxing, and perfect after a day of exploring. I definitely made the most of it! The location was also ideal, just a pleasant 10-minute walk to the village, which made it easy to enjoy the local shops, restaurants, and atmosphere without needing to drive. John and Kristi were fantastic hosts—friendly, responsive, and clearly committed to creating a great guest experience. I would absolutely stay here again and highly recommend it to anyone visiting the area!

South Wind - Modern Condo in Collingwood - Sleep 5
We had a great stay here. The hosts were responsive and helpful. The place is very clean and had everything we needed for our stay.

2 Bedroom, 2 Level Condo on Blue Mountain!
Richard was an extremely gracious and helpful host who responded immediately upon my reservation request. He answered every question I had in a very timely manner and helped me to get in contact with Airbnb when I had a separate issue that had nothing to do with his booking. When we arrived at the bnb, there was a complimentary bottle of white wine waiting in the fridge for us. Shortly after we checked out, he reached out to let me know that I had left one of my belongings in the closet and offered to return it to me. He also gave me a discount for our stay due to an unforeseen circumstance that was beyond his control. He was very generous and helpful and went above and beyond to accommodate us! Our stay was quiet, clean, comfortable and cozy! We will stay there again when we visit Collingwood and highly recommend it!

Lovely Open Concept Friday Harbor Resort Condo
If you’ve never been to Friday Harbour it’s an amazing weekend escape with beaches, pools, bars and restaurants and light shopping. We spent our 10th anniversary at Marks Condo in the Harbour and loved every minute of it. Mark’s condo in Friday Harbour really is a gem. It’s on the top floor of a quiet building just steps away from the main boardwalk, hiking trails, and everything else Friday Harbour has to offer. The building complex offers communal BBQs and fire pits that are available and easy to use. The condo itself is very clean, bright, with its own balcony and everything you could possibly need. Marks check-in instructions are very detailed and thorough and is great at communication should anything come up. It was an incredible weekend and we will 100% come back.

Marina view at Friday Harbour 2bd/2bth Pool option
Immaculately clean, spacious, and Beautiful condo. It had everything we need and a few steps to the marina. Easy instructions to get inside and parked. I highly recommend!

Resort Condo in Friday Harbour
Great place to stay! Close to everything!
Quick stats about holiday rentals that are kid-friendly in Midland
Total rentals
50 properties
Nightly prices starting at
$52 SGD 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
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- Blue Mountain Village
- Port Carling Golf & Country Club
- Osler Bluff Ski Club
- Horseshoe Resort
- Devil's Glen Country Club
- Georgian Bay Islands National Park
- Beaver Valley Ski Club
- Mount St. Louis Moonstone
- Snow Valley Ski Resort
- Lake Joseph Golf Club
- Muskoka Lakes Golf and Country Club
- The Georgian Peaks Club
- The Club At Bond Head
- Muskoka Bay Resort
- Rocky Crest Golf Club
- Alpine Ski Club
- National Pines Golf Club
- Barrie Country Club
- Windermere Golf & Country Club
- The Georgian Bay Club
- Craigleith Ski Club
- Muskoka Highlands Golf Links
- South Muskoka Curling and Golf Club
- Mansfield Ski Club