
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
Had a lovely stay! Lisa was so accommodating! Beautiful location.

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.
My husband and I had a great experience here. Kerin was a great host, even putting snacks out for us which was a nice touch. She was highly responsive if I had any questions. The place was cozy and comfortable, as described. It was very clean, which I appreciated. Highly recommend for couples looking to relax!

Bright basement apt with private entrance, Barrie
Everything was great down to every little detail. Soaps, shampoo, Conditioner, towels, toothpaste and new brushes in case you forgot yours. Coffee, tea and sugar, water bottles and ice in the freezer. Every detail was perfect. We would definitely stay again when in the area. Only negative... is you can hear the main level apartment (living space) people walking around if heavy footed... but in general that was not a problem and not a complaint. Just an FYI for future renters.

Spacious Barrie Basement with Separate Entrance
Place is nice and clean! Fridge is kind of loud but not a dealbreaker. Would recommend

Georgian Bay Water/Beach front Cottage
wonderful hosts! Derek was so accommodating and flexible. The location is beautiful and the house itself was perfect for a long or short stay. We absolutely loved being here, and felt very well taken care of by the hosts. Highly recommend.
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!

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!

Blue Mountain Studio Retreat
Natalie’s place is excellent! The studio was super clean and very nice. We felt right at home!! It had everything we needed and was close to all the local attractions. Natalie provided a guide ahead of our trip with information about the AirBnb, as well as local recommendations for food and things to do. She was extremely kind and responsive. Would definitely stay here again! Thanks Natalie!!
Family-friendly apartment rentals

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!
This place was beautiful! As soon as we walked in, we felt at home. All the amenities listed were in the property and in good condition. Richard was very helpful and responsive when we had questions for him. There were extra pillows for people who sleep with more than just one lol. The ceiling fan in the loft really cooled down the place and kept the place at a good temperature. The area is also lovely, with a nearby tennis court on the resort. My friends and I spent most of our time there playing pickleball and tennis. Also, Blue Mountain village is about a 20 minute walk from the resort, so my friends and I went to visit at night. Overall, this was a lovely place to stay for the weekend and I would definitely come back again!

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!

Horseshoe 2BR | 4 Beds+Pool+BBQs+Resort Access
Justin was very accommodating and helpful when we had questions! The responses were so fast and informative. We loved everything about this place, it was peaceful, nice location and the pool was clean and very nice! Definitely will be back!!
Quick stats about holiday rentals that are kid-friendly in Midland
Total rentals
50 properties
Nightly prices starting at
$51 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 Club At Bond Head
- The Georgian Peaks Club
- Muskoka Bay Resort
- Alpine Ski Club
- Rocky Crest Golf 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