
Pet-friendly holiday rentals in Midland
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Top-rated pet-friendly home rentals in Midland
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Popular amenities for Midland pet-friendly home rentals
Pet-friendly house rentals

Large 4 Br - 4.5 Bath; Sauna/Heated Pool/2 King
Visited with 4 couples for a few nights away. Beautiful location. Would recommend

Paradise Point Steps from Georgian Bay Great WIFI
Very cozy and well equipped home. Had an awesome time staying at Angela’s place

Driftwood on 6th Heritage Downtown Collingwood
I wish this was my house. Truly, that’s my only complaint. The entire place is stunning, but the backyard is a true oasis. The photos don’t even come close to doing it justice. It’s peaceful, beautifully set up, and the kind of space you’ll find yourself daydreaming about long after you leave. Inside, everything was spotless, stylish, and thoughtfully put together. The bed was super comfortable, the location was ideal, and every little detail felt intentional and warm. It’s one of those rare places that feels like home the second you walk in. I already can’t wait to come back. Seema - if you ever decide to sell, please call me first. ❤️

Waterfront Cottage Over-the-Water view w fast Wifi
Chelsea’s place was absolutely beautiful ! Upon walking in the house, the view of the water is breathtaking and did not get old each morning while sipping our coffees. The home itself was very homey, and a great wide open space for gathering with friends. Chelsea was super helpful when booking, made recommendations and was super responsive during our stay with any questions we had. I would highly recommend a stay here - can’t get much closer to being “on the lake”!

King Bed*Pool*Fireplace*BBQ*Smart TV
Absolutely amazing stay, Tristan’s place truly went above what our expectations were and blew us away, amazing balcony that was private and quiet, clean rooms, lots to do in the area. I cannot recommend this place enough!

JJ’s Collingwood bar & games house.
Jer was an outstanding host! The house was everything we needed it to be! Great location! Would definitely recommend.

King Bed Farmhouse- w/ Fire-pit, 75" TV, Ping Pong
Thank you for being a great Host to our group.

Lakefront detached house on the little lake
Shiyu was a great host. What an amazing and peaceful cottage. We made some great memories there. Shiyu was very responsive and helpful. The place looks exactly, even better than pictures in real life. Shiyu accommodated us in best way possible. Totally worth getting this place for the weekend and spending time with family. Definitely booking it again soon. I would recommend 100% this property if you want to spend quality time with your loved ones.
Pet-friendly home rentals with a pool

The Snowbridge Lookout on Monterra Golf Course
We had a wonderful stay at this Airbnb! The place was very comfortable, spotlessly clean, and the temperature inside was just perfect. We really enjoyed our time here and felt right at home. The only small downside was that the Wi-Fi was a bit slow, but everything else was great. We would definitely love to come back. Highly recommended!

Treehouse on private, isolated forest (300 acres)
Ollie and Frank were tremendous hosts. We loved the log cabin and all their recommendations were exceptional. We will be back!!!

Cozy 1-Bedroom Romantic Retreat with full Kitchen
Had a great stay! Very comfortable, clean and great communication from Vlad! Had a high chair available for use which was a nice touch! The only feedback we would give would be it would be nice to have more than two towels for a family especially being that there’s a pool but that was no big deal! Thanks for a great stay!

Utopia Villa and Spa
We stay for 2 nights it was a perfect getaway for us. Lots to do inside and outside our little ones really enjoyed. The host was super nice and responsive. The house was very clean and the detail of the house was very homey. We really enjoyed our stay. Most recommended to book this it was very worth it.

Mackenzie Cottage
We stayed from 4 night, and despite having almost 72 hours of light but constant rain (it looked like a veil of rain when looking over the fields), we were very comfortable and cozy in the cottage. The trails attached to the cottage are a nice gateway into the surrounding forests. They are and thick with trees that sheltered us from the rain (and any cabin fever). This location also prvoided us easy access (via bike) to the Durham mountain bike trails in the area when the rain let up finally, near the end of our stay.

Sunny Pines Farm Studio Tennis Court/Bruce Trail
had a wonderful stay! The countryside location is absolutely beautiful – peaceful, scenic, and perfect for relaxing. The surroundings are great for walks and enjoying nature. The host was welcoming and helpful, making everything easy and comfortable. Highly recommended to anyone looking for a quiet getaway with amazing views!

Modern Condo at Friday harbour/Pet Friendly
Had a great stay place was beautiful. Great communication with host would def recommend. Both me and my wife can’t wait to come back again in the future.

Lake Simco penthouse at Friday Harbour resort
great location, lots to do in the area. Anastasia was very communicative and a great host. highly recommend
Private, pet-friendly home rentals

A-Frame in the Woods of GeorgianBay, Muskoka
We had a wonderful time celebrating our friend’s bachelorette. We’ll definitely have to come back one day when it’s a little warmer!

Deerleap Glamping Dome
Everything is good ! The host would reply your messages !

Private Loft w Sauna, Fireplace, Wi-Fi & Projector
Paul and Lindsey were phenomenal hosts; helpful, responsive, accommodating, and very friendly! The place is very unique and you definitely get the full experience of the amenities and much more. A very unique space and experience, would definitely recommend!

A modern retreat on Georgian Bay STRTT-2025-062
Beautiful home! We absolutely loved the living area. It felt cozy with all the natural light coming in through the ceiling windows. The dining area was great on a snowy day. We played the games and enjoyed the views of the snow-covered pine trees! Loved the location and the house. Would recommend!

Georgian Bay retreat - apartment in Midland
Tatiana's place is great for a couple or singles. She is incredibly kind and accommodating. Her place is in a nice residential neighborhood. Midland is a great community with lots to do on Georgian Bay.

Relax at Lakefront Follie’s Cove Cottage
This cottage is perfection. Liane & James are just SO lovely. If you're reading this, don't look any further. Just book it. We couldn't have had a better week at Follie's Cove. The cottage was the perfect mix of modern and rustic. Clean, comfortable, and thoughtfully equipped. We felt at home instantly. The sunroom was the perfect chill spot for us and our two big dogs to get out of the sun/rain without feeling cooped up indoors. The beach was heaven for our dogs, and on a quiet end of the lake, so we saw few other people all week. The quintessential Muskoka experience! Liane and James were *beyond* wonderful. They set us up with a ton of breakfast food and desserts. Even offered to return the day after check-in to drop off more coffee. It truly felt like renting from friends. Highly recommend renting the pontoon boat from them and puttering around the lake. Wish I had more space to gush about the space and their incredible hospitality. We would book again in a heartbeat!

Cozy Comfort by the Bay w/Jacuzzi
We were 7 adults., Us 2 from Australia visiting sister and her 2 daughters of which one lives with my sister in Kitchener and one who lives in Toronto. The 2 daughters were joined by their partners we hadn’t met so everyone was on their best behaviour and made a great impression on us. We hadn’t met the nieces partners so a fantastic time was enjoyed sitting around chatting, having some wine and whisky. The nieces and their partners used the hot tub the last evening and thoroughly enjoyed the experience. This townhouse was fantastic with everything one needs and more. We can definitely recommend this to any future guests.

The Beach House, Georgian Bay, Beach View w/ Sauna
My family and I had a great time at Adam’s cottage! Incredible view of the lake, the lake water was crystal-clear. Beach house was well maintained and very clean, the interior decor was stunning! Beach house/garage had all the amenities you will need! The 2 paddle boards and 2 bikes were a great edition! we enjoyed walks/bike rides through the trails in the neighbourhood. We will definitely come back, HIGHLY recommend! Adam was very helpful, insightful, and gave fast replies! Great host!
Quick stats about holiday rentals that are pet-friendly in Midland
Total rentals
80 properties
Nightly prices starting at
₹4,305 before taxes and fees
Total number of reviews
2.4K reviews
Family-friendly rentals
70 properties are a good fit for families
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Destinations to explore
- Grand River Holiday rentals
- Brampton Holiday rentals
- Muskoka Lakes Holiday rentals
- Vaughan Holiday rentals
- Georgian Bay Holiday rentals
- Markham Holiday rentals
- Tobermory Holiday rentals
- Kitchener Holiday rentals
- Waterloo Holiday rentals
- Mississauga Holiday rentals
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- Rentals with lake access Midland
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- Rentals with a hot tub Midland
- House rentals Midland
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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
- Craigleith Ski Club
- The Georgian Bay Club
- Muskoka Highlands Golf Links
- South Muskoka Curling and Golf Club
- Mansfield Ski Club