
Pet-friendly holiday rentals in Midland
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Midland
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Popular amenities for Midland pet-friendly home rentals
Pet-friendly house rentals

Sunnyside Stay-3bdrm w/ Gym!
We had a wonderful stay here in Midland. The house is very clean and spacious and the master bedroom is a great space to unwind and relax. The house did not disappoint and I would book again for our next trip to Midland. Nicole is a great host, and excellent communicator and was very helpful.

Tiny House in Penetanguishene
Lovely tiny home in Penetanguishene. Very clean and the host was very helpful. Fully equipped house with everything we required. Love that it was dog friendly. Unfortunately there’s not much within walking distance of the home so a car is needed to get to the local towns.

Simcoe Retreat
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!

Driftwood on 6th Heritage Downtown Collingwood
We thoroughly enjoyed our time here. Seema's home is even more lovely than in pictures. The kitchen was fully stocked with everything you could possibly need. The beds were very comfortable and linens were high quality. This is always a make or break deal for me. The living room with big screen TV and comfy furniture was the perfect spot for us girls to relax and catch up. One thing to note is that both bathrooms are on the main floor. If you are one to get up through the night, she has installed 3 motion lights that come on as you go down the stairs. We really appreciated this safety measure. The backyard looked gorgeous. Unfortunately, we didn't have the best weather so we could not enjoy it. We'll look forward to using it the next time we book Seema's lovely home as we will most definitely be back!

Waterfront Cottage Over-the-Water view w fast Wifi
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

Brand New Entire Home in Southgate ( Dundalk)
Ruth was an amazing hosts, beautiful house and friendly positive person to deal with. Thank you!

JJ’s Collingwood bar & games house.
Jer was a very good host, the place was beautiful, bunch of games to play, had a lot of fun. The surroundings are beautiful 10 min walk to park and beach. 10 minutes drive to blue mountain. The place was really good.

Lakefront detached house on the little lake
It was really a wonderful experience. We didn’t face any problem and we enjoyed a lot with beautiful view of lake. I recommend all of you to must stay here.
Pet-friendly home rentals with a pool

Farmhouse GUEST SUITE- Pool, hot tub, horses
We stayed at Amanda and Mike’s Airbnb in Minesing for a 3-day cottage vacation and had an amazing time! The farmhouse was the perfect size for the two of us. The place was very clean. The kitchen was fully stocked with everything we needed, and the hot tub very nice and the instructions given for operating were easy to follow. It was very quiet, peaceful, and the perfect relaxing getaway from the city. We would definitely recommend this place to friends and family and would love to come back again!

Large 4 Br - 4.5 Bath; Sauna/Shuttle Bus/2 King bd
This was a great home with lots to do inside. We enjoyed all of the games and pool table. Shuttle service was easy to use and only a short ride away to the village. The beds were comfortable and lots of space inside for our family. Brendan was friendly and responsive!

Serene mountainside home View/Shuttle Bus/Pool
We had a wonderful stay - Brendan's place was clean, organized and in a great area (close to village). Brendan was responsive and helpful and I would recommend this place to relax and enjoy Collingwood.

*Haven on Blue*- Hot Tub, Heated Pool & Sauna
Great place - cozy and so close to the hill. Didn’t have a chance to use the sauna so hopefully next time :)

Mackenzie Cottage
A really lovely character-filled home. Look forward to another stay one day!

Great kitchen, comfy beds, games, walk 2 village +
Jason and Tanya saved our trip after the first Airbnb we checked into was dirty and had mice! They had a last minute cancellation and allowed us to check in right away! They were super helpful in getting us moved over to their place. When we got inside it was beyond clean and comfortable. The kitchen was the best of any airbnb I've stayed in with spotless dishes and useable pots/pans and appliances. The unit is spacious and the beds & linens were extremely comfortable. A million thanks for saving our trip for us! Would highly recommend to anyone.

Blue Mountain Escape! Pool&HotTub. Walk to Village
One of the best staycation. My siblings and I are really feel grateful especially the host are very cooperative. Everything in the house are good and the place is perfect! Will recommend it 💯%. Thank you very much!

King Bed*Pool*Fireplace*BBQ*Smart TV
Tristan’s unit was exactly as described, clean bathroom, spacious living room, lots of boardgames for entertainment. Nice boardwalk and views! Would love to be back again!
Private, pet-friendly home rentals

Woodski Mountain Retreat w/Pool & 3+ Private Acres
We had an amazing stay at this cozy cottage for the weekend! It was beautifully decorated, super clean, and had everything we needed. The peaceful location was perfect for relaxing, yet close to nearby attractions. Our host was thoughtful and communicative, making sure we had a great experience. We can’t wait to return!

Blue Mountain Studio, 2 Queen Beds, Lake Huron
Great place with a wonderful host. Can’t wait to stay here again

Cozy 4 Season Family Cottage
Anthony’s place was the perfect spot for a nice weekend! We really enjoy having a relaxing fire in the backyard with plenty of wood. We would definitely consider staying here in the future!

Memories Are Made Here
Great place in such a beautiful cozy community! Communication with Ali was fast and easy and his cottage was clean and bunch of useful amenities. 10 min walk from beach, overall great experience!

3 Bdrm Family Cottage Private Beach, Thunder Beach
We absolutely loved the cottage it was perfect for our week at the beach. The beach itself was just steps away and was absolutely beautiful with calm,clear water and friendly neighbours. There is a strong sense of community in the area. We really loved the outdoor shower which was a family favourite. We will defiantly come back to this cottage again and again if we can.

Quaint and Cozy -your home away from home!
Cathy's place is wonderful. The home is open and spacious with a great layout. Everything was comfortable and just right. The home is in an ideal location to get to both Wasaga and Collingwood and also right in town if need anything. I would definitely book here again next time I am in town. Thank you Cathy!

Muskoka Lakefront Family Paradise *Hot Tub*
My husband, 3&1/2 year old daughter, two dogs and I just returned from the most incredible cottage stay in Bracebridge, Muskoka, and we’re already counting down the days until we can go back! The host, James, was truly exceptional - responsive, organized, and went above and beyond to make our stay feel like a home away from home. From the moment we walked in, we were blown away by the thoughtful touches and extra details that made our stay so special. The Christmas tree was beautifully decorated with different lighting options, and the abundance of board games and video games kept us entertained for hours, regardless of the weather outside. The hot tub was immaculately clean and the perfect spot to relax and unwind, and the home itself was spotless and tidy. It's clear that James takes great pride in his property and goes to great lengths to ensure guests have an unforgettable stay. I'm so grateful to have found this little slice of heaven in Muskoka! Highly recommend!

Romantic Cabin Getaway with Hot Tub
“Hostess with the mostest” is an understatement for Sandra. When she says all you need to bring is your overnight bag and groceries, she means it! Her and Dejay are lovely people, offering an incredible getaway. The attention to detail and commitment to their guests is unmatched. 10/10 would recommend and return!
Quick stats about holiday rentals that are pet-friendly in Midland
Total rentals
80 properties
Nightly prices starting at
£38 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
- Markham Holiday rentals
- Georgian Bay Holiday rentals
- Waterloo Holiday rentals
- Kitchener Holiday rentals
- Oakville Holiday rentals
- Mississauga Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Rentals with a hot tub Midland
- Family-friendly rentals Midland
- Cottage rentals Midland
- Rentals with an EV charger Midland
- Rentals with a patio Midland
- Rentals with beach access Midland
- Rentals with a kayak Midland
- Rentals with lake access Midland
- Rentals with outdoor seating Midland
- Flat rentals Midland
- Waterfront rentals Midland
- Cabin rentals Midland
- Rentals with a washing machine and dryer Midland
- House rentals Midland
- Rentals with a fireplace Midland
- Rentals with a firepit Midland
- Family-friendly rentals Midland
- Beachfront rentals Midland
- Rentals with pools Midland
- Fitness-friendly rentals Midland
- Pet-friendly rentals Simcoe County
- Pet-friendly rentals Ontario
- Pet-friendly rentals Canada
- Yurt Rentals United States
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- Castle Rentals United States
- Houseboats United States
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- Private Island Rentals United States
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- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
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- Beach Houses United Kingdom
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- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Blue Mountain Village
- Horseshoe Resort
- Mount St. Louis Moonstone
- Port Carling Golf & Country Club
- Snow Valley Ski Resort
- Osler Bluff Ski Club
- Georgian Bay Islands National Park
- Muskoka Lakes Golf and Country Club
- Beaver Valley Ski Club
- Devil's Glen Country Club
- Lake Joseph Golf Club
- Muskoka Bay Resort
- Alpine Ski Club
- National Pines Golf Club
- Windermere Golf & Country Club
- South Muskoka Curling and Golf Club
- Toronto Ski Club
- The Georgian Bay Club
- The Georgian Peaks Club
- Rocky Crest Golf Club
- Shanty Bay Golf Club
- The Club At Bond Head
- Muskoka Highlands Golf Links
- Mansfield Ski Club