Pet-friendly holiday rentals in Midland

Find and book unique pet-friendly homes on Airbnb

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Popular amenities for Midland pet-friendly home rentals

Pet-friendly house rentals

Superhost
Home in The Blue Mountains
4.89 out of 5 average rating, 225 reviews

Large 4 Br - 4.5 Bath; Sauna/Heated Pool/2 King

PamelaRating, 5 stars2 weeks ago
Visited with 4 couples for a few nights away. Beautiful location. Would recommend
Top guest favourite
Home in Port McNicoll
4.96 out of 5 average rating, 25 reviews

Paradise Point Steps from Georgian Bay Great WIFI

SidRating, 5 stars9 months ago
Very cozy and well equipped home. Had an awesome time staying at Angela’s place
Top guest favourite
Home in Collingwood
4.96 out of 5 average rating, 113 reviews

Driftwood on 6th Heritage Downtown Collingwood

LianneRating, 5 stars1 day ago
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. ❤️
Superhost
Home in Orillia
4.82 out of 5 average rating, 259 reviews

Waterfront Cottage Over-the-Water view w fast Wifi

EmilyRating, 5 stars4 weeks ago
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”!
Guest favourite
Home in Innisfil
4.88 out of 5 average rating, 184 reviews

King Bed*Pool*Fireplace*BBQ*Smart TV

Braeden.Rating, 5 stars1 month ago
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!
Guest favourite
Home in Collingwood
4.9 out of 5 average rating, 199 reviews

JJ’s Collingwood bar & games house.

AmyRating, 5 stars1 week ago
Jer was an outstanding host! The house was everything we needed it to be! Great location! Would definitely recommend.
Superhost
Home in Barrie
4.86 out of 5 average rating, 116 reviews

King Bed Farmhouse- w/ Fire-pit, 75" TV, Ping Pong

BradRating, 5 stars2 weeks ago
Thank you for being a great Host to our group.
Guest favourite
Home in Little Lake
4.87 out of 5 average rating, 103 reviews

Lakefront detached house on the little lake

OrrebRating, 5 stars1 week ago
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

Guest favourite
Townhouse in The Blue Mountains
4.9 out of 5 average rating, 156 reviews

The Snowbridge Lookout on Monterra Golf Course

T TRating, 5 stars4 weeks ago
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!
Guest favourite
Treehouse in Port Perry
4.98 out of 5 average rating, 555 reviews

Treehouse on private, isolated forest (300 acres)

DanielaRating, 5 stars4 months ago
Ollie and Frank were tremendous hosts. We loved the log cabin and all their recommendations were exceptional. We will be back!!!
Superhost
Apartment in Oro
4.78 out of 5 average rating, 102 reviews

Cozy 1-Bedroom Romantic Retreat with full Kitchen

KristenRating, 5 stars1 week ago
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!
Guest favourite
Cottage in Innisfil
4.9 out of 5 average rating, 214 reviews

Utopia Villa and Spa

AngeloRating, 5 stars3 weeks ago
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.
Guest favourite
Guest suite in Uxbridge
4.96 out of 5 average rating, 208 reviews

Mackenzie Cottage

OzrenRating, 5 stars3 weeks ago
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.
Guest favourite
Guest house in Orangeville
4.95 out of 5 average rating, 354 reviews

Sunny Pines Farm Studio Tennis Court/Bruce Trail

DhillonRating, 5 stars3 days ago
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!
Top guest favourite
Flat in Innisfil
4.99 out of 5 average rating, 105 reviews

Modern Condo at Friday harbour/Pet Friendly

BlairRating, 5 stars2 weeks ago
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.
Guest favourite
Apartment in Innisfil
4.88 out of 5 average rating, 214 reviews

Lake Simco penthouse at Friday Harbour resort

JonRating, 5 stars2 weeks ago
great location, lots to do in the area. Anastasia was very communicative and a great host. highly recommend

Private, pet-friendly home rentals

Top guest favourite
Home in Georgian Bay
4.99 out of 5 average rating, 86 reviews

A-Frame in the Woods of GeorgianBay, Muskoka

BecciRating, 5 stars2 weeks ago
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!
Superhost
Dome in East Gwillimbury
4.89 out of 5 average rating, 226 reviews

Deerleap Glamping Dome

Hiu ChingRating, 5 stars2 days ago
Everything is good ! The host would reply your messages !
Top guest favourite
Farm stay in Uxbridge
4.97 out of 5 average rating, 174 reviews

Private Loft w Sauna, Fireplace, Wi-Fi & Projector

LongRating, 5 starstoday
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!
Superhost
Cottage in Tiny
4.9 out of 5 average rating, 52 reviews

A modern retreat on Georgian Bay STRTT-2025-062

KaterynaRating, 5 stars5 months ago
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!
Guest favourite
Holiday home in Midland
4.88 out of 5 average rating, 42 reviews

Georgian Bay retreat - apartment in Midland

TrevorRating, 5 stars1 month ago
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.
Guest favourite
Cottage in Port Severn
5 out of 5 average rating, 35 reviews

Relax at Lakefront Follie’s Cove Cottage

MeghRating, 5 stars10 months ago
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!
Top guest favourite
Townhouse in Midland
5 out of 5 average rating, 13 reviews

Cozy Comfort by the Bay w/Jacuzzi

IetjeRating, 5 stars1 day ago
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.
Guest favourite
Cabin in Tiny
5 out of 5 average rating, 12 reviews

The Beach House, Georgian Bay, Beach View w/ Sauna

SamRating, 5 stars1 day ago
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

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