
Pet-friendly holiday rentals in Caledon
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Top-rated pet-friendly home rentals in Caledon
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Pet-friendly house rentals

Hot Tub - Cozy - Guelph 3 Bed 1 Bath Loft House
Punit’s place was warm, welcoming and well maintained. The home is close to a busy road but punit provided ear plugs in the bathroom. The thought and care going into the property was well demonstrated through the amenities and touches. Punit was responsive and eager to help when questions arose. Our dog was very happy to stay there and we enjoyed the backyard, fire pit and hot tub thoroughly. Thank you for having us!

Mono Mills Home next to the County Great Getaway
We were displaced by a fire and lucky to find this spot to call home until we found our forever home. Trudy and Ray were both friendly and supportive. Big backyard was nice for our little guy to play in, safe and quiet spot as well. Thank you for having us!

The Walnut - Steps to Canoe Launch & Downtown
Katherine's place is stunning! The home honours its heritage with updated amenities. The pictures from the listing are accurate. Our stay away allowed us to celebrate family time with our adult children and their spouses. We enjoyed cooking food in the expansive kitchen and playing games at the dining room table together. The town of Paris is a quick walk to awesome shops, with beautiful views of the Grand River along the way. We would highly recommend a stay here!

Spacious 3-Bed Home near Airport. Parking Backyard
We loved staying at her place. The host was friendly and was replying to my questions as soon as possible. The neighbourhood was peaceful and quiet.

Hockley Valley - Jazzy Pines - 4 BR with Pool
We had such a wonderful time staying at John’s place—it honestly couldn’t have been better. The home was gorgeous, spotless, and felt so warm and inviting. You can tell a lot of care went into making it a space where guests can truly unwind and feel at home. The private pool was a dream. Surrounded by trees and completely peaceful, it felt like our own hidden escape. We spent hours swimming and lounging by the water, and since it was deep enough to dive, it added that extra bit of fun we didn’t expect but absolutely loved. John was an incredible host—super responsive and kind. Any time I had a question, he got back to me right away and made sure everything went smoothly. It was so reassuring to know he was just a message away. If 10 stars were an option, we’d give them in a heartbeat. This stay set the bar so high, and we’re already talking about coming back. Huge thanks to John for making it such a memorable getaway!

Studio Apartment
Sahar was very helpful and nice. The place was very neat I will be back for sure, Highly recommended

JJ’s small town country retreat
I recently stayed at Jer’s Airbnb with a group of seven friends, and we had an incredible experience. The amenities truly made the stay unforgettable. We spent hours enjoying the pool table, foosball, darts, and old-school arcade machines. The private sauna and jacuzzi were perfect for unwinding, and the outdoor BBQ and fire pit setup created the ideal space for evening hangouts. Everything was spotless, well-organized, and located in a quiet, safe neighborhood. Jer was an excellent host, very responsive and clearly committed to providing a top-tier experience. I highly recommend this property to anyone planning a getaway with friends or family. We had an amazing time and would absolutely stay here again. Thanks, Jer! One thing worth highlighting is that the pictures don’t do this place justice. As great as it looks online, the property is 100 times better in person — more spacious, more comfortable, and filled with thoughtful touches that aren’t fully captured in photos.

Elora Heritage House
We had a great time visiting Elora for a night while staying at this listing. My husband and I stayed overnight with our 8 month old and Yorkie dog and were more than comfortable. The location is very walkable so we were able to pop in and out of the airbnb throughout our stay. There are great little shops and restaurants very close by. The Airbnb was very quaint and peaceful. We’d definitely recommend staying here.
Pet-friendly home rentals with a pool

Stunning Waterfront Estate with private beach
We had an excellent stay here. The location is incredible with a gorgeous lake view and amazing sunset view. Indoors it was spacious and very nicely decorated. We particularly appreciated that the airbnb was stocked with everything from kitchen supplies, washroom, even BBQ supplies - we didn’t need to bring a thing. Very well thought out. Gary was an excellent host, very responsive and attended to any question right away. Would definitely recommend a stay here!

Free parking 10 min walk to Falls & attractions!
A truly fantastic stay! Frank and Zoltan’s attention to detail shines through from their gorgeous home, to their detailed instructions, to the homey atmosphere they created for check in. A beautiful home, and great pool. Very close walk to Clifton Hill and you can see the fireworks over the falls from the backyard. I would definitely recommend!

Experience Country Living at Firefly Ridge
We really enjoyed our stay here. The place is exactly what we are looking for. Very cozy and quiet, nice hikes and most of all, the amazing animals. The girls spent hours hanging out with the horses and the pigs. Our time here was very memorable. There are amazing hikes nearby, small towns like Markdale and Flasherton and both have small restaurants, shops and cafes. John and Andrea are simply great! They are extremely kind and generous with their time. Excellent advice all the time, great conversations and will offer anything to make our stay more enjoyable. John let us help with the daily shores and feeding the animals. He also gave us excellent ideas for hikes, local attractions, etc. We are really looking forward to going there again next spring or summer.

Large 4 Br - 4.5 Bath; Sauna/Heated Pool/2 King
Great stay at Blue Mountain. The kiddos really enjoyed the game room and the pool table. it was also super convenient to be able to schedule free shuttle to pick up and drop off to and from the village. Even if couldn't catch the shuttle it's only 20 min walk.

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!!!

Beautiful Penthouse with Breathtaking View
Wafa was an incredible host and was always responsive and attentive to any questions we had. The place was just as described, clean, and had a wonderful view. Would definitely book again!

Heated Pool-tub Open 365 Days
We had a great stay! The house was spotless and very well maintained. Having three full bathrooms was incredibly convenient for our group, and the hot tub was a perfect. Highly recommend this place for a comfortable and enjoyable stay!

Utopia Villa and Spa
We had a wonderful stay at Shahrzad’s cottage in Innisfil! The place was cozy, clean, and exactly as described. It had everything we needed for a relaxing getaway. Shahrzad was a fantastic host—very responsive and thoughtful. The location was peaceful and close to the lake, which made it perfect for a weekend escape. We would definitely stay here again. Highly recommended!
Private, pet-friendly home rentals

Kempenhaus- Lake Simcoe Cottage & Spa
We had a wonderful two-night stay at this cozy cottage! The highlight was definitely the hot tub — perfect for relaxing after a day outdoors. The BBQ setup was great and made evening meals easy and enjoyable. The cottage was clean, well-equipped, and surrounded by beautiful nature views, making it a peaceful escape from the city. We especially loved sitting on the deck and taking in the quiet, scenic surroundings. Would definitely come back for another getaway!

Stonewell Farm Guest House
Stonewell Farm is an absolutely beautiful spit. The grounds were beautiful and the home was beautifully decorated in a tasteful not cluttered way. The beds, linens and towels were lovely. The only drawback was the bbq. It wasn’t clean and it was very slow for cooking. It just didn’t get very hot. I would not hesitate to book Stonewell Farm again.

Loft Where City Meets Country With Hot Tub
The loft is amazing, exactly as described and the hottub was incredible the pond/lake was awesome with the paddle boat, board, and kayaks. Theres so much space so even with all the other guests camping around you and shared space, it still feels super private. We also didn't realize they provided firewood and fresh eggs to help yourself to which was awesome!!

Charming and Peaceful Retreat with Hot Tub
My family (5 adults, 1 child, 1 infant) came to town for a wedding and were So Lucky to have stayed in this Beautiful home for 5 days last month. The house is spotless, modern, well maintained, and so spacious with plenty of very comfortable, well appointed rooms (4 upstairs, 2 basement) and bathrooms (2 upstairs, 1 basement, 1/2 main floor). The cozy living room is equipped with ample seating and board games. The dining room is large with a great table easily accommodating 10 people. The kitchen is huge and we found all we needed there. There is also a laundry room and mud room leading to the Fabulous hot tub in its own "house" on the outside deck. This Beautiful house is situated on a Gorgeous piece of property with Incredible views all around. The co-host, Brendan, was easy to communicate with and gave us clear instructions. This was the Perfect place for our day-trip into Toronto, "hiking day" in the Island Lake Conservation area, and relax-at-home day, before the wedding.

Romantic studio in a peaceful setting
Lissette was very considerate of our time and cared about our say. The unit was very clean, well decorated and nice personal touches to make it feel like a home which made our stay very comfortable.

Stunning 5 Bedroom Family Home
Tave was super responsive and flexible with our early check in request. The place was very clean and the beds and pillows were really comfortable. Nice modern kitchen with all the amenities.

Guest Suite in Hockley Valley
This was one of the most beautiful places I've ever stayed! I attended a wedding in the area and my only wish is that I had more time on the property. I would recommend this place to anyone and I hope I can stay again.

Explore 4BR 3BA Cottage Surrounded By Nature
Great place to stay, quiet. If you like being away from all of the city noise this is the place to be! We will be back. Thank you, DH
Quick stats about holiday rentals that are pet-friendly in Caledon
Total rentals
300 properties
Total number of reviews
7.4K reviews
Family-friendly rentals
170 properties are a good fit for families
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
190 properties have a dedicated workspace
Wifi availability
280 properties include access to wifi
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- Rogers Centre
- Scotiabank Arena
- CN Tower
- University of Toronto
- Budweiser Stage
- Blue Mountain Village
- Distillery District
- Port Credit
- Metro Toronto Convention Centre
- TPC Toronto at Osprey Valley
- Toronto Zoo
- Exhibition Place
- The Danforth Music Hall
- Harbourfront Centre
- CF Toronto Eaton Centre
- Massey Hall
- BMO Field
- Whistle Bear Golf Club
- Trinity Bellwoods Park
- Casa Loma
- Royal Woodbine Golf Club
- Dufferin Grove Park
- Royal Ontario Museum
- Royal Botanical Gardens