
House holiday rentals in Caledon
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Top-rated house rentals in Caledon
Guests agree: These houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Caledon house rentals
House rentals with a pool

Luxury House with a Bright Sunroom & a heated pool
A perfect spot for a large group! The pool was great and the common space was large and comfortable! Bedrooms were good size and beds were comfy! Our host was gracious and even brought a birthday cake for my husband. Would definitely stay again!

Award Winning Luxury Home with Heated Pool + Sauna
My group and I truly loved this home ! It was quiet and in the perfect area for us! We will definitely be back!

Home away from home with a hot tub and pool
lovely spot for some quiet outside time. backyard is spacious and welcoming. plenty of options for seating to enjoy sun or shade. kitchen was absolutely amazing to prepare food in, well organized and nicely laid out. rooms were tidy and clean, plenty of space to sleep 6 comfortably. would highly recommend this spot

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!

Luxury Hockley Estate Spa
It was a great location and hosted a large group. Very nice place in a remote area, giving us the feeling of an outdoor oasis.

WhiteOrchid LuxuryHome WithSaltHeatedSwimmingPool
Beautiful place. The hosts were so kind and helpful. The area is safe and so close to the outlets which was a huge plus for us ladies! Hope to stay there again one day!

Heart of Kimberley - with views and a hot tub
We had an amazing experience. It’s a beautiful home with modern amenities and a beautiful outdoor area. We arrived in a cozy town with nearby restaurants and general store. It was a very clean and well prepped home. Our host was amazing. She was accommodating and very kind, always responsive and very welcoming. We highly recommend this stay. 10/10 experience.

Boutique Wine Country Home with Pool and Hot Tub
The place is gorgeous, clean peaceful and at close proximity to everything. The hosts were easy to reach out to and made sure our stay was everything we were hoping for. The pictures don’t even do justice to how adorable the place is. I highly recommend booking this place if you want to take full advantage of what Niagara-on-the-Lake has to offer! Thank you again for having us :)
Weekly house rentals

Stunning Luxury Home
Very peaceful location. Had a nice time at this place.

4BR Ultra-Modern Retreat – Fully Renovated & Chic!
A really well furnished placed to stay at. Had a couple requests which were handled by the host team quickly. They checked up on us during our stay and helped us out whenever needed. Would definitely recommend.

3BR Spacious Home - KING BED
Brigitte's place was amazing! Very beautiful property, very spacious and inviting! Very clean and she has everything labeled which is very helpful! Has everything you could think of and more. We traveled with a group of 4 grown men for a golf trip and it was more than enough space for everyone! Having 2 full bathrooms is a must and the en-suite attached to the master has a beautiful soaker tub. Very beautiful deck with BBQ and comfortable patio furniture and the front yard has a nicely landscaped firepit which we didn't use this time but will next time as we will definitely be back! Great place for families and it is even pet friendly! Brigitte is an amazing host, very attentive and knowledgeable of the surrounding area. Nicest Air BnB I've ever personally stayed at! Solid 9/10

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.

Home Away from Home
Bayo’s place was amazing! It’s a beautiful, modern, and brand-new home. The location is in a newly developed area, so while it shows up on Google Maps, some delivery apps like Uber or DoorDash may not recognize it yet just a heads-up for future guests. I’m sure this will be resolved by the apps over time. The home was stocked with all the essentials, along with thoughtful touches from the host. Easy access to the main road and Caledon made getting around a breeze. Would definitely stay here again!

Luxury Home - 5 min from airport, 15 to downtown
This was our second time staying here. Love this location and home. Tina is an excellent communicator and host. Highly recommend.

Central OVille,3 bed Victorian, walk to Lake, pets
We loved staying at George’s place. Easy to find and clean. Host was great. We will be back!

HomeSweetHome!
This is the second time I stayed at Allison’s place and it is a lovely spot. The house is clean and comfortable and the kitchen well equipped. It is a perfect home away from home.
Private house rentals

Charming Farmhouse Stunning Views & Hot tub
Top notch and 100% what I had envisioned. My family stayed for 3 nights and it was worth the drive. The location was remote on a farm but close enough to the city as we were able to run into the city to get any items we needed. But once you entered the gate, it felt like a nice country get away. I loved every minute of my stay and would do it again in a heartbeat. There was more than enough room for us to relax and enjoy ourselves. Thank you for allowing us to host my special day. It was definitely a weekend to remember.....

Debonair Luxury Stays
We had a very comfortable stay at this conveniently located Airbnb, just minutes from Pearson International Airport with easy access to other parts of the city. The space was beautifully decorated with elegant touches and thoughtful details throughout. Do note that there are stairs to reach the main and lower levels, which may be important for some guests to consider. Check out process is simple and easy. Danielle was an exceptional host—very responsive and attentive to our needs. Highly recommend!

Contemporary Design | Spotless | Cozy | Workspace
This house is just awesome! Really enjoyed our stay. Thank you for allowing us to use your space! It nice clean and just simply awesome. Thanks again everyone!!

100% Private & Spotless ~3BR, 3.5WR ~Trinity Plaza
Great home and secure area close to shops , supermarket and mall I am recommend this house. It was clean house

#1 Best Deal in Brampton
beautiful house in a fantastic location. felt right at home. the house was very clean and I would love to stay here in the future. Pawan was very responsive and helpful

Entire Lower Level Home 3500 Sq Walk Out
“Hands down the best AirBnB I have stayed at! It’s gorgeous, clean, extremely spacious, and well decorated with a beautiful modern touch. My friends and I were in awe of the space. All the photos turned out so well thanks to the large ceiling to floor windows which made the lighting impeccable. We didn’t even notice the family on the upper floor —it truly feels like a separate, private place. Our host Sophia was also incredibly responsive and kind throughout the process. I am most definitely going to recommend to all my friends. Highly, highly recommend!”

Luxurious Prince Mansion
Honestly, this house was well worth the cost. I would have preferred unattended checkin (mostly because we arrived so late and I felt bad for Aziz!) but he was punctual and didn't complain a whit about the hour. The shower was so fancy (3 showerheads, 4 knobs!) that it likely would have taken me another day to fully figure out all the permutations. The house overall was exquisite, from furnishing to location, we couldn't have asked for more. There were a host of restrictions about "partying" but honestly this was a family trip and not a concern for us. The family still enjoyed the hot tub until 1am while older members of the group went off to a perfectly peaceful sleep before 10pm. There was room enough for everyone to have their own way and plenty of spaces in which to come together.

Ravine Home | Spotless Retreat by Toronto and YYZ
It was our pleasure to once again stay at this Airbnb while visiting for a Horse Show at Caledon Equestrian Park. A quick 10 min drive to the park, spacious and comfortable layout - we have already booked twice more!
Quick stats about house rentals in Caledon
Total rentals
1.2K properties
Total number of reviews
13K reviews
Family-friendly rentals
400 properties are a good fit for families
Pet-friendly rentals
190 properties allow pets
Rentals with a pool
40 properties have a pool
Rentals with dedicated workspaces
560 properties have a dedicated workspace
Destinations to explore
- Niagara Falls Holiday rentals
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- Niagara-on-the-Lake Holiday rentals
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- Rentals with a fire pit Caledon
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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