
Holiday rentals with a patio in Caledon
Find and book unique Holiday Accommodation with Outdoor Verandahs on Airbnb
Top-rated Holiday Accommodation with Outdoor Verandahs in Caledon
Guests agree: These Holiday Homes with Outdoor Verandahs are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Caledon Holiday Houses with Outdoor Verandahs
Apartment rentals with a patio

Cozy Upper Apartment with Private Deck at RBG
We had a great stay. The neighborhood is quiet and quaint. It was fun to walk around and explore the neighborhood. The place was clean, quiet and the beds were very comfortable.

Stylish Private Suite
Really enjoyed Blake’s house, so cute!! Blake was easy to communicate with. Would definitely stay there again.

Discover our new apartment in the Heart of Milton
Great place to stay. Within walking distance to downtown Milton. Beautiful basement apartment just like the pictures. The TV big-screen was amazing! Tito was a very responsive host and very helpful. Thanks again!

Lovely bachelor apartment with a patio
Has everything you need for a few days, clean and cozy.

Lovely 2 Bedroom Apartment attached to Main House
Mary was very nice and accommodating. The place was clean and felt right at home. Will stay here again, if the opportunity presents itself :)

Mill View one bedroom apartment . Upper level
Thank you so much for all the little extras. Loved the location, loved the bed. Have already booked another stay. Rachelle

Separate Basement Apartment
The place is so well kept and looks fabulous. We had a wonderful stay there, and it is worth the price!

Charming Apt w/ Private Deck in a 1890s Victorian
This space was very cozy with beautiful light and a great location. The host is friendly, communicative, and accommodating. We would stay here again!
Holiday House Rentals with a Verandah

Cozy Home
Staying at Sagana’s place was a joy for my family and I. The space was open, clean and better than what we even expected. Thank you for allowing us a flexible check in time and always responding to messages quickly!

Luxury 3+1 Bedrooms Home…
Great place to stay. Very clean and host was very accommodation and friendly!

Cozy 2-Bedroom Home with Patio
The house was exactly as described in the photos and, in fact, more beautiful. It was very organized and, above all, the owner was really very friendly and helpful. We stayed for several months but it was really a pleasure.

Brand New!
Jesse was an amazing host, ended up having a delay in our job which made us have to stay in town for longer than expected. Couldn’t renew our current Airbnb and booked with Jesse super late notice, he was able to make the stay happen, couldn’t believe it. The house is super nice and clean. Multiple snow showers while we were in town, every day when we got back from work the driveway, walkway, stairs, and porch were shoveled and salted. Jesse really cares about his guests and it shows. Hands down the best host I’ve had in the years with Airbnb. 1000/5, if you need a place this is it.

3 Bedroom with ensuites. Newly Renovated. Spacious
We had a great few nights at the house. The unit was perfect for the 6 of us to have our own space and also spend time together eating and enjoying conversations. Too cold to enjoy the fire pit but it looked lovely nestled among the vines. Definitely worth booking again if you’re wanting to explore the Bench.

Luxurious 2-Bedroom Space
Cody was friendly and very accommodating with our last minute booking. He was available whenever we needed to communicate with him.

kids paradise, extra storage, fenced, pet friendly
We loved staying here! There was SO much space, it felt very homey and cozy. The backyard was beautiful! This is an amazing home to stay in with tons and tons of room.

Professionally designed townhome
Cheryl's place is a nice, clean and comfortable home. Good location, easy to find and beds were really comfortable.
Holiday condos with a patio

Lovely 3 Bedroom Condo with Stunning View and Pool
We have a wonderful time at Sabine's place, which was an ideal space in every way. It was beautiful, well laid out, and had everything we needed. Sabine was very responsive and accommodating. We would gladly go back when we are next at Blue Mountain.

Cityscape Oasis w/ Private Patio & Parking
Bharat and his team are very responsive. We had a fridge issue and they were there the same evening with a solution and had the issued resolved as quickly as was possible. Lovely unit and a fantastic terrace with amazing views of the city. High end building and amenities (unfortunately the pool was closed for renovations) including a kids play room and extensive fitness facilities.

Loft Condo Resort Style Living in FRidAy HarBOUR
Ashley was quick to respond to messages and the room was very clean. It is somewhat far from surrounding towns. This is the ideal place for a quiet and cozy stay.

Modern Downtown Condo Free Parking/ Walk to Lake
Jessica was one of the best Airbnb hosts I’ve had in a long time! I celebrated my three-year anniversary here with my partner, and it was absolutely perfect. Jessica went above and beyond by setting up the room beautifully with flowers, rose petals, and electric candles—my partner was overjoyed. She was incredibly accommodating, allowing us to check in early and responding quickly to all my requests. The space itself was spotless, smelled amazing, and was incredibly comfortable. As a same-sex couple, safety is always a consideration when booking accommodations, but this location felt extremely secure. My partner and I were out late at night and felt completely at ease. The apartment has a double lock for added security, and the building itself is well-monitored. On top of all that, the view of downtown and the CN Tower was stunning. I highly recommend this stay, especially for couples—10/10!

Luxurious Friday Harbour Condo
Great listing, was surprised there were 2 showers one in each washroom, amazing view and Aaron went above and beyond to make sure we were good.

Luxurious 2 bedroom condo
Beautiful place! Easy check in! Felt very safe and comfortable! Around more than enough food options to choose from! Very responsive host! Was always readily available to answer any question I had! Would most certainly stay again!

Exceptional 2+1 ground floor condo @Friday Harbour
Shai was a great host. It is a beautiful location. We loved that there was a late check- out for 5 pm. I would definitely come back to stay.

Million Dollar Views, Free Parking, Gym, WiFi
We had an absolute amazing time staying at Gregory’s place in Toronto. The location was incredible and was within walking distance of so many restaurants and places to visit. We were able to visit the top of the CN Tower, see the Blue Jays and Maple Leafs play, and visit the Hockey Hall of Fame. We also spent time exploring the PATH and sampling the delicious food options. Throughout our stay, Gregory was in constant contact with us to ensure that everything was going well. We felt at home and could have spent another week there just admiring the beautiful view from the condo. The pictures were exactly what we hoped for with a spectacular view of the downtown and Lake Ontario both during the day and at night. The rooms were comfortable and having a grocery store within the building was awesome, especially when we wanted a late night snack. Our time at Gregory’s place was so much fun. We can’t recommend a better place, so stop looking and book your stay!
Quick stats about holiday rentals with a patio in Caledon
Total rentals
530 properties
Total number of reviews
13K reviews
Family-friendly rentals
240 properties are a good fit for families
Pet-friendly rentals
120 properties allow pets
Rentals with a pool
40 properties have a pool
Rentals with dedicated workspaces
320 properties have a dedicated workspace
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- Rogers Centre
- Scotiabank Arena
- CN Tower
- Blue Mountain Village
- Budweiser Stage
- Port Credit
- Horseshoe Resort
- University of Toronto
- Metro Toronto Convention Centre
- The Danforth Music Hall
- CF Toronto Eaton Centre
- Exhibition Place
- Toronto Zoo
- TPC Toronto at Osprey Valley
- Royal Woodbine Golf Club
- Massey Hall
- Snow Valley Ski Resort
- Whistle Bear Golf Club
- Harbourfront Centre
- Yonge-Dundas Square
- Osler Bluff Ski Club
- Trinity Bellwoods Park
- Royal Ontario Museum
- Casa Loma