
Holiday rentals with outdoor seating in Caledon
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Top-rated Holiday Houses with Outdoor Seating in Caledon
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.
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Holiday House Rentals with Outdoor Seating

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!

Hot Tub & Private Suite - Casa Facciolo
This was a wonderful place to stay and was exactly where I needed to be after long, hectic days. Sherry is a great host - very friendly, accommodating and making sure I was comfortable. Her gardens make it seem like paradise when you walk from the driveway to the private entrance - love love love the lilac trees beside the parking space ❤️ This felt like I was staying with a friend rather than in a stranger’s place. Thanks Sherry for all your hospitality!

Log Cabin in the heart of downtown Elora
We stayed at Andrew’s log cabin in Elora and had a such a fantastic time. Firstly, the cabin was so beautiful, thoughtfully appointed and very comfortable. Andrew provided timely recommendations on food and activities. I would highly recommend the Cabin and Cove.

RivertrailRetreat | Unique Deck + Skiing + Theatre
My family absolutely loved Paul’s place. Clean, modern, well stocked and beautifully decorated. The accommodation met and exceeded our expectations. It has to be the best ABNB accommodation we have stayed in. Communication with Paul was professional yet friendly. I would have absolutely no hesitation in recommending Paul’s Rivertrail house.

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.

Beach House-S/W Exposure! Hot Tub, Sandy Water!
We stayed at Dylan’s place for the weekend with 13 adults and 4 kids. There was enough rooms and beds for all of us with adequate bedding and space. The house was clean and well equipped for our weekend! Before the stay we had lots of questions and Dylan was very responsive and answered everything in a timely manner and with lots of details. He was always following up during the weekend as well. The dock is beautiful and amazing! It was a bit buggy but that’s expected near the waters. We used the kayaks and boat and had a wonderful time!

Modern Custom Home w/ Pool, Games & Parking
I was more than lucky to have found Natalie’s place, it’s in a great neighbourhood, place was exactly like the photos & as described, and the most amazing host I’ve ever encountered in this app. Natalie was always more than accommodating with my requests & responded on time. She is also such a great person herself, she will not let you down. A million thank yous Natalie 🥰

Spacious & Modern space with Yard, TT, PS4, Piano
I had a fantastic stays at this spacious and spotless house. The home was very clean and well maintained, with plenty of room to relax and feel comfortable. Everything was just as described, and the check in process was smooth. I would definitely recommend this place to anyone visiting and I would happy to stay here again!!
Apartment rentals with outdoor seating

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!

hidden gem hot tub and igloo st-catharines
This place was awesome! Just as described. Would absolutely stay here again. Our luggage was delayed and the host was so gracious in helping us get that squared away. So thankful!

The Hilton BnB Adult Luxury Suite
My husband and I spent our first year anniversary at Lanny & Jennifer’s beautiful property. Right from the start, they made us feel right at home by greeting us and giving us a walk through of the property. We never felt so at home at an air b n b! The place is so well kept - clean, smelled great & had all the essentials. We felt safe and at home throughout the stay. The pool was well kept and the laundry was an amazing addition. The neighbour hood is quiet and close to all the stores. The hosts were extremely personable and made sure we had everything we needed for our stay. We highly recommend this property and we will be back!

Beautiful Riverside Country Apartment
The gardens and creek were just lovely…the apartment was clean & pretty much had all I needed. In particular the bed was excellent- had a great sleep. Would stay here again, if needed. Wendy was easy to communicate with & prompt with her replies & very accommodating to my schedule. Thank you, Wendy!

Vintage Dreams | Mid-Century Design in artsy area
We had a wonderful time! Would highly recommend!

Bright and Spacious 2 bedroom. Quiet house.
Lovely home very detailed and helpful instructions. Thank you Marina.

Comfort, Style and Privacy.
Such a beautiful and clean place. Very quiet and private. My husband and I loved everything about it. Can’t wait to come back!!

As seen on HGTV! 2-Bedroom Luxury Apartment
We had a pleasant experience. The apartment was super clean and was stocked with everything you might need. We will definitely stay there again.
Condo rentals with outdoor seating

Bright MCM 2 Bedroom Walk Up with Private Deck/BBQ
I rented unit for my parents and they absolutely loved their stay! The place was clean, nicely decorated, and had everything they needed for a comfortable visit. The host was incredibly welcoming and responsive, making check-in was nice and easy. The location was perfect—quiet, yet close to everything. Would definitely stay here again and highly recommend to anyone visiting the area!

Lovely 2-bedroom at Friday Harbour
Gorgeous condo! Wonderful People, highly recommend

“Elysium” Where happiness is real!
David was a wonderful host. He responded immediately with clear instructions. The place had thoughtful, generous touches to it, making one feel at home and/or like a very welcomed guest. The shower was amazing, I want it! :)

Entire Condo - 20min from Toronto Airport
Yassine and Amela are exceptional hosts. They were very responsive and provided all the check-in information I needed to enter the condo especially since I arrived late at night. The condo is beautifully furnished and very clean. The kitchen has all the amenities needed and is well stocked with tea, coffee, and hot chocolate. It is located in a quiet neighborhood, close to grocery stores, a shopping mall, and great restaurants. It is conveniently located to major highways leading to the airport, Toronto, and Niagara Falls. I had a great stay and look forward to returning. Thank you Yassine and Amela for being such warm and welcoming hosts!

Exceptional 2+1 ground floor condo @Friday Harbour
Loved this place so much! Shai was amazing. Definitely will be coming back!

Lovely Open Concept Friday Harbor Resort Condo
If you’ve never been to Friday Harbour it’s an amazing weekend escape with beaches, pools, bars and restaurants and light shopping. We spent our 10th anniversary at Marks Condo in the Harbour and loved every minute of it. Mark’s condo in Friday Harbour really is a gem. It’s on the top floor of a quiet building just steps away from the main boardwalk, hiking trails, and everything else Friday Harbour has to offer. The building complex offers communal BBQs and fire pits that are available and easy to use. The condo itself is very clean, bright, with its own balcony and everything you could possibly need. Marks check-in instructions are very detailed and thorough and is great at communication should anything come up. It was an incredible weekend and we will 100% come back.

Resort Condo in Friday Harbour
Great place to stay! Close to everything!

SpectacularPenthouse VIEWS/ POOL /free Parking
Judy's one bedroom apartment felt like a home away from home. We never heard our neighbors or any disturbing sounds through the walls. The other residents of the building were friendly and helpful. The property is an easy five-minute walk from the subway and buses. We were able to visit all the Toronto destinations on our list, then we could retreat to this haven in the sky. The bed was very comfortable. There were plenty of bed and bath linens. The kitchen included all we needed to cook and dine. It would have been handy to have more regular-size spoons and forks. We enjoyed a swim in the pool and a soak in the hot tub.
Quick stats about holiday rentals with outdoor seating in Caledon
Total rentals
260 properties
Total number of reviews
11K reviews
Family-friendly rentals
140 properties are a good fit for families
Pet-friendly rentals
70 properties allow pets
Rentals with a pool
30 properties have a pool
Rentals with dedicated workspaces
190 properties have a dedicated workspace
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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