
Holiday rentals with outdoor seating in Caledon
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
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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Popular amenities for Caledon outdoor seating rentals
Holiday House Rentals with Outdoor Seating

Luxury Home I Mins from Falls I Pool & Pong Table
Had an amazing time here. Very responsive, and clean. Had lots of space to fit the 12 in my group. A great area with lots of different types of food, and a nice walk to Clifton Hill. Highly recommend staying here.

Sunlight.
Suzanne’s place was excellent! Bright, clean and quiet - perfect for our weekend stay. It had everything we needed to cook meals for ourselves and Suzanne was kind enough to let us check out late to accommodate my son’s swim meet schedule. We would 100% stay there again!

Country Oasis in the Village - 4 bed - 2 bath home
We booked our stay for a wedding at the Elora Mill and this place was a great spot for a group of 4!

Family Home Near St Clair W and Public Transport
Great for our family of 4…easily holds family of 5 because of 2 beds in the 3rd room. Well stocked and very clean. Perfect location for visiting family and being close enough to downtown. Great hosts - would recommend.

Garden House.
Edu is a great host and he provide us all the information about the area and showed us exact places to see and places for free parking, Really enjoyed his place with our guests also enjoyed a lot. Thank you Edu for everything you did for us.

Debonair Luxury Stays
Long weekend with family here. Was perfect. Thank you. Exactly as advertised. Clean and very functional for us. Highly recommended.

Victorian Home Downtown Toronto, Cabbagetown
We came as a group for a raptors game and Sarah’s place was the perfect accommodation! There was adequate space and it was one of the most comfortable spots. Overall, u a great stay!

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.
Apartment rentals with outdoor seating

Modern Lakefront Apartment
Doreen and Derek were excellent hosts. They were warm, friendly and receptive. The place was clean, nicely furnished and the kitchen had all necessary amenities. The neighbourhood was quiet and beautiful. We would like to visit the place again if the opportunity arises.

Cute Private Apartment near University of Toronto
Rhuland's place was exactly what we needed! We were attending an event nearby and it was perfect. So clean and comfortable! In a nice and quiet neighbourhood as well so if you want a place that isn't right in the hustle and bustle of the city, but close enough to it to be convenient, this is the place for you.

One bedroom vacation rental at The Beaches
Very responsive and welcoming host! Would definitely stay again in the future 😊

Mill View one bedroom apartment . Upper level
Shannon’s place is a great place to stay in Elora. Walking distance to all attractions. She is super responsive and helpful. Left us some treats that were very much appreciated. Will definitely be back 🙏🏼

CY3 Icing on the Cake--Chic DT Basement Unit
A great deal with friendly hosts and very smooth check-in process. The interior is well-decorated and the kitchen is fully equipped. Worth for a visit and thank you very much for the nice place.

AirBnB Elora : Victoria Street Retreat
Christine was a fantastic host! We loved our stay at her Elora Airbnb. It had enough space for my family (we have 8-month-old baby) to get comfy and relax while we were in elora for a wedding at the Mill. The place was spotless and came with any and every amenity we could need (e.g., an iron to crisp up our wedding attire). The Airbnb is so conveniently located to the Elora Mill, and a very short walk to elora’s main restaurants and shops. We loved everything about this stay!

Charming Apt w/ Private Deck in a 1890s Victorian
Kate's place is fantastic. It's exactly as described. It's one of the cleanest airbnb's we've stayed at in several years. In fact, it's one of those rare places where we felt we didn't need to wash all the dishes before using them. The bathroom was spotless. The bed was also very comfortable, and Kate was friendly, proactive and responsive.

Hygge Hidden Gem Apartment
The place was cozy and comfortable. The host was very responsive and made sure I had everything I needed. I would stay there again when visiting in the area. It felt like home.
Condo rentals with outdoor seating

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.

2BR Getaway at Friday Harbour All Season Resort
Brilliant location for the harbour everything in walkable distance, clean and well stocked kitchen . Responsive host would recommend.

Close to Village, 2 Bedrooms , Rivergrass
We had a great girls weekend away at Bruce’s place! It was very cute and homey, well stocked and very comfortable. Great location too - the shuttle service was a bonus! Unfortunately we had to deal with a wide spread power outage while there but the place was equipped with emergency lights and we made the most out of it. Will definitely be back.

Beautiful Condo, 2 Bedrooms and a Den in a Resort!
Shahed's place at Friday Harbour is beautiful and well appointed. He gave very clear instructions for entry and parking, including photos. The condo was clean and had all the amenities needed, even extra charging cables for devices! The space was comfortable and uncluttered. Shahed was great at communicating and always responded quickly to any questions. Friday Harbour has activities and restaurants available on weekends in the winter and is a fun engaging place by the harbour in the spring, summer and early fall. We were there in the early part of the week in February so the harbourfront was quiet but still nice for a stroll. We spent time in both Barrie (20 minutes away) and Orillia (about 50 minutes away).

Exceptional 2+1 ground floor condo @Friday Harbour
Shai was a wonderful host — everything was great from start to finish! The place was clean, comfortable, and exactly as described. Highly recommend!

Friday Harbour Luxury Condo Escape, Sleeps 4
My boyfriend and I stayed the weekend, it was a great location, Joe was very responsive and friendly! We had only 1 concern with the bbq that was not clean, but it has been handled with effectively. Overall space was very clean, it was easy to find kitchen supplies, and other items in the house! A great location with stores, restaurants at a walking distance, and other attractions within a 30 minute drive

Marina view at Friday Harbour 2bd/2bth Pool option
Immaculately clean, spacious, and Beautiful condo. It had everything we need and a few steps to the marina. Easy instructions to get inside and parked. I highly recommend!

Lake Simco penthouse at Friday Harbour resort
my friends and I had a fantastic stay at Anna's place. It is a beautiful condo in a great location, with lots of great places to eat and very safe and walkable. we enjoyed the balcony and the spacious and eclectic interior for a bachelorette hang out. Anna was very responsive and kind. highly recommend!
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
- Blue Mountain Village
- Budweiser Stage
- Distillery District
- Port Credit
- Horseshoe Resort
- Metro Toronto Convention Centre
- The Danforth Music Hall
- Exhibition Place
- CF Toronto Eaton Centre
- Toronto Zoo
- TPC Toronto at Osprey Valley
- Massey Hall
- Whistle Bear Golf Club
- Royal Woodbine Golf Club
- Harbourfront Centre
- Yonge-Dundas Square
- Snow Valley Ski Resort
- Trinity Bellwoods Park
- BMO Field
- Royal Ontario Museum