
Vacation rentals with outdoor seating in Caledon
Find and book unique outdoor seating rentals on Airbnb
Top-rated outdoor seating rentals in Caledon
Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Caledon outdoor seating rentals
House rentals with outdoor seating

Hot Tub - Cozy - Guelph 3 Bed 1 Bath Loft House
Wonderful spot! Had a great time :)

Stunning 4-BDRM Home-Toronto Area - Quiet Location
House was clean and Spacious Cody is a great host. Highly recommend

Austrian Log house
The Austrian Log House is a little slice of heaven. We enjoyed every minute of our stay, and really hope we will get to go back again someday. The location is peaceful and quiet with beautiful views. The log house was very clean, had everything we needed, super comfortable beds. This place is absolutely stunning!! And our host was super friendly, helpful, and made us feel so welcome. It was a truly magical weekend away at the beautiful Austrian Log House.

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.

Modern Lakefront Cottage In The City With Hot Tub
We really enjoyed our stay. It was very clean, peaceful and can’t wait to book again!

JJ’s small town country retreat
the house has been in the family since 1934, however has been updated and additions built that adds to the charm. Super cool sauna lay out and the bedrooms were spacious and clean...we had a great stay and even managed a few cider tours in the surrounding area. so fun...

Luxurious Spacious Dream Home with Parking!
Romalis place was Beautiful comfortable, so spacious and clean!!

Fun living space
We had the great fortune to host my wedding at Ankush's place. He was very responsive and accommodating to all our needs. We hosted some pre events at the house and all the guests loved the venue. I would highly recommend this place if you are looking to host your wedding. Even if not, the house offers a great escape from our otherwise monotonous routine. The house is equipped with pool table, table tennis, soccer, darts, fully equipped bar, cricket pitch, putting turf and so so much. Thank you to the hosts for a flawless stay!
Apartment rentals with outdoor seating

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!

hidden gem hot tub and igloo st-catharines
Excellent spot. Exactly as described: hot tub is indeed hot (and clean and works well), beds are very comfortable, it is easy manage temperature, the shower was great, and kitchen well stocked. All just perfect. Isabelle was very kind and helpful, too. Would recommend and would return!

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

The Upper Deck
Words can hardly capture the magic of Cathy’s BnB in Wasaga. From the moment we pulled into the driveway, we knew we were about to experience something special. This isn’t just a place to stay — it’s a destination in itself, a beautifully curated space that feels like stepping into the pages of an artist’s journal. The first thing that struck us was the atmosphere — peaceful, welcoming, and infused with personality. Every inch of the property is meticulously thought out and bursting with creativity. You can feel Cathy’s heart in every detail. It’s clear that this isn’t just a business for her — it’s a lifelong passion project rooted in artistry and hospitality. Cathy’s background in the arts and event world shines through in the most delightful ways. If you’re looking for something more than just a rental, if you want to stay somewhere that feeds your soul as much as it rests your body, Cathy’s BnB is it. Thank you so much for our stay!

Bright and Spacious 2 bedroom. Quiet house.
We had such a wonderful stay. The space is absolutely spotless. It is in a wonderful area. I would absolutely recommend Marinas's place and I hope to stay again as well.

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
Janet’s place was perfect and exactly like the photos. Very cozy and homey feel. It is a basement suite and it was nice that she had a space heater and fireplace to keep us warm. She even had a basket of snacks for us when we arrived which the kids loved. This was very helpful as we arrived on our flight at almost 1am and needed a little snack. We highly recommend Janet’s place to anyone wanting a nice private place near the airport and a peaceful place to rest. Thank you Janet!

The Evelyn Suites - Suite B - Petit Pied-a-Terre
We felt right at home at the Evelyn Suites. We were in town for a wedding at the Mill and the location was walkable to the wedding venue. Also super close to all the amenities in town. We would definitely stay here again!
Condo rentals with outdoor seating

Lovely 2-bedroom at Friday Harbour
Lovely stay as described! Would recommend

“Elysium” Where happiness is real!
everything was as described bed was comfortable and clean I would stay there again if necessary

Designer Condo with beautiful harbour view.
Very beautiful place and surroundings. Host was very helpful with giving us advice and answering any questions we had

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
Shai’s place is beautiful and he was very easy to communicate with. Wonderful stay.

Lovely Open Concept Friday Harbor Resort Condo
We stayed at Mark & Lisa’s place for a night and had a great night. Mark’s very responsive and gave very detailed instructions before the check-in. The place is nice and has all amenities one needs. We didn’t get to use most of them such as BBQ, patio furnitures, dishwasher, coffee machine, etc , due to limited time there, but these are all available.

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

SpectacularPenthouse VIEWS/ POOL /free Parking
Very nice apartment, with exceptional views, pool and gym, public land and visible from the apartment which is not far from it. Very nice bedding. Good location, next to the subway. Bonus: parking included. Excellent concierge and thank you to Harit the receptionist. A perfect stay.
Quick stats about vacation 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
Destinations to explore
- Niagara Falls Vacation rentals
- Grand River Vacation rentals
- St. Catharines Vacation rentals
- Niagara Falls Vacation rentals
- Brampton Vacation rentals
- London Vacation rentals
- Buffalo Vacation rentals
- Niagara-on-the-Lake Vacation rentals
- Pocono Mountains Vacation rentals
- Mississauga Vacation rentals
- Greater Toronto and Hamilton Area Vacation rentals
- Greater Toronto Area Vacation rentals
- Bungalow rentals Caledon
- Rentals with a fireplace Caledon
- Smoking-friendly rentals Caledon
- Pet-friendly rentals Caledon
- Condo rentals Caledon
- Rentals with lake access Caledon
- House rentals Caledon
- Kid-friendly rentals Caledon
- Rentals with a patio Caledon
- Apartment rentals Caledon
- Bed and breakfasts Caledon
- Rentals with a fire pit Caledon
- Rentals with a hot tub Caledon
- Townhouse rentals Caledon
- Family-friendly rentals Caledon
- Rentals with an EV charger Caledon
- Private suite rentals Caledon
- Rentals with breakfast Caledon
- Guesthouse rentals Caledon
- Waterfront rentals Caledon
- Rentals with pools Caledon
- Fitness-friendly rentals Caledon
- Rentals with a washer and dryer Caledon
- Rentals with outdoor seating Regional Municipality of Peel
- Rentals with outdoor seating Ontario
- Rentals with outdoor seating Canada
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- 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
- Trinity Bellwoods Park
- Whistle Bear Golf Club
- Casa Loma
- Royal Woodbine Golf Club
- Dufferin Grove Park
- Royal Ontario Museum
- Royal Botanical Gardens