
Vacation rentals with outdoor seating in Caledon
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Top-rated outdoor seating rentals in Caledon
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House rentals with outdoor seating

Stunning 4-BDRM Home-Toronto Area - Quiet Location
We have stayed in a few of Cody's places and have had nothing but positive experiences. This house is in a quiet neighborhood and we enjoyed the back deck after work to relax on. Close to major places to eat and shop. 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...

Stunning Luxury Estate - Your Memorable Retreat
We had a great experience renting this home. We stayed for 2 months. A lot of space for entertaining/ bonding with family. Really enjoyed having 2 separate kitchens. Very spacious house and huge backyard. Everything was perfect.

Luxurious Spacious Dream Home with Parking!
Host is very friendly and responsive! The place was perfect for us!

Beach House-S/W Exposure! Hot Tub, Sandy Water!
Wonderful stay! Our host Dylan was very quick to respond and extremely accommodating. The home fit our large group comfortably. The home was spotless, beds were very comfortable and we appreciated all the little extras (lots of towels, warm blankets, coffees, teas, little treats) Hot tub was very relaxing and clean. Lots to do, we all enjoyed ourselves and we’re already planning our return 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!

Beautiful Riverside Country Apartment
I enjoyed a peaceful 2 weeks at this beautiful Airbnb! The setting is surreal surrounded by nature and a river! I had everything I needed and I enjoyed a few nights with a cozy fire in the wood stove. The bed and couches were very comfortable. The No Frills in Shelburne was a great grocery store nearby. Wendy was always very responsive and helpful. As clearly noted in the description, there is no cell service but not a big deal as there is wifi. I hope to be back again one day! A true gem!

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
This was a perfect setting for us - we particularly enjoyed the patio, it was a comfortable place to enjoy nature and good conversations.

The Evelyn Suites - Suite B - Petit Pied-à-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

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
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
Charmant endroit pour relaxer et profiter du bon temps. Il était très facile d’accéder au logement et j’ai apprécié avoir accès à une petite cour. Le condo était propre et commode. Je recommande à tous.

SpectacularPenthouse VIEWS/ POOL /free Parking
Très bel appartement, avec une vue exceptionnelle, piscine et salle de sport , terrain public et visible depuis l’appartement qui est non loin de la. Très bonne literie. Bien situé, à côté du métro . Petit plus : parking inclus. Conciergerie au top et merci à Harit la réceptionniste. Séjour parfait

Elora Grandeur: The Pinnacle Retreat"
Would definitely stay at John’s place again! The location was extremely close to downtown Elora, as well as the Elora Mill (where we were attending a wedding). The place was perfect for 5 to stay, with lots of room and great amenities. John was very responsive and accommodating. Thank you for your hospitality, and for an amazing weekend!
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
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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
- Trinity Bellwoods Park
- Whistle Bear Golf Club
- Casa Loma
- Royal Woodbine Golf Club
- Dufferin Grove Park
- Royal Ontario Museum
- Royal Botanical Gardens