
House holiday rentals in Pickering
Find and book unique houses on Airbnb
Top-rated house rentals in Pickering
Guests agree: these houses 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 house rentals in Pickering
House rentals with a pool

Beautiful Cottage in Ajax
This was the perfect place for our family to celebrate my father's 90th birthday! This home is spacious, clean, and has all the extra's that you need! The kitchen is well stocked and beautiful. There are plenty of windows for natural light! The backyard is a peaceful oasis where we enjoyed the large pool and fireplace. It is located minutes from grocery stores etc, but it feels like you are far from the busyness of the city. Sabesan was a fantastic host, responding quickly to questions and making sure we had the best experience possible. I highly recommend this property and we hope to be back again!

Award Winning Luxury Home with Heated Pool + Sauna
My group and I truly loved this home ! It was quiet and in the perfect area for us! We will definitely be back!

Home away from home with a hot tub and pool
lovely spot for some quiet outside time. backyard is spacious and welcoming. plenty of options for seating to enjoy sun or shade. kitchen was absolutely amazing to prepare food in, well organized and nicely laid out. rooms were tidy and clean, plenty of space to sleep 6 comfortably. would highly recommend this spot

Ultimate Privacy In The City | 4 Bdrms 4 Washrooms
We had a delightful stay at Jasmine’s place. The space was impeccably clean and thoughtfully decorated, making it feel like a true home away from home. Jasmine was an exceptional host—attentive, communicative, and always ready with helpful replies with my questions. I highly recommend her place to anyone visiting the area and would love to return in the future.

Heated Pool-tub Open 365 Days
We had a great stay! The house was spotless and very well maintained. Having three full bathrooms was incredibly convenient for our group, and the hot tub was a perfect. Highly recommend this place for a comfortable and enjoyable stay!

Private Pool + BBQ + PS4: 5 Bedooms, 3 Bathrooms!
Neil was an amazing host for my large group! Extremely responsive and helpful with any questions you might have and the Airbnb + pool are lovely! The home was clean and as pictured in the listing would highly recommend!!!

Ravine Paradise ! heated pool and hot tub!
this was one of the best airbnbs we stayed at. the place was clean and even more beautiful than described. Preston communicated with me months before we rented, through tech difficulties, before during and after the stay. they were understanding, courteous, and helpful. would stay here again, even my sister who visited inquired for the future.

Toronto Vacation Pool/Park/Zoo/Casino
House was well situated for our purposes and rooms were spacious and clean. Nice to be able to turn on fireplace in one of the sitting rooms. Enjoyed our stay.
Weekly house rentals

Private Bedroom, Bathroom, Kitchen -Basement Apt
Ana is a great host and was caring and responsive. I stayed there a couple of months and felt at home. It was really great to have a private unit all to myself and for relatively reasonable price. The location is very convenient, with public transit, grocery stores, libraries, and lots of other stores very close by. The unit is quite spacious. The kitchen is probably more suitable for light cooking or heating of food, and there’s not a ton of refrigerator space. My only discomfort during my stay was that when the weather was very cold, the heat in the room was very warm, especially at night. But it made the laundry dry quickly, which was good. All in all, I’m glad I found this place and I really enjoyed my stay.

Just Like Home- Brand New 4 Bedroom Home
Jason is responsive and easy to communicate. We are happy with our stay. The house is great very comfortable and clean. His place is very peaceful. I like the community. Thank you Jason, I highly recommend your house.

Holiday Hideout Basement Unit
Sobia was a great host, very friendly and pleasant to deal with.

Private Suite - Ajax by the Lake
Lovely place and lovely hosts. Honestly couldn't have asked for more. We felt very welcome and Nadia and Ifte were always available for help and information. Would definitely recommend.

Modern cozy living.
Our family enjoyed a super clean and comfortable at Noor’s place! Location was fantastic and walkable to grocery stores, plazas, and the highway. The place itself was spotless and spacious. Couldn’t be happier with our stay!

Lavishing & Modern Apt. with Free Parking
This is a cute apartment conveniently situated. It is well thought out for travelers.

Beautiful 2 Bedroom Home Suite
Nice basement, very clean and updated fixtures

1 bedroom cozy basement apt with separate entrance
Sonia was a wonderful host and was really nice and understanding.
Private house rentals

Sunlight.
Very clean and spacious. Great location. Lots of amenities close by. Perfect for our group of 5 in Toronto for a tournament.

Family Friendly Apartment with Private Entrance
Very polite and communicative and responsive. The basement of the home is a very nice unit. Very clean. Hosts were excellent and very polite. Would recommend to anyone coming to Oshawa or Whitby area for a lengthy stay (we did 4 days).

3 bedroom bungalow in South Ajax
my stay at Mrinals place was amazing! it looks exactly like the photos and was so clean. my family stayed here before moving out of the country and it was literally stocked with anything you’d need! anything we needed in the kitchen they had as well as laundry detergent and cleaning supplies. there was so many extra towels, sheets, and bedding. the check in was super easy and everything was exactly like the photos. The driveway has good space as well, me and my family were able to fit 2 SUV’s. Mrinal was an amazing host and very responsive and kind. I highly recommend!

6 beds Full house W ravine view
Jeya’s home was perfect for our group! It was clean, well kept, spacious, and comfortable. Check-in was easy, wifi worked great, and Jeya answered questions quickly and effectively. I highly recommend staying here!

Cheery 1941 Historic Home in Ajax
Such a beautiful home Marie has, it was spotlessly clean with all amenities and more. Above all Marie was extremely responsive and friendly, simply an amazing host. Thank you Marie for the awesome experience.

Elegance and Comfort
The place was great for us four folks. The location is close enough to Frenchman's Bay where we paddled each day. The house is 5 min to highway 401 making access to anywhere pretty easy. The place was very clean and spacious. It is a little chilly being downstairs, but with the two space heaters and the gas fireplace, the place warms up pretty quickly. We would stay there again next year if we return to Pickering. Thanks Oliver!

Cozy Guest Suite Basement Apartment
A home truly like home. Imran was very kind and responsive. Will stay again!

Basement in Ajax w/ Private Entrance
Charvi was really kind and the place was very spacious. It had everything I needed and made for a very comfortable stay.
Quick stats about house rentals in Pickering
Total rentals
980 properties
Total number of reviews
16K reviews
Family-friendly rentals
410 properties are a good fit for families
Pet-friendly rentals
180 properties allow pets
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
590 properties have a dedicated workspace
Destinations to explore
- Niagara Falls Holiday rentals
- Grand River Holiday rentals
- St. Catharines Holiday rentals
- Niagara Falls Holiday rentals
- Brampton Holiday rentals
- Buffalo Holiday rentals
- Pocono Mountains Holiday rentals
- Mississauga Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Hudson Valley Holiday rentals
- Montreal Holiday rentals
- Smoking-friendly rentals Pickering
- Pet-friendly rentals Pickering
- Rentals with pools Pickering
- Rentals with beach access Pickering
- Rentals with a firepit Pickering
- Rentals with an EV charger Pickering
- Rentals with a fireplace Pickering
- Cottage rentals Pickering
- Rentals with lake access Pickering
- Family-friendly rentals Pickering
- Fitness-friendly rentals Pickering
- Rentals with a hot tub Pickering
- Rentals with a patio Pickering
- Family-friendly rentals Pickering
- Apartment rentals Pickering
- Flat rentals Pickering
- Private suite rentals Pickering
- Waterfront rentals Pickering
- Guest house rentals Pickering
- Rentals with breakfast Pickering
- Rentals with a washing machine and dryer Pickering
- Townhouse rentals Pickering
- Beachfront rentals Pickering
- Rentals with outdoor seating Pickering
- House rentals Regional Municipality of Durham
- House rentals Ontario
- House rentals 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
- 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
- Casa Loma
- Royal Woodbine Golf Club
- Jackson-Triggs Niagara Estate
- Dufferin Grove Park
- Royal Ontario Museum
- Cobourg Beach
- Toronto City Hall