
House holiday rentals in Pickering
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Top-rated house rentals in Pickering
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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!

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.

King West Victorian Studio Gem
What an absolute gem of a house! I felt right at home and so relaxed with the cherry tree blooming in the back yard. Kathleen added thoughtful details and helpful instructions. The house was within walking distance of amazing restaurants, cafes and shops.

New Cstm Bld 2 BDRM Cozy Suite-Heated Flrs-Game Rm
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 🥰
Weekly house rentals

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).

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.

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.

2 Bd 1 Bth Walkout Bsmt Apartment with Ravine View
Amazing simply amazing would definitely recommend. I'll be booking again for sure.

peace and tidy second floor unit separate entrance
I had a wonderful stay at this charming apartment! The space is beautifully maintained, thoughtfully decorated, and incredibly comfortable. Every detail—from the cozy furnishings to the fully equipped kitchen—made it feel like a true home away from home. The host was outstanding: warm, responsive, and genuinely caring. They went above and beyond to ensure I had everything I needed and made the entire experience seamless and enjoyable. The amenities were top-notch and exactly as described—everything was clean, modern, and in perfect working order. I especially appreciated the little touches that showed real attention to detail. I would absolutely stay here again and highly recommend this place to anyone looking for a relaxing and enjoyable stay!

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

1 bedroom cozy basement apt with separate entrance
Great spot, great host, highly recommended

Cozy Entire 3-Bedroom Townhouse in Pickering!
Great stay, very responsive and easy going, would definitely recommend
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.

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.

Cozy private backyard garden studio
Beautiful, spacious apartment with all the comforts. The host was quick to respond to our questions and very helpful. A nice base about 1 km walk from the station, with which you can reach Toronto in 40 minutes by train. Nearby a small supermarket and restaurants. We recommend a walk along the bay and in the Port restaurant you can have a delicious dinner. It's busy, so booking is recommended, but you can also go on the bonnefooi. The temperature in the apartment 24 degrees is too hot for us, so we just opened the door. We could indeed hear people walking, but for us that was not disturbing. A beautiful place we definitely recommend.

Full Detached House: Luxurious, Bright & Spacious
Very nice place to stay , all perfect.

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!

Seasons Vacation: Cozy 4B/2.5B,Kitchen,Parking,5G!
We stayed at this property to attend a family reunion. Even though the reunion was at a different city, we would be meeting family and friends after a long time. This property was ideal for us since we were able to invite a couple of families for tea and were able to catch up. The bright sunshine coming in through the windows, was my favorite. The kitchen and living room with a door to the small patio was ideal. We did not do much cooking except making coffee and tea, for which this kitchen is well equipped. The bedrooms upstairs with 2 full baths were comfortable and bright. The laundry was a big advantage. But bring your own detergent. Pickering is a city adjacent to Ajax. Both these cities are rich in ethnic diversity. A big plus!

Cheery 1941 Historic Home in Ajax
Thank you for such a beautiful stay!

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!
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
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- 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