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House holiday rentals in Pickering

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Popular amenities for house rentals in Pickering

House rentals with a pool

Guest favourite
Home in Ajax
4.94 out of 5 average rating, 48 reviews

Beautiful Cottage in Ajax

JaniceRating, 5 stars2 days ago
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!
Guest favourite
Home in North York
5 out of 5 average rating, 13 reviews

Award Winning Luxury Home with Heated Pool + Sauna

OnyxRating, 5 stars2 weeks ago
My group and I truly loved this home ! It was quiet and in the perfect area for us! We will definitely be back!
Guest favourite
Home in Port Perry
4.93 out of 5 average rating, 220 reviews

Home away from home with a hot tub and pool

CourtneyRating, 5 stars1 week ago
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
Top guest favourite
Home in Scarborough
4.98 out of 5 average rating, 48 reviews

Ultimate Privacy In The City | 4 Bdrms 4 Washrooms

JoannalynRating, 5 stars6 days ago
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.
Top guest favourite
Home in The Beaches
4.99 out of 5 average rating, 148 reviews

Heated Pool-tub Open 365 Days

CaitlynRating, 5 stars2 weeks ago
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!
Superhost
Home in Pickering
4.84 out of 5 average rating, 50 reviews

Toronto Vacation Pool/Park/Zoo/Casino

ElizabethRating, 5 stars2 weeks ago
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.
Guest favourite
Home in Niagara
4.91 out of 5 average rating, 303 reviews

King West Victorian Studio Gem

JessieRating, 5 stars1 month ago
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.
Guest favourite
Home in Scarborough
4.95 out of 5 average rating, 104 reviews

New Cstm Bld 2 BDRM Cozy Suite-Heated Flrs-Game Rm

ZaimaRating, 5 stars1 week ago
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

Top guest favourite
Home in Ajax
5 out of 5 average rating, 30 reviews

Family Friendly Apartment with Private Entrance

RobinRating, 5 stars2 days ago
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).
Guest favourite
Home in Pickering
5 out of 5 average rating, 16 reviews

Just Like Home- Brand New 4 Bedroom Home

LhannieRating, 5 stars6 days ago
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.
Guest favourite
Home in Ajax
4.88 out of 5 average rating, 43 reviews

Private Suite - Ajax by the Lake

JoshuaRating, 5 stars2 weeks ago
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.
Superhost
Home in Pickering
4.74 out of 5 average rating, 35 reviews

2 Bd 1 Bth Walkout Bsmt Apartment with Ravine View

AyletRating, 5 stars8 months ago
Amazing simply amazing would definitely recommend. I'll be booking again for sure.
Guest favourite
Home in Pickering
4.94 out of 5 average rating, 17 reviews

peace and tidy second floor unit separate entrance

Julien.BriceRating, 5 stars1 month ago
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!
Top guest favourite
Home in Ajax
5 out of 5 average rating, 20 reviews

Cozy Guest Suite Basement Apartment

Sarah C.R.Rating, 5 stars1 month ago
A home truly like home. Imran was very kind and responsive. Will stay again!
Superhost
Home in Whitby
4.75 out of 5 average rating, 80 reviews

1 bedroom cozy basement apt with separate entrance

SeanRating, 5 stars1 week ago
Great spot, great host, highly recommended
Superhost
Home in Pickering
4.74 out of 5 average rating, 23 reviews

Cozy Entire 3-Bedroom Townhouse in Pickering!

KeenynRating, 5 stars2 months ago
Great stay, very responsive and easy going, would definitely recommend

Private house rentals

Guest favourite
Home in Pickering
4.92 out of 5 average rating, 13 reviews

Sunlight.

RobRating, 5 stars2 weeks ago
Very clean and spacious. Great location. Lots of amenities close by. Perfect for our group of 5 in Toronto for a tournament.
Superhost
Home in North York
4.83 out of 5 average rating, 6 reviews

Private Bedroom, Bathroom, Kitchen -Basement Apt

AnatRating, 5 stars1 month ago
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.
Guest favourite
Home in Pickering
4.82 out of 5 average rating, 17 reviews

Cozy private backyard garden studio

CorrieRating, 5 stars1 month ago
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.
Guest favourite
Home in Whitby
4.93 out of 5 average rating, 40 reviews

Full Detached House: Luxurious, Bright & Spacious

CedricRating, 5 stars1 month ago
Very nice place to stay , all perfect.
Top guest favourite
Home in Ajax
4.97 out of 5 average rating, 29 reviews

3 bedroom bungalow in South Ajax

SamoriaRating, 5 stars2 months ago
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!
Superhost
Home in Pickering
4.7 out of 5 average rating, 10 reviews

Seasons Vacation: Cozy 4B/2.5B,Kitchen,Parking,5G!

JaishreeRating, 5 stars3 weeks ago
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!
Top guest favourite
Home in Ajax
4.93 out of 5 average rating, 59 reviews

Cheery 1941 Historic Home in Ajax

SarahRating, 5 stars3 weeks ago
Thank you for such a beautiful stay!
Top guest favourite
Home in Ajax
4.9 out of 5 average rating, 29 reviews

Modern cozy living.

ChanelRating, 5 stars3 weeks ago
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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