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House holiday rentals in Pickering

Find and book unique houses on Airbnb

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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 stars3 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 Port Union
4.98 out of 5 average rating, 48 reviews

Ultimate Privacy In The City | 4 Bdrms 4 Washrooms

JoannalynRating, 5 stars1 week 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 Rouge
4.92 out of 5 average rating, 74 reviews

Ravine Paradise ! heated pool and hot tub!

CelesteRating, 5 stars2 weeks ago
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.
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 West Queen West
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.

Weekly house rentals

Guest favourite
Home in Pickering
4.82 out of 5 average rating, 17 reviews

Cozy private backyard garden studio

MikuenRating, 5 stars1 month ago
C’est la meilleure place où rester, surtout lorsque nous partons avec notre chien 🐶! Très convivial et pratique pour les déplacements vers Toronto.
Guest favourite
Home in Pickering
5 out of 5 average rating, 16 reviews

Just Like Home- Brand New 4 Bedroom Home

LhannieRating, 5 stars1 week 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 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
4.74 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.
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!
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 Ajax
4.8 out of 5 average rating, 45 reviews

2 bed, 2 bath beside Golf Course

AdamRating, 5 stars1 month ago
Clear check in instructions. The place was very clean. Very comfortable and affordable

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.
Guest favourite
Home in Whitby
4.93 out of 5 average rating, 14 reviews

Urban Zen Retreat/Ontario Largest Spa 15min Walk

KelechiRating, 5 stars1 week ago
I recommend this house . Best place for a family vacation . Everything you will need is in this house . Host was responsive . And it’s 3 mins walk to Walmart and other stores
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.
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!
Guest favourite
Home in Pickering
4.95 out of 5 average rating, 21 reviews

Elegance and Comfort

NealRating, 5 stars2 weeks ago
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!
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!
Guest favourite
Home in Ajax
4.94 out of 5 average rating, 52 reviews

Entire Home - Spacious 4 BR Detached with Office

NormanRating, 5 stars2 months ago
We stayed at Lisa’s place for an extended period of time while waiting for our new home to close… The home has all the amenities to accommodate long stays.. The home office was perfect and private so being on Zoom and otherwise was easy.. We had our family pet with us and the house was just a couple doors down from a large park so it was convenient to walk the dog.. Lisa was also accommodating and accepted our early check in request but also gave us a an extremely long window to check in which was amazing.. It’s a very clean home wth lots of space… I definitely would return and strongly recommend Lisa’s place… Regards, Norman
Top guest favourite
Home in Ajax
4.98 out of 5 average rating, 51 reviews

Modern Cozy Vacation house in Ajax, GTA ON Canada

OsamuedeRating, 5 stars1 month ago
My family and I truly loved our state. We were blown away with the cleanliness and how stunning the house actually was. I’ll highly recommend this anyone looking for a peaceful 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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