Holiday rentals with a pool in Pickering

Find and book unique homes with a pool on Airbnb

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Popular amenities for Pickering rentals with a pool

House rentals with a pool

Guest favourite
Home in North York
5 out of 5 average rating, 14 reviews

Award Winning Luxury Home with Heated Pool + Sauna

SymphoneeRating, 5 stars4 days ago
Lovely home. In close proximity to most of the things we wanted to visit. The kids loved the pool and arcade, and Ryan was very responsive if we had questions or concerns
Superhost
Home in Oshawa
4.81 out of 5 average rating, 31 reviews

Private Pool + BBQ + PS4: 5 Bedooms, 3 Bathrooms!

KajaRating, 5 stars1 week ago
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!!!
Superhost
Home in Scarborough
4.92 out of 5 average rating, 76 reviews

Ravine Paradise ! heated pool and hot tub!

BrittanyRating, 5 stars2 days ago
Preston was very helpful throughout the entire stay. He gave local recommendations for restaurants and was very communicative. Whenever I had a question, he responded fast and accurately. The amenities were exactly as described, and the house came with everything you needed for a short- or long-term stay. Preston was friendly and interactive just as much as you allowed him to be. Would recommend this air bnb for anyone looking for a fun getaway with their friends just as I was!
Guest favourite
Home in Uxbridge
5 out of 5 average rating, 34 reviews

Redwood Haven East: Your Dream Getaway in Uxbridge

SarahRating, 5 stars2 weeks ago
This is a wonderful Airbnb in a really special place away from the hustle and bustle of everyday life. You are in a quiet location within easy access of trails where you can run or walk and if you like to ride, there are plenty of equestrian places providing this facility including part of the Airbnb itself. Youssef and his family were welcoming and on hand to provide advice as needed. That said, they were never intrusive. The accommodation is spacious and homely and you certainly do not feel like rushing out but rather enjoying the facilities. There is everything that you could need for a short or extended stay. Towels were plentiful as were shampoo and lots of extras in the bathrooms and kitchen. The heated pool is a real bonus for children or adults that like a daily swim and although shared with the family, I never felt restricted in its use and loved the fact that it was heated so was comfortable regardless of the external temperature. A wonderful stay and perfect host.
Guest favourite
Home in North York
4.85 out of 5 average rating, 75 reviews

Toronto Pool Retreat

JasonRating, 5 stars1 month ago
Meysam’s place was a great fit for our large group. The location was convenient for getting around, and the house offered everything we needed for a comfortable stay. There was plenty of space to cook and hang out together, and the hot tub was a nice feature. Overall, a solid spot for a group getaway.
Superhost
Home in Mimico-Queensway
4.87 out of 5 average rating, 47 reviews

private backyard SPA oasis in Toronto

JJRating, 5 stars2 days ago
⭐️⭐️⭐️⭐️⭐️ Absolutely Outstanding Stay! This was hands down one of the best Airbnb experiences I’ve ever had. The home was spotless, beautifully designed, and had every amenity I could’ve asked for. The attention to detail—from the cozy linens to the fully stocked kitchen—truly made it feel like a home away from home. The host was incredibly responsive, thoughtful, and made check-in a breeze. The neighborhood was quiet and safe, yet close to everything we needed. The Hot Tubs, Sauna, and pool all came in hand when recovering from the Ice Hockey Tournament. I’m already looking forward to booking again next year—it’s become a new favorite! Thank you for making this such a memorable and seamless experience.
Guest favourite
Home in Niagara
4.91 out of 5 average rating, 305 reviews

King West Victorian Studio Gem

TamerRating, 5 stars1 week ago
It was great to stay at Kathleen's. The place is very spacious and perfect for a one person or a couple. The location is very close to a lot of nice restaurants, coffee shops, bars, and a lot more. I like the neighborhood a lot. In the summer, you can also enjoy the park right across the street. The place was very clean, and Kathleen was a great communicator - on top of everything. It really felt like home. I stayed there for one month as I was in between places and honestly I wish I could have stayed more.
Guest favourite
Home in Port Credit
5 out of 5 average rating, 11 reviews

Oakwood Haven

DianeRating, 5 stars8 months ago
The house was beautiful, clean with lots of space and facilities. It's located a few houses up from the lake, and a very short walk from a park, shops and restaurants in Port Credit. The neighbourhood is quiet and felt very safe at night. It's around a 15 minute walk to the train station to get to down town Toronto within 30 minutes. The host was very helpful and available on messages and was flexible with check in/out which helped having later flights!

Condo rentals with a pool

Superhost
Condo in Davisville Village
4.85 out of 5 average rating, 106 reviews

1Brm 2beds 5*Cozy, Hot tub, Midtown, Subway 5mins

NhatRating, 5 stars2 days ago
Great location, the place is clean and the host is very responsive.
Guest favourite
Condo in Unionville
4.91 out of 5 average rating, 114 reviews

Downtown Markham Unionville

AndreaRating, 5 stars3 months ago
We had a great stay at Thomas' place. He met us at check in, showed us the building, parking and any details we needed to know. He was very responsive, provided early check in, and coordinated parking spots for both our vehicles. The place was very clean and quiet. We would definitely stay again!
Superhost
Condo in Downtown Toronto
4.89 out of 5 average rating, 101 reviews

Beautiful Condo Across CN Tower and MTCC

Daniela Rating, 5 stars5 months ago
I really enjoyed staying at William’s airbnb. Host was always responsive, professional and nice. The instructions were clear and easy to follow. Really recommend it!
Guest favourite
Condo in Toronto
4.93 out of 5 average rating, 152 reviews

Hidden gem in Humber bay shores Toronto w/ parking

RebeccaRating, 5 stars2 months ago
Super convenient area for getting around the city. Very clean and super friendly host.
Top Guest favourite
Condo in Fort York
4.98 out of 5 average rating, 192 reviews

Stylish Downtown Toronto Condo with Free Parking

NickRating, 5 stars1 week ago
Great place and location. As described, no issues and responsive host.
Guest favourite
Condo in Fort York
4.98 out of 5 average rating, 121 reviews

Artsy and Comfy Home with a View

YomiRating, 5 stars1 week ago
Great Location if you're visiting the city close to everything downtown. Great view as well being on the 20th floor. Very clean apartment. The host used white sheets, pillowcases and towels which is always a plus in my opinion. Free parking was a HUGE plus for me (Parked my car and walked everywhere). I would definitely stay again and would recommend to anyone.
Guest favourite
Condo in Fort York
4.86 out of 5 average rating, 249 reviews

Luxury 2 Bdrm, CNTower/Lake View +Parking+Pool+Gym

NoomenRating, 5 stars2 weeks ago
The view on CN tour by night is the best feature and i really recommend this place.
Top Guest favourite
Condo in Downtown Toronto
4.99 out of 5 average rating, 135 reviews

Luxury Downtown Condo For 6 (Near CN Tower)

SusanRating, 5 stars6 days ago
Excellent property in a convenient location of a beautiful city! Condo was just as advertised and perfect for our family of four. Two teens were very pleased with lodging. Had everything we needed for occasional meal prep and laundry. Clean and bright with good window darkening available. Walkable and central. Right across from Rogers Centre and CN Tower. Easy access to public transportation as well. I would recommend to anyone looking for a wonderful urban getaway. Bri and Mike were very responsive to any questions we had! Overall, one of our best AirBnB experiences!

Quick stats about holiday rentals with a pool in Pickering

  • Total rentals

    50 properties

  • Nightly prices starting at

    $33 NZD before taxes and fees

  • Total number of reviews

    770 reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. Canada
  3. Ontario
  4. Regional Municipality of Durham
  5. Pickering
  6. Rentals with pools