
Vacation rentals with a pool in Church-Wellesley, Old Toronto
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Church-Wellesley, Old Toronto
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Popular amenities for Church-Wellesley, Old Toronto rentals with a pool
House rentals with a pool

Award Winning Luxury Home with Heated Pool + Sauna
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

Modern 5 Bedroom Home with Pool & Jacuzzi
We had a wonderful stay at Angie's house. The place is amazing—clean, bright, and welcoming. The host is incredibly sociable, friendly, positive, helpful, and proactive. Overall, we had a fantastic time, and I just want to say thank you!

Toronto Pool Retreat
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.

private backyard SPA oasis in Toronto
⭐️⭐️⭐️⭐️⭐️ 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.

Luxury 2bedroom Unit in the city/heated salt pool.
If you are thinking of visiting Toronto and don’t want to stay in the chaos of the city or simply like the suburbs more, this is definitely the place to go. Not only is the neighborhood beautiful and so is the place, it’s also a very useful area. It has good stores and pubs and restaurants within 10-15 minutes walks. Only a few minutes from a bus stop that runs every ten minutes will take you to Kipling station, from there you can metro anywhere in the city for only a few bucks. (Definitely get a presto card on your phone, more reliable than a card). Bessa herself was awesome, in my excitement of booking flights for my first international trip, I got into the country way earlier than the check in time and Bessa worked hard to have the place ready as early as she can for me and was very quick to let me know when it’s available. When I had questions about the area she was very quick to answer with useful information. All in all, this place and its host made my trip to Canada amazing.

The Retreat
My family and I had the pleasure of staying here for two weeks recently, and we loved our time here. The interior design of this house is stunning and creates a very cozy and relaxing vibe as the light pours in through the many skylights. The kitchen is a chef’s dream while the outdoor space, bbq and patio sections are perfect for a summer family gathering. Taking a dip in the lagoon shaped pool while looking up at the forrest canopy makes you feel like you’re at a remote cottage. Highly recommended!

King West Victorian Studio Gem
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.

Modern Custom Home w/ Pool, Games & Parking
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 🥰
Condo rentals with a pool

Luxury heart of downtown by CN Tower/ MTCC/Union
Lovely place , felt right at home . Crystal was very helpful and responsive, given it was a very last minute booking. The street was very quiet and so was the building itself . Very cozy getaway in the heart of downtown Toronto for an incredibly good price . Thank you so much for making our short stay nothing short of AMAZING !

Hidden gem in Humber bay shores Toronto w/ parking
Super convenient area for getting around the city. Very clean and super friendly host.

Trendy King West townhome
Karina’s apartment is really spacious and nice. I love it when it is stocked with everything you need. Very spacious as well and the bed is the most comfortable ever! Karina is super responsive and helped me with everything! Definitely recommend!!

Charming Condo w Parking, CN Tower View & Pool
This is my second time staying with Ali and he never disappoints. He is a wonderful host with an even more wonderful airbnb. He is super helpful and responsive and will work to accommodate all of your needs! Very responsive and knowledgeable of the area. The building and amenities are amazing, veey few places in the city can compete. Highly recommend!

Luxury 1BR Executive Condo • Panoramic City Views
We thoroughly enjoyed our stay in this beautiful apartment. It was exactly as described and even nicer than the photos. The unit was spotless and beautifully appointed. The large windows provide lots of natural light and the views of downtown Toronto were spectacular. (From the pool there is a great view of the CN Tower too!). The unit is located at the end of the hallway so there was no noise from people walking by or getting off the elevators. It was very peaceful and we had great sleeps. You can’t beat this location with the proximity to Rogers Stadium, the conference centre, a short walk to the Toronto Island ferries, Queen Street and Eaton Centre for shopping, Kensington and St Lawrence Markets. We walked everywhere. There are also excellent restaurants and coffee shops in the immediate neighbourhood. Mackenzie was a fantastic host who communicated in a timely, helpful, and friendly manner. Check in and check out was a breeze. We loved our time here and hope to be back!

Artsy and Comfy Home with a View
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.

Luxury 2 Bdrm, CNTower/Lake View +Parking+Pool+Gym
The view on CN tour by night is the best feature and i really recommend this place.

Closest condo to Rogers Centre/CN tower in Toronto
Host was very communicative and helpful. The unit was clean and was accurate to the post. The only problem I had was that it wasn’t self check-in, as advertised, as you must check in with concierge with photo ID, so be wary of that. I had to wait a bit for the host’s reply to get everything cleared up, but once she was aware of the issue, it was cleared up quickly and went smoothly after that. Would recommend.
Quick stats about vacation rentals with a pool in Church-Wellesley, Old Toronto
Total rentals
100 properties
Nightly prices starting at
G$2,091 GYD before taxes and fees
Total number of reviews
780 reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
40 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
- Clifton Hill
- TPC Toronto at Osprey Valley
- Toronto Zoo
- Exhibition Place
- The Danforth Music Hall
- Harbourfront Centre
- CF Toronto Eaton Centre
- BMO Field
- Massey Hall
- Trinity Bellwoods Park
- Niagara Falls State Park
- Legends on the Niagara Golf Course
- Casa Loma
- Dufferin Grove Park
- Jackson-Triggs Niagara Estate
- Royal Woodbine Golf Club