
Vacation rentals with a pool in Greater Toronto and Hamilton Area
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Greater Toronto and Hamilton Area
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Greater Toronto and Hamilton Area rentals with a pool
House rentals with a pool

Home in Orillia
4.95 out of 5 average rating, 20 reviewsCute and Cozy House
Anzhelika's place was a wonderful cozy retreat in winter. We love the games and ample space to enjoy some girls time and make memories! Thank you so much for having us! We would stay again!

Home in The Blue Mountains
4.89 out of 5 average rating, 205 reviewsLarge 4 Br - 4.5 Bath; Sauna/Shuttle Bus/2 King bd
We had an excellent stay at Brendon’s place. The place was cozy right in the lap of wonderful view of blue mountains. We were here with our parents and our kids and this place had something to offer for all of us. Having private Sauna definitely stood out for us. Brendon was helpful for all the questions and he was also kind enough to accommodate a late checkout for us. We will definitely be back here and highly recommend to anyone looking for a staycation.

Home in Eden
5 out of 5 average rating, 3 reviewsCitrus! Heated pool sleeps 14
We rented both orange and clementine houses and was a great space for our large family in town for a wedding in Orchard Park. The host was quick to respond and flexible with check-in and out times and kept the pool open for us for our later September visit and we got to really enjoy it!

Home in Port Perry
4.94 out of 5 average rating, 216 reviewsHome away from home with a hot tub and pool
We had the most wonderful stay in such a clean and beautiful home. Perfectly equipped with everything we needed for a family of 6 to have a comfortable stay. A bedroom full of toys kept our little kids very entertained. Instructions were very clear and the hosts were very quick to respond to questions. The property was very close to everything we needed: walmart, restaurants, shopping. Felt like a safe and peaceful area. We would love to stay here again when visiting family.

Home in Niagara Falls
4.96 out of 5 average rating, 284 reviewsSauna/POol/hot tub/Relax, have fun in Niagara
Jered’s place was super clean all of the amenities well organized and easy to find. Beautiful house, great location, decor was super cozy and modern. Had full stock kitchen with appliances and utensils. Hot tub and sauna in the snow was amazing. Will definitely be booking again in future.

Home in Chatsworth
4.89 out of 5 average rating, 144 reviewsStonehaven - large country retreat, with pool*
Steve’s property was ideal for our large group of 20. It was very well equipped with everything that was required to make our stay comfortable from the kitchen appliances, pots, cups, dishes, to the bed linens, towels etc. Lots of space on the main level. 6 bedrooms above with plenty of space to stay (one is a very small room). We enjoyed Tobogganing on the slope on the large property. Overall great fun. Steve communicated very well during our stay. Recommended for a large group of family, friends.

Home in Peterborough
4.91 out of 5 average rating, 66 reviewsNew Adventures Edinburgh House/large heated pool
Sarah’s property is one of the most dreamiest places for families. It ticks off so many boxes for everyone in your party. Communication with the host very timely and much appreciated.

Home in Mississauga
5 out of 5 average rating, 17 reviewsFamily Oasis with Pool and Hot Tub
We had a wonderful 11 day stay at Caitlin’s. Extremely well appointed in terms of comfort and amenities (you could quite easily just enjoy the beautiful backyard and stay home). House was very spacious and, if you are travelling with children, Caitlin had lots of games, books and toys for their entertainment. As a multigenerational group we all enjoyed our stay and very much hope we can return very soon. Caitlin is an excellent host who takes her guests’ needs and comfort very seriously.
Condo rentals with a pool

Condo in The Blue Mountains
4.98 out of 5 average rating, 141 reviewsLovely 3 Bedroom Condo with Stunning View and Pool
Perfect stay. Perfect location and amazing views. We were there for a weekend event so it was a quick 5 minute walk over to the conference area with the village being behind it. No more than a 10 minute walk to the village. The host provided perfect directions and helpful info on the app and at the Airbnb. No complaints. I would only recommend a full length mirror for the upstairs master bedroom.

Condo in Toronto
4.96 out of 5 average rating, 130 reviewsModern Downtown Condo Free Parking/ Walk to Lake
We stayed here while in town to see Taylor Swift. The location was an easy and safe walk to Rogers Centre and the CN Tower. We had no issues getting a 4am Uber to the airport at this location. Jessica was very friendly and accommodating to an early check in. I asked several questions in the weeks leading up to our stay and she always answered quickly and thoroughly. I’m so sad our plans only had us in the AirBnb for a few short hours because it was absolutely lovely with amazing views of the city. We loved the city and hope to return—we will absolutely stay here again!

Condo in Innisfil
4.89 out of 5 average rating, 139 reviewsFriday Harbor Upscale 1Bed+Sofabed+Pool Option
Kevin was a responsive and friendly host, and his place is clean and comfortable and very close to Friday Harbour. We loved the balcony for breakfast and coffee, and the condo itself was full of friendly folks. We can't wait to go back sometime!

Condo in Innisfil
4.91 out of 5 average rating, 138 reviewsBeautiful Condo, 2 Bedrooms and a Den in a Resort!
Great place to stay. Very clean and comfortable with a stocked kitchen. Perfect location with a short walk to the harbour. Loved having the secured underground parking. We would definitely stay here again.

Condo in Toronto
4.87 out of 5 average rating, 23 reviewsEntire 2BR Condo Downtown + Skyline View + Parking
Great place , very well located and a great view. Host was equally great very easy to communicate with

Condo in Blue Mountains
4.92 out of 5 average rating, 326 reviews2 Bedroom, 2 Level Condo on Blue Mountain!
A quiet gem. Private with a beautiful forest view. The perfect winter getaway. Pristinely clean and all the amenities a family of 4 would need. Ski in and out access is a plus (snow dependent). My family plans to return.

Condo in Innisfil
4.93 out of 5 average rating, 108 reviewsExceptional 2+1 ground floor condo @Friday Harbour
Apartment was even beyond our expectations. It was the most amazing place we have ever rented on New Year holidays. There were 6 people and the place was big and comfortable enough for everybody. Moreover, the apartment was extremely clean and had everything in it to live for short or long terms without any issues. The apartment is located in Friday Harbour which is the perfect place to live in. There are lots of shops, restaurants, a beautiful marina, pool , beach club nearby. We also went for skiing to Horseshoe resort, which took us approx 30 minutes to get there. Shai is a wonderful host, he was in touch during the entire period of our stay in his apartment. He left us a bottle of wine and chocolates as a present, it was so cute. Thank you so much for your attention and care. We will definitely rent your apartment again.

Condo in Innisfil
4.94 out of 5 average rating, 115 reviewsFriday Harbour Luxury Condo, Sleeps 4
My boyfriend and I stayed the weekend, it was a great location, Joe was very responsive and friendly! We had only 1 concern with the bbq that was not clean, but it has been handled with effectively. Overall space was very clean, it was easy to find kitchen supplies, and other items in the house! A great location with stores, restaurants at a walking distance, and other attractions within a 30 minute drive
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