Vacation rentals with a pool in Greater Toronto and Hamilton Area

Find and book unique homes with a pool on Airbnb

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Popular amenities for Greater Toronto and Hamilton Area rentals with a pool

House rentals with a pool

Guest favorite
A pristine in-ground pool is surrounded by a well-maintained patio and grassy area. The house features a modern exterior with a sloped roof and accessible steps leading to a deck adorned with planters. Sunlight reflects off the water, creating a calming ambiance.

Home in Orillia

4.95 out of 5 average rating, 20 reviews

Cute and Cozy House

MeaganRating, 5 stars1 week ago
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!
Superhost

Home in The Blue Mountains

4.89 out of 5 average rating, 205 reviews

Large 4 Br - 4.5 Bath; Sauna/Shuttle Bus/2 King bd

HusainRating, 5 stars1 week ago
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.
Superhost
An inviting inground pool is surrounded by a spacious patio area. Colorful pool floats rest on the water's surface. To one side, a raised ranch home features large windows and an elevated balcony. A fenced yard adds privacy to the outdoor space.

Home in Eden

5 out of 5 average rating, 3 reviews

Citrus! Heated pool sleeps 14

TeresaRating, 5 stars16 months ago
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!
Guest favorite
An outdoor pool is surrounded by a stone patio, featuring landscaping elements including flower beds and a small bush. Seating options are provided by chairs placed around the pool area, and a decorative birdbath is visible nearby.

Home in Port Perry

4.94 out of 5 average rating, 216 reviews

Home away from home with a hot tub and pool

KristinaRating, 5 stars2 months ago
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.
Guest favorite
A private deck features a hot tub alongside a refreshing pool, surrounded by lush greenery. Comfortable loungers offer relaxation options under the sun, while a bright beach ball adds a playful touch to the inviting outdoor space.

Home in Niagara Falls

4.96 out of 5 average rating, 284 reviews

Sauna/POol/hot tub/Relax, have fun in Niagara

ValerieRating, 5 stars3 weeks ago
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.
Superhost

Home in Chatsworth

4.89 out of 5 average rating, 144 reviews

Stonehaven - large country retreat, with pool*

SameerRating, 5 stars1 month ago
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.
Superhost
A private salt-water pool is depicted with a colorful pink flamingo float and a multi-colored inflatable lounge. A shaded gazebo with seating is visible in the background, surrounded by lush greenery. The pool area features brick paving and well-maintained landscaping.

Home in Peterborough

4.91 out of 5 average rating, 66 reviews

New Adventures Edinburgh House/large heated pool

TerriRating, 5 stars5 months ago
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.
Guest favorite
A private backyard features a sparkling pool surrounded by a spacious patio. A large dining table with bright green chairs is shaded by a vibrant umbrella. Grassy areas and tall trees offer a serene, enclosed atmosphere, enhancing the outdoor living experience.

Home in Mississauga

5 out of 5 average rating, 17 reviews

Family Oasis with Pool and Hot Tub

SallyRating, 5 stars6 months ago
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

Guest favorite

Condo in The Blue Mountains

4.98 out of 5 average rating, 141 reviews

Lovely 3 Bedroom Condo with Stunning View and Pool

RachelRating, 5 stars3 weeks ago
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.
Guest favorite
An indoor pool area is visible, featuring a large, rectangular pool surrounded by tiled flooring. Floor-to-ceiling windows allow natural light to fill the space. Lounge chairs are positioned along the edges, and a seating area can be seen in the background.

Condo in Toronto

4.96 out of 5 average rating, 130 reviews

Modern Downtown Condo Free Parking/ Walk to Lake

JennyRating, 5 stars2 months ago
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!
Guest favorite

Condo in Innisfil

4.89 out of 5 average rating, 139 reviews

Friday Harbor Upscale 1Bed+Sofabed+Pool Option

DaveRating, 5 stars4 months ago
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!
Superhost
The image showcases a spacious outdoor area featuring a swimming pool surrounded by landscaped gardens. Modern buildings with balconies are visible in the background. Seating areas with tables and chairs are arranged around the pool, providing a relaxed atmosphere for guests.

Condo in Innisfil

4.91 out of 5 average rating, 138 reviews

Beautiful Condo, 2 Bedrooms and a Den in a Resort!

StevenRating, 5 stars1 month ago
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.
Superhost
A serene bedroom is illuminated by city lights visible through large windows. The bed is neatly made, and a dresser appears nearby. Beautifully draped curtains gently frame the view, enhancing the tranquil setting at night.

Condo in Toronto

4.87 out of 5 average rating, 23 reviews

Entire 2BR Condo Downtown + Skyline View + Parking

IanRating, 5 stars1 week ago
Great place , very well located and a great view. Host was equally great very easy to communicate with
Guest favorite
A modern living area is featured, showcasing a grey sofa and two armchairs. A coffee table sits in front of the seating arrangement, and a wall-mounted television is positioned above a linear fireplace. Natural light streams through large windows, illuminating the space.

Condo in Blue Mountains

4.92 out of 5 average rating, 326 reviews

2 Bedroom, 2 Level Condo on Blue Mountain!

KateRating, 5 stars2 days ago
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.
Guest favorite
An outdoor pool area features a modern design with lounge chairs positioned along the water's edge. A wooden pergola provides shaded seating. Surrounding greenery and contemporary building façades enhance the space, creating a relaxing setting for guests.

Condo in Innisfil

4.93 out of 5 average rating, 108 reviews

Exceptional 2+1 ground floor condo @Friday Harbour

ZoyaRating, 5 stars1 month ago
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.
Guest favorite
The image shows a private pool surrounded by modern architecture, with a spacious deck area composed of large stone tiles. Planters with greenery are positioned along the edges, enhancing the serene atmosphere. The pool features light blue water and is set against a backdrop of multi-story buildings.

Condo in Innisfil

4.94 out of 5 average rating, 115 reviews

Friday Harbour Luxury Condo, Sleeps 4

SoniaRating, 5 stars4 months ago
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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