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
Home in Port Perry
4.93 out of 5 average rating, 218 reviews

Home away from home with a hot tub and pool

LornaRating, 5 stars3 days ago
Had a great time at Angie's place! Everything was very clear, clean and easy—instructions were left out and amenities were provided. The hot tub was a great bonus to the weekend. We even had a delayed car picking us up, and Angie was very accommodating and understanding about letting us stay slightly longer while waiting for its arrival.
Superhost
Home in St. Catharines
4.84 out of 5 average rating, 242 reviews

Stunning Large Character Family home

CatherineRating, 5 stars1 month ago
The house was easy to find. The lock was having trouble but then we were able to get in. The next day realized the lock on the house was malfunctioning and that was why we had trouble getting in. Texted the owner and someone was immediately sent to fix(replace the lock). Great customer service from the owners.
Superhost
Home in East Gwillimbury
5 out of 5 average rating, 3 reviews

10 Acre Farmhouse with Pool + 5 Bedrooms/3 Baths

PaulRating, 5 stars3 months ago
This place was absolutley spotless and communication was amazing even though nothing was needed til checkout. Would love to have enjoyed pool but tough in January. Minimal amount of snow fell and they had someone come shovel and salt.
Guest favorite
Home in Niagara Falls
4.96 out of 5 average rating, 299 reviews

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

RuthRating, 5 stars1 week ago
Great stay. Beautiful backyard. We will definitely return if we are ever in the Niagara Falls area.
Top guest favorite
Home in Mississauga
5 out of 5 average rating, 17 reviews

Family Oasis with Pool and Hot Tub

SallyRating, 5 stars8 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.
Superhost
Home in Pickering
4.85 out of 5 average rating, 46 reviews

Toronto Vacation DecemberPromotion/Park/Zoo/Casino

Huy LongRating, 5 stars1 month ago
Great host! Great response time and services!
Guest favorite
Home in Niagara-on-the-Lake
4.96 out of 5 average rating, 24 reviews

Stunning 3 Bdrm for 6 Guests - In-Ground Pool NOTL

AmyRating, 5 stars7 months ago
We had a great stay at Shawn's house. The house was somehow even nicer in person than in the pictures. It was very clean and comfortable. We felt right at home and really enjoyed our time in Niagara-on-the-Lake. Would definitely come back!
Top guest favorite
Home in Alton
4.97 out of 5 average rating, 92 reviews

Cheerful 3 bedroom home with outdoor pool & hottub

KelliRating, 5 stars3 weeks ago
We loved our time at Paige's beautiful home. Such a comfortable, cozy, unique home. The stone fireplace with the wrapping stairs is so pretty. You feel you are staying somewhere special. With being out of our home for a renovation Paige provided many staples to make day to day comfortable. We definitely will recommend staying here to our friends and family.

Condo rentals with a pool

Guest favorite
Condo in The Blue Mountains
4.98 out of 5 average rating, 151 reviews

Lovely 3 Bedroom Condo with Stunning View and Pool

SusanRating, 5 stars1 month ago
We have a wonderful time at Sabine's place, which was an ideal space in every way. It was beautiful, well laid out, and had everything we needed. Sabine was very responsive and accommodating. We would gladly go back when we are next at Blue Mountain.
Guest favorite
Condo in Toronto
4.96 out of 5 average rating, 132 reviews

Modern Downtown Condo Free Parking/ Walk to Lake

StephanieRating, 5 stars1 month ago
Jessica was one of the best Airbnb hosts I’ve had in a long time! I celebrated my three-year anniversary here with my partner, and it was absolutely perfect. Jessica went above and beyond by setting up the room beautifully with flowers, rose petals, and electric candles—my partner was overjoyed. She was incredibly accommodating, allowing us to check in early and responding quickly to all my requests. The space itself was spotless, smelled amazing, and was incredibly comfortable. As a same-sex couple, safety is always a consideration when booking accommodations, but this location felt extremely secure. My partner and I were out late at night and felt completely at ease. The apartment has a double lock for added security, and the building itself is well-monitored. On top of all that, the view of downtown and the CN Tower was stunning. I highly recommend this stay, especially for couples—10/10!
Guest favorite
Condo in Innisfil
4.89 out of 5 average rating, 139 reviews

Friday Harbor Upscale 1Bed+Sofabed+Pool Option

DaveRating, 5 stars6 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
Condo in Innisfil
4.91 out of 5 average rating, 139 reviews

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

LoriRating, 5 stars1 month ago
Shahed's place at Friday Harbour is beautiful and well appointed. He gave very clear instructions for entry and parking, including photos. The condo was clean and had all the amenities needed, even extra charging cables for devices! The space was comfortable and uncluttered. Shahed was great at communicating and always responded quickly to any questions. Friday Harbour has activities and restaurants available on weekends in the winter and is a fun engaging place by the harbour in the spring, summer and early fall. We were there in the early part of the week in February so the harbourfront was quiet but still nice for a stroll. We spent time in both Barrie (20 minutes away) and Orillia (about 50 minutes away).
Guest favorite
Condo in Toronto
4.9 out of 5 average rating, 31 reviews

Entire 2BR Condo Downtown + Skyline View + Parking

JordanRating, 5 stars2 weeks ago
Great condo in a great location. Lovely view of Toronto. Walking distance to all amenities.
Guest favorite
Condo in Blue Mountains
4.92 out of 5 average rating, 338 reviews

2 Bedroom, 2 Level Condo on Blue Mountain!

LaharRating, 5 stars4 days ago
The property was as advertised. It was clean and functional. We asked for help a couple of times and were given prompt and immediate answers. Highly recommended!
Guest favorite
Condo in Innisfil
4.93 out of 5 average rating, 109 reviews

Exceptional 2+1 ground floor condo @Friday Harbour

ZoyaRating, 5 stars3 months 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
Condo in Innisfil
4.94 out of 5 average rating, 115 reviews

Friday Harbour Luxury Condo, Sleeps 4

SoniaRating, 5 stars7 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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