Vacation rentals with a pool in Midtown Toronto, Old Toronto

Find and book unique homes with a pool on Airbnb

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Popular amenities for Midtown Toronto, Old Toronto rentals with a pool

House rentals with a pool

Guest favourite
Home in Mississauga
4.93 out of 5 average rating, 15 reviews

Luxury House with a Bright Sunroom & a heated pool

MarianneRating, 5 stars4 days ago
We had a wonderful stay. Everything was up to standard. House was clean and well set up.
Guest favourite
Home in Vaughan
5 out of 5 average rating, 5 reviews

Vacation Getaway with Heated Spa-Pool Open365 Days

YasminRating, 5 stars3 weeks ago
I had an amazing experience staying at this beautiful home. The property was exactly as described, and even better in person! It was clean, spacious, and thoughtfully decorated, making it feel like a home away from home. The host was incredibly welcoming and responsive, ensuring that we had everything we needed for a comfortable stay. The location was perfect, with easy access to local attractions and amenities. I highly recommend this place to anyone looking for a relaxing and enjoyable stay. Can't wait to return!
Guest favourite
Home in Lakeview
4.88 out of 5 average rating, 25 reviews

Lakeside Luxury Retreat | Pool & Putting Green

MelissaRating, 5 stars2 months ago
Virinder was super responsive, and the place was lovely for our one night stay!
Guest favourite
Home in North York
5 out of 5 average rating, 13 reviews

Luxe, Family-Friendly Oasis Home With Pool

SergeRating, 5 stars3 months ago
Great place with all the amenities for a family of 5. Easy access from airport. Great host that was responsive throughout our stay. Would highly recommend.
Superhost
Home in Central Etobicoke
4.89 out of 5 average rating, 9 reviews

Luxury 2bedroom Unit in the city/heated salt pool.

TanyaRating, 5 stars7 months ago
We had a great time at Bessa’s. The house was beautifully decorated. The pool and back yard were amazing. We will definitely be back. I would highly recommend staying here.
Guest favourite
Home in Niagara
4.91 out of 5 average rating, 299 reviews

King West Victorian Studio Gem

MRating, 5 stars5 days ago
One of the best Airbnb stays! I love the character of the space, the location is fantastic, and the availability of amenities all around. The best part was the softness of the bed sheets! I value a good night sleep, and the bed was so comfortable. Wi-Fi was extremely fast and made working from home a breeze. The kitchen is well stocked with everything needed to make yourself at home. Thank you Kathleen. I'll definitely book again in the future.
Guest favourite
Home in Port Credit
5 out of 5 average rating, 10 reviews

Oakwood Haven

DianeRating, 5 stars6 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!
Top guest favourite
Home in North York
4.87 out of 5 average rating, 77 reviews

Casa Meya - Toronto Poolhouse Villa

CathrynRating, 5 stars1 week ago
We stayed at Rooz’s home for our son’s wedding at Graydon Hall Manor. It was the perfect location and only a seven minute drive. The house was beautiful! It was very comfortable and quiet inside. The neighborhood was also safe and quiet. It had well supplied kitchen and bathrooms. The beds were super comfy. I highly recommend this home to anyone traveling to Toronto, especially if attending an event at Graydon Hall Manor.

Condo rentals with a pool

Superhost
Condo in Downtown Toronto
4.88 out of 5 average rating, 122 reviews

Luxury Downtown 2Bed by ScotiaBank Arena + Parking

KarenRating, 5 stars1 month ago
You cannot beat this location! The Airbnb exceeded our expectations. It was spacious with all the amenities you could want. An amazing space with spectacular views, and a patio to enjoy our time even more. Close to absolutely everything. We walked everywhere, took in a hockey game and felt like we were living in downtown Toronto. A perfect weekend getaway. Highly recommended!
Guest favourite
Condo in Fort York
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 favourite
Condo in Fort York
4.97 out of 5 average rating, 115 reviews

Luxury Waterfront Downtown Condo w/ Pool & Parking

KaylaRating, 5 stars2 weeks ago
We had a great stay. The place was clean and very nice. I love how parking was included with our stay. That was convenient. Highly recommend!
Guest favourite
Condo in Fort York
4.89 out of 5 average rating, 414 reviews

Lakeside Condo Studio In Downtown Toronto

IeishaRating, 5 stars2 weeks ago
Very clean and great locations for nights in downtown Toronto
Guest favourite
Condo in Downtown Toronto
4.93 out of 5 average rating, 150 reviews

3BR Rooftop Pool-Gym-Steps-MTCC-CN Tower-Parking

BhalchandraRating, 5 stars1 week ago
very clean apartment, walkable to everything, across the street from CN tower. Matthew was very proactive with communication. ours was kind of last minute reservation, but Matthew was very fast is getting back to us with confirmation and provided all the instructions for checkin. The apartment building has security and was fully gated, which made us feel very safe.
Top guest favourite
Condo in Fort York
4.98 out of 5 average rating, 186 reviews

Stylish Downtown Toronto Condo with Free Parking

DavidRating, 5 stars1 month ago
stayed here a few times, always a pleasure. host is so nice and place is just as pictured.
Top guest favourite
Condo in Downtown Toronto
5 out of 5 average rating, 125 reviews

Luxury Downtown Condo For 6 (Near CN Tower)

LauraRating, 5 stars5 days ago
Clean, very conveniently located, and always quick communication before and during the trip from Bri and Mike! Great set up for our family (2 adults and 2 kids). Would definitely stay here again if returning to Toronto.
Top guest favourite
Condo in Davisville Village
4.93 out of 5 average rating, 264 reviews

SpectacularPenthouse VIEWS/ POOL /free Parking

SelyaRating, 5 stars1 week ago
Great condo with lots of amenities. Very clean and great location. Very convenient to have parking included however instructions were a bit unclear and it’s hard to find parking and space (need to get inside Loblaws parking and then locate P3). Otherwise really nice condo and kind host.

Quick stats about vacation rentals with a pool in Midtown Toronto, Old Toronto

  • Total rentals

    330 properties

  • Nightly prices starting at

    $14 CAD before taxes and fees

  • Total number of reviews

    4.7K reviews

  • Family-friendly rentals

    70 properties are a good fit for families

  • Pet-friendly rentals

    80 properties allow pets

  • Rentals with dedicated workspaces

    170 properties have a dedicated workspace

Destinations to explore

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  3. Ontario
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  5. Midtown Toronto
  6. Rentals with pools