Vacation rentals with a pool in Midtown Toronto, Old Toronto

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Midtown Toronto, Old Toronto

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Apartment in Downtown Toronto

4.96 out of 5 average rating, 45 reviews

Ambient Vibe Downtown | CN Tower + Lake View Condo

The most exclusive condo where you can set the vibe by changing all the lights to your favourite colour. The perfect getaway and a home away from home. Immerse yourself in this two bedroom, two washroom Airbnb, with the perfect view of the CN Tower, lake and city skyline from the private balcony. Enjoy one of the only rooftop pools/terrace with unparalleled views of the city and cabanas/sun beds available to all guests, with everything you need to make your stay exceptional. Best location in TO

Top guest favorite

Home in The Beaches

4.99 out of 5 average rating, 140 reviews

Heated Pool-tub Open 365 Days

** Ask about MID WEEK Specials. Welcome to the Toronto Beach. We are right next to the lake and have a HEATED private pool and spa that are both open year round. Explore local shops on the high street and swim, kayak (provided), volleyball, basketball and tennis courts right beside us. In winter, an outdoor ice rink (skates provided), cross-country ski trails (bring your own equipment) and lots of walking to be had. We decorate for for holidays, and the house has a real wood burning fireplace.

Top guest favorite

Guesthouse in Brampton

5 out of 5 average rating, 47 reviews

Bright and Airy Guest Suite with Pool and Sauna

Large windows, high ceilings, fresh modern decor and backyard pool best describes our Garden Suite. Spoil yourself in everything this space has to offer. Featuring a comfy queen size bed sheeted with luxury cotton and down duvet. A large queen pull-out couch offers space for extra sleepers. Take some time to refine your culinary skills with the well appointed kitchen. Don't overpack, your in-unit washer and dryer will keep your clothes clean. Pool is closed for season. Will re-open May 20, 2025.

Top guest favorite

Apartment in Mississauga

4.95 out of 5 average rating, 111 reviews

Luxury Stay w/phenomenal view!

Enjoy a stylish experience at this centrally located property. Sunset lovers are going to love this one! Starbucks, restaurants, grocery shops, dentists, pharmacies, and much more ON THE MAIN FLOOR. Walking distance to Mississauga’s largest mall Square one. 15 mins drive from airport. 20 mins drive to Downtown Toronto. Lakeshore south view from balcony. Gym, swimming pool, jacuzzi, sauna, piano room, cards room, stretching room, outdoor bbq, and much more in this unique one of a kind property.

Top guest favorite

Home in Central Etobicoke

5 out of 5 average rating, 10 reviews

Luxe Haven Heated Pool Sauna Gym

Welcome to our luxurious 4-bedroom estate, perfect for families, friends, or couples. Enjoy a heated pool, private gym, and sauna for ultimate relaxation. Unwind in premium massage chairs and cook in the gourmet kitchen with high-end appliances. Elegant living spaces, high-speed Wi-Fi, smart TVs, and a state-of-the-art sound system ensure comfort and entertainment. Fresh linens, towels, and toiletries are provided .This luxurious retreat is more than just a place to stay – it's an experience.

Guest favorite

Guest suite in Lorne Park

4.92 out of 5 average rating, 153 reviews

Full apt on Upper floor near HWY - S Mississauga

Get the privacy & convenience of a hotel and comfort of a home. Many of our guests are repeat guests as they find a lot of value in staying here. In Lorne Park in S. Mississauga, the apartment is on the upper floor of a house with a separate entrance. One minute to QEW, 17 minutes from the airport, & 20 minutes to downtown Toronto, this spacious apartment is self-sufficient with a new, full kitchen with appliances, bathroom, laundry & parking. Ideal for all types of stays. No smoking please.

Guest favorite

Villa in North York

5 out of 5 average rating, 11 reviews

Award Winning Luxury Home with Heated Pool + Sauna

Winner of the 2023 RESA Home Staging Industry Award, my house was professionally designed to ensure my guests have a 5-star atmosphere to enjoy their stay. It has 3 bedrooms with 4 beds total, as well as 3.5 bathrooms and a sauna. It is fully equipped with everything you'll need including comfortable Fairmont Royal beds, high-speed WiFi, several 4K TV's, spacious rooms and a large backyard in a ravine lot. It has been recently renovated and has a brand new deck to relax on by the pool.

Superhost

Home in Scarborough

4.94 out of 5 average rating, 16 reviews

Lakeview Cottage in the City with Pool

Cottage in the City with gorgeous Lake Ontario view, specious land for 50 people with pool within a safe city area. A cottage in the city is a rare and delightful find, a tranquil oasis amidst the hustle and bustle of urban life. Cottage in the City is located 5 minutes away from the Beaches Area where you can find delicious ice cream, multiple restaurants, and local stores and 20 minutes away from downtown Toronto, CN Tower, and the Distillery district. Parking for 4 cars is available.

Guest favorite

Guest suite in Mississauga

4.99 out of 5 average rating, 139 reviews

Modern Luxe Flat • Near YYZ Airport & Downtown T.O

MSG FOR DIRECT RATES Welcome to this modern and inviting 1 bed, 1 bath unit that boasts a bright and spacious atmosphere. With an open concept layout, this unit is designed to maximize both comfort and functionality. Located above ground, this unit receives an abundance of natural light that complements the modern aesthetic. Nestled in a tranquil ravine setting, this apartment offers a unique & serene environment that combines the beauty of nature with the comfort of modern living.

Top guest favorite

Home in Erin Mills

5 out of 5 average rating, 17 reviews

Family Oasis with Pool and Hot Tub

Bring the whole family to this great place with lots of room for fun. Enjoy the private backyard with a fenced in pool, trampoline, hot tub, outdoor has fire pit and sitting area. Private parking for two cars. Lots of space to spread out and enjoy. 2 family rooms with tvs, access to laundry, huge kitchen, and large dinning room for family dinners. Family friendly neighbourhood. Restaurants and shopping nearby. Backyard is private and exclusive to you only.

Superhost

Home in Pickering

4.85 out of 5 average rating, 46 reviews

Toronto Vacation DecemberPromotion/Park/Zoo/Casino

Welcome to our newly renovated 4-bedroom home. This spacious and stylish accommodation offers both a living room and a family room for your comfort and convenience. Dive into relaxation with access to our private heated pool. We take pride in upholding high cleanliness standers to ensure your stay is comfortable and enjoyable. Whether you’re here for a family getaway or a group retreat, our home provides the perfect blend of comfort and convenience.

Guest favorite

Home in North York

4.91 out of 5 average rating, 68 reviews

Toronto Pool Retreat

Experience prestige and privacy in our spacious, well-maintained family home. Enjoy resort-like living with a private yard featuring an inviting pool, hot tub, and large deck. Plus, indulge in additional entertainment options like air hockey and ping pong. Perfect for entertaining! Steps away from ravines, parks, and nature trails, plus easy access to amenities and transportation. Your ideal Toronto getaway awaits!

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What guests are saying

Harbour Waterfront luxury Condo

5 out of 5 average rating, 13 reviews8 months ago

There were a few options out there but none can be compared to what Matthew’s location has to offer. With the description mirroring what is shown, this location is 20 minutes away from the city with local gems within walking distance. As for the host, Matthew. He was kind/ attentive, throughout our stay and prior to. Matthew made sure all of our needs as a family of five were met.

Apartment in Lakeview

What guests are saying

Stylish Condo with Patio + Gym, Rooftop Pool!

4.94 out of 5 average rating, 18 reviews2 weeks ago

Great little apartment in the heart of downtown. Hosts were kind and responsive, the place was super clean and had everything you need. I loooved all of the plush pillows, blankets and carpet as the weather was cold while I was there but I felt so cosy in the apartment. Would stay again!

Apartment in Downtown Toronto

What guests are saying

NEW Gorgeous 2Bed 2Bath by SQ1

5 out of 5 average rating, 39 reviews3 days ago

I had an amazing stay at this apartment! Everything was exactly as described — clean, stylish, and incredibly comfortable. The host provided clear, detailed instructions which made check-in super easy, and communication was always prompt and helpful. You can tell a lot of thought and care was put into making this space welcoming. I truly appreciated how smooth and stress-free everything was. Highly recommend this place and would definitely stay again. Thank you Makan for a wonderful experience!

Condo in Mississauga

What guests are saying

Quiet & Cozy Oasis in the Heart of Oakville Uptown

4.89 out of 5 average rating, 90 reviews1 month ago

This condo apartment was perfect for my stay-- great little kitchen, quiet, spotlessly clean, and easy parking. Grocery stores literally across the street, and many restaurant options for those who want to eat out. The location is a little unusual, in that it's a brand new development, so lots of unbuilt lots and a lot of open parking, but if you are looking for a quiet spot to rest and work, it's great. My unit was on the 11th floor, and had views to the horizon from the nearly floor to ceiling windows. Felipe was also very responsive and flexible when my plans changed at the last minute, which I really appreciate.

Condo in Oakville

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