Vacation rentals with a pool in Greater Toronto Area

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Greater Toronto Area

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

%{current} / %{total}1 / 1
Guest favorite
Vibrant autumn foliage displays shades of yellow and orange surrounding a geodesic dome. A pathway of stone steps leads through a lawn covered in colorful leaves, creating a serene outdoor setting amidst lush greenery.
Dome in Bradford West Gwillimbury
4.96 out of 5 average rating, 419 reviews

Four season glamping dome under the stars

Whether you are looking for a romantic getaway for two, a solo remote work week in solitude surrounded by nature, or a family adventure, this 4-season geodesic dome is just the right place. Explore picturesque trails of Scanlon Creek Conservation Area, enjoy inground pool in summer, experience breathtaking sunsets over the farm fields, the starry skies by the bonfire, mesmerizing dance of fireflies in June, and let the frogs and crickets lull you to sleep in the place where time stands still...

Guest favorite
A spacious loft area features a cozy sleeping space with a large bed, complemented by a decorative light fixture overhead. A television is positioned for viewing, and natural light fills the area through multiple windows. A comfortable seating area and soft textures contribute to the serene environment.
Loft in Niagara-on-the-Lake
4.9 out of 5 average rating, 468 reviews

Luxury In The Heart Of Wine Country

Hidden along the shores of the Niagara River, Grayden Estate is nestled on a quiet dead end street in beautiful Queenston/Niagara on the Lake. A short drive to Old Town and within a few minute walk or bike to world class wineries, art galleries, farmers markets, hiking trails, parks and the waterfront, Grayden Estate is the ideal location for a peaceful quiet getaway for anyone looking to surrender to the simple living quiet life. Complimentary tour bikes are available for use. Lic # 112-2023

Top guest favorite
A glass table is set on a balcony, featuring an ice bucket holding a bottle of sparkling wine, accompanied by two elegant glasses. Soft string lights provide gentle illumination, enhancing the cozy atmosphere. A potted plant adds a touch of greenery.
Condo in Innisfil
4.99 out of 5 average rating, 179 reviews

Fire & Ice Spa w/ Private Sauna!

Welcome to the most unique suite at Friday Harbour Resort! Relax, refresh and unwind in your very own private spa experience which includes large infrared sauna, 3 indoor fireplaces and outdoor fire table. Kiss those winter blues away while you warm up in the most cozy suite, perfect for a romantic getaway. Every stay includes a bottle of bubbly to toast with the one who is most important to you! Make Fire & Ice your next vacation destination and reconnect in a most romantic, relaxing suite!

Guest favorite
A modern living area features a large window with expansive views of the cityscape and surrounding landscape. A flat-screen television is mounted on the wall opposite a comfortable sofa and a coffee table, creating a welcoming space for relaxation.
Apartment in Mississauga
4.94 out of 5 average rating, 152 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.

Guest favorite
Five alpacas are seen walking across a grassy area in front of a large, restored barn. The barn features a dark roof and wooden siding, with a door visible on the lower level. A clear blue sky and scattered clouds provide a bright backdrop.
Farm stay in Caledonia
4.97 out of 5 average rating, 103 reviews

Alpaca farm stay and bunkie getaway.

A farm stay on your way to soaking up all that our county has to offer. The bunkie is located next to a restored century barn and an outdoor pool. The property is home to 5 alpacas, mini goats, chickens and our family dog. The bunkie is on a shared property with our home. It's 1 hour from Toronto, 20 minutes from Hamilton, 1-hour from Niagara-on-the-lake and 10 minutes from the historic Ancaster village. Antiquing, hiking, nature tours, golfing, wine tours, farmers markets and more close by.

Top guest favorite
A charming two-story cabin is nestled among lush greenery, with a pathway leading to the entrance. Tall trees and well-maintained hedges surround the home, creating a sense of privacy. Soft sunlight illuminates the cabin, enhancing its rustic appeal.
Cabin in Mono
4.95 out of 5 average rating, 329 reviews

The Trails Retreat (Private Cabin)

Beautifully renovated 2-story private hilltop cabin for romantic getaway, family stay or friends' retreat, experience a taste of the country together. Backed by forest and trails and set away from our family home, minutes to the Bruce Trail, Hockley Ski & Golf Resort, Mansfield Ski Club and charming Orangeville. Enjoy total guest privacy & spectacular sunrises. Guests are welcome to share our heated pool in season:) Add a playful Yoga/Functional Movement class or chef's dinner to your stay!

Top guest favorite
The exterior of a modern two-story home is displayed, featuring a brick and stone facade. A well-maintained driveway leads to a double garage with decorative doors. Bright flower pots are positioned near the entrance, while lush green landscaping surrounds the property.
Apartment in Newmarket
4.99 out of 5 average rating, 197 reviews

The Hilton BnB Adult Luxury Suite

Experience the elegance of the Hilton BnB nestled in Newmarket’s prestigious Stonehaven Estates, just 30 minutes from downtown Toronto. This beautifully decorated open concept walkout suite in a two-story home offers unparalleled comfort and amenities for 1-2 adult guests. Indulge in dining by the fireplace during winter or unwind with a poolside BBQ in the summer amidst breathtaking grounds. The suite boasts spaciousness and a uniquely designed interior that exudes luxury at every corner.

Guest favorite
The indoor swimming pool area features a tiled pool surrounded by natural light from large skylights. Two colorful floats are positioned on the water surface, and glass doors provide a view of the outdoors, enhancing the open and airy feel of the space.
Villa in Toronto
4.94 out of 5 average rating, 176 reviews

Toronto Vacation | ➊ The One Toronto Villa

The One is a unique luxurious private midle-century modern villa escape in the center of north Toronto. Having a stunning and spacious lawn for events and social gathering, this modern house is featured a thermostatic indoor swimming pool. Being inspired from a farmhouse building, the house offering a traditional touch on the vintage furniture and a rustic interior that gives a warm and cozy feelings. It is a great escape from the hustle and bustle of city life without going out of town.

Guest favorite
A cozy sitting area is presented with a blue checkered sofa and a striped armchair, adorned with nautical-themed cushions. Light is provided by two lamps on either side, illuminating the artwork and rustic wooden beams above.
Guesthouse in Erin
4.96 out of 5 average rating, 137 reviews

The Captain's Cottage at Willow Pond

You will have your own private one bedroom cottage on our 17 acre property. Your countryside getaway can be as quiet or as busy as you make it. You will have access to our tennis court, swimming pool, hot tub, gazebo, pond, garden and woodland trails. Adults are welcome to use the exercise studio. There is a flock of heritage chickens, guinea hens and quail who lay beautiful eggs for your breakfast. We also have bees who produce delicious honey for our guests.

Top guest favorite
The serene backyard features a heated saltwater pool surrounded by a stone deck, bordered by lush greenery and blooming trees. A patio area includes outdoor seating and a grill, while large windows overlook the pool, enhancing natural light in the adjacent indoor space.
Home in Toronto
4.99 out of 5 average rating, 161 reviews

Year-Round Heated Pool & Hot Tub Family Oasis

Enjoy a private, year-round heated pool and spa only steps from the lake. Kayak, volleyball, tennis and basketball gear all ready for you-plus skates and ski trails when snow falls. Inside you'll find a gourmet kitchen, wood-burning fireplace and four comfy bedrooms that sleeps the whole crew. Pool & hot tub heated to 87-102 F, 365 days. Winter rink, summer pickle-ball courts. Please respect quiet hour 11pm-7am so everyone can relax.

Top guest favorite
The exterior of a cabin is depicted, featuring wooden siding and a stone base. A small wreath decorates the entrance, which is flanked by a snow-covered landscape. Tall trees stand in the background, hinting at the surrounding nature.
Cabin in Hamilton
4.98 out of 5 average rating, 165 reviews

The Fox's Retreat - A Cozy Cabin for Two

Escape to this open concept cabin in Flamborough, Ontairo. Get to Flamborough Downs Casino and Racetrack, McMaster University, African Lion Safari, Valens and Christie's Conversation Areas, Westfield Heritage Village, and Dundas Waterfalls and multiple Golf Courses in under 15 minutes. Modern amenities provide all the comforts necessary for a relaxing stay, quiet remote work, or a unique space to get wedding ready.

Guest favorite
A modern living area is shown with a light-colored sectional sofa featuring dark blue accent pillows. A sleek, black coffee table contrasts against the soft, patterned rug. Abstract artwork adorns the wall, complemented by an open layout that invites natural light.
Condo in Mississauga
4.84 out of 5 average rating, 292 reviews

Beautiful Cozy 1 BR Condo👌🔥 Steps to SQ1! 👍

This beautiful sunfilled condo is newly furnished and well cared for, equipped with everything you need to make you feel right at home! Free Wifi included with Netflix access and underground parking. Amenitites in the building include a swimming pool and gym. located very conveniently in the heart of Mississauga, steps to Square one, Hwy 403, Pearson Airport and only a short drive to Downtown Toronto.

Popular amenities for Greater Toronto Area rentals with a pool

Destinations to explore