Vacation rentals with a pool in Greater Toronto and Hamilton Area

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Greater Toronto and Hamilton Area

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

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Guest favorite

Dome in Bradford West Gwillimbury

4.98 out of 5 average rating, 216 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...

Dec 12 – 19

G$24,995 GYD per night

Guest favorite

Guesthouse in Orangeville

4.95 out of 5 average rating, 310 reviews

Sunny Pines Farm Studio Tennis Court/Bruce Trail

Perfect for a getaway in the country. A bright, spacious, open-concept designer studio featuring beautiful rolling-hill vistas, queen bed, 3-piece bathroom, dedicated bbq, heat/AC plus a wood burning stove, wet bar with a Nespresso machine, deluxe counter-top oven & bar fridge and all new tennis court, laundry available upon request. Mono Cliffs, Boyne Valley, Hockley Valley Nature Reserve Prov. Parks & Mansfield Recreation Centre are minutes away. Ideal hiking, cycling, snowshoeing and xcsking.

Oct 15 – 22

G$32,362 GYD per night

Guest favorite

Loft in Niagara-on-the-Lake, Canada

4.9 out of 5 average rating, 250 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

Oct 2 – 9

G$23,930 GYD per night

Guest favorite

Treehouse in Port Perry, Canada

4.98 out of 5 average rating, 533 reviews

Treehouse on private, isolated forest (300 acres)

You will feel like you're a thousand miles from Toronto. Your own private space with several ponds for swimming, gazebo, fire pits, running water, hot shower, mtn bike and hiking trails. With 300 acres at your door step, you can choose not to see another soul during your stay or venture to a nearby winery, restaurants, shopping, horse farms, golf courses or ski hills! We are just 1 hour from Toronto with easy access off the 407. We also have an amazing log cabin for rent on the same 300 acres.

Jan 19 – 26

G$78,168 GYD per night

Guest favorite

Condo in Innisfil, Canada

4.97 out of 5 average rating, 111 reviews

•#TheFridayFlat Luxury Poolside Retreat for Summer

Enjoy access to all of Friday Harbour's world-class amenities, including a golf course and sandy beach. Take a dip in the outdoor pool and explore the kilometres of scenic walking trails that wind through the Nature Preserve Located just a short drive from Toronto, Friday Harbour offers the perfect escape from city life. Spend your days exploring the shops and restaurants of the promenade, or venture out onto the lake. Come experience the ultimate waterfront getaway at Friday Harbour!

Jun 13 – 20

G$23,383 GYD per night

Guest favorite

Cottage in Wainfleet, Canada

4.97 out of 5 average rating, 119 reviews

Niagara's Little Cottage on the Lake.

Luxurious Cottage rental Perfect for 2 friends or a Cozy Romantic getaway Located on the Beach of Lake Erie Country setting near Morgan's Point Conservation Area Private beach front, located on quiet dead-end street Private pool with Exclusive Use for renters Wake up to beautiful sunrise..the Birds and the sound of Waves every day Stunning evening sunsets over the Lake Active Lifestyles -Trails and hiking on site Close to everything Niagara Falls has to offer. LICENCE #: STR-034-2024

Mar 22 – 29

G$33,622 GYD per night

Guest favorite

Villa in Toronto, Canada

4.94 out of 5 average rating, 116 reviews

➊ The One Toronto Villa - Indoor Pool&Tennis Court

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.

Jan 27 – Feb 3

G$216,035 GYD per night

Guest favorite

Guesthouse in Lincoln, Canada

4.97 out of 5 average rating, 101 reviews

Dancing Fields on Tintern

Opened in august 2021, this Country setting loft in wine country - is surrounded by fields and close to local scenic Ball's Falls and golf courses. Minutes from numerous wineries and five minute drive from the Bench. Unique open concept space created with timeless features with touches of modern charm. Perfect for long week get away, 1 hour away from the hustle and bustle of (Toronto) city life, 25 minutes from Niagara falls/Niagara on the Lake - 1 hour from the US border (Buffalo)

Oct 22 – 29

G$17,385 GYD per night

Guest favorite

Farm stay in Essa

4.99 out of 5 average rating, 119 reviews

The Schoolhouse

Kick back and relax in this calm, stylish space. This school portable turned into a modern guest home is situated on acreage boasting with gorgeous views of forests, fields, grazing animals and sunsets. In warmer months, cool off in the stock tank pool, play on the volleyball court, and enjoy meals on the deck accessed from the bedroom and main entry. Relax by the campfire, walk nearby trails, visit restaurants, markets and shops. Planning your wedding? Ask about our wedding package!

Mar 4 – 11

G$36,973 GYD per night

Guest favorite

Guesthouse in Kawartha Lakes

4.92 out of 5 average rating, 248 reviews

The Loft on Sturgeon Lake

Enjoy the lakeside lifestyle on Sturgeon Lake! This beautiful custom loft features one spacious bedroom with a queen bed and large, bright windows. The suite has a private washroom with a large walk-in shower. There is a full kitchen available and living space with a pull out couch. Experience stunning sunsets over Sturgeon Lake from your private balcony or by the lake at the dockside fire pit. There is an outdoor pool that can be used when available and canoes and kayaks.

Sep 9 – 16

G$28,744 GYD per night

Guest favorite

Cabin in Mono

4.94 out of 5 average rating, 273 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 and yoga studio, minutes to the Bruce Trail, Hockley Ski & Resort, and Mansfield Ski Club, enjoy total guest privacy & spectacular sunrises. Guests are welcome to share our heated pool in season:) Chef's creations and Private yoga and group classes available

Apr 29 – May 6

G$34,875 GYD per night

Guest favorite

Apartment in Newmarket, Canada

5.0 out of 5 average rating, 141 reviews

The Hilton BnB Adult Luxury Suite

A beautifully decorated open concept walkout suite in an elegant 2-story home with all the amenities, accommodates 1-2 adult guests, in Newmarket’s prestigious Stonehaven Estates. The Hilton BnB is located just 30 minutes from downtown Toronto. Dine by the warmth of a fireplace in the winter or relax and have a BBQ poolside in the summer. The suite is spacious and the grounds are breathtaking. Uniquely designed with luxury in mind!

Nov 2 – 9

G$22,951 GYD per night