
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.

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...

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.

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

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!

Utopia villa and spa
Welcome to Utopia B&B, a peaceful retreat where lasting memories are created with family and friends. Just minutes from the beach, grocery stores, gas stations, and all everyday essentials. With so much to enjoy, you may never want to leave! Spend your day savoring good food by the fireplace, relaxing in the hot tub, unwinding in the sauna, and having fun in the game room. Indulge yourself with an unforgettable stay. : No smoking or eating in the hot tub. Any violation will result $500 fine.

Ultimate Georgian Bay Vacation Getaway
Come and stay at our beautifully renovated *all-season* beachfront cottage and enjoy a breathtaking panoramic view of Georgian Bay! You'll discover the cottage sitting atop a sand dune, right on one of the most stunning freshwater beaches in the world. This rare location hosts a private covered deck hovering over the white sand, in a beach house closer to the bay than anywhere else around! Summer guests also enjoy use of a heated salt water pool and large resort deck created by Paul Lafrance.

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.

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!

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.

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.

Home away from home with a hot tub and pool
This spacious home is a short walk to downtown Port Perry. Enjoy your time around the pool or hot tub, relaxing by the outdoor fireplace, lounging at the bar or just spending your time under a large covered deck ( rain or sunshine, uv ray protection). Port Perry offers shopping, fun at the lake (fishing and boating), skiing, hiking, local brewery, many restaurant choices and easy access to the Blue Heron casino. Check local web site for the many events going on around town.

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.
Popular amenities for Greater Toronto Area rentals with a pool
House rentals with a pool

Serene mountainside home with View/Shuttle Bus

Comfortable &Stylish 4BD Stay Near Toronto Airport

Oriole Ridge Retreat, Hot Tub, King Suite

WhiteOrchid LuxuryHome WithSaltHeatedSwimmingPool

California Chic +Breathe +Unwind +Restore

sunset 1100

Chic King West Studio – TIFF & FIFA at Your Door

Modern Custom Built Walkout to Marble Pool Game RM
Condo rentals with a pool

1Brm 2beds 5*Cozy, Hot tub, Midtown, Subway 5mins

Hidden gem in Humber bay shores Toronto w/ parking

Stylish Downtown Toronto Condo with Free Parking

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

Large & Bright 2BR+Den in Midtown w/ Free Parking

Luxury 2 Bdrm, CNTower/Lake View +Parking+Pool+Gym

Luxury Downtown Condo For 6 (CN Tower View)

Beautiful & Cozy 2Bed 2Bath Condo Steps to Square1
Other vacation rentals with a pool

The King's Rest

Cozy Private Suite with Year-Round Hot Tub

The Farmer's Cottage

Bright and Airy Guest Suite with Pool

Charming and Luxurious 2BR+1Bath Guest Suite

Comfy suite with private pool(4-6)

The Beach Deck Retreat

Cozy getaway for two with hot tub!
Destinations to explore
- Greater Toronto and Hamilton Area Vacation rentals
- Mississauga Vacation rentals
- Pocono Mountains Vacation rentals
- Capital District, New York Vacation rentals
- Island of Montreal Vacation rentals
- Grand River Vacation rentals
- Northeast Ohio Vacation rentals
- St. Catharines Vacation rentals
- Niagara Falls Vacation rentals
- Pittsburgh Vacation rentals
- Erie Canal Vacation rentals
- Laurentides Vacation rentals
- Rentals with an accessible height bed Greater Toronto Area
- Campsite rentals Greater Toronto Area
- Loft rentals Greater Toronto Area
- Rentals with a soaking tub Greater Toronto Area
- Rentals with a washer and dryer Greater Toronto Area
- Cottage rentals Greater Toronto Area
- Rentals with lake access Greater Toronto Area
- Rentals with an EV charger Greater Toronto Area
- Farmstay rentals Greater Toronto Area
- Vacation home rentals Greater Toronto Area
- Rentals with a fire pit Greater Toronto Area
- Aparthotel rentals Greater Toronto Area
- Bungalow rentals Greater Toronto Area
- Ski-in/ski-out rentals Greater Toronto Area
- Chalet rentals Greater Toronto Area
- Pet-friendly rentals Greater Toronto Area
- Tiny house rentals Greater Toronto Area
- Family-friendly rentals Greater Toronto Area
- RV rentals Greater Toronto Area
- Apartment rentals Greater Toronto Area
- Dome rentals Greater Toronto Area
- Rentals with a patio Greater Toronto Area
- Rentals with a kayak Greater Toronto Area
- Townhouse rentals Greater Toronto Area
- Private suite rentals Greater Toronto Area
- Luxury rentals Greater Toronto Area
- Smoking-friendly rentals Greater Toronto Area
- Boutique hotels Greater Toronto Area
- Rentals with a sauna Greater Toronto Area
- Rentals with a hot tub Greater Toronto Area
- Fitness-friendly rentals Greater Toronto Area
- House rentals Greater Toronto Area
- Hotel rooms Greater Toronto Area
- Waterfront rentals Greater Toronto Area
- Serviced apartment rentals Greater Toronto Area
- Beachfront rentals Greater Toronto Area
- Cabin rentals Greater Toronto Area
- Rentals with beach access Greater Toronto Area
- Bed and breakfasts Greater Toronto Area
- Condo rentals Greater Toronto Area
- Guesthouse rentals Greater Toronto Area
- Villa rentals Greater Toronto Area
- Rentals with breakfast Greater Toronto Area
- Rentals with a fireplace Greater Toronto Area
- Rentals with outdoor seating Greater Toronto Area
- Rentals with an accessible height toilet Greater Toronto Area
- Rentals with a home theater Greater Toronto Area
- Rentals with pools Ontario
- Rentals with pools Canada
- Rogers Centre
- CN Tower
- Scotiabank Arena
- Union Station
- University of Toronto
- Metro Toronto Convention Centre
- Port Credit
- BMO Field
- Distillery District
- The Danforth Music Hall
- Nike Square One Shopping Centre
- Harbourfront Centre
- Exhibition Place
- Toronto Eaton Centre
- Toronto Zoo
- Trinity Bellwoods Park
- Snow Valley Ski Resort
- Mount St. Louis Moonstone
- Massey Hall
- Financial District
- Casa Loma
- Lakeridge Ski Resort
- Dufferin Grove Park
- Downsview Park
- Things to do Greater Toronto Area
- Nature and outdoors Greater Toronto Area
- Food and drink Greater Toronto Area
- Sports activities Greater Toronto Area
- Art and culture Greater Toronto Area
- Sightseeing Greater Toronto Area
- Things to do Ontario
- Food and drink Ontario
- Art and culture Ontario
- Nature and outdoors Ontario
- Sports activities Ontario
- Sightseeing Ontario
- Entertainment Ontario
- Tours Ontario
- Things to do Canada
- Food and drink Canada
- Entertainment Canada
- Sports activities Canada
- Tours Canada
- Art and culture Canada
- Sightseeing Canada
- Nature and outdoors Canada




