Holiday 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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Top Guest favourite
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
4.97 out of 5 average rating, 502 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 favourite
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, 562 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

Guest favourite
A swimming pool is surrounded by a decorative coping with steps leading into the water. A slide is positioned at one end, alongside poolside seating. Lush greenery and a wooden fence enclose the pool area, creating a private outdoor space for relaxation and enjoyment.
Home in Niagara Falls
4.93 out of 5 average rating, 100 reviews

Niagara Farmhouse Cottage with Attic & Heated Pool

Nestled in the heart of Chippawa town, our newly farmhouse-style residence exudes timeless charm and modern comfort. Situated in close proximity to the enchanting Welland River, the location offers a tranquil escape with picturesque surroundings. Our spacious home ensure comfort and ample space for all. Spacious parking lot could park for up to 8 cars and RV/Trailers. Just a short drive and easy access to Niagara's main attractions. Grocery store, restaurants , and much more In walking distance

Guest favourite
The image features a diamond-shaped solar-heated swimming pool reflecting the soft colors of sunset. Comfortable blue lounge chairs are positioned nearby, overlooking a serene lake. The distant skyline can be faintly seen across the water, blending into the horizon.
Home in Hamilton
4.81 out of 5 average rating, 129 reviews

California Chic +Breathe +Unwind +Restore

Enter through the grand foyer with a winding staircase, pass the kitchen, and step into the relaxing backyard featuring an in-ground, diamond-shaped, solar-heated swimming pool and a stunning lake. The view of the lake is beautiful! The area is quiet and scenic, with the soothing sounds of the lake lulling you to sleep. You are just 30 minutes away from Niagara Falls and 1 hour from Toronto. On a clear day, you can even see the Toronto skyline. It's the perfect place for a group or family of 9.

Top Guest favourite
Apartment in Niagara Falls
4.98 out of 5 average rating, 487 reviews

The Grand Garden Suites 1 *free parking (licensed)

Our property is a duplex ( 2 units) located just steps away from Casino Niagara as well as just one block from the main tourist area. Many restaurants are just steps away as well as the Niagara river where the famous Niagara Falls is located. As close as we are to it all you will still feel tucked away in your own little piece of heaven surrounded by so much beauty with gardens to fill all your senses. And not to mention a backyard oasis with an inground heated pool ( May 1st- September 30th)

Superhost
A serene view of the villa is captured from the edge of the natural spring-fed pond, showcasing its spacious, multi-level design. Surrounding greenery, including trees and landscaped gardens, adds to the tranquility of the setting. Fluffy clouds drift across a bright blue sky.
Villa in Cambridge
4.88 out of 5 average rating, 135 reviews

Luxury Villa for Accommodation

★★★ SUPERHOST for 6+ years ★★★ Escape to this stunning, secluded villa for exquisite accommodation or hosting memorable events. ✔ Secluded villa on 8.8-acre lot ✔ Private 17 ft deep natural spring-fed pond + hot tub ✔ 4000 sqft living space ✔ Full access ✔ 4 bedrooms, 7 beds ✔ High-end finishes: Offers comfort & elegance. ✔ BBQ ✔ Next to Whistle Bear Golf Club & Langdon Hall (Relais & Châteaux, 5 Diamond dining), Cambridge Mill, walking trails, scenic Blair Creek. ✔ 401 easy access

Guest favourite
A tree house is nestled among tall trees, featuring a wooden structure with a balcony and staircase. Soft sunlight filters through the branches, highlighting the natural wood finish and the serene forest surroundings.
Treehouse in Port Perry
4.98 out of 5 average rating, 566 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.

Superhost
A serene backyard is highlighted by a clear swimming pool surrounded by natural stone coping. Comfortable seating arrangements with dark wicker chairs and a sleek table are positioned nearby, offering a relaxing spot. Lush greenery frames the area, providing a peaceful atmosphere.
Guesthouse in Mississauga
4.89 out of 5 average rating, 116 reviews

“CasaDeLeon”- Modern and cozy Lakeview guesthouse

Forget your worries in this quiet,, spacious & serene space. King+queen air/4 twin , lrg patio doors overlooking lush greenery in private backyard oasis. Enjoy in/outdoor living & access to private basketball court, trampoline. Landscaped backyard w deck, bbq, tons of board games, 4K projector (stream from G00gle chromecast) for large screen media / movies, and wine fridge, espresso bar, fridge w ice maker, full bathroom, heated flooring. IMPORTANT: You MUST read “Other Details To Note”

Guest favourite
A private pool is surrounded by a secure fence, featuring a concrete deck with steps leading into the water. Comfortable lounge chairs are positioned nearby, set against a backdrop of lush greenery and a clear blue sky.
Home in Niagara-on-the-Lake
4.9 out of 5 average rating, 124 reviews

Wine country Cottage 15 min drive to old Town NOTL

Welcome to our modern, spacious vacation rental, featuring a stylish interior and a private backyard pool, all situated in a safe and quiet neighborhood. Conveniently located just 15 minutes drive from the world-famous Niagara Falls and the charming downtown area of Niagara-on-the-Lake—one of Canada’s prettiest towns. Enjoy great wineries, restaurants, golf courses, and outlet shopping nearby, as well as a post office, grocery and hardware stores, and a park with a children’s playground.

Top Guest favourite
Home in Niagara-on-the-Lake
4.92 out of 5 average rating, 137 reviews

Lake & Vine Collection | Poolside Retreat

Welcome to Poolside Retreat, Lake & Vine Collection’s premier summer escape. This private vacation home features a large in-ground swimming pool, expansive backyard, inviting outdoor living spaces, and thoughtfully designed interiors for families and groups. Whether you’re swimming, dining outdoors, or simply relaxing by the pool, this home offers the perfect setting for an unforgettable Niagara-on-the-Lake getaway. It's really an ideal destination for creating lasting memories.

Guest favourite
Condo in Innisfil
4.96 out of 5 average rating, 184 reviews

Upscale Spa w/ Hot Tub-Private Sauna-Penthouse

Welcome to our most Dramatic & Romantic Penthouse Spa Getaway Suite! Reconnect with your loved one or celebrate that special milestone in our professionally designed to play with all your senses spa suite, this escape will leave you feeling refreshed and rejuvenated! Cozy up to any of 3 fire elements and then cleanse and detox in your own private in-suite Infrared Sauna! Cook up a gourmet meal in our fully equipped chef's dream kitchen and year round Weber BBQ for grilling!

Top Guest favourite
Guesthouse in Breslau
4.97 out of 5 average rating, 227 reviews

House on the Hill

What makes The House unique? How about: - a year-round heated indoor pool & sauna - private 2-bedroom + loft guesthouse with private entrance - fully-equipped kitchen - homey living area with electric fireplace - 27 gorgeous acres with 2 ponds - private patio & BBQ There's so much more! Come join your hosts Frances & Rod and experience a country retreat in the middle of the city... all this within 5km to Waterloo Int'nl Airport & 15 min to tri-cities & 401.

Popular amenities for Greater Toronto and Hamilton Area rentals with a pool

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