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

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...

FamilyLocationHeating

4.97 out of 5 average rating, 506 reviews

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

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

FamilyLocationGetting around

4.89 out of 5 average rating, 568 reviews

Top Guest favourite

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

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!

ValueLocationDecor

5.0 out of 5 average rating, 237 reviews

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

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

ValueFamilyParks

4.93 out of 5 average rating, 102 reviews

Top Guest favourite

Apartment in Niagara Falls

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)

LocationValueParking

4.98 out of 5 average rating, 489 reviews

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

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.

LocationFamilyView

4.98 out of 5 average rating, 567 reviews

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

“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”

ValueFamilyAccess

4.89 out of 5 average rating, 116 reviews

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

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.

FamilyLocationDecor

4.9 out of 5 average rating, 125 reviews

Guest favourite

A modern condominium building is showcased from a street view, highlighting two tall, sleek towers with an expansive glass façade. The ground level features a multi-story section with large windows and contemporary architectural elements, set against a clear blue sky.

Condo in Mississauga

Beautiful & Cozy 2Bed 2Bath Condo Steps to Square1

Welcome to this exquisite 2-bedroom 2 bathroom condo, a blend of modern sophistication and breathtaking views. Nestled in the heart of downtown Mississauga this private-corner unit is everything you’re looking for. Everything in this unit is brand new. Cleanliness and providing a 5 star stay is our priority. All necessities are provided to make you feel at home. Amenities are available to all guests including a gym, pool, hot-tub, sauna, yoga room, music room, game room and much more.

LocationValueWalkability

4.9 out of 5 average rating, 170 reviews

Top Guest favourite

Home in Niagara-on-the-Lake

L&V | Poolside Retreat | Pool & Spacious Deck

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.

ValueFamilyComfort

4.92 out of 5 average rating, 139 reviews

Top Guest favourite

Guesthouse in Breslau

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.

ValueLocationHiking

4.97 out of 5 average rating, 228 reviews

Top Guest favourite

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 The Beaches

Luxury 4BR: 365 Days Open- Heated Pool & Hot Tub

A Private Luxury Getaway in Toronto’s Most Coveted Neighbourhood Escape to an extraordinary 4-bedroom luxury home in Toronto’s iconic Beaches, where sophisticated design meets relaxed lakeside living. This top 1% rated Airbnb property offers an unforgettable weekend experience—perfect for families, couples, or a curated group of friends seeking both comfort and wow-factor. A year round private heated pool and hot tub are yours to enjoy !

LocationValueBarbecue

4.99 out of 5 average rating, 187 reviews