Holiday rentals with a pool in Oakville

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Top-rated rentals with a pool in Oakville

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

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Top guest favourite
This inviting bedroom features a spacious bed adorned with soft linens and a textured throw. A large armoire stands alongside, complemented by decorative plants and soft lighting. Natural light is welcomed through an adjacent glass door leading to a private entrance.
Guest suite in Orangeville
4.92 out of 5 average rating, 829 reviews

HotTub & Cozy Fireplace - Headwaters Retreat

Escape to our rustic-modern Queen Suite, perfect for your getaway. Relax in the private hot tub right outside your door, unwind by the fireplace & enjoy Netflix & Amazon TV. This cozy retreat features a private entrance, ensuite bathroom, and a second bedroom with twin beds. Steps from scenic hiking trails, minutes from the town center, your stay is ideal for outdoor adventures, wine tours, weddings, work trips or just quiet escape away. Book now for your ultimate getaway in comfort and nature!

Top guest favourite
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.
Flat in Mississauga
4.94 out of 5 average rating, 162 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.

Top guest favourite
A spacious living area features light wood flooring and large windows allowing natural light to fill the space. A comfortable sectional couch is arranged with wooden chairs and tables. A ceiling fan offers a cooling breeze, while lush greenery is visible outside through the windows.
Guest suite in Lorne Park
4.92 out of 5 average rating, 165 reviews

Full apt on Upper floor near HWY - S Mississauga

Get the privacy & convenience of a hotel and comfort of a home. Many of our guests are repeat guests as they find a lot of value in staying here. In Lorne Park in S. Mississauga, the apartment is on the upper floor of a house with a separate entrance. One minute to QEW, 17 minutes from the airport, & 20 minutes to downtown Toronto, this spacious apartment is self-sufficient with a new, full kitchen with appliances, bathroom, laundry & parking. Ideal for all types of stays. No smoking please.

Guest favourite
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, 104 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.

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.
Apartment in Mississauga
4.9 out of 5 average rating, 137 reviews

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.

Guest favourite
A scenic lake view is presented, featuring a wooden bench positioned on a grassy area beside the water. The sun reflects off the lake's surface, and a clear blue sky is adorned with a few fluffy clouds, creating a serene atmosphere.
Guest suite in Bronte
4.84 out of 5 average rating, 185 reviews

Stylish Basement Hideaway*1 BR Suite*Near Lake

Our guest suite is licensed by Town of Oakville & 1 BLOCK AWAY FROM THE LAKE. New Flooring, Luxurious and spacious suite with ABOVE GRADE WINDOWS, heated flooring, bathroom, WIFI, Kitchenette &50” smart TV. Steps away from Bronte Harbor, Coronation Park, shopping, restaurants, nightlife and GO station. 1hr drive to NIAGARA FALLS and 35mins drive to downtown Toronto. Our place is suitable for all kinds of travelers. Solar heated pool can be accessed from 10am to 8pm (June to Sep)

Top guest favourite
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.
Guest house in Erin
4.97 out of 5 average rating, 144 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.

Superhost
A backyard oasis features a sun-drenched inground pool surrounded by lush perennial gardens. A stone patio is equipped with shaded lounge areas and outdoor seating, creating an inviting space for relaxation. The two-story house overlooks the pool, complementing the tranquil environment.
Flat in Milton
4.82 out of 5 average rating, 200 reviews

Backyard Oasis Guesthouse.

POOL IS CLOSED TILL MAY 2026 Welcome to our cozy walk-out basement apartment with no kitchen. It is a completely private unit with separate entrance. Perfect for making some memories at this unique and family-friendly place. Backing on to the Sixteen-mile creek, this backyard oasis has a sun-drenched inground pool surrounded by mature perennial gardens, a new manufactured stone patio, with upper and lower shaded lounge areas.

Top guest favourite
An outdoor hot tub is nestled beneath a wooden pergola, featuring jets and seating. In the background, a swimming pool is visible, surrounded by greenery and blue skies, evoking a relaxing atmosphere.
Cottage in Niagara-on-the-Lake
4.89 out of 5 average rating, 325 reviews

Modern Farmhouse XL Hot Tub NOTL 15Mins- Falls

Indulge in the rejuvenating health benefits of a mid-week retreat at our Outdoor Spa. Immerse yourself in the refreshing autumn ambiance, relishing the crisp cool air, snug days, and enchanting evenings amidst the fragrant scents of fall in our picturesque outdoor setting. Discover the myriad ways to savor the essence of fall at our spa. Unwind with an overnight stay at our Modern Farm House in charming Niagara-on-the-Lake.

Top guest favourite
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, 172 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.

Superhost
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.
Apartment in Mississauga
4.84 out of 5 average rating, 298 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.

Superhost
A spacious bedroom features large windows, allowing natural light to fill the room. A comfortable bed is centered against a dark accent wall, complemented by minimal artwork. A round mirror hangs on the adjacent wall, and warm lighting is provided by a bedside lamp.
Flat in Mississauga
4.88 out of 5 average rating, 114 reviews

Condo in Heart of Mississauga

Just an 8-minute walk to Square One Mall, this cozy condo is perfectly located — 15 minutes from Pearson Airport, with easy access to highways and public transit. Downtown Toronto is just a 30-minute drive away (traffic permitting). Inside, you’ll find a comfortable bed, a private terrace to relax on, and the convenience of one free designated parking spot included with your stay.

Popular amenities for Oakville rentals with a pool

When is the best time to visit Oakville?

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Avg. price€ 110€ 106€ 105€ 120€ 138€ 137€ 205€ 131€ 126€ 118€ 121€ 119
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Quick stats about holiday rentals with a pool in Oakville

  • Total holiday rentals

    Explore 50 holiday rentals in Oakville

  • Nightly prices starting at

    Oakville holiday rentals start at € 34 per night before taxes and fees

  • Verified guest reviews

    Over 690 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    50 of Oakville holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Oakville rentals

  • 4.8 Average rating

    Oakville stays are highly rated by guests – averaging 4.8 out of 5!

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