
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.

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.

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.

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.

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.

Five Star Hayloft Suite
This open space home is in the top level of a century-old bank barn. Witness the beautiful architecture while enjoying modern amenities like an open-concept kitchen, projector & movie lounge, and more! Enjoy 180 degree views from the bay window in the living room during your stay. Five Star Ranch offers a year-round getaway in a beautiful country setting. Situated on a working farm, and surrounded by gardens, animals and beautiful forest, it is a perfect destination for seclusion and peace.

Modern 1 Bed Condo Mississauga
Welcome, new, stylish condo in the heart of Mississauga! This 1Bed/1Bath unit offers a cozy and convenient stay, perfect for both business and leisure travelers. Centrally located in Mississauga, you'll be close to public transport, shopping malls, restaurants, and major highways, making it easy to explore the city. The bedroom features a queen-sized bed. Smart TV and high-speed internet, perfect for relaxing or working remotely. Private Balcony to enjoy the city views. One parking spot.

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.

Luxury 4BR Oasis Year Round Heated Pool & Hot Tub
Unwind in style at my all year-round heated pool & soothing hot tub—the heart of this luxury 4-bed family oasis. Inside you’ll find plush beds, smart TVs, speedy Wi-Fi and a fully stocked chef’s kitchen. Outside, enjoy the fenced backyard with BBQ, lounge seating and night lighting. Pool & hot tub open 365 days Baby gear: crib, high-chair, safety gates Games galore: board games, books & playroom Seconds to beaches, shops and dining—yet peaceful enough for stargazing.

“Amazing 2 Bedrooms Condo” in Downtown Toronto”
Enjoy your luxury condo in heart of Entertainment District. Best location in the downtown! Very close to all major attractions but silence and comfortable to enjoy city life. Breathtaking view, step away from CN Tower, Aquarium, Metro Convention Centre, Rogers Centre, TiFF, Union Station, Scotiabank Arena, Lake Ontario and others NOTE : The pool, steam room, and hot tub are temporarily closed for seasonal maintenance. The newly renovated gym is available for use.

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.

Cozy Country Spring Getaway | HotTub + Fire Pit
Escape to the countryside this spring 🌸 Unwind in the hot tub, enjoy cozy fires under the stars, and soak in the peaceful charm of Alton. Perfect for a relaxing getaway, girls weekend, or quiet work-from-home retreat. • Sleeps up to 8 guests comfortably • 3 cozy bedrooms (2 with private decks!) • 1.5 bathrooms • Fully equipped kitchen + BBQ patio for year-round grilling • Stylish living room with fireplace & smart TV • Fast Wi-Fi, workspace-friendly

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.
Popular amenities for Oakville rentals with a pool
House rentals with a pool

Luxury House with a Bright Sunroom & a heated pool

Modern Luxury House w/EV Charger & Heated Pool

Four seasons Pool Retreat near downtown!

*5BR 4Bath Family GetAway near Lake & Harbor*

Luxurious 6BR Poolside Paradise with huge backyard

The Bayfront Flat - Harbour Views + Private Pool!

Comfortable &Stylish 4BD Stay Near Toronto Airport

Chic King West Studio – FIFA at Your Door
Condo rentals with a pool

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

2BR by Union, Scotia Bank Arena CN Tower + Parking

Downtown Markham Unionville

Beautiful Condo Across CN Tower and MTCC

The Penty: Luxurious Penthouse with Pool, Hot Tub

WaterfrontCondoPool/HotTub/FreeParking/BMO Feild

Humber Bay Family Friendly condo w Terrace&Parking

Hidden gem in Humber bay shores Toronto w/ parking
Other holiday rentals with a pool

Luxury 2.5Br-2Bath 1 Prk Condo SQ1 Striking Views

Central downtown condo next2 CNtower+free parking

Luxury 2BDR modern private condo in Toronto

Charming and Luxurious 2BR+1Bath Guest Suite

Cheerful 3 Bedrooms Available for Renting!

Milton Home- a Family Oasis

Urban Escape • High-Rise • SQ1• Free Parking

Luxury Designer Condo | Downtown Toronto Retreat
When is the best time to visit Oakville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $190 AUD | $184 AUD | $183 AUD | $207 AUD | $240 AUD | $238 AUD | $355 AUD | $228 AUD | $218 AUD | $205 AUD | $210 AUD | $206 AUD |
| Avg. temp | -3°C | -3°C | 2°C | 8°C | 14°C | 20°C | 23°C | 22°C | 18°C | 11°C | 5°C | 0°C |
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 $58 AUD 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 and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
50 of Oakville holiday rentals include Wi-Fi 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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- Rogers Centre
- CN Tower
- Scotiabank Arena
- Union Station
- University of Toronto
- Metro Toronto Convention Centre
- BMO Field
- The Danforth Music Hall
- Distillery District
- Harbourfront Centre
- Nike Square One Shopping Centre
- Exhibition Place
- Toronto Eaton Centre
- Toronto Zoo
- Trinity Bellwoods Park
- Financial District
- Niagara Falls State Park
- Massey Hall
- Wilfrid Laurier University
- Casa Loma
- Downsview Park
- Horseshoe Falls
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