
Holiday rentals with a pool in Oakville
Find and book unique homes with a pool on Airbnb
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.

“CasaDeLeon”- Modern and cozy Lakeview guesthouse
YES Hot tub and heated pool are open! Forget your worries in this 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. **25+ ID & waiver req**

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.

The Penty: Luxurious Penthouse with Pool, Hot Tub
Welcome to our modern & luxurious corner penthouse! Stylishly designed with lush greenery and upscale touches, this bright space offers comfort, elegance, and a relaxed tropical vibe. Take in stunning panoramic city views and unwind with premium amenities including an outdoor pool, hot tub, and steam room sauna. Just a 15-min drive to downtown. Public transit at the doorstep. 10-min drive to Rogers Stadium. Perfect for discerning guests seeking an elevated stay in Toronto’s vibrant urban core

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.

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.

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.

FIFA Cottage Monthly avail. 12 Max Hot Tub Pool
Max 12 ADULTS* *Unfenced pool = NOT suitable for toddlers & non-swimmers. Young adult (13yrs.+) swimmers welcome. Inquire re weekend or weekly availability. - COTTAGE-Vibe Secluded - POOL OPEN mid-June to Oct. - HOT TUB all year - Ping pong/pool table - AC/furnace - BBQ+fuel - Private enter. - Short walk to lake - Towels avail, guests bring BEACH towels, lawn chairs NO parties, events, unregistered guests. Pool & Hot Tub close @ 10:30 PM NALOXONE kit avail.

Bright and Airy Guest Suite with Pool
Large windows, high ceilings, fresh modern decor, cedar sauna, fitness room and backyard pool best describes our Garden Suite. Spoil yourself in everything this space has to offer. Featuring a comfy queen size bed sheeted with luxury cotton and down duvet. A large queen pull-out couch offers space for extra sleepers. Take some time to refine your culinary skills with the well appointed kitchen. Don't overpack, your in-unit washer and dryer will keep your clothes clean.

FIFA: 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 !

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.

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

3 bedroom home close to downtown with Pool!

Modern Luxury House w/EV Charger & Heated Pool

Ravine Paradise ! heated pool and hot tub!

The Bayfront - Harbour Views + Private Pool!

private backyard SPA oasis in Toronto

Victorian Charm – Prime FIFA Base in King West

Boutique Wine Country Home with Pool and Hot Tub

Cozy Country Spring Getaway | HotTub + Fire Pit
Condo rentals with a pool

Luxury 2BR Condo w/ Skyline Views & Balcony

FIFA fan zone Pool/HottubFree parking walk to BMO

Stylish 1BR on Toronto’s Harbourfront

Humber Bay Family Friendly condo w Terrace&Parking

Stylish Downtown Toronto Condo + Free Parking

Charming Condo w Parking, CN Tower View & Pool

Luxury Downtown Condo For 4 (CN Tower Views)

Stylish 1+1 Corner Suite |Steps to Lake&Downtown
Other holiday rentals with a pool

Tropical Beach House with 2 level Pool & Hot Tub!

20th Floor Condo w/ Celebration Square Views

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

Four seasons Pool Retreat near downtown!

Modern Toronto Home w/ Pool, Hot Tub, Sauna | 4BR

Executive 2BR/2BA Condo Near Square One

Comfortable &Stylish 4BD Stay Near Toronto Airport

Milton Home- a Family Oasis
When is the best time to visit Oakville?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $150 AUD | $183 AUD | $184 AUD | $203 AUD | $234 AUD | $233 AUD | $347 AUD | $223 AUD | $213 AUD | $200 AUD | $206 AUD | $202 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 40 holiday rentals in Oakville

Nightly prices starting at
Oakville holiday rentals start at $57 AUD per night before taxes and fees

Verified guest reviews
Over 630 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
40 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
- University of Toronto
- Metro Toronto Convention Centre
- Union Station
- BMO Field
- Downsview Park
- The Danforth Music Hall
- Harbourfront Centre
- Toronto Eaton Centre
- Niagara Falls State Park
- Toronto Zoo
- Exhibition Place
- Scarborough Town Center
- Nike Square One Shopping Centre
- Niagara Falls
- Trinity Bellwoods Park
- Massey Hall
- Casa Loma
- Enercare Centre
- Yorkdale Shopping Centre
- Elora Gorge
- York University





