
Holiday rentals with a pool in Oakville
Find and book unique homes with a pool on Airbnb
Quick stats about holiday rentals with a pool in Oakville

Total holiday rentals
Explore 30 holiday rentals in Oakville

Nightly prices starting at
Oakville holiday rentals start at £22 per night before taxes and fees

Verified guest reviews
Over 620 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
10 properties have a dedicated workspace

Wifi availability
30 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!
Top-rated rentals with a pool in Oakville
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Luxurious 2 bdr suite near SQ1, UTM, parking/pool
Fully renovated 2 bedroom walkout basement modern suite(1,100 sqft), increased in size windows, feels like ground floor, 20x30 swimming pool. 3 minutes to UTM. This home is in a quiet, peaceful neighborhood that offers access to scenic walks and parks nearby. 2 minutes to HWY. DWTN Toronto and DWTN Mississauga is close which makes dining at great restaurants, browsing boutique shops, shopping malls and general sightseeing both easy and convenient. Pool/seasonal/notHeated LICENSE# 2022-000188-STA

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.

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.

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.

“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”

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.

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.

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.

Spacious, Pet Friendly Basement Apartment
Quiet, pet-friendly private basement suite designed for comfort and easy stays. Features a queen bed, sofa bed, fully equipped kitchen, dining area, in-suite laundry, free Wi-Fi, and complimentary coffee & tea. Guests enjoy a shared backyard with a seasonal pool and barbecue in summer. Loved for its privacy and comfort while being steps from a park, grocery store, pharmacy, bank, and nearby restaurants—perfect for short or extended stays.
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

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

private backyard SPA oasis in Toronto

Hamilton Lakeside Haven ~ 4BR Home ~ Swimming pool

Cozy Country Escape w/ Hot Tub, Fire Pit & Pool

Victorian Charm – Prime FIFA Base in King West

The Serenity Home Pool/Yoga/Game Room by the Lake
Apartment rentals with a pool

Luxury 2BR Condo w/ Skyline Views & Balcony

Beautiful Penthouse with Breathtaking View

**30%OFF** Lake view property ❤️ of downtown

Humber Bay Family Friendly condo w Terrace&Parking

Sky-High 2BR/2BA Condo | Best City Views+Parking

Stylish Downtown Toronto Condo + Free Parking

Fort York- Lake View Studio Condo + Indoor Parking

Luxury Downtown Condo For 4 (CN Tower Views)
Other holiday rentals with a pool

Tropical Beach House with 2 level Pool & Hot Tub!

Bright & Spacious 3Br/2Bth Suite Private Entrance

The Bayfront - Harbour Views + Private Pool!

Sky High Luxe Stay | SQ1 | LakeView | Gym Pool Pkg

Comfortable &Stylish 4BD Stay Near Toronto Airport

Fun Villa | Pool, Theatre, Gym & BBQ | Sleep 14

Luxury Comfort | Feels 5-Star

Milton Home- a Family Oasis
When is the best time to visit Oakville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £78 | £95 | £96 | £105 | £122 | £121 | £180 | £116 | £111 | £104 | £107 | £105 |
| 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 |
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- Rogers Centre
- CN Tower
- Scotiabank Arena
- University of Toronto
- Union Station
- Metro Toronto Convention Centre
- Downsview Park
- The Danforth Music Hall
- Harbourfront Centre
- Toronto Eaton Centre
- Niagara Falls State Park
- Toronto Zoo
- Scarborough Town Center
- Exhibition Place
- Niagara Falls
- Nike Square One Shopping Centre
- Trinity Bellwoods Park
- Casa Loma
- Yorkdale Shopping Centre
- Massey Hall
- Elora Gorge
- Enercare Centre
- York University
- Sheppard–Yonge Station





