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

Total vacation rentals
Explore 30 vacation rentals in Oakville

Nightly prices starting at
Oakville vacation rentals start at ﺩ.ﺇ 110 per night before taxes and fees

Verified guest reviews
Over 620 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Oakville vacation 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!
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.

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.

Spacious 3BR +2BT w/ 1 Parking! Spectacular Views!
Enjoy this spacious, bright, and centrally located condo with free underground parking in the heart of Mississauga downtown. Walking distance to Square One Shopping Centre, Celebration Square, Sheridan College, Restaurants, nightlife, and more. Close to major highways 403, 401, and 407. Short distance to Toronto Pearson Airport and Downtown Toronto. This 3 bedroom beautiful condo comes with a fully functional kitchen, on-suite washer/dryer, fast wireless internet, and smart TV with Netflix.

Stunning Skyline View Condo, Steps to CN Tower
Stay in the heart of downtown Toronto in this modern one-bedroom condo just steps from the CN Tower, Rogers Centre, and the waterfront. The unit features a comfortable queen bed in the bedroom and a sofa bed in the living room, perfect for couples or small groups. Enjoy skyline views through floor-to-ceiling windows or relax on the private balcony. The condo includes a full kitchen, smart TV, high-speed Wi-Fi, and in-suite washer and dryer. Guests also have access to a gym and outdoor pool .

“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 & Spacious 3Br/2Bth Suite Private Entrance
Modern 3-bedroom basement apartment with private entrance. Perfect for families, small groups, or business travelers. Enjoy a fully equipped kitchen with stainless steel appliances, open living room with smart TV, and two full bathrooms (one with shower, one with tub). Bright, newly renovated space with comfortable beds, high-speed WiFi, and cozy décor. Convenient location near Dundas and Trafalgar, offering both comfort and privacy for your stay.

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.

🔥Charming 1 BR Condo🔥 Steps To Square One!👌
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.
Popular amenities for Oakville rentals with a pool
House rentals with a pool

King West Studio – TIFF, Dining & Nightlife

Beautiful Home with Heated Pool

Cozy Family Retreat near LAKE&Harbour* 3BR 2Bath

3 bedroom home close to downtown with Pool!

Modern Luxury House w/EV Charger & Heated Pool

Luxury 4BR Retreat with Pool, Piano, Spa & Games

Panoramic Lake Views | Hot Tub • Beach • Firepit

Custom Built Modern 5BDR Home with Pool Oasis
Condo rentals with a pool

Luxury 2BR Condo w/ Skyline Views & Balcony

Luxury Downtown Condo For 4 (CN Tower Views)

The Penty: Luxurious Penthouse with Pool, Hot Tub

Luxury Downtown Condo For 6 (CN Tower View)

Lakeside Condo /Pool/ Walking Trail/Parking/CNE

Toronto CN Tower 2 Bed 2 B w Master King w Parking

Luxury Downtown Condo For 6 (Near CN Tower)

3BR Penthouse with Panoramic Views + Large Terrace
Other vacation rentals with a pool

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

Tropical Beach House with 2 level Pool & Hot Tub!

CN Tower Views, Indoor Pool & Gym Condo

Stylish Condo Downtown Mississauga Steps to SQ1

Luxury House with a Bright Sunroom & a heated pool

Oakwood Haven

Milton Home- a Family Oasis

Luxury 2.5Br-2Bath 1 Prk Condo SQ1 Striking Views
When is the best time to visit Oakville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 386 | ﺩ.ﺇ 470 | ﺩ.ﺇ 474 | ﺩ.ﺇ 492 | ﺩ.ﺇ 746 | ﺩ.ﺇ 705 | ﺩ.ﺇ 892 | ﺩ.ﺇ 573 | ﺩ.ﺇ 547 | ﺩ.ﺇ 514 | ﺩ.ﺇ 529 | ﺩ.ﺇ 518 |
| 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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- CN Tower
- Rogers Centre
- Scotiabank Arena
- University of Toronto
- Union Station
- Downsview Park
- Metro Toronto Convention Centre
- The Danforth Music Hall
- Harbourfront Centre
- Niagara Falls State Park
- Toronto Eaton Centre
- Niagara Falls
- Scarborough Town Center
- Nike Square One Shopping Centre
- Toronto Zoo
- Exhibition Place
- Elora Gorge
- Yorkdale Shopping Centre
- Casa Loma
- Trinity Bellwoods Park
- Sheppard–Yonge Station
- York University
- Massey Hall
- The International Centre





