
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 €26 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.

Beautiful Home with Heated Pool
Welcome to your Burlington retreat! This spacious bungalow blends style and comfort—perfect for families or groups. Backyard Oasis: Lounge by the heated saltwater pool, host an outdoor movie night, or stay cozy by the patio heater. Prime Location: Enjoy the peace of a residential neighborhood while staying incredibly connected. Just 5 mins to the GO Train for traffic-free trips to Toronto or Niagara Falls. Fully Equipped: Kitchen, laundry, plus all linens and toiletries included. Book today!

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.

Cozy Family Retreat near LAKE&Harbour* 3BR 2Bath
Relax with the whole family at this peaceful place to stay. 1 BLOCK AWAY FROM THE LAKE. Luxurious and spacious upper unit, Master bedroom with ensuite and 2 more spacious rooms and additional 3pc full bathroom, WIFI, Kitchen & TV. Steps away from lake, Bronte Harbor, Coronation Park, shopping, restaurants, nightlife and GO station. About an hour drive to NIAGARA FALLS and 45mins drive to downtown Toronto. Our place is suitable for all kinds of travelers. Shared Solar heated pool (June to Sep)

“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.

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

King West Studio – TIFF, Dining & Nightlife

3 bedroom home close to downtown with Pool!

Luxury House with a Bright Sunroom & a heated pool

The Bayfront - Harbour Views + Private Pool!

Indoor Pool & Hot Tub Villa | Sleeps 14

Panoramic Lake Views | Hot Tub • Beach • Firepit

Modern 6 Bedroom/3 Bath Pool Home Near the Lake

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

Beautiful Penthouse with Breathtaking View

Luxury 2BR Condo w/ Skyline Views & Balcony

The Penty: Luxurious Penthouse with Pool, Hot Tub

Luxury Downtown Condo For 6 (Near CN Tower)

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

Luxury Downtown Condo For 4 (CN Tower Views)

Lakeside Condo /Pool/ Walking Trail/Parking/CNE

Rooftop Pool Condo with CN Tower View
Other holiday rentals with a pool

Sunset Retreat | 2BR/2BA | CN Tower View + Parking

Skyline Retreat-| 2BR/2BA | Panoramic Views | SQ 1

Tropical Beach House with 2 level Pool & Hot Tub!

Milton Home- a Family Oasis

Stylish Condo Downtown Mississauga Steps to SQ1

CN Tower Views, Indoor Pool & Gym Access

Luxury Penthouse Suite SQ1

Luxury 2BR | Free Parking | Walk to Square 1
When is the best time to visit Oakville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €91 | €110 | €111 | €116 | €175 | €165 | €209 | €134 | €128 | €121 | €124 | €122 |
| 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
- Toronto Eaton Centre
- Niagara Falls State Park
- Scarborough Town Center
- Nike Square One Shopping Centre
- Toronto Zoo
- Exhibition Place
- Elora Gorge
- Yorkdale Shopping Centre
- Casa Loma
- Sheppard–Yonge Station
- Trinity Bellwoods Park
- York University
- The International Centre
- Coca Cola Coliseum





