
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.

Sleeps 12 ADULT private hot tub pool Walk to Lake
Max 12 ADULTS* - Price VARIES with # of guests*. (Add correct # for price accuracy.) - Cottage Vibe, Cozy, secluded - POOL mid-June to October - HOT TUB open all year - Ping pong/pool table - AC/furnace. NEW! - BBQ + fuel - Private entrance - Short walk to the lake - Towels: Provided (guests bring beach towels). *ADULTS ONLY. Unfenced pool = RISK to toddlers/non-swimmers. **No parties, events, unregistered guests. ** Pool & Hot Tub close @ 10:30 PM NALOXONE kit avail.

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.

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.

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.

Stylish Basement Hideaway*1 BR Suite*Near Lake
Our guest suite is licensed by Town of Oakville & 1 BLOCK AWAY FROM THE LAKE. New Flooring, Luxurious and spacious suite with ABOVE GRADE WINDOWS, heated flooring, bathroom, WIFI, Kitchenette &50” smart TV. Steps away from Bronte Harbor, Coronation Park, shopping, restaurants, nightlife and GO station. 1hr drive to NIAGARA FALLS and 35mins drive to downtown Toronto. Our place is suitable for all kinds of travelers. Solar heated pool can be accessed from 10am to 8pm (June to Sep)

Stylish 1+1 Corner Suite |Steps to Lake&Downtown
Modern Corner Unit with Stunning Views | 1+1 BR at 209 Fort York – Prime Downtown Location Step outside and you're just minutes from Toronto’s top attractions: 🗼 CN Tower & Ripley’s Aquarium ⚾ Rogers Centre & Scotiabank Arena 🎡 Exhibition Place & BMO Field 🌊 Harbourfront Centre & Toronto Islands Ferry 🌳 Coronation Park & Martin Goodman Trail 🛍️ Queen West & King West Everything downtown is easily accessible with steps away from public transportation.

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.

🔥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.

Backyard Oasis Guesthouse.
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

Modern Luxury House w/EV Charger & Heated Pool

Ask re: FALL Specials-Heated Pool-tub Open 365 Day

The Bayfront Flat - Harbour Views + Private Pool!

WhiteOrchid LuxuryHome WithSaltHeatedSwimmingPool

The Nautical Nook | Luxury Beach House

Family Oasis with Pool and Hot Tub

Gorgeous Getaway in Oakville

Victorian Charm – TIFF/FIFA Base in King West
Condo rentals with a pool

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

Lux Spacious 3 Beds w CN Tower View (Free Parking)

Beautiful Condo Across CN Tower and MTCC

Lux Waterfront Condo by Rogers -IndoorPool-Parking

Lakeside Condo Studio In Downtown Toronto

Chic, High-Rise Apartment with CN Tower Views

Stylish Downtown Toronto Condo with Free Parking

Luxury 1BR Executive Condo • Panoramic City Views
Other holiday rentals with a pool

Spacious 3BR +2BT w/ 1 Parking! Spectacular Views!

Luxury House with a Bright Sunroom & a heated pool

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

Beautiful Condo with Parking Mississauga Downtown

Stylish 11th-Floor Condo

Condo-mansion with large terrace

City Centre Lodge ( Downtown)

Luxury 2 bedroom + den full condo in Square One
When is the best time to visit Oakville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $225 NZD | $218 NZD | $216 NZD | $246 NZD | $284 NZD | $282 NZD | $390 NZD | $407 NZD | $294 NZD | $218 NZD | $206 NZD | $258 NZD |
| 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 $69 NZD per night before taxes and fees

Verified guest reviews
Over 750 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, Wi-Fi 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
- Budweiser Stage
- Distillery District
- Metro Toronto Convention Centre
- Port Credit
- Clifton Hill
- The Danforth Music Hall
- Exhibition Place
- Harbourfront Centre
- Toronto Zoo
- Financial District
- CF Toronto Eaton Centre
- Trinity Bellwoods Park
- BMO Field
- Massey Hall
- Niagara Falls State Park
- Casa Loma
- Whistle Bear Golf Club
- Dufferin Grove Park
- Legends on the Niagara Golf Course
- Casino Niagara