
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.

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.

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)

Backyard Oasis Guesthouse.
POOL IS CLOSED TILL MAY 2026 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.

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.

Beautiful Cozy 1 BR Condo👌🔥 Steps to SQ1! 👍
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.

Condo in Heart of Mississauga
Just an 8-minute walk to Square One Mall, this cozy condo is perfectly located — 15 minutes from Pearson Airport, with easy access to highways and public transit. Downtown Toronto is just a 30-minute drive away (traffic permitting). Inside, you’ll find a comfortable bed, a private terrace to relax on, and the convenience of one free designated parking spot included with your stay.

The Homelands Suite, 2 Bedroom with Pool.
Forget your worries in this 1200 sq ft spacious and serene place. We are happy to be able to host you in our pleasant Homelands suite. Every inch of this space has come to life through love, attention and hard work! It has many personal touches while also considering all of your needs in order to have a stress free and comfortable experience.

4BR-Year-Round Heated Pool & Hot Tub Family Oasis
Make lifelong memories in this 4-bed oasis right next to the lake with a heated pool & hot tub open all year Sleeps 10 in 4 comfy bedrooms Pool, hot tub, fire-pit & BBQ outside Kids covered: crib, bath & safety gates Fast Wi-Fi, full kitchen and shops 5 min away keep everyone happy. Book your stay before your dates disappear!

Luxury Penthouse Suite SQ1
Enjoy a Stylish Penthouse Experience with Breathtaking Views in the Heart of Square One! Steps to Shopping, Transit, Highway, Restaurants, Movies And More! Comes Fully Furnished, with Full Access to Amenities (Gym, Pool, Hot-tub), 2 FREE Parkings and Ultra Fast Fibre Internet.
Popular amenities for Oakville rentals with a pool
House rentals with a pool

newly renovated, close to airport, washer/dryer

Modern Luxury House w/EV Charger & Heated Pool

The Bayfront Flat - Harbour Views + Private Pool!

Lake Ontario Waterfront House 15 Min To DT Toronto

private backyard SPA oasis in Toronto

California Chic +Breathe +Unwind +Restore

Cozy Modern Suite•Heated Flrs•Game Rm•Free Pkg

Chic King West Studio – TIFF & FIFA at Your Door
Condo rentals with a pool

Lux Waterfront Condo Pool Hot Tub Free Parking

Humber Bay Family Friendly condo w Terrace&Parking

Luxury Condo with FreeParking. CN Tower Lake View

Stylish Downtown Toronto Condo with Free Parking

Beautiful Lake View Studio Condo + 1 free Parking

Charming Condo w Parking, CN Tower View & Pool

Luxury 2 Bdrm, CNTower/Lake View +Parking+Pool+Gym

Luxury Downtown Condo For 6 (Near CN Tower)
Other holiday rentals with a pool

Tranquil Lakeside Suite Toronto

Skyline Views Penthouse, Gym, Pool & Sauna

Luxry Prvte Appartment highrise near train/Bus TTC

Stylish 11th-Floor Condo

Luxury 1BD Condo w/ Stunning Views - Toronto

Luxury Lakeview Condo free parking

City Centre Lodge ( Downtown)

Luxury Condo w. Pool @ Yorkdale, Free Parking!
When is the best time to visit Oakville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $194 AUD | $188 AUD | $186 AUD | $212 AUD | $244 AUD | $243 AUD | $362 AUD | $233 AUD | $222 AUD | $186 AUD | $177 AUD | $222 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 50 holiday rentals in Oakville

Nightly prices starting at
Oakville holiday rentals start at $60 AUD per night before taxes and fees

Verified guest reviews
Over 690 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
50 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!
Destinations to explore
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Mississauga Holiday rentals
- Pocono Mountains Holiday rentals
- Grand River Holiday rentals
- Northeast Ohio Holiday rentals
- St. Catharines Holiday rentals
- Niagara Falls Holiday rentals
- Pittsburgh Holiday rentals
- Erie Canal Holiday rentals
- Detroit Holiday rentals
- Columbus Holiday rentals
- Rentals with a hot tub Oakville
- Rentals with lake access Oakville
- Private suite rentals Oakville
- Rentals with a fireplace Oakville
- Rentals with a fire pit Oakville
- Fitness-friendly rentals Oakville
- Townhouse rentals Oakville
- Apartment rentals Oakville
- Cottage rentals Oakville
- Rentals with beach access Oakville
- Rentals with a patio Oakville
- Rentals with outdoor seating Oakville
- House rentals Oakville
- Rentals with breakfast Oakville
- Condo rentals Oakville
- Waterfront rentals Oakville
- Rentals with a washing machine and dryer Oakville
- Pet-friendly rentals Oakville
- Rentals with an EV charger Oakville
- Family-friendly rentals Oakville
- Rentals with pools Halton
- Rentals with pools Ontario
- Rentals with pools Canada
- Rogers Centre
- CN Tower
- Scotiabank Arena
- Union Station
- University of Toronto
- Metro Toronto Convention Centre
- Distillery District
- Port Credit
- The Danforth Music Hall
- Nike Square One Shopping Centre
- Bay Station
- BMO Field
- Harbourfront Centre
- Exhibition Place
- Toronto Zoo
- Toronto Eaton Centre
- Trinity Bellwoods Park
- Financial District
- Massey Hall
- Niagara Falls State Park
- Casa Loma
- Dufferin Grove Park
- Toronto City Hall
- Casino Niagara




