
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.

Spacious, Pet Friendly Basement Apartment
Spacious and private basement apartment. This pet-friendly retreat features a cozy queen bed and sofa bed. Enjoy cooking in the fully equipped kitchen and gather around the dining table. You'll appreciate the convenience of in-unit laundry, along with complimentary coffee, tea, and free Wi-Fi. Step outside to relax in the large backyard, with access to a pool and BBQ for an additional fee (subject to availability). Located near grocery stores, restaurants, and just steps from a lovely park!

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.

The Fort York Flat
Welcome to the Fort York Flat! This 2 Bedroom, 1 Bathroom space has been thoughtfully renovated using a mixture of modern and contemporary decor to create a relaxing, upscale place to kick back while enjoying everything Downtown Toronto has to offer. Our location and smart lockbox located at the front doors makes checking into the flat easier than ever, no need to worry about fussing with the front desk staff or waiting for elevators.

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.

Modern 1 Bed Condo Mississauga
Stylish and central 1 Bed condo in Downtown Mississauga, steps to Square One, Celebration Square, Sheridan College, and transit. This modern unit features a bright open layout, full kitchen, fast Wi-Fi, smart TV, in-suite laundry, private balcony, and free parking. Walk to top restaurants, shops, events, and entertainment. Perfect for business travel, weekend getaways, shopping trips, and long stays.

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.
Popular amenities for Oakville rentals with a pool
House rentals with a pool

Luxury House with a Bright Sunroom & a heated pool

newly renovated, close to airport, washer/dryer

Modern Luxury House w/EV Charger & Heated Pool

*5BR 4Bath Family GetAway near Lake & Harbor*

4BR-Year-Round Heated Pool & Hot Tub Family Oasis

The Bayfront Flat - Harbour Views + Private Pool!

Lake Ontario Waterfront House 15 Min To DT Toronto

private backyard SPA oasis in Toronto
Apartment rentals with a pool

Stylish 2 Bdrm Gorgeous CN Tower View w/Parking!

Lux Waterfront Condo Pool Hot Tub Free Parking

Humber Bay Family Friendly condo w Terrace&Parking

Luxury Condo with FreeParking. CN Tower Lake View

Beautiful Lake View Studio Condo + 1 free Parking

Large & Bright 2BR+Den in Midtown w/ Free Parking

Lakeside Downtown Condo for upto 4 ppl

Charming Condo w Parking, CN Tower View & Pool
Other holiday rentals with a pool

Rare 1BR - Rooftop Pool, Next to MTCC & CN Tower

Stellar Humber Bay 2BD/2BTH Large Patio & Parking

Luxry Prvte Appartment highrise near train/Bus TTC

Stylish 11th-Floor Condo

Condo-mansion with large terrace

City Centre Lodge ( Downtown)

Luxury Condo w. Pool @ Yorkdale, Free Parking!

Pleasant stay Mississauga
When is the best time to visit Oakville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £97 | £94 | £93 | £106 | £123 | £122 | £182 | £117 | £111 | £93 | £89 | £111 |
| 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 £30 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 & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
50 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!
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 firepit Oakville
- House rentals Oakville
- Flat rentals Oakville
- Cottage rentals Oakville
- Private suite rentals Oakville
- Rentals with a fireplace Oakville
- Rentals with lake access Oakville
- Rentals with beach access Oakville
- Rentals with a washing machine and dryer Oakville
- Fitness-friendly rentals Oakville
- Townhouse rentals Oakville
- Rentals with a hot tub Oakville
- Rentals with a patio Oakville
- Rentals with outdoor seating Oakville
- Pet-friendly rentals Oakville
- Apartment rentals Oakville
- Family-friendly rentals Oakville
- Waterfront rentals Oakville
- Rentals with an EV charger Oakville
- Rentals with breakfast 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




