
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 In The Heart Of Wine Country
Hidden along the shores of the Niagara River, Grayden Estate is nestled on a quiet dead end street in beautiful Queenston/Niagara on the Lake. A short drive to Old Town and within a few minute walk or bike to world class wineries, art galleries, farmers markets, hiking trails, parks and the waterfront, Grayden Estate is the ideal location for a peaceful quiet getaway for anyone looking to surrender to the simple living quiet life. Complimentary tour bikes are available for use. Lic # 112-2023

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.

“CasaDeLeon”- Modern and cozy Lakeview guesthouse
YES Hot tub and heated pool are open! Forget your worries in this 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. **25+ ID & waiver req**

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.

Five Star Hayloft Suite
This open space home is in the top level of a century-old bank barn. Witness the beautiful architecture while enjoying modern amenities like an open-concept kitchen, projector & movie lounge, and more! Enjoy 180 degree views from the bay window in the living room during your stay. Five Star Ranch offers a year-round getaway in a beautiful country setting. Situated on a working farm, and surrounded by gardens, animals and beautiful forest, it is a perfect destination for seclusion and peace.

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 and Airy Guest Suite with Pool
Large windows, high ceilings, fresh modern decor, cedar sauna, fitness room and backyard pool best describes our Garden Suite. Spoil yourself in everything this space has to offer. Featuring a comfy queen size bed sheeted with luxury cotton and down duvet. A large queen pull-out couch offers space for extra sleepers. Take some time to refine your culinary skills with the well appointed kitchen. Don't overpack, your in-unit washer and dryer will keep your clothes clean.

Private NOTL Retreat • Pool • Quiet Escape
Enjoy a private Niagara-on-the-Lake retreat, now offered as an entire home. This peaceful property features two King bedrooms with ensuite bathrooms, plus a Queen bedroom with its own dedicated full bathroom. Relax in bright living spaces, unwind in the cozy lower-level family room with a smart TV, or enjoy the spacious backyard with a pool, deck, and pergola area. Perfect for families or small groups seeking comfort, privacy, and a quiet getaway.

Backyard Oasis Guesthouse.
POOL IS OPEN 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

Vineyard Estate by the River with Pool!

Luxury Family Oasis W/ GameRoom/King Bed/Hot Tub

Toronto Backyard w/ Pool, Hot Tub & Sauna | 4BR

Comfortable &Stylish 4BD Stay Near Toronto Airport

private backyard SPA oasis in Toronto

Wine country Cottage 15 min drive to old Town NOTL

Hot Tub/Outdoor Sauna/Heated Pool/5 Min To Falls

Victorian Charm – Prime FIFA Base in King West
Apartment rentals with a pool

Luxury 2BR Condo w/ Skyline Views & Balcony

Beautiful Condo Across CN Tower and MTCC

1 Bedroom + Den (Office/Bidet/Balcony) near Rogers

FIFA fan zone pool/ HottubFree parking walk to BMO

Stylish 1BR on Toronto’s Harbourfront

Humber Bay Family Friendly condo w Terrace&Parking

Stylish Condo | Walk to BMO Field + FIFA Festivals

Beautiful Lake View Studio Condo + 1 free Parking
Other holiday rentals with a pool

20th Floor Condo w/ Celebration Square Views

Beautiful High Rise View Condo W/Pool&Free Parking

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

The Farmhouse – Pool, Orchards, Dog-Friendly

Walk-Out Suite | Airport 22m | BMO Field 38m w/ GO

CN Tower View Penthouse | Pool, Gym & World Cup

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

Milton Home- a Family Oasis
When is the best time to visit Oakville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £78 | £95 | £96 | £106 | £122 | £121 | £181 | £116 | £111 | £104 | £107 | £105 |
| 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 £30 per night before taxes and fees

Verified guest reviews
Over 630 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
40 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!
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- Rogers Centre
- CN Tower
- Scotiabank Arena
- Union Station
- University of Toronto
- Enercare Centre
- Metro Toronto Convention Centre
- BMO Field
- The Danforth Music Hall
- Harbourfront Centre
- Nike Square One Shopping Centre
- Toronto Eaton Centre
- Niagara Falls State Park
- Downsview Park
- Exhibition Place
- Toronto Zoo
- Trinity Bellwoods Park
- Niagara Falls
- Casa Loma
- Wilfrid Laurier University
- Massey Hall
- Scarborough Town Center
- York University
- Casino Niagara





