
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 40 holiday rentals in Oakville

Nightly prices starting at
Oakville holiday rentals start at $71 NZD 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 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, 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.

3 bedroom home close to downtown with Pool!
This unique home offers its own charm, just minutes from the lake and walking distance to restaurants, shopping, cafes, and more. A quiet yet central neighborhood. Relax in our backyard and pool with your family. Our kitchen and kitchenette are fully equipped for a large family. Enjoy the comfort of high-end mattresses in a thoughtfully decorated home. Hosting is my passion, and as a Super host for six years in a row, we’re committed to providing you the same comfort we’ve offered our guests!

Modern Luxury House w/EV Charger & Heated Pool
Modern, clean, detached home in Burlington, perfect for families. * Open-concept design with ultra fast WiFi (1GBPS) and reliable mesh WiFi * 3 bedroom w/Two king beds for comfort & space * L2 electric car charger (NEMA 14-30) & 3-car private parking * Centrally located: 32 mins to Toronto, 30 mins to wine country * Palmer neighborhood: Top 10 family-friendly (Zoocasa 2023), #1 community (Maclean’s 2019) Relax by the heated saltwater pool (May - October) or cozy up by the Indoor gas fireplace.

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.

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.

FIFA Cottage Monthly avail. 12 Max Hot Tub Pool
Max 12 ADULTS* *Unfenced pool = NOT suitable for toddlers & non-swimmers. Young adult (13yrs.+) swimmers welcome. Inquire re weekend or weekly availability. - COTTAGE-Vibe Secluded - POOL OPEN mid-June to Oct. - HOT TUB all year - Ping pong/pool table - AC/furnace - BBQ+fuel - Private enter. - Short walk to lake - Towels avail, guests bring BEACH towels, lawn chairs NO parties, events, unregistered guests. Pool & Hot Tub close @ 10:30 PM NALOXONE kit avail.

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.

FIFA: 4BR: 365 Days Open- Heated Pool & Hot Tub
A Private Luxury Getaway in Toronto’s Most Coveted Neighbourhood Escape to an extraordinary 4-bedroom luxury home in Toronto’s iconic Beaches, where sophisticated design meets relaxed lakeside living. This top 1% rated Airbnb property offers an unforgettable weekend experience—perfect for families, couples, or a curated group of friends seeking both comfort and wow-factor. A year round private heated pool and hot tub are yours to enjoy !

Modern Farmhouse XL Hot Tub NOTL 15Mins- Falls
Indulge in the rejuvenating health benefits of a mid-week retreat at our Outdoor Spa. Immerse yourself in the refreshing autumn ambiance, relishing the crisp cool air, snug days, and enchanting evenings amidst the fragrant scents of fall in our picturesque outdoor setting. Discover the myriad ways to savor the essence of fall at our spa. Unwind with an overnight stay at our Modern Farm House in charming Niagara-on-the-Lake.
Popular amenities for Oakville rentals with a pool
House rentals with a pool

Four seasons Pool Retreat near downtown!

Ravine Paradise ! heated pool and hot tub!

The Bayfront - Harbour Views + Private Pool!

Comfortable &Stylish 4BD Stay Near Toronto Airport

private backyard SPA oasis in Toronto

Victorian Charm – Prime FIFA Base in King West

Boutique Wine Country Home with Pool and Hot Tub

Cozy Country Spring Getaway | HotTub + Fire Pit
Condo rentals with a pool

Luxury 2BR Condo w/ Skyline Views & Balcony

Modern 1+Den condo steps away from CN Tower & Lake

FIFA fan zone Pool/HottubFree parking walk to BMO

Humber Bay Family Friendly condo w Terrace&Parking

Stylish Downtown Toronto Condo + Free Parking

Luxury Downtown Condo For 4 (CN Tower Views)

Charming Condo w Parking, CN Tower View & Pool

Closest condo to Rogers Centre/CN tower in Toronto
Other holiday rentals with a pool

Tropical Beach House with 2 level Pool & Hot Tub!

20th Floor Condo w/ Celebration Square Views

Private 1 bed/1.5 bath in-law suite in a house!

Modern Toronto Home w/ Pool, Hot Tub, Sauna | 4BR

Luxurious 6BR Poolside Paradise with huge backyard

Midtown Penthouse - Toronto City Skyline View

Exec 2.5Br-2bath 1 Prk Condo SQ1 Stunning Views!

Modern 6 Bedroom/3 Bath Pool Home Near the Lake
When is the best time to visit Oakville?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $186 NZD | $227 NZD | $229 NZD | $252 NZD | $291 NZD | $289 NZD | $431 NZD | $276 NZD | $264 NZD | $248 NZD | $255 NZD | $250 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 |
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- Rogers Centre
- CN Tower
- Scotiabank Arena
- University of Toronto
- Metro Toronto Convention Centre
- Union Station
- BMO Field
- Downsview Park
- The Danforth Music Hall
- Harbourfront Centre
- Toronto Eaton Centre
- Niagara Falls State Park
- Toronto Zoo
- Exhibition Place
- Scarborough Town Center
- Nike Square One Shopping Centre
- Niagara Falls
- Trinity Bellwoods Park
- Massey Hall
- Casa Loma
- Enercare Centre
- Yorkdale Shopping Centre
- Elora Gorge
- York University





