Vacation rentals with a pool in Oakville

Find and book unique homes with a pool on Airbnb

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Popular amenities for Oakville rentals with a pool

House rentals with a pool

Superhost
Home in Burlington
5 out of 5 average rating, 13 reviews

Modern Luxury House w/EV Charger & Heated Pool

DidiRating, 5 stars7 months ago
Our stay at this Airbnb in Burlington, Ontario, was truly a home away from home. From the moment we arrived, we felt completely at ease in this beautiful and peaceful space. The home itself is lovely, with warm, inviting decor and thoughtful touches that made us feel instantly comfortable. The location in Burlington was ideal for us as a family. We enjoyed exploring the nearby , taking peaceful walks along the waterfront, and visiting the local parks. Burlington’s small-town charm paired with its scenic beauty was a perfect match for our family’s needs. The hosts were exceptional—always responsive and so kind, which really enhanced our experience. They went above and beyond to ensure we had everything we needed, and their hospitality made us feel genuinely welcomed. We left with wonderful memories, and we wouldn’t hesitate to stay here again on future visits to Burlington. Highly recommended for families or anyone seeking a peaceful retreat in a beautiful area
Superhost
Home in Aldershot
4.83 out of 5 average rating, 46 reviews

Four seasons Pool Retreat

KarenRating, 5 stars4 days ago
This house was spacious, just perfect for our large group! This may sound strange but the house had a crockpot which was equally perfect for us. We could go all day to see the sights and return to a ready-to-eat meal. The neighborhood was very quiet and beautiful. We could easily access the highways to get to Toronto, Niagara Falls, and other points of interest.
Superhost
Home in St. Catharines
4.83 out of 5 average rating, 247 reviews

Stunning Large Family home

AlettaRating, 5 stars3 weeks ago
Went for a weekend away and the place was a great stay. It was clean and communication was great. They even left us snacks and a nice note.
Guest favorite
Home in Niagara-on-the-Lake
4.79 out of 5 average rating, 230 reviews

WhiteOrchid LuxuryHome WithSaltHeatedSwimmingPool

ChandraRating, 5 stars3 weeks ago
Beautiful place. The hosts were so kind and helpful. The area is safe and so close to the outlets which was a huge plus for us ladies! Hope to stay there again one day!
Top guest favorite
Home in Ancaster
5 out of 5 average rating, 16 reviews

Loft Apartment

ShannonRating, 5 stars2 weeks ago
This cozy studio was the perfect get away for us. We felt relaxed, at ease and comfortable. Milena is a gracious host, the home is stunning, welcoming and it was very well stocked with everything we needed, just like home. It was the perfect location for us to hike the waterfall trails, experience the Botanical gardens and visit with family and friends in Hamilton and Burlington. Will certainly book again for future vacations.
Superhost
Home in Mimico-Queensway
4.87 out of 5 average rating, 47 reviews

private backyard SPA oasis in Toronto

JJRating, 5 stars3 days ago
⭐️⭐️⭐️⭐️⭐️ Absolutely Outstanding Stay! This was hands down one of the best Airbnb experiences I’ve ever had. The home was spotless, beautifully designed, and had every amenity I could’ve asked for. The attention to detail—from the cozy linens to the fully stocked kitchen—truly made it feel like a home away from home. The host was incredibly responsive, thoughtful, and made check-in a breeze. The neighborhood was quiet and safe, yet close to everything we needed. The Hot Tubs, Sauna, and pool all came in hand when recovering from the Ice Hockey Tournament. I’m already looking forward to booking again next year—it’s become a new favorite! Thank you for making this such a memorable and seamless experience.
Superhost
Home in Hamilton
4.78 out of 5 average rating, 95 reviews

California Chic +Breathe +Unwind +Restore

DomarRating, 5 stars1 week ago
Thank you for providing the opportunity to enjoy this 2 night which exceed our expectations, we had a wonderful stay in your place . What a beautiful place!!!! It was great to relax and enjoy. The view is like none other, fantastic location. We loved this place. The place is equipped with everything. We can’t wait until we come back.
Superhost
Home in Central Etobicoke
4.9 out of 5 average rating, 10 reviews

Luxury 2bedroom Unit in the city/heated salt pool.

GrantRating, 5 stars2 days ago
If you are thinking of visiting Toronto and don’t want to stay in the chaos of the city or simply like the suburbs more, this is definitely the place to go. Not only is the neighborhood beautiful and so is the place, it’s also a very useful area. It has good stores and pubs and restaurants within 10-15 minutes walks. Only a few minutes from a bus stop that runs every ten minutes will take you to Kipling station, from there you can metro anywhere in the city for only a few bucks. (Definitely get a presto card on your phone, more reliable than a card). Bessa herself was awesome, in my excitement of booking flights for my first international trip, I got into the country way earlier than the check in time and Bessa worked hard to have the place ready as early as she can for me and was very quick to let me know when it’s available. When I had questions about the area she was very quick to answer with useful information. All in all, this place and its host made my trip to Canada amazing.

Condo rentals with a pool

Superhost
Condo in North York
4.8 out of 5 average rating, 106 reviews

Chic Studio w/ Pool | Near Lawrence West Subway

KayodeRating, 5 stars6 days ago
Andrews Place is perfect for a solo traveler. The property is clean, private, and offers excellent transport access to very interesting places. You can catch a direct bus from Toronto YYZ Airport with no need to change buses, and it's just less than a 10-minute walk to the property from the bus stop. It was truly great value for money.
Superhost
Condo in Burlington
4.88 out of 5 average rating, 52 reviews

Modern Luxury Condo - Go Station, Gym, Pool+

JohnRating, 5 stars5 months ago
Our Go To Place to stay in Burlington. Stephanie goes above and beyond in terms of responsiveness. Being so close to the GO TRAIN made commutes to Union Station a breeze. Will definitely be staying again.
Top guest favorite
Condo in Fort York
4.98 out of 5 average rating, 192 reviews

Stylish Downtown Toronto Condo with Free Parking

NickRating, 5 stars1 week ago
Great place and location. As described, no issues and responsive host.
Guest favorite
Condo in Mississauga
4.9 out of 5 average rating, 52 reviews

Mississauga Square One Condo

IbRating, 5 stars1 week ago
Property was exactly as listed. Very comfortable and extremely clean, there was even cleaning supplies in the cabinet which was great. Parking was a maze but the instructions were very clear. I will be staying at Tulashi's place every time I go to Canada ❤️
Superhost
Condo in Mimico-Queensway
5 out of 5 average rating, 5 reviews

Luxury 1BD Condo w/ Stunning Views - Toronto

WilliamRating, 5 stars1 week ago
Staying at Stephanie’s was amazing. It was a great location from the airport and the local station. Close to a supermarket for food and essentials. The host was extremely helpful with a fantastic information pack provided upon arrival with everything you need to know about the apartment and the local area. It was a very clean apartment. Beautiful views and very affordable with great value for money. I would recommend staying at this accommodation to anyone visiting Toronto. I will be coming back here for sure. Thank you for being such a great host.
Guest favorite
Condo in Fort York
4.98 out of 5 average rating, 121 reviews

Artsy and Comfy Home with a View

YomiRating, 5 stars1 week ago
Great Location if you're visiting the city close to everything downtown. Great view as well being on the 20th floor. Very clean apartment. The host used white sheets, pillowcases and towels which is always a plus in my opinion. Free parking was a HUGE plus for me (Parked my car and walked everywhere). I would definitely stay again and would recommend to anyone.
Guest favorite
Condo in Fort York
4.86 out of 5 average rating, 249 reviews

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

NoomenRating, 5 stars2 weeks ago
The view on CN tour by night is the best feature and i really recommend this place.
Guest favorite
Condo in Downtown Toronto
4.98 out of 5 average rating, 102 reviews

“Amazing 2 Bedrooms Condo” in Downtown Toronto”

PeterRating, 5 stars1 day ago
Erkan's apartment was the perfect base for us to explore Toronto. It is really close to Union Station, the CN Tower, the shoreline, all the shops, great restaurants. Everything we were looking for. We'll definitely be back next time we visit the city.

Quick stats about vacation rentals with a pool in Oakville

  • Total rentals

    60 properties

  • Total number of reviews

    840 reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    60 properties include access to wifi

Destinations to explore

  1. Airbnb
  2. Canada
  3. Ontario
  4. Regional Municipality of Halton
  5. Oakville
  6. Rentals with pools