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

Guest favorite
Home in Mississauga
4.93 out of 5 average rating, 15 reviews

Luxury House with a Bright Sunroom & a heated pool

MarianneRating, 5 stars4 days ago
We had a wonderful stay. Everything was up to standard. House was clean and well set up.
Superhost
Home in Burlington
5 out of 5 average rating, 3 reviews

2 living rms | 3 TVs | Foosball | Family fun!

AlexRating, 5 stars4 months ago
This was our home away from home through renovations and cannot be more thankful for Helena and Matt allowing us to use their home. We had two extensions and the team was more than accommodating - communication was quick and easy! Thank you so much again for opening your home to us! Happy Holidays!
Guest favorite
Home in Vaughan
5 out of 5 average rating, 5 reviews

Vacation Getaway with Heated Spa-Pool Open365 Days

YasminRating, 5 stars3 weeks ago
I had an amazing experience staying at this beautiful home. The property was exactly as described, and even better in person! It was clean, spacious, and thoughtfully decorated, making it feel like a home away from home. The host was incredibly welcoming and responsive, ensuring that we had everything we needed for a comfortable stay. The location was perfect, with easy access to local attractions and amenities. I highly recommend this place to anyone looking for a relaxing and enjoyable stay. Can't wait to return!
Superhost
Home in Burlington
5 out of 5 average rating, 13 reviews

Modern Luxury House w/EV Charger & Heated Pool

DidiRating, 5 stars5 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
Guest favorite
Home in Niagara
4.91 out of 5 average rating, 299 reviews

King West Victorian Studio Gem

MRating, 5 stars5 days ago
One of the best Airbnb stays! I love the character of the space, the location is fantastic, and the availability of amenities all around. The best part was the softness of the bed sheets! I value a good night sleep, and the bed was so comfortable. Wi-Fi was extremely fast and made working from home a breeze. The kitchen is well stocked with everything needed to make yourself at home. Thank you Kathleen. I'll definitely book again in the future.
Top guest favorite
Home in North York
4.87 out of 5 average rating, 77 reviews

Casa Meya - Toronto Poolhouse Villa

CathrynRating, 5 stars1 week ago
We stayed at Rooz’s home for our son’s wedding at Graydon Hall Manor. It was the perfect location and only a seven minute drive. The house was beautiful! It was very comfortable and quiet inside. The neighborhood was also safe and quiet. It had well supplied kitchen and bathrooms. The beds were super comfy. I highly recommend this home to anyone traveling to Toronto, especially if attending an event at Graydon Hall Manor.
Guest favorite
Home in St. Catharines
4.95 out of 5 average rating, 39 reviews

Upscale 3BR Designer House with POOL!

AmyRating, 5 stars8 months ago
This is a wonderful little house that suited our needs. So clean it was amazing the pool was great and the downstairs tv room was perfect to congregate all together. We could not fault Greg’s communication he was quick to respond and the helpful guide sent before check in was great. I walked the neighbourhood some afternoons and it was lovely with beautiful trees and gardens and a park at the end of the street. Very quick to anywhere in town by car and out to vineyards etc. We would highly recommend this house to anyone! Thank you
Guest favorite
Home in Clarkson
4.94 out of 5 average rating, 16 reviews

Modern 6 Bedroom/3 Bath Pool Home Near the Lake

AmyRating, 5 stars4 months ago
Wonderful hosts, house was accurately represented per the description. We held our team offsite for 2025 planning and had team members come in from all over North America and local as well. House was perfectly set up for this. Great location for team to come together, but also big enough that team members would have their own space. Fast and easy communication with hosts and sparkling clean!

Condo rentals with a pool

Superhost
Condo in Downtown Toronto
4.88 out of 5 average rating, 122 reviews

Luxury Downtown 2Bed by ScotiaBank Arena + Parking

KarenRating, 5 stars1 month ago
You cannot beat this location! The Airbnb exceeded our expectations. It was spacious with all the amenities you could want. An amazing space with spectacular views, and a patio to enjoy our time even more. Close to absolutely everything. We walked everywhere, took in a hockey game and felt like we were living in downtown Toronto. A perfect weekend getaway. Highly recommended!
Guest favorite
Condo in Fort York
4.96 out of 5 average rating, 132 reviews

Modern Downtown Condo Free Parking/ Walk to Lake

StephanieRating, 5 stars1 month ago
Jessica was one of the best Airbnb hosts I’ve had in a long time! I celebrated my three-year anniversary here with my partner, and it was absolutely perfect. Jessica went above and beyond by setting up the room beautifully with flowers, rose petals, and electric candles—my partner was overjoyed. She was incredibly accommodating, allowing us to check in early and responding quickly to all my requests. The space itself was spotless, smelled amazing, and was incredibly comfortable. As a same-sex couple, safety is always a consideration when booking accommodations, but this location felt extremely secure. My partner and I were out late at night and felt completely at ease. The apartment has a double lock for added security, and the building itself is well-monitored. On top of all that, the view of downtown and the CN Tower was stunning. I highly recommend this stay, especially for couples—10/10!
Guest favorite
Condo in Fort York
4.97 out of 5 average rating, 115 reviews

Luxury Waterfront Downtown Condo w/ Pool & Parking

KaylaRating, 5 stars2 weeks ago
We had a great stay. The place was clean and very nice. I love how parking was included with our stay. That was convenient. Highly recommend!
Guest favorite
Condo in Fort York
4.89 out of 5 average rating, 414 reviews

Lakeside Condo Studio In Downtown Toronto

IeishaRating, 5 stars2 weeks ago
Very clean and great locations for nights in downtown Toronto
Guest favorite
Condo in Downtown Toronto
4.93 out of 5 average rating, 150 reviews

3BR Rooftop Pool-Gym-Steps-MTCC-CN Tower-Parking

BhalchandraRating, 5 stars1 week ago
very clean apartment, walkable to everything, across the street from CN tower. Matthew was very proactive with communication. ours was kind of last minute reservation, but Matthew was very fast is getting back to us with confirmation and provided all the instructions for checkin. The apartment building has security and was fully gated, which made us feel very safe.
Top guest favorite
Condo in Fort York
4.98 out of 5 average rating, 186 reviews

Stylish Downtown Toronto Condo with Free Parking

DavidRating, 5 stars1 month ago
stayed here a few times, always a pleasure. host is so nice and place is just as pictured.
Guest favorite
Condo in Fort York
4.9 out of 5 average rating, 31 reviews

Entire 2BR Condo Downtown + Skyline View + Parking

JordanRating, 5 stars2 weeks ago
Great condo in a great location. Lovely view of Toronto. Walking distance to all amenities.
Top guest favorite
Condo in Downtown Toronto
5 out of 5 average rating, 125 reviews

Luxury Downtown Condo For 6 (Near CN Tower)

LauraRating, 5 stars5 days ago
Clean, very conveniently located, and always quick communication before and during the trip from Bri and Mike! Great set up for our family (2 adults and 2 kids). Would definitely stay here again if returning to Toronto.

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