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Vacation 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.

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Condo in Mississauga

4.87 out of 5 average rating, 107 reviews

Mississauga sq1 lovely 1 bedroom condo with pool

lovely 1 Bedroom condo with 1 undergroud parking parking. centrally located in downtown Mississauga, A shopping mall with hundreds retail stores, bankings, Restaurants bars and night clubs and within a kilometre to a central highway. ~20 minute drive to DT toronto. ~15 Minutes drive to airport. Some highlights within walking distances include: ~Moxie's Grills and bar ~REDS ~All stars Wings & Ribs ~Scaddabush Italian Kitchen and Bar ~Jack Astors Bar& Grill ~ Chinese Restaurants ***No party

Condo in Davisville Village

4.93 out of 5 average rating, 250 reviews

SpectacularPenthouse VIEWS/ POOL /free Parking

Sparkling clean, lovely Penthouse Unit with panoramic city view. Lots of amenities, great neighbourhood. The building is 2 mins from subway-which leads you to Downtown Toronto- in ten minutes. Lots of amazing restaurants and pubs in the area for your enjoyment and entertainment. There is a gym, salt water pool and sauna on the 4th floor and 24 hour security; a secured parking garage with a spot for guests to park free; and there is additional paid public parking in the underground.

Guest suite in Lorne Park

4.93 out of 5 average rating, 149 reviews

Full apt on Upper floor near HWY - S Mississauga

Get the privacy & convenience of a hotel and comfort of a home. In the heart of Lorne Park in S. Mississauga, the apartment is built on the upper floor of a house with a separate entrance from the rear. 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. A lot of our guests are repeat guests. No smoking property.

Guest suite in Bronte West

4.84 out of 5 average rating, 185 reviews

Stylish Basement Hideaway*1 BR Suite*Near Lake

Our guest suite is licensed by Town of Oakville & 1 BLOCK AWAY FROM THE LAKE. New Flooring, Luxurious and spacious suite with ABOVE GRADE WINDOWS, heated flooring, bathroom, WIFI, Kitchenette &50” smart TV. Steps away from Bronte Harbor, Coronation Park, shopping, restaurants, nightlife and GO station. 1hr drive to NIAGARA FALLS and 35mins drive to downtown Toronto. Our place is suitable for all kinds of travelers. Solar heated pool can be accessed from 10am to 8pm (June to Sep)

Villa in St. Catharines

4.8 out of 5 average rating, 101 reviews

Stunning Waterfront Estate with private beach

This feels like paradise, this feels like home, this truly is 'Harmony by the Lake'. Relax and enjoy this stunning property with 60 feet of private shore line with breathtaking views of Lake Ontario and Toronto Skyline. Imagine the bliss, sitting by the water, with the sounds of nature and serenity as the backdrop. Its conveniently located 1 minute from QEW, 20 minutes from Niagara Falls/Clifton Hill and an hour drive from Toronto. Pool Closed from Oct 15th to April 30th.

Home in The Beaches

4.99 out of 5 average rating, 118 reviews

Vacation Getaway:Heated Pool-Hottub Open 365 Days

Welcome to the Toronto Beach and to this century old home, right on the beach with a private pool and spa that is open year round. Explore local shops on the high street and swim, kayak (provided), volleyball, basketball and tennis courts right beside us. In winter, an outdoor ice rink (skates provided), cross-country ski trails (bring your own equipment) and lots of walking to be had. We decorate for for holidays, and the house has a real wood burning fireplace.

Condo in Mississauga

4.76 out of 5 average rating, 206 reviews

Benetton Suite - Square One - 1 BR+Den+1 Parking

The Benetton Suite - Square One - 1 BR + Den + 1 Parking located in the heart of Mississauga, 600m from Square One Mall and 300m from Living Arts Centre. This centrally air-conditioned apartment. includes complimentary high speed wi-fi and 1 private parking free on site. Furnished in top quality style, the apartment has 2 bedrooms, a flat screen TV (with Netflix!), a fully equipped kitchen, dishwasher, microwave, washing machine, dryer with 1 bathroom with a bath.

Guest suite in Grimsby

4.95 out of 5 average rating, 255 reviews

Bright, spacious 2 bedroom apartment

Nestled just below the Niagara escarpment, in the heart of wine country, this is the perfect place to relax after a busy day. A 4 season vacation destination, you will never find a shortage of activities to do in the area. A short drive or bike ride away from numerous wineries, restaurants and hiking. A 5 minute drive to Lake Ontario, and the beach. We are a 25 minute drive to iconic Niagara Falls and a 45 minute drive to downtown Toronto.

Rental unit in Burlington

4.79 out of 5 average rating, 119 reviews

Quiet 2-bdrm, family-friendly apt with cont. bfast

Welcome to Pjila'si Home (Mi'kmaq word meaning Welcome, come in and sit down is prounced ep' ee-laa-chi). Great basement apartment, conveniently-located within a 15-minute drive of the beach, forests, farms and the mall. Less than an hour of Niagara Falls, Canada's Wonderland, 5 airports, and downtown Toronto. Continental Breakfast fixings included in your stay which includes pastries, cereal, juice, cheese, fresh fruit, coffee and tea.

Rental unit in Milton

4.83 out of 5 average rating, 104 reviews

Backyard Oasis Guesthouse.

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. NOTE:POOL IS CLOSED FOR THE SEASON

Cabin in Rural Flamborough

4.98 out of 5 average rating, 104 reviews

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.

Condo in Mississauga

4.85 out of 5 average rating, 193 reviews

🔥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.

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Popular amenities for Oakville rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Mississauga

5 out of 5 average rating, 5 reviews

6 Bedroom Luxury House with a Bright Sunroom

Home in Aldershot

4.88 out of 5 average rating, 17 reviews

Four seasons Pool Retreat

Home in Ancaster

5 out of 5 average rating, 8 reviews

Loft Apartment

Home in Aldershot

4.92 out of 5 average rating, 25 reviews

Holiday Retreat with Pool

Home in Cooksville

5 out of 5 average rating, 13 reviews

The Retreat

Home in Niagara

4.91 out of 5 average rating, 291 reviews

King West Victorian Studio Gem

Home in Port Credit

5 out of 5 average rating, 10 reviews

Maple Garden Lakeside Retreat

Home in Clarkson

4.94 out of 5 average rating, 33 reviews

Carrera Cove - Spacious 3BR - 5 Mins to Go Train

Condo rentals with a pool

Condo in Downtown Toronto

4.93 out of 5 average rating, 206 reviews

College Park :2Bd+2bth + Free parking

Condo in Unionville

4.91 out of 5 average rating, 105 reviews

Downtown Markham Unionville

Condo in Fort York

4.95 out of 5 average rating, 125 reviews

One Of A Kind Downtown Sanctuary w/ CN Tower View

Condo in Fort York

4.89 out of 5 average rating, 404 reviews

Lakeside Condo Studio In Downtown Toronto

Condo in Downtown Toronto

4.95 out of 5 average rating, 196 reviews

Upscale Luxurious Condo Free Parking

Condo in Downtown Toronto

4.97 out of 5 average rating, 235 reviews

Chic, High-Rise Apartment with CN Tower Views

Condo in Downtown Toronto

4.87 out of 5 average rating, 105 reviews

Luxury 1BR Executive Suite with Stunning Views!

Condo in Fort York

4.89 out of 5 average rating, 124 reviews

Lakeside Downtown Oasis accommodating 4 ppl

Quick stats about vacation rentals with a pool in Oakville

Total rentals
60 properties
Total number of reviews
760 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