The heart of Windsor, Canada, is its ever-present youth. The University of Windsor draws in students with a stellar education, and the rest of the city serves this bright-eyed and energetic population with a myriad of arts and culture. As a visitor, you too will benefit from the plethora of sights and sounds. Whether you’re 18 years old or 80, the art of Windsor Sculpture Park, the sweeping history of Willistead Manor, the excitement of a casino, and the vibrancy of one of the many festivals set in the city are sure to awaken a thrill. What better way to complete a vacation there than to splash in the swimming pool? For relaxing accommodation options, check out the top Airbnbs with pool in Windsor, Canada.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to pool. The image galleries get refreshed with the latest updates regularly. They were last updated on December 18, 2024.
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1. High-tech mansion in a historic neighborhood
Set in the historic neighborhood of Victoria Avenue, the property has seven bedrooms that can sleep up to sixteen guests. You’ll have access to a sleek kitchen for culinary experiments with your friends, a living area with plush furnishings, fun board games, and Nintendo Wii for entertainment.
The cherry on top is the 16 x 32 ft (4.9 x 9.8 m) private outdoor pool, heated for your convenience. The owner has thoughtfully included pool towels in the package as well. The seasonal pool is typically operational in May until it snows, so don’t forget to double-check with the host if you want to use this swimming facility in the gated yard. The 24-hour pool includes sun loungers and pool toys and can be accessed via the patio doors.
A six-seater hot tub is at your disposal too if you prefer a soothing soak.
Windsor, Ontario, Canada
2.02 km (1.3 mi) from Jackson ParkSuperhost
Accommodates: 16
Top guest reviews
Host:
hosts are welcoming and accommodatinglouis and mariah were amazing hostslouis is an amazing host just like his homelouis is amazing host'louis was extremely response and is a great hostLocation:
great location and the pool is amazingamazing place fully stocked with everything you could possibly needeveryone enjoyed the location and amenitieseasy check in/checkout spacious parking and convenient locationit’s the perfect place to be with friends and family and have an intimate gatheringCleanliness:
a very clean spacious houseit was extremely clean and organizedso clean and very well equippedit was very clean enough beds for everyone to sleep comfortablyit was clean modern and accommodated everyone perfectly with room to spareRead more reviewsAmenities & Room:
the furniture in the back yard is comfortable and stylishstay was great internet was fast and the pool was really nicethe pool area is beautiful as is the entire houselouis was an incredibly helpful host for our two families - we had a blast and were very comfortablebeds were comfortable
2. Relaxing family home with a patio (from USD 254)
Perfect for those who want a large space for their family, this newly renovated house features a spacious backyard with a sparkling blue outdoor pool. Guests are welcome to sport their swimsuits in this fenced leisure facility and enjoy a refreshing dip!
The property itself has four bedrooms and a fully stocked kitchen. There’s also a wooden patio with a barbecue grill, so you have a choice to have fun cookouts under the stars. When swimming tires you and the kids out, the TV takes care of your quiet-time entertainment as it is equipped with Chromecast, Netflix, and YouTube.
Windsor, Ontario, Canada
2.67 km (1.7 mi) from Jackson ParkAccommodates: 8
Top guest reviews
Host:
troy was a very helpful host who provided thorough and easy to follow check in instructions for my employeeswe had a great time in windsor and appreciate you hosting useasy to communicate with and very accommodatingLocation:
the location is good close to restaurants and on a pretty quiet streetgreat location lovely home and pool will stay again for future trips to windsorit was a busy weekend and the location was perfect for attending the woodward dream cruise in detroitgood place if you are looking for a getaway for a cheap priceRead more reviewsCleanliness:
pool and house were both clean and maintainedthe interior and exterior upkeep/cleanliness of the property was outstanding
3. Sports-themed suite with barbecue facilities (from USD 52)
If you’re a fan of athletics, this novelty two-bedroom suite is certainly the place to be. The walls are plastered with posters of athletes and sports memorabilia, awakening a fun, competitive spirit, especially if there’s a game to watch with your friends. The bungalow has the perfect area for it, too: the living room with the huge, flat-screen TV, pliant leather couches, and a fireplace in the corner for cold nights.
Outside, a broad saltwater pool awaits your competitive games of Marco Polo and Atomic Whirlpool. The seasonal pool is heated, making it ideal when the weather gets too cold. Don’t forget—you’ll be sharing it with other guests, so it’s also a great opportunity to make friends.
A built-in grill and a bar table are available for you to roast some meat, and there are poolside lounge chairs perfect for sunbathing.
Windsor, Ontario, Canada
1.96 km (1.3 mi) from Jackson ParkAccommodates: 4
Top guest reviews
Host:
host was responsive without interferingthe hosts were super friendly and helpfulthanks for being an awsome host francogreat host and a comfortable staygreat host extremely friendly and accommodatingLocation:
good location near storesexcellent location place and overall experiencethis basement apartment is a great place to stayeasy location to get around town with or without a carbedrooms and the bathroom were great very close to local things caesars was maybe 8 mins awayCleanliness:
great place and very cleanexpect for a very clean and enjoyable stayplace is good and cleanthe place was beautiful and spotlessawesome spot - hosts are very friendly space is clean - highly recommendRead more reviewsAmenities & Room:
very comfortable suite wonderful backyard amenitiesquiet comfortable and it really exceeded my expectationsour favorite part was the sparkling heated pool and landscaped yardthe quiet atmosphere and comfortable beds make for a great night sleeptotally recommended for a comfortable stay in windsor
4. Quaint house with a garden
Ideal for family trips, this little grey house has everything you need for a relaxing weekend getaway. The property has two bedrooms and three beds, able to sleep up to six people. It features an indoor playroom for your little ones, complete with posters, picture books, stuffed toys, and a trampoline. Outside is even better: you get your own 12 x 4 ft (3.7 x 1.2 m) above-ground pool! You won’t be sharing it with neighbors, and your kids can splash around to their heart’s content.
The verdant garden also houses a tiny playground with a dining area nearby—perfect for afternoon meals when the children get hungry.
Windsor, Ontario, Canada
4.74 km (3.0 mi) from Jackson ParkAccommodates: 6
5. Tranquil house in the middle of the city
Looking for a romantic getaway with your spouse? In this elegant one-bedroom house, you’ll be able to have all the one-on-one time that you need to reconnect with your partner. While the location is in the midst of the city, you’ll be surprised because the neighborhood is quiet, and you’ll be able to have your privacy.
Guests will be provided with a complimentary hot breakfast. However, if you want to try your hand at cooking, the kitchen is fully functional and spacious enough that you won’t be bumping elbows with your loved one as you create a meal together.
In the yard filled with verdant greenery, you’ll find a swimming pool. You can dip your feet in the cool water as you eat snacks on the poolside or get on some floaties while sipping drinks and conversing. You’re sure to have a wonderful time!
Windsor, Ontario, Canada
5.83 km (3.7 mi) from Jackson ParkAccommodates: 4
Top guest reviews
Host:
great space - amazing hostsbrent was communicative and respectfulnice private dog friendly space above a garage separate from the owner's houseLocation:
very convenient and central location that served as a great home base while we visited family in windsorRead more reviewsCleanliness:
clean and very spaciousthe unit was clean and quietbig and super cleanclean spacious apartment - added bonus that dogs are allowed
Savor a relaxing dip after touring around Windsor
As the southernmost city in Canada, Windsor also has the warmest climate in Ontario. When summer rolls around, there’s nothing more perfect than taking a refreshing dip in the pool. Book one of these top Airbnbs with pool where you can recharge after exploring the city’s attractions.
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