
Vacation rentals with a pool in Windsor
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Windsor
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
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Popular amenities for Windsor rentals with a pool
House rentals with a pool
Superhost

Home in Detroit
4.82 out of 5 average rating, 49 reviewsCute & Cozy 3bdrm, 1 bath. 12 mins to Downtown.
SeQuanaRating, 5 stars1 day ago
House is nice! The yard and pool was surprisingly huge! What a great entertainment space! Just what my daughter needed for her 18th birthday 🎂 🥳 pool party
Superhost

Home in Windsor
4.33 out of 5 average rating, 18 reviewsLuxury at its finest (Windsor) Swimming Pool
MadisonRating, 5 starstoday
Beautiful house and pool. Lots of space and comfortable beds, would definitely stay again
Guest favorite

Home in Kingsville
4.9 out of 5 average rating, 29 reviewsModern lake-town cottage
ErinRating, 5 stars2 months ago
Great spot very convenient and walkable to town, nice open space, and I liked that it had workout equipment too in the basement. Check in and check out was extremely easy.
Guest favorite

Home in Amherstburg
4.77 out of 5 average rating, 35 reviewsLittle heaven
AdnanRating, 5 stars1 week ago
My family and I were pleasantly surprised when we first explored the Airbnb. The house was even better than described! The little details really made it an over the top experience. The backyard, with the pool and river, was breath taking. There was plenty of space for our party of 7 and everyone enjoyed every moment. We will be coming back! Adnan
Superhost

Home in Ruscom Station
4.86 out of 5 average rating, 14 reviewsLakeshore Weekend Getaway
NiloojiniRating, 5 stars1 day ago
We had a fantastic stay at Nik’s place! The property was perfect for both adults and kids. We loved the pool and BBQ setup—it made for some great outdoor family time. The pool table was a fun bonus for evenings, and the firepit by the pond created such a relaxing vibe. The kids especially enjoyed the giant tic-tac-toe game! One of the highlights was the amazing view of the patty field—it was spacious, scenic, and made the whole experience even better. Nik was a great host—responsive and welcoming. Would definitely recommend this place for anyone looking to unwind and have fun. Thanks again, Nik!
Superhost

Home in Kingsville
4.85 out of 5 average rating, 26 reviewsPrivate Poolside Escape near Point Pelee
Chrystal MargaretRating, 5 stars1 week ago
You will not find a more beautiful, cozy place in Leamington/Essex County with a pool. The entire backyard is a ‘get-a-way’ in itself! The location is wonderful- outside of the ‘busy towns’ but so close you can get to restaurants, shops etc.. very quickly. For those who are looking to go to point pelee, the home comes with a pass which is just a lovely bonus. Beds were comfortable, bedding was clean and cozy. Kitchen well equipped and LOTS of room for your food if you plan on cooking. Great place for kiddos as well - fenced in yard, bunk beds, games… The hosts were EXTRA accommodating with our different needs and very prompt if we had a question or needed anything. This is the place for you and your family for a vacation or staycation. Recommending to everyone and would definitely come back!
Top guest favorite

Home in Belle River
4.97 out of 5 average rating, 78 reviewsBelanger Air BnB
EvettRating, 5 stars3 weeks ago
We stayed 2 nights at Dave's place and enjoyed the swimming pool and the outside fire pit was great because the weather was chilly and it helped to spend time outdoors in the backyard. Kitchen was well-equipped for basic needs. Will come back.
Guest favorite

Home in Kingsville
4.95 out of 5 average rating, 78 reviewsSunny Days Estate ✦ Large Saltwater Pool ✦ Hot Tub
JonathanRating, 5 stars8 months ago
I would stay with Vik anywhere he chooses to have a rental. It was a pleasure to connect with such a pleasant host. The kingsville area could keep us coming back for years. The wineries are world class and the restaurants know how to make you feel like a king, while also have a small town vibe. Highest of recommendations
Quick stats about vacation rentals with a pool in Windsor
Total rentals
50 properties
Nightly prices starting at
G$4,184 GYD before taxes and fees
Total number of reviews
840 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Ford Field
- Little Caesars Arena
- Point Pelee National Park
- Comerica Park
- Michigan Stadium
- Oakland Hills Country Club
- Detroit Golf Club
- Wesburn Golf & Country Club
- Detroit Zoo
- Warren Community Center
- Roseland Golf & Curling Club
- University of Michigan Museum of Art
- Grosse Ile Golf & Country Club
- Bloomfield Hills Country Club
- Maumee Bay State Park
- University of Michigan Golf Course
- Rolling Hills Water Park
- Motown Museum
- Seven Lakes State Park
- Country Club of Detroit
- Essex Golf & Country Club
- Ambassador Golf Club
- Franklin Hills Country Club
- Coachwood Golf & Country Club