Vacation rentals with a pool in Windsor

Find and book unique homes with a pool on Airbnb

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Popular amenities for Windsor rentals with a pool

House rentals with a pool

Superhost
A circular above-ground pool with clear blue water is set against a grassy area. The pool's surrounding area features a smooth gravel bed, while a wooden fence and a two-story home are visible in the background.
Home in Detroit
4.82 out of 5 average rating, 49 reviews

Cute & 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
The exterior of a single-story home is shown, featuring a spacious driveway lined with paving stones. Lush greenery, including a large evergreen tree and manicured shrubs, frames the entrance, which includes a blue door and large front windows under a lightly clouded sky.
Home in Windsor
4.33 out of 5 average rating, 18 reviews

Luxury 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
A modern kitchen area is highlighted with a central island, pendant lighting, and a small dining space. The room features large windows providing natural light, with a view of the outdoors. Stylish blue chairs add a pop of color against light wood flooring.
Home in Kingsville
4.9 out of 5 average rating, 29 reviews

Modern 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 reviews

Little 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
A hot tub is located on a wooden deck under a string of warm lights. The water is illuminated in blue, creating a calming ambiance. A ceiling fan is positioned above the tub, and the surrounding area is enclosed with latticework for privacy.
Home in Ruscom Station
4.86 out of 5 average rating, 14 reviews

Lakeshore 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
A large, inviting saltwater pool extends across the backyard area, surrounded by lush green landscaping. The home is visible in the background, featuring a grey roof and light-colored exterior. Poolside lounge chairs are positioned for relaxation under the clear blue sky.
Home in Kingsville
4.85 out of 5 average rating, 26 reviews

Private 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
A clear blue swimming pool is framed by a textured concrete deck. A diving board extends from one side, with poolside furniture visible in the background. Vibrant greenery surrounds the area, enhancing the outdoor space.
Home in Belle River
4.97 out of 5 average rating, 78 reviews

Belanger 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
The exterior of the home features a brick facade complemented by vibrant green landscaping. Lush trees and shrubs create a welcoming entrance, while a well-maintained lawn adds to the overall appeal. The front door, framed by natural stone accents, invites guests into the property.
Home in Kingsville
4.95 out of 5 average rating, 78 reviews

Sunny 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

Destinations to explore

  1. Airbnb
  2. Canada
  3. Ontario
  4. Essex County
  5. Windsor
  6. Rentals with pools