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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Top guest favorite

The exterior features a rustic wooden facade with archways framing the entrance. A stone pathway leads to the front door, surrounded by grassy areas and decorative landscaping elements. Two windows, with trimmed edges, are positioned symmetrically beside the door.

Barn in Tilbury

4.94 out of 5 average rating, 90 reviews

Cowbarn Cabin

We have converted this cow barn into a charming open concept country cabin, 5 mins from the 401. Relax with your morning coffee on the patio or on the raised pool deck watching the sun rise overlooking the countryside. Enjoy the warm glow of the gas fireplace while watching TV and sitting on the leather reclining loveseat. For the fishermen, you are 5 mins to 2 boat launches that enter the Thames River into Lake St. Clair, ample parking for vehicles, boats, trailers and outside hydro outlets.

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

The perfect place to enjoy all that this little town on the lake has to offer! Two blocks from the best restaurants in the area, a local coffee roaster, and a wellness spa. Seven blocks from Lake Erie, on the wine route close to 14 wineries & breweries, and a prime spot for bird enthusiasts. Welcome to this newly renovated 2-bed, 2-bath home in Kingsville, the southern most town in Canada! Enjoy your morning coffee poolside from the walk-out deck, hike or bike the Greenway or the at-home Peloton

Superhost

A spacious living area showcases comfortable seating and a modern kitchen with essential appliances. The outdoor patio features cozy furniture under a large umbrella, perfect for relaxation. Lush greenery surrounds the area, emphasizing the tranquility of the private resort setting.

Place to stay in Belle River

4.83 out of 5 average rating, 54 reviews

Whitty’s at Rochester Boat•Golf •Fish•Swim

Everything provided, cottage is situated in a private resort on the 16th green of a premier public golf course. 1 bedroom and easily sleeps 4, including a sofa bed. Beautiful backyard includes patio with furniture, outdoor dinning, bbq & fire pit. Easy access to boat launch & wells, outdoor pool & playground. Minutes walk to Parkside Grille 5 star restaurant with lounge and live music. Enjoy scenic ecosystem of river & lake access to boat, fish, paddle on Lake St.Clair. Sandy beach nearby!

Superhost

An inviting outdoor area showcases a glistening in-ground oval pool framed by a spacious deck. Comfortable lounge chairs are situated nearby, and the house features large windows that allow for ample natural light. A dining set is visible under the covered patio, ideal for outdoor meals.

Home in Riverside

4.79 out of 5 average rating, 204 reviews

Beautiful Oasis w/Heated Private Pool & Sunroom!

*HEATED POOL IS OPEN APRIL 1 - OCT 31* Welcome to Windsor’s largest and coziest stay! This gorgeous home blends modern design with comfort, featuring an inviting sunroom with soaring ceilings and natural light, perfect for morning coffee or quiet evenings. The chic decor creates a stylish, yet homey feel :) Unwind in a private backyard oasis with a 15x30, 8’ deep, in-ground oval pool with a brand NEW heater and BBQ lounge! Our backyard designed for a unique and relaxing family experience!

Top guest favorite

The exterior of a brick bungalow is visible, framed by a variety of lush greenery and colorful flower beds. A small set of steps leads to the entrance, which is accentuated by a welcoming porch and neatly arranged planters.

Guest suite in Windsor

4.91 out of 5 average rating, 125 reviews

Beautiful 2 bdrm Entire Level Sport Themed Suite

This private spacious 2 bedroom lower level sport themed/sport pool backyard getaway is nestled in the heart of South Windsor, ON Canada. This space is unique, clean and well maintained and is sure to exceed your expectations! This quiet and safe neighborhood is conveniently centered near everything -International bridge, major roads highways & expressway, shopping, restaurants & casino. Ideal for workers, couples, business traveller’s. Come enjoy the space but absolutely NO CRAZY PARTIES

Guest favorite

The exterior of a two-story brick home features large windows framed by wooden shutters. A stone pathway leads to the entrance steps, which are flanked by neatly landscaped flower beds and ornamental plants in decorative pots. The entrance is inviting, with a warm color palette.

Home in Malden

4.91 out of 5 average rating, 116 reviews

The Ambassador Estate Inn

A warm “welcome back” to all our previous guests and “greetings” to our new friends! A luxurious executive 7 bedroom estate property located on Windsor’s finest golf course and minutes from the Ambassador Bridge to Detroit Michigan. A beautifully appointed home nestled among rare Carolinian Forest. All the amenities of a 5 star resort with the privacy and serenity of a country estate. If you are looking for quality and relaxing luxury, then look no further than the Ambassador Estate.

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

4.57 out of 5 average rating, 30 reviews

Luxury at its finest (Windsor) Swimming Pool

Enjoy a stylish experience at this centrally located home. 5 bedrooms. 6 beds. 1 is a pull out couch. 3 full bathrooms. - Minutes from the battery plant - Massive driveway can fit a trailer - Fully renovated - Heated outdoor sports pool - Sun room - Massive backyard - 5 Spacious bedrooms - 3 smart TV's - Jenn-Air appliances - Can't beat the neighbourhood - Garage for parking and a driveway that can fit 6 cars - PRIVACY! Very private backyard and is located on a cul-de-sac

A comfortable living space features a gray sofa adorned with decorative pillows. A wooden coffee table rests on a patterned rug, and a small lamp provides soft lighting. Wall decor adds character, while a closet and hooks for belongings are visible in the background.

Condo in Allen Park

4.75 out of 5 average rating, 48 reviews

Cozy Condo fully furnished!

This cozy 1 bedroom condo is a perfect stay for a couple on vacation or for a working traveler. Our condo is in a great location! We're 12 minutes from Metro Airport (DTW) and 15 minutes from Downtown Detroit! There are several bars and restaurants within minutes of us as well as multiple shopping centers, grocery stores, and convenience stores. This condo is nicer than the hotels in the area with more amenities for our guests. We'd love for you to call our place home.

Guest favorite

A serene outdoor space features a salt-water pool surrounded by lush greenery, lounge chairs, and shaded seating areas. Natural stone accents are present near the water's edge, with steps leading up to a covered patio area. Tree silhouettes frame the background, enhancing the tranquil setting.

Guest suite in Windsor

4.92 out of 5 average rating, 395 reviews

Lakeshore Hidden Oasis (heated pool / jacuzzi)

Located in Lakeshore, minutes from Windsor / Detroit, a perfect oasis for the couple looking for a quiet escape. The suite's private jacuzzi tub makes it the ideal place in any season! The suite is fully equipped, including a complete kitchenette, Smart TV, etc. A private BBQ is at your door. During your stay you will have access, day and night, to our heated salt water pool. It is open from mid March to early November at 32°C (90°F). The hot tub is open year round.

Guest favorite

A spacious living room features a large gray sectional sofa, two mustard yellow armchairs, and a round coffee table. Natural light brightens the space through large windows, enhancing the light-colored walls and wooden flooring. A lush green plant adds a touch of nature to the decor.

Home in Windsor

4.96 out of 5 average rating, 25 reviews

Main Unit Luxury South Windsor Oasis

Welcome to your Southwood Lakes retreat ✨ A true luxury oasis with a private heated pool, where you can relax and unwind with loved ones. Centrally located, our home offers easy access to Windsor Airport, the Ambassador Bridge (12 minutes), and nearby conveniences like Costco, Starbucks, Devonshire Mall, and Caesars Casino. Enjoy full privacy: private entrance, backyard, and pool. Basement is owner-occupied, no shared spaces • Smoke-Free Home — Outdoor Smoking Only

Superhost

A modern retreat is highlighted by a sleek, heated pool reflecting the evening sky. Floor-to-ceiling windows provide glimpses of illuminated indoor spaces, while a rooftop terrace is accessible. A landscaped patio is bordered by a wooden fence, offering privacy.

Home in Windsor

4.56 out of 5 average rating, 18 reviews

Architectural Gem | Direct-Entry Pool

Welcome to Windsor’s hidden gem. This modern 2-bedroom retreat stuns with a unique sunken living room, soaring patio doors, and a heated pool just steps away. The main floor features an open-concept layout with a sleek kitchen and access to a tree-top terrace lounge. Upstairs, unwind in a spa-like bedroom with a soaker tub, rainfall shower, and rooftop retreat. With two private terraces and unforgettable design, this is more than a stay—it’s an experience.

Guest favorite

A spacious living area features a comfortable sofa and loveseat, complemented by decorative pillows. A wooden coffee table sits in front, with a remote control placed on top. Nearby, a dining table with four chairs is visible, alongside bar stools positioned at a countertop.

Apartment in Tecumseh

5 out of 5 average rating, 5 reviews

Impressive Furnished All-inclusive Apartment

Welcome to your peaceful retreat! This 2-bedroom, 2-bathroom apartment is located in a calm and quiet building close to the waterfront, shops, and restaurants. Enjoy seasonal access to an outdoor pool and tennis courts, perfect for unwinding. The apartment is stocked with essentials, making it a comfortable choice for business travelers, family visits, or anyone seeking a relaxing break. Settle in and make yourself at home