Vacation rentals with a pool in Windsor

4.96 out of 5 average rating, 70 reviews

The exterior of a modern cottage is displayed, featuring a patio area with seating for four under a shaded umbrella, a lounge area with cushioned seating, and easy access to the surrounding greenery. Large windows reflect the natural light, while a serene pond is visible in the background.

Cottage in Lakeshore

Cottage @ Rochester Place Golf Club and Resort

Modern cottage located on a pond with view of the 17th green in Rochester Place Golf Club and Resort. Guests have called our location serene as it is one of the most private cottages in the resort. Open concept with 2 bedrooms; sleeps 6 including a sofa bed. Dock your boat on the resort's canal where you then have access to beautiful Lake St. Clair. Golf on the 18 hole championship course. Enjoy a BBQ on our beautiful patio or take advantage of the many family amenities the resort has to offer.

4.89 out of 5 average rating, 87 reviews

The Cedarwood Suite features a modern design with a spacious bed adorned with a patterned coverlet. A flat-screen television is mounted on the wall opposite. Natural light filters through curtains, illuminating a small dining area equipped with a table and chairs.

Guest suite in Windsor

Cozy Cedarwood Suite ☆Terrace ☆ heated salt pool

Modern private suite with its own entrance and a gorgeous terrace. The space has a fully equipped kitchenette, a bathroom with shower. a 65" Roku HDTV : chromecast, Disney+, Netflix, Amazon Prime, ... The heated outdoor pool and a dining area with BBQ is accessible. These are shared with our family and guests. 20 minutes from the Detroit, Michigan border and downtown Windsor with its Caesars Casino. Ideal for a travelling couple or a contract worker looking for a cozy place to call home.

Place to stay in Belle River

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.

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!

4.8 out of 5 average rating, 209 reviews

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

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!

4.94 out of 5 average rating, 154 reviews

A spacious living area features a light-colored sectional sofa adorned with dark blue and white blankets. A rustic barn door, made of wood, adds character and leads to the bedroom. Two round mirrors are mounted on the wall, reflecting natural light.

Cottage in Lakeshore

Waterfront Luxurious Cottage in Lakeshore, Ontario

Waterfront Modern Executive Cottage with lots of natural light and stunning views. This cottage is a breath of fresh air and provides all of the comforts and conveniences that you need in a luxurious relaxing getaway . The cottage boasts a unique layout that sleeps 4 with a bright fully stocked kitchen and dinette, master bedroom, an eclectic second bedroom, barn doors, Smart TV and plenty of closet space, gas fireplace, swimming pool and giant waterfront backyard with lake access to swim.

4.91 out of 5 average rating, 116 reviews

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

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.

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.

4.58 out of 5 average rating, 31 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

An indoor swimming pool is set within a bright space featuring a high ceiling. Large windows line the walls, allowing natural light to fill the area. A stone fireplace is positioned at one end, providing a cozy focal point.

4.66 out of 5 average rating, 68 reviews

ultimate getaway

Get ready for the ULTIMATE getaway! this ppty features a beautiful indoor pool , big back yard a gazebo and a gas fire place, this ppty is close to all amenities lots of restaurants and shopping around and right across from the airport , the indoor pool is heated only in the winter and fall from the month of oct till may and temp is set to 84 degrees .it is for a single family enjoyment and NOT A PARTY VENUE , THERE IS A 2000 DOLLAR PENALTY IF A PARTY TAKES PLACE AT THIS PPTY.

4.92 out of 5 average rating, 398 reviews

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

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.

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.

4.96 out of 5 average rating, 27 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

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.

4.58 out of 5 average rating, 19 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.

4.94 out of 5 average rating, 64 reviews

An outdoor area features a rectangular swimming pool surrounded by a spacious deck. Comfortable seating arrangements consist of dark wicker furniture with soft cushions. A wooden table sits center stage, complemented by a grill nearby. Lush green grass highlights the backyard setting.

Townhouse in Amherstburg

Family Oasis w/ Heated Pool, BBQ and Smoker

**POOL HEATER (out of service)** ***Waterfall not working *** :( Relax with the whole family at this getaway oasis for kids and adults alike. Perfect getaway location with everything for everyone! 5 Minutes to downtown Amherstburg! Close to many restaurants, horseback riding, golf courses, kayaking, LCBO, beaches and don't forget the wonderful wineries/breweries this area has to offer. Fully equipped kitchen with BBQ and SMOKER

Popular amenities for Windsor rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.85 out of 5 average rating, 61 reviews

A modern living room features two black leather sofas positioned adjacent to a glass-top coffee table. The space is illuminated by natural light through two windows, accented by light grey walls and a plush area rug underneath.

Home in Detroit

Cute & Cozy 3bdrm, 1 bath. 12 mins to Downtown.

The exterior of a two-story brick house is showcased, featuring symmetrical windows and a prominent entrance flanked by greenery. The well-maintained lawn is complemented by decorative shrubs and stones, while a parked car is visible in the driveway leading to a two-car garage.

4.63 out of 5 average rating, 27 reviews

Memories to Remember/free parking/upper unit

4.86 out of 5 average rating, 97 reviews

A two-story cottage with a light grey exterior is showcased, featuring a welcoming front porch with white railings. A spacious yard surrounds the home, with a gravel driveway leading up to it. Lush green grass complements the serene environment.

Home in Amherstburg

Cottage Escape by the Water

4.95 out of 5 average rating, 19 reviews

A heated sports pool, surrounded by a spacious patio area, is complemented by comfortable seating options including loungers and umbrellas. A contemporary pool house with large windows is visible in the background, featuring a clean design that enhances the outdoor space.

Home in Belle River

The Grand River Retreat. Pool/ hot tub avail Sep

4.84 out of 5 average rating, 51 reviews

A spacious home is illuminated by exterior lighting, featuring a covered patio and large windows that showcase the interior. Lush green grass surrounds a swimming pool in the backyard, reflecting the evening sky, contributing to a serene setting.

Home in Amherstburg

Little heaven

A two-story house is set against a backdrop of tall trees, with a well-maintained lawn leading up to the entrance. The home's covered porch features white columns, and large windows reflect the daylight. A paved path runs alongside the house.

5 out of 5 average rating, 5 reviews

River front view

4.85 out of 5 average rating, 74 reviews

A vibrant outdoor area features a pool surrounded by sun loungers and colorful chairs. String lights adorn the space, enhancing the evening ambiance. A pool table is positioned nearby, offering additional recreational options. The backdrop includes a spacious house with multiple windows reflecting soft twilight.

Home in Remington Park

Staycation Windsor

4.98 out of 5 average rating, 91 reviews

A spacious outdoor pool is highlighted under clear blue skies. Several lounge chairs are positioned poolside, providing ample seating for relaxation. The surrounding area features well-maintained greenery and a fence that encloses the space.

Home in Belle River

Belanger Air BnB

Other vacation rentals with a pool

4.86 out of 5 average rating, 7 reviews

New place to stay

Walkerville Retreat: 4BR Home w/ Pool & Hot Tub

A spacious living area is arranged with a large, neutral-colored sectional sofa. A flat-screen television is mounted on the wall across from the seating. Natural light flows in through large windows, accompanied by two modern lamps placed on side tables.

Condo in Detroit

Downtown Water front Penthouse Sport Areas Close

Home in Belle River

4.5 out of 5 average rating, 4 reviews

! Lake St. Clair Golf Resort Getaway !

The image captures a serene view of a river at dusk, with city lights reflecting on the water's surface. Silhouettes of buildings can be seen along the waterfront, while the distant skyline features illuminated towers in red and green, contrasting against the twilight sky.

Condo in Detroit

5 out of 5 average rating, 3 reviews

Lovely one bedroom condo with International Views

A serene view of the illuminated pool surrounded by a partially landscaped patio area. Lounge chairs are arranged beside the pool, with soft lighting reflecting off the water. Trees and a fence frame the background, adding privacy to the outdoor space.