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

A circular pool is surrounded by a wooden deck, reflecting the clear blue sky above. Lush greenery, consisting of tall trees, creates a natural barrier in the background, enhancing the peaceful outdoor setting.

Barn in Tilbury

4.94 out of 5 average rating, 85 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

Guest favorite

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

4.96 out of 5 average rating, 67 reviews

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.

Superhost

Home in Riverside

4.8 out of 5 average rating, 198 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!

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, 124 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

Superhost

A private pool is surrounded by a wooden deck, featuring steps leading into the water. The lush greenery adds to the tranquil environment, with two red chairs positioned nearby for relaxation. The house and outdoor seating area are visible in the background.

Home in Amherstburg

4.86 out of 5 average rating, 92 reviews

Cottage Escape by the Water

Perfectly positioned on the outskirts of the historic town of Amherstburg and with beautiful views of the Detroit river. A cozy cottage 5 mins from great restaurants, coffee shops and boutique shops of Amherstburg. Relax by the pool or head into town for a walk along the water front. This is the perfect relaxation spot for couples and families! Windsor/Essex is well known for the wonderful wineries/ breweries and sight seeing in that area and our Air BnB is not far from all that and more.

Top guest favorite

An outdoor area is illuminated by warm lights at dusk, featuring a heated plunge pool and a circular fire pit with seating. Lounge chairs are arranged along the poolside, while large glass doors reveal a cozy indoor space. Lush greenery surrounds the area.

Barn in Kingsville

4.99 out of 5 average rating, 101 reviews

Nature Resort - Sauna + Heated Pool open til Nov 2

*Pool open & heated Easter - Thanksgiving sauna open all year Escape to Kings Woods Lodge — your private retreat in Ontario wine country! Immerse yourself in nature and enjoy a heated plunge pool, barrel sauna, screened lounge, and endless games. Inside, find a chef’s kitchen, cozy fireplace, smart TVs and woodland themed bedrooms. Planning a boutique wedding, shower, or celebration? Kings Woods Hall, our stylish on-site event venue, is just steps away and available to add to your stay!

Guest favorite

An aerial view captures a spacious outdoor area featuring a blue swimming pool surrounded by landscaped gardens. Several shaded seating areas are visible, along with a gazebo and a patio. Trees provide a lush backdrop, creating a serene environment for relaxation.

Home in LaSalle

4.91 out of 5 average rating, 115 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

4.54 out of 5 average rating, 28 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

Superhost

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

Guest suite in Windsor

4.92 out of 5 average rating, 393 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.

Superhost

The modern structure features multiple expansive glass doors that open to a serene outdoor area with a heated pool. The evening sky casts a gentle glow over the property, highlighting the rooftop terrace and the sleek design elements of the surrounding space.

Home in Windsor

4.75 out of 5 average rating, 12 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.