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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Guest favorite

A vibrant pool area is framed by a wooden deck with lounge chairs in bright colors. The crystal-clear pool reflects the sky, surrounded by potted plants. A shaded seating area is visible, inviting relaxation. The backdrop features a charming wooden structure and neighboring homes.

Home in The Core

4.9 out of 5 average rating, 67 reviews

Staycation Windsor

A unique STAYCATION offering like no other. Pack up the kids and grandparents and invite your friends and spend time, not money, on a fun and relaxation stress free staycation . Make memories at this unique and family-friendly place. If you get tired of shuffle board, ping pong, pool, darts, corn hole, swimming in the pool, or Ms Pac Man; get the game boards out, play cards or work on your jig saw puzzle. All while listening to Music Videos on 7 Tv/s. Finish the day off in the 7 person hot tub.

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

4.95 out of 5 average rating, 63 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.

Guest favorite

A comfortable living area is arranged with dark leather sofas surrounding a coffee table atop a patterned area rug. Mirrored walls reflect natural light, and a doorway leads to the kitchen. Potted plants add greenery to the space.

Apartment in Windsor

4.91 out of 5 average rating, 11 reviews

3 Bedroom- 3 Bath Penthouse

This spacious Penthouse is located within 5 minutes of downtown Windsor, the University of Windsor campus, and the Aquatic Centre. The penthouse has 3 bedrooms, each with it's own separate bathroom. There is fully equipped kitchen suitable for preparing any meal, whether a simple breakfast, quick snack or a three-course gourmet dinner. Spacious countertops and the central kitchen island provide plenty of room to work your MasterChef magic. FREE WiFi, Smart TV, infant change table, and more.

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

4.8 out of 5 average rating, 193 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, 122 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

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

4.92 out of 5 average rating, 112 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

4.46 out of 5 average rating, 24 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

Guest favorite

Guest suite in Windsor

4.92 out of 5 average rating, 392 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

4.78 out of 5 average rating, 9 reviews

Architectural Gem | Heated 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.

Top guest favorite

Barn in Kingsville

4.99 out of 5 average rating, 98 reviews

KingsWoods Lodge | Wilderness Resort + Event Venue

Escape to Kings Woods Lodge — your private retreat on 55 forested acres 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!

Superhost

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, 3 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

Top guest favorite

A spacious living room features a large sectional couch and a coffee table, with a television displaying a beach scene. Bright natural light enters through the window, which is complemented by light curtains. The polished wooden floor adds warmth to the space.

Home in Riverside

5 out of 5 average rating, 13 reviews

Spacious Family Getaway w/ Pool -Sleeps 12 - 2 TVs

Welcome to our family home nestled in the quiet neighbourhood of Riverside, Windsor. Enjoy the private, fenced-in backyard with an above ground pool, a fully equipped kitchen, 7 beds that sleep 12 in total, in-suite laundry, parking for 3 mid-size cars and garage access and plenty of space for entertaining. Our home is about 13km from the Windsor International Airport, and close to many grocery stores and restaurants.