Vacation rentals with a pool in Windsor

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.

Cozy & Spacious Family Home w/Fireplace & 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!

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

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.

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.

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

Cozy Forest Retreat • Sauna • Hiking • Event Space

Escape to Kings Woods Lodge for a cozy winter getaway! Enjoy hiking in the woods, bird watching, crackling fires, heated blankets, rejuvenating sauna sessions, and nights filled with board games and shuffleboard. Surrounded by peaceful forest views, it’s the perfect spot to relax and reconnect. Hosting an event? Kings Woods Hall, our boutique on-site venue, is just steps away and can host up to 80 guests. Great for Christmas parties, bridal or baby showers or intimate weddings.

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.

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.

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.

Midtown Gem – Walkable & Bright Hotel Style Unit

Stylish hotel-style apartment in the heart of vibrant Midtown Detroit! Walkable to Wayne State University and top hospitals like Henry Ford and DMC, this thoughtful space offers ultimate convenience. Enjoy stunning views of the Detroit skyline, take advantage of the attached bar and restaurant (Common Pub), and visit the pool without ever leaving the building. An absolutely perfect spot to explore or work in Midtown - whatever your visit entails!

Downtown Winter Escape w/City Views

Experience timeless style in this mid-century modern 1BR in the heart of downtown. Bright, airy, and tastefully furnished with vintage flair, it features a plush queen bed, full kitchen, spa-like bath, and high-speed Wi-Fi. Steps from dining, shops, and attractions, yet a peaceful retreat to relax after exploring. Enjoy seamless check-ins, laundry located inside the building, and everything you need for a stylish, comfortable stay