Holiday rentals with a pool 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.

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!

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.

Cottage-Belle River (Rochester Place #718) WiFi

Nestled on one of the most picturesque lots, this beautiful property overlooks the stunning 17th green. Upper patio with comfortable lounge seating, perfect for enjoying sunsets. Lower patio featuring a dining table and chairs. Relax by the concrete fire pit surrounded by 6 cozy Muskoka chairs—ideal for evenings under the stars. Boat launch as well as 4 kayaks available to travel down the canal. Great fishing with quick access to Lake St.Clair. Heated salt water pool on grounds!!

5-bedroom Victorian Home Saltwater

Recently renovated 5 Bedroom, 4 full bathrooms and a salt water pool. The Kingsville House is private, fully automated, and has easy access to the best of Kingsville & surrounding areas. This home is filled with amenities including a large outdoor deck with an eating area and lounge area, natural gas bbq, parking for 5 cars, grand living room, dining room, fully stocked eat in kitchen with dishwasher and more! Enjoy all that this home has to offer. **Pool is available May - October

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.

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

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.