Holiday rentals with a pool in Windsor

The Ambassador Estate Inn

Welcome home to all our previous guests and greetings to all our new friends across the globe. A luxurious 6 bedroom estate property located on Windsor’s finest golf course and just minutes from both the Ambassador Bridge and the brand new Gordie Howe Bridge International Bridge. With all the amenities of a 5 star resort, yet the privacy and serenity of a large country estate, you need look no further than the Ambassador Estate Inn to make your vacation or business travel a memorable experience!

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.

Penthouse, Queen beds, Pool, Gym, Arcade, Downtown

Welcome to our luxurious 2-bedroom Penthouse loft in the heart of downtown Wyandotte!! Some highlights include: -A HUGE, residents-only pool -A well-equipped gym -Enhance your golf skills on the rooftop putting green -Arcade with 14 Games -City views from the private balconies -Sunbathe or relax in rooftop cabanas -Spacious kitchen, ready to tackle any culinary challenge with finesse Immerse yourself in the convenience of being within walking distance from events and a diverse culinary scene.

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.

Hummingbird Haven Cottage - Rochester Place Resort

Make some memories at this unique and family-friendly place. Families, fisherman and couples will love Rochester Resort. It has something for everyone! Included is a heated pool, boat ramp, firepit and patio on sight, playground, weekly entertainment and kids activities. Also available for $ is an 18 Hole Golf Course, Boat Docks, Golf Cart rentals, snack store, Parkside Grille Restaurant and Patio and extra firewood. Be sure to keep an eye on the Hummingbird Feeders for their frequent visitors!

Beautiful 2 bdrm Lower 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

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!!

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

Gorgeous Poolhouse! Spacious Family Home w/Sunroom

*HEATED POOL IS READY!* 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!

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.

Windsor Luxury Stay Oasis

Welcome to your Southwood Lakes retreat — a true private oasis in one of Windsor’s most peaceful neighbourhoods. This spacious 4-bedroom, 2.5-bath home offers 5 beds with premium bedding, a seasonal heated saltwater pool, gazebo, BBQ, sunroom, workspace, and parking for up to 6 vehicles. Guests enjoy private use of the main home, backyard, pool, and driveway. The owner-occupied basement is fully separate with its own entrance; no spaces are shared.

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!