Holiday rentals with a pool in Windsor

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.

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!

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

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 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.

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.

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

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.