Vacation rentals with a pool in Lakeshore

Cowbarn Cabin

We have converted this cow barn into a charming open concept country cabin, 5 mins from the 401. Relax with your morning coffee on the patio or on the raised pool deck watching the sun rise overlooking the countryside. Enjoy the warm glow of the gas fireplace while watching TV and sitting on the leather reclining loveseat. For the fishermen, you are 5 mins to 2 boat launches that enter the Thames River into Lake St. Clair, ample parking for vehicles, boats, trailers and outside hydro outlets.

Little Country Charmer

Enjoy some relaxation while soaking up the country side in this one bedroom apartment located in the midst of a hobby farm. Watch the ducks and chickens roam free while you enjoy a unique outdoor space. The peaceful country view from the balcony upstairs is unique and very beautiful. The downstairs outdoor sitting room by the pool has a charm all its own. Firetable for use. You can also have a campfire in The Pavillion! There's firepit and pizza oven in the pavilion, very relaxing 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.

Whitty’s at Rochester Boat•Golf •Fish•Swim

Everything provided, cottage is situated in a private resort on the 16th green of a premier public golf course. 1 bedroom and easily sleeps 4, including a sofa bed. Beautiful backyard includes patio with furniture, outdoor dinning, bbq & fire pit. Easy access to boat launch & wells, outdoor pool & playground. Minutes walk to Parkside Grille 5 star restaurant with lounge and live music. Enjoy scenic ecosystem of river & lake access to boat, fish, paddle on Lake St.Clair. Sandy beach nearby!

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.

*Victoriana* - Entire upper King suite@MicroLux

MicroLux micro hotel. Center of it all. Walk to downtown restaurants nightlife all around Walk to a park or 2 or the Detroit zoo! Included with your stay: ✅️Self check in ✅️Free off street parking ✅️Open concept design ✅️King bedroom w new memory foam mattress ✅️Laundry free in suite ✅️Stainless and granite kitchen ✅️Ice maker and water filter ✅️Access to patio with hot tub ✅️Lighted mirror ✅️Heated tile ✅️Netflix ✅️Coffee, tea, breakfast ✅️Mood lighting ✅️Bedding, towels, linens, soap

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.

Woodland Retreat with Pool, Sauna & Event Space

Set on a peaceful woodland property just minutes from Kingsville wine country, Kings Woods Lodge and Hall offers a relaxed, immersive escape designed for both getaways and gatherings. Enjoy light-filled interiors, outdoor living spaces, a seasonal heated pool (open April–October), and barrel sauna — all in a setting that feels calm and quietly special. An on-site event space is available as an optional add-on for those looking to host a meaningful celebration while staying together.

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.