Holiday rentals with a pool in Essex County

Modern lake-town cottage

The perfect place to enjoy all that this little town on the lake has to offer! Two blocks from the best restaurants in the area, a local coffee roaster, and a wellness spa. Seven blocks from Lake Erie, on the wine route close to 14 wineries & breweries, and a prime spot for bird enthusiasts. Welcome to this newly renovated 2-bed, 2-bath home in Kingsville, the southern most town in Canada! Enjoy your morning coffee poolside from the walk-out deck, hike or bike the Greenway or the at-home Peloton

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.

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 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.

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.

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.

LOFT Escape Apartment Onsite Beach Dock Waterfront

Full Water view (front and back), boat dock and beach access This 82’ waterfront property provides an infinite view of Lake Erie, Ohio & Michigan. Jump off the dock into the lake, direct access to the lake from our private boat ramp. Full Water view on both front & back yard. The newly renovated 350 square feet 2nd floor loft APARTMENT with modern cottage theme. Perfect place for couple (up to 3 person capacity).