Holiday rentals with a pool in Essex County

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.

The Ambassador Estate Inn

Welcome home to all our previous guests and greetings to all our new friends across the globe. A luxurious 7 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!

Casa Azul: Your Lake Erie Cottage Oasis

Welcome to Casa Azul This beautiful all-season Lakehouse is near Point Pelee National Park, Erie Shores Gold, and Country Club. Our lakehouse is a luxury 3-bedroom, 2-bathroom home on Lake Erie in Leamington Ontario. Completely renovated with modern amenities and furnishing keeping comfort in mind. The two sofa beds easily accommodate 10 guests in total. Inside is a fully equipped kitchen where you can cook all your delicious meals. A Hot tub awaits you outside. We look forward to hosting you

Lake_House_OASIS

POOL IS OPEN AND HEATED UNTIL MID NOVEMBER Escape to a stunning lakeside retreat on Lake Erie where luxury meets relaxation. Enjoy breathtaking views, a heated pool, and a hot tub—perfect by day or under the stars. The spacious 10-person bar with BBQ, ice machine, and mini fridges makes hosting effortless. Ideal for family getaways, special occasions, or weekends with friends, this one-of-a-kind escape delivers comfort, style, and unforgettable memories. ✨ —Point Pelee family pass available

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 Cottage | Private Pool |Lakeshore

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.

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 late 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.

Walk to Downtown | Saltwater Pool + 5BR Wine Retre

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

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!

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

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!

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.

Sunny Days Estate ✦ Large Saltwater Pool ✦ Hot Tub

**Seasonal pool open May 11 to Oct 1, 2026** Nestled within Lake Erie North Shore Wine County, Sunny Days Estate is a newly furnished 4 bedroom home with a beautiful backyard and a large heated saltwater pool and self cleaning hot tub. Sunny Days Estate is the perfect destination for groups and families visiting beautiful Kingsville and area. Visit and explore the surrounding beaches, birding hotspots, exciting wineries, local breweries or just relax and unwind.