Holiday rentals with a pool in Windsor

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Windsor

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite

Home in Kingsville

4.9 out of 5 average rating, 29 reviews

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

Guest favourite

Loft in Wyandotte

4.88 out of 5 average rating, 16 reviews

4 Bed Penthouse Downtown, Pool, Gym, 2 Balconies

Welcome to our luxurious 4-bedroom penthouse loft in the heart of downtown Wyandotte! Some highlights include: -An expansive, residents-only pool -A well-equipped gym -Enhance your golf skills on the rooftop putting green -Scenic city views from 2 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 local events and a diverse culinary scene.

Superhost

Place to stay in Belle River

4.88 out of 5 average rating, 32 reviews

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!

Superhost

Home in Riverside

4.81 out of 5 average rating, 180 reviews

Beautiful Modern Oasis w/Heated Pool & Sunroom!

*POOL IS OPEN MAY 1 - SEPT 30* Welcome to one of Windsor’s largest and coziest stays! This 3500+ sq.ft home blends modern design with warmth, featuring an inviting sunroom with soaring ceilings and natural light—perfect for morning coffee or quiet evenings. The updated kitchen and chic decor create a stylish yet homey feel. Unwind in the private backyard oasis with a 15x30 in-ground oval pool and BBQ lounge. Every corner is thoughtfully designed for a unique and relaxing family experience!

Guest favourite

Guest suite in Windsor

4.92 out of 5 average rating, 118 reviews

Covid Clean 2 bdrm Entire Lower Level Sport Themed

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

Guest favourite

Home in Amherstburg

4.89 out of 5 average rating, 76 reviews

Cottage Escape by the Water

Perfectly positioned on the outskirts of the historic town of Amherstburg and with beautiful views of the Detroit river. A cozy cottage 5 mins from great restaurants, coffee shops and boutique shops of Amherstburg. Relax by the pool or head into town for a walk along the water front. This is the perfect relaxation spot for couples and families! Windsor/Essex is well known for the wonderful wineries/ breweries and sight seeing in that area and our Air BnB is not far from all that and more.

Top guest favourite

Home in LaSalle

4.92 out of 5 average rating, 105 reviews

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.

Guest favourite

Home in Kingsville

4.95 out of 5 average rating, 78 reviews

Sunny Days Estate ✦ Large Saltwater Pool ✦ Hot Tub

**Seasonal pool opening May 2nd to October 13th, 2025** 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.

Guest favourite

Guest suite in Windsor

4.92 out of 5 average rating, 369 reviews

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 late March to early November at 32°C (90°F). The hot tub is open year round.

Guest favourite

Cabin in Lakeshore

4.87 out of 5 average rating, 103 reviews

Resort- # 500 - midnight Blue * Prime Location *

Enjoy this brand new modern cottage at Rochester Place Golf Resort. This cottage is located just steps away from the golf course and all the amenities it has to offer. There is something for everyone whether its boating, relaxing by the heated pool & splash area for the children with new playground, activities for the children all day. PS..If you are not in the mood to cook you can treat yourself to The Parkside Grille 5 star restaurant overlooking the golf course.

Top guest favourite

Home in Tilbury

5 out of 5 average rating, 25 reviews

Magical, Oasis Heated inground pool, hottub &fun

Discover a magical Airbnb oasis with an 20x40 heated in ground pool, spa hot tub, and enchanting lit backyard. Perfect for ANY event, or OUT OF TOWN WORKERS. 40 mins to windsor, and casino, 25 mins to Chatham. Lightly travelled highways. Home sleeps 9+ with additional space for cots. I have a queen air mattress also. Features include indoor and outdoor games, a spacious field, two BBQs, two patio tables, and pergola. # NOTE# POOL closes November

Superhost

Loft in Amherstburg

4.85 out of 5 average rating, 147 reviews

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).