Vacation 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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Top guest favourite

Barn in Tilbury

4.94 out of 5 average rating, 82 reviews

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.

Superhost

Guesthouse in Windsor

4.73 out of 5 average rating, 55 reviews

Cozy cityscape Guesthouse

Safe neighbourhood in the town of Lasalle. Nature and trees around backyard, great for bird watching. 3 minutes to 401 highway, highway 3, & Ec-Row highway. 10 minutes to Ambassador bridge to Detroit. 15 minutes to underground tunnel to downtown Detroit. 15 minutes to downtown Caesars Casino. 3 minutes to outlet mall, shopping plazas, gym, and grocery stores. 6 minutes to waterfront. 10 minutes to Devonshire mall 5 minutes to seven lakes golf course. Police station & fire station 5 minutes away.

Superhost

Home in The Core

4.88 out of 5 average rating, 57 reviews

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.

Guest favourite

Cottage in Lakeshore

4.95 out of 5 average rating, 58 reviews

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.

Superhost

Home in Riverside

4.81 out of 5 average rating, 181 reviews

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!

Top guest favourite

Barn in Kingsville

4.99 out of 5 average rating, 86 reviews

Private Nature Resort w/ Event Space, Pool & Sauna

Escape to Kings Woods Lodge — your private retreat on 55 forested acres in Ontario wine country! Immerse yourself in nature and enjoy a heated plunge pool, barrel sauna, screened lounge, and endless games. Inside, find a chef’s kitchen, cozy fireplace, smart TVs and woodland themed bedrooms. Host unforgettable events in our elegant forest-view venue for up to 80 guests—perfect for boutique weddings, showers, birthdays, and more. Nature, luxury, and connection all in one stunning getaway.

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

4.9 out of 5 average rating, 77 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.

Guest favourite

Home in LaSalle

4.92 out of 5 average rating, 106 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

Guest suite in Windsor

4.92 out of 5 average rating, 375 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 mid March to early November at 32°C (90°F). The hot tub is open year round.

Superhost

Cabin in Lakeshore

4.86 out of 5 average rating, 104 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.

Guest favourite

Home in Riverside

5 out of 5 average rating, 5 reviews

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.