Holiday rentals with a pool in Windsor

4.96 out of 5 average rating, 70 reviews

The exterior of a modern cottage is displayed, featuring a patio area with seating for four under a shaded umbrella, a lounge area with cushioned seating, and easy access to the surrounding greenery. Large windows reflect the natural light, while a serene pond is visible in the background.

Cottage in Lakeshore

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.

4.88 out of 5 average rating, 88 reviews

The Cedarwood Suite features a modern design with a spacious bed adorned with a patterned coverlet. A flat-screen television is mounted on the wall opposite. Natural light filters through curtains, illuminating a small dining area equipped with a table and chairs.

Guest suite in Windsor

Cozy Cedarwood Suite ☆Terrace ☆ heated salt pool

Modern private suite with its own entrance and a gorgeous terrace. The space has a fully equipped kitchenette, a bathroom with shower. a 65" Roku HDTV : chromecast, Disney+, Netflix, Amazon Prime, ... The heated outdoor pool and a dining area with BBQ is accessible. These are shared with our family and guests. 20 minutes from the Detroit, Michigan border and downtown Windsor with its Caesars Casino. Ideal for a travelling couple or a contract worker looking for a cozy place to call home.

4.96 out of 5 average rating, 49 reviews

A well-maintained cottage with a gray exterior is surrounded by a landscaped yard. Colorful blue chairs are arranged around a firepit, set on a gravel area. A patio door leads into the cottage, while lush green trees provide shade on a clear day.

Cottage in Belle River

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!

4.8 out of 5 average rating, 211 reviews

Home in Riverside

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!

4.86 out of 5 average rating, 97 reviews

A two-story cottage with a light grey exterior is showcased, featuring a welcoming front porch with white railings. A spacious yard surrounds the home, with a gravel driveway leading up to it. Lush green grass complements the serene environment.

Home in Amherstburg

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.

4.94 out of 5 average rating, 155 reviews

A spacious living area features a light-colored sectional sofa adorned with dark blue and white blankets. A rustic barn door, made of wood, adds character and leads to the bedroom. Two round mirrors are mounted on the wall, reflecting natural light.

Cottage in Lakeshore

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.

4.91 out of 5 average rating, 117 reviews

The exterior of a two-story brick home features large windows framed by wooden shutters. A stone pathway leads to the entrance steps, which are flanked by neatly landscaped flower beds and ornamental plants in decorative pots. The entrance is inviting, with a warm color palette.

Home in Malden

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.

5 out of 5 average rating, 20 reviews

A circular concrete area is shown, featuring six red Muskoka chairs positioned around a central fire pit. The green grass surrounds the seating area, and a light tree canopy filters sunlight onto the space, creating a relaxed outdoor setting.

Tiny home in Belle River

Cottage-Belle River (Rochester Place #718) WiFi

Nestled on one of the most picturesque lots, this beautiful property overlooks the stunning 17th green. Upper patio with comfortable lounge seating, perfect for enjoying sunsets. Lower patio featuring a dining table and chairs. Relax by the concrete fire pit surrounded by 6 cozy Muskoka chairs—ideal for evenings under the stars. Boat launch as well as 4 kayaks available to travel down the canal. Great fishing with quick access to Lake St.Clair. Heated salt water pool on grounds!!

4.99 out of 5 average rating, 111 reviews

Barn in Kingsville

Cozy Forest Retreat w/ Sauna + Event Space

Escape to Kings Woods Lodge for a cozy winter getaway! Enjoy hiking in the woods, bird watching, crackling fires, heated blankets, rejuvenating sauna sessions, and nights filled with board games and shuffleboard. Surrounded by peaceful forest views, it’s the perfect spot to relax and reconnect. Hosting an event? Kings Woods Hall, our boutique on-site venue, is just steps away and can host up to 80 guests. Great for Christmas parties, bridal or baby showers or intimate weddings.

An indoor swimming pool is set within a bright space featuring a high ceiling. Large windows line the walls, allowing natural light to fill the area. A stone fireplace is positioned at one end, providing a cozy focal point.

4.66 out of 5 average rating, 68 reviews

ultimate getaway

Get ready for the ULTIMATE getaway! this ppty features a beautiful indoor pool , big back yard a gazebo and a gas fire place, this ppty is close to all amenities lots of restaurants and shopping around and right across from the airport , the indoor pool is heated only in the winter and fall from the month of oct till may and temp is set to 84 degrees .it is for a single family enjoyment and NOT A PARTY VENUE , THERE IS A 2000 DOLLAR PENALTY IF A PARTY TAKES PLACE AT THIS PPTY.

4.93 out of 5 average rating, 403 reviews

A serene outdoor space features a salt-water pool surrounded by lush greenery, lounge chairs, and shaded seating areas. Natural stone accents are present near the water's edge, with steps leading up to a covered patio area. Tree silhouettes frame the background, enhancing the tranquil setting.

Guest suite in Windsor

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.

A spacious living room features a large gray sectional sofa, two mustard yellow armchairs, and a round coffee table. Natural light brightens the space through large windows, enhancing the light-colored walls and wooden flooring. A lush green plant adds a touch of nature to the decor.

4.96 out of 5 average rating, 27 reviews

Main Unit Luxury South Windsor Oasis

Welcome to your Southwood Lakes retreat ✨ A true luxury oasis with a private heated pool, where you can relax and unwind with loved ones. Centrally located, our home offers easy access to Windsor Airport, the Ambassador Bridge (12 minutes), and nearby conveniences like Costco, Starbucks, Devonshire Mall, and Caesars Casino. Enjoy full privacy: private entrance, backyard, and pool. Basement is owner-occupied, no shared spaces • Smoke-Free Home — Outdoor Smoking Only

Popular amenities for Windsor rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Belle River

4.5 out of 5 average rating, 4 reviews

! Lake St. Clair Golf Resort Getaway !

The exterior of a two-story brick house is showcased, featuring symmetrical windows and a prominent entrance flanked by greenery. The well-maintained lawn is complemented by decorative shrubs and stones, while a parked car is visible in the driveway leading to a two-car garage.

4.63 out of 5 average rating, 27 reviews

Memories to Remember/free parking/upper unit

4.95 out of 5 average rating, 19 reviews

A heated sports pool, surrounded by a spacious patio area, is complemented by comfortable seating options including loungers and umbrellas. A contemporary pool house with large windows is visible in the background, featuring a clean design that enhances the outdoor space.

Home in Belle River

The Grand River Retreat. Pool/ hot tub avail Sep

The exterior of a single-story home is shown, featuring a spacious driveway lined with paving stones. Lush greenery, including a large evergreen tree and manicured shrubs, frames the entrance, which includes a blue door and large front windows under a lightly clouded sky.

4.58 out of 5 average rating, 31 reviews

Luxury at its finest (Windsor) Swimming Pool

4.85 out of 5 average rating, 53 reviews

A spacious home is illuminated by exterior lighting, featuring a covered patio and large windows that showcase the interior. Lush green grass surrounds a swimming pool in the backyard, reflecting the evening sky, contributing to a serene setting.

Home in Amherstburg

Little heaven

A serene view of the illuminated pool surrounded by a partially landscaped patio area. Lounge chairs are arranged beside the pool, with soft lighting reflecting off the water. Trees and a fence frame the background, adding privacy to the outdoor space.

4.73 out of 5 average rating, 15 reviews

Luxury Modern smart home for vacation

A two-story house is set against a backdrop of tall trees, with a well-maintained lawn leading up to the entrance. The home's covered porch features white columns, and large windows reflect the daylight. A paved path runs alongside the house.

5 out of 5 average rating, 5 reviews

River front view

4.85 out of 5 average rating, 74 reviews

A vibrant outdoor area features a pool surrounded by sun loungers and colorful chairs. String lights adorn the space, enhancing the evening ambiance. A pool table is positioned nearby, offering additional recreational options. The backdrop includes a spacious house with multiple windows reflecting soft twilight.

Home in Remington Park

Staycation Windsor

Condo rentals with a pool

A spacious living area is arranged with a large, neutral-colored sectional sofa. A flat-screen television is mounted on the wall across from the seating. Natural light flows in through large windows, accompanied by two modern lamps placed on side tables.

Condo in Detroit

4.86 out of 5 average rating, 7 reviews

Downtown Water front Penthouse Sport Areas Close

5 out of 5 average rating, 16 reviews

A modern kitchen features a sleek, multi-colored granite countertop with a built-in sink. An island with bar stools offers additional seating. Stainless steel appliances are present, complemented by contemporary cabinetry and pendant lighting that enhances the functional space.

Condo in Canton

Luxury Condo in the Heart of Canton

4.83 out of 5 average rating, 193 reviews

A stylish living area features a modern electric fireplace beneath an elegantly detailed mantle. Natural light enters through a large window adorned with sheer curtains. A chandelier hangs from the ceiling, complementing a light-colored tufted sofa and accompanying chair.

Condo in Royal Oak

*Victoriana* - Entire upper King suite@MicroLux

4.82 out of 5 average rating, 130 reviews

A cozy living area features two plush sofas and a single accent chair, arranged around a modern electric fireplace. Large windows allow natural light to enter, and a piece of art with colorful fruits adds a vibrant touch to the gray walls.

Condo in Royal Oak

*Cook!* Entire 2 King BR suite at MicroLux

A comfortable living space features a gray sofa adorned with decorative pillows. A wooden coffee table rests on a patterned rug, and a small lamp provides soft lighting. Wall decor adds character, while a closet and hooks for belongings are visible in the background.

Condo in Allen Park

4.76 out of 5 average rating, 51 reviews

Cozy Condo fully furnished!

4.5 out of 5 average rating, 16 reviews

A stylish living area features a black sofa with colorful cushions, complemented by a round coffee table atop a vibrant area rug. A plush armchair adds additional seating, with soft lighting enhancing the modern decor. Natural light filters through the nearby sliding door.

Condo in Utica

Sterling Condo at the Crossroads

The image captures a serene view of a river at dusk, with city lights reflecting on the water's surface. Silhouettes of buildings can be seen along the waterfront, while the distant skyline features illuminated towers in red and green, contrasting against the twilight sky.

Condo in Detroit

5 out of 5 average rating, 3 reviews

Lovely one bedroom condo with International Views

4.88 out of 5 average rating, 205 reviews

A private rooftop terrace features a hot tub surrounded by scenic views of autumn foliage and nearby homes. A cushioned lounge area with red and black accents provides a comfortable spot to relax. The entrance to the suite is visible in the background.

Condo in Royal Oak

*Zen* Entire King suite w rooftop spa, @MicroLux

Other holiday rentals with a pool

A comfortable living area is presented with a light-colored sofa and armchair, paired with a sleek coffee table. Natural light filters through expansive windows framed by elegant curtains, highlighting the room's spaciousness. A decorative lamp and minimalistic decor enhance the inviting ambiance.

Cottage in Belle River

4.64 out of 5 average rating, 11 reviews

Rochester Place Resort 527

4.92 out of 5 average rating, 26 reviews

A spacious living area features large windows that allow natural light to fill the room, offering views of the cityscape. A comfortable sectional sofa is arranged around a stylish area rug, with a mounted television visible on the wall. A well-equipped kitchen area is partially seen in the background.

Loft in Wyandotte

4 Bed Penthouse Downtown, Pool, Gym, 2 Balconies

4.8 out of 5 average rating, 40 reviews

The spacious bedroom features a large bed dressed in white linens, complemented by a gray throw blanket. A desk with a chair is positioned beside a stylish lamp. Natural light filters through sheer curtains, illuminating the soft color palette of the room.

Apartment in Detroit

Modern Hotel-Inspired Midtown Stay

4.94 out of 5 average rating, 16 reviews

An open kitchen space is equipped with modern appliances, including a stainless steel refrigerator and oven. A spacious island is accompanied by two gold-accented stools. Large windows provide ample natural light and views of the surrounding area, enhancing the airy atmosphere.

Loft in Wyandotte

Loft, Open Concept, Balcony 2 Bed, Pool Gym, Wifi

Home in Rivertown - Warehouse District

New place to stay

Windsor Gem – 4BHK Home with Pool, Comfort & Style

A cozy bedroom features a spacious bed with a light-colored blanket. A nightstand stands beside the bed, with a lamp casting soft light. Light-filtering curtains frame a window with blinds, and a decorative basket adds interest to the carpeted floor.

Paradise near the water

The living area features a light-colored couch and a recliner positioned across from a wooden coffee table. A textured carpet covers the floor, and natural light enters through windows on the far wall. An open kitchen area is visible to the left.

Apartment in Belle River

Bachelor Apt. On the Belle River