Vacation rentals with a pool in Essex County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Essex County

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

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Top guest favorite

The exterior features a rustic wooden facade with archways framing the entrance. A stone pathway leads to the front door, surrounded by grassy areas and decorative landscaping elements. Two windows, with trimmed edges, are positioned symmetrically beside the door.

Barn in Tilbury

4.96 out of 5 average rating, 113 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.

Top guest favorite

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 LaSalle

4.92 out of 5 average rating, 124 reviews

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!

Guest favorite

Home in Leamington

4.9 out of 5 average rating, 20 reviews

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

Top guest favorite

The exterior of a brick bungalow is visible, framed by a variety of lush greenery and colorful flower beds. A small set of steps leads to the entrance, which is accentuated by a welcoming porch and neatly arranged planters.

Guest suite in Windsor

4.91 out of 5 average rating, 134 reviews

Beautiful 2 bdrm Lower 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

Guest favorite

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

4.89 out of 5 average rating, 44 reviews

The Grand River Retreat. Pool/ hot tub avail Sep

Luxury Riverfront Retreat 5BR/3BA with private Pool, Hot Tub, Basketball Court & More! Welcome to your dream getaway! Step outside and enjoy the best of waterfront living! Your private dock allows you to park your boat, access to lake St Clair. The L-shaped heated sports pool (May to Oct (heated June to Sept)), kayak or paddleboard through the river, 6 persons hot tub (Sept - June) Marina is 4 minutes drive, offers a beach, park, and bike trail. Close to city restaurants and grocery store

Guest favorite

A clear view of a seasonally available swimming pool bordered by a sun-soaked patio. Outdoor seating is arranged under a wooden covered area. The vibrant greenery and lake beyond provide a relaxing backdrop, enhancing the inviting ambiance of the outdoor space.

Cottage in Lakeshore

4.94 out of 5 average rating, 180 reviews

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.

Top guest favorite

Barn in Kingsville

4.99 out of 5 average rating, 142 reviews

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.

Top guest favorite

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

5 out of 5 average rating, 24 reviews

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!!

Guest favorite

An inviting outdoor area showcases a glistening in-ground oval pool framed by a spacious deck. Comfortable lounge chairs are situated nearby, and the house features large windows that allow for ample natural light. A dining set is visible under the covered patio, ideal for outdoor meals.

Home in Windsor

4.82 out of 5 average rating, 240 reviews

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!

Superhost

A spacious living area showcases comfortable seating and a modern kitchen with essential appliances. The outdoor patio features cozy furniture under a large umbrella, perfect for relaxation. Lush greenery surrounds the area, emphasizing the tranquility of the private resort setting.

Place to stay in Belle River

4.77 out of 5 average rating, 65 reviews

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!

Top guest favorite

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

4.93 out of 5 average rating, 460 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.

Guest favorite

The exterior of the home features a brick facade complemented by vibrant green landscaping. Lush trees and shrubs create a welcoming entrance, while a well-maintained lawn adds to the overall appeal. The front door, framed by natural stone accents, invites guests into the property.

Home in Kingsville

4.95 out of 5 average rating, 92 reviews

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.