Holiday 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 favourite

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

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.

ValueLocationAmenities

4.96 out of 5 average rating, 116 reviews

Top Guest favourite

A landscaped outdoor area showcases a serene pool surrounded by lush greenery and decorative rocks. A pathway of stone pavers leads to a shaded seating area with an outdoor gazebo. Vibrant fall foliage frames the scene, adding warm color to the tranquil setting.

Home in LaSalle

The Ambassador Estate Inn

Welcome home to all our previous guests and greetings to all our new friends across the globe. A luxurious 6 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!

FamilyValueBarbecue

4.92 out of 5 average rating, 128 reviews

Top Guest favourite

A hot tub is positioned outdoors, surrounded by a privacy fence. The clear blue water reflects the sky, while a tree with a broad canopy casts a gentle shadow. Lake Erie is visible in the background, adding to the relaxing atmosphere.

Cottage in Leamington

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

FamilyLocationView

4.91 out of 5 average rating, 53 reviews

Guest favourite

Home in Leamington

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

FamilyValueCondition

4.9 out of 5 average rating, 31 reviews

Top Guest favourite

A lakeside deck features two black Adirondack chairs, positioned for unobstructed views of the tranquil water. The blue horizon meets a clear sky, while surrounding greenery and rocks enhance the natural setting.

Cottage in Amherstburg

Stranded Paddle -Waterfront/ Hot Tub/ Wine country

Escape to a peaceful Lake Erie waterfront cottage in the heart of Essex County wine country. Relax in your private hot tub overlooking the lake, enjoy beautiful sunsets from the waterfront deck, or explore nearby wineries and charming towns. Perfect for couples, two couples or a small family, with 2 bedrooms, each with a queen bed. Holiday Beach Conservation Area is next door, and two adult bikes are included for exploring the area. A quiet, relaxing getaway made for slowing down and unwinding.

FamilyLocationHot tub

4.99 out of 5 average rating, 91 reviews

Guest favourite

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

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

FamilyLocationComfort

4.91 out of 5 average rating, 135 reviews

Superhost

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

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

ValueFamilyIndoor spaces

4.87 out of 5 average rating, 45 reviews

Guest favourite

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

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!

ValueFamilyOutdoor spaces

4.82 out of 5 average rating, 245 reviews

Top Guest favourite

Barn in Kingsville

Woodland Retreat | Heated Pool, Sauna, Event Space

Set on a peaceful woodland property just minutes from Kingsville wine country, Kings Woods Lodge offers a relaxed escape for getaways and gatherings. This fall, enjoy the private heated pool through the end of October, unwind in the barrel sauna, and gather around the fire under the trees. Light-filled interiors and inviting outdoor spaces make it special in every season. An on-site event space is available as an optional add-on for intimate weddings & milestone celebrations.

FamilyLocationView

4.99 out of 5 average rating, 145 reviews

Top Guest favourite

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.

FamilyValueShared spaces

4.93 out of 5 average rating, 465 reviews

Guest favourite

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

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.

LocationFamilyCheckout

4.95 out of 5 average rating, 95 reviews

Guest favourite

Home in Kingsville

Northshore Beach Estate Salt water pool & Hot Tub

The North Shore Beach House is a luxury retreat with 190 feet of private Lake Erie shoreline. Panoramic views frame the grand living room, sunroom, and harvest dining table. A gourmet kitchen with high-end appliances makes entertaining effortless. Four bedrooms, including two king suites, a bunk room, and a cozy daybed room, ensure restful nights. Outdoors, enjoy the saltwater pool, hot tub, and fire pit. In the heart of the Lake Erie North Shore Wine Region.

LocationValueAir conditioning

4.91 out of 5 average rating, 66 reviews