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.

0 of 0 items showing

1 of 3 pages

Guest favorite

Barn in Tilbury

4.92 out of 5 average rating, 61 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.

Guest favorite

Home in Kingsville

4.92 out of 5 average rating, 26 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

Superhost

Home in Windsor

4.81 out of 5 average rating, 162 reviews

The Modern Oasis: Beautiful Home w/Pool & Sunroom!

*POOL IS OPEN MAY 1 - SEPT 30* Enjoy the LUXURIOUS feel of a spacious, modern home! Beautifully decorated and featuring over 3500 sq.ft of living space! Designed with open-concept and modern approach, this home features new and chic furniture, a state-of-the-art kitchen and a unique, high-ceiling, spacious sunroom! One of the largest Airbnbs in Windsor! An updated kitchen, a king bed, a 15x30 in-ground oval pool and SO MUCH MORE! Come home and nestle in the warmth of this clean & comfy home!

Guest favorite

Barn in Kingsville

4.99 out of 5 average rating, 71 reviews

Kings Woods Lodge - Prviate Resort w/ Sauna + Pool

Welcome to Kings Woods Lodge, an unforgettable escape in the heart of Ontario's renowned wine country! This stunning luxury lodge is located on a 55-acre estate and offers a serene sanctuary with breathtaking forest views. Immerse yourself in nature while enjoying the lavish comforts & amenities that this exceptional property has to offer. Whether you're seeking a peaceful getaway, small event space or a memorable vacation with friends & family, Kings Woods Lodge is the perfect destination!

Guest favorite

Guest suite in Windsor

4.91 out of 5 average rating, 117 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 favorite

Home in Amherstburg

4.89 out of 5 average rating, 64 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 favorite

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 favorite

Cottage in Lakeshore

4.95 out of 5 average rating, 55 reviews

Cottage @ Rochester Place Golf Club and Resort

"Unique modern cottage located on a pond with view of the 17th green in Rochester Place Golf Club and Resort. Open concept with 2 bedrooms; sleeps 6 including a sofa bed. Dock your boat on the resort's private canal where you then have access to fishing and boating on Lake St. Clair. Spend a day golfing on the completely renovated 18 hole championship course culminating in a relaxing BBQ on our beautiful patio or visit the 5 star restaurant and patio overlooking the golf course."

Guest favorite

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 favorite

Guest suite in Windsor

4.92 out of 5 average rating, 354 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 favorite

Home in Kingsville

4.95 out of 5 average rating, 20 reviews

NoRtHsHoRe BeAcH Estate - Salt water pool- Hot Tub

The North Shore Beach House, a luxurious lakeside retreat on Lake Erie stunning 4-bedroom estate, with 2 king rooms, 1 queen room, and a bunk room, offers breathtaking panoramic views from every window. Enjoy the gourmet kitchen, grand living room with fireplace, and sunroom. Relax in the saltwater pool, hot tub, or around the fire table. With private beach access and proximity to the best vineyards, nature trails, and local produce stands, it's the perfect getaway.

Guest favorite

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.