Holiday rentals with a pool in Essex County

4.94 out of 5 average rating, 82 reviews

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.

4.85 out of 5 average rating, 13 reviews

Home in Ruscom Station

Lakeshore Weekend Getaway

Welcome to Your Dream Countryside Retreat: Where Relaxation Meets Adventure. Perfectly blending modern luxury with the tranquility of nature, this property is the perfect for any Event or Family Reunions, Groups of Friends, or Couples seeking a romantic getaway. Whether you're seeking adventure, relaxation, or a bit of both, this countryside retreat is the perfect place to create unforgettable memories. Book your stay today and experience the ultimate blend of luxury, comfort and natural beauty.

4.73 out of 5 average rating, 55 reviews

Guest house in Windsor

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.

4.95 out of 5 average rating, 58 reviews

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.

4.95 out of 5 average rating, 42 reviews

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!

Place to stay in Belle River

4.83 out of 5 average rating, 35 reviews

Whitty’s at Rochester Boat•Golf •Fish•Swim

Everything provided, 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!

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!

4.99 out of 5 average rating, 86 reviews

Barn in Kingsville

KINGS WOODS LODGE - Nature Resort + Venue

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.

4.92 out of 5 average rating, 118 reviews

Guest suite in Windsor

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

4.9 out of 5 average rating, 77 reviews

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.

4.92 out of 5 average rating, 106 reviews

Home in LaSalle

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.

4.92 out of 5 average rating, 374 reviews

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.

Holiday rentals for every style

Get the amount of space that is right for you

Flats

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Houses

A space that's all yours, with room for everyone

Popular amenities for Essex County rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Essex

4.73 out of 5 average rating, 74 reviews

Cheerful 5 bedroom home | Heated Indoor Pool!

YvetteRating, 5 stars1 month ago

Excellent host. Great and convenient location.

4.62 out of 5 average rating, 26 reviews

Memories to Remember/free parking/upper unit

TrevorRating, 5 stars1 month ago

Stayed there while fishing the Detroit River. The fishing wasn't great, but the place was very close to the launch and you can park a truck with a 19ft boat on the trailer in the driveway. Great for this type of trip

4.29 out of 5 average rating, 17 reviews

Luxury at its finest (Windsor) Swimming Pool

SheenaRating, 5 stars10 months ago

Fawaz was great to communicate with and so very helpful. Beautiful property and great area. Look forward to returning in the future! Thank you!

5 out of 5 average rating, 28 reviews

Home in Tilbury

Magical, Oasis Heated inground pool, hottub &fun

Dasvanth ReddyRating, 5 stars1 week ago

We recently stayed at this Airbnb and had a fantastic experience! The place is absolutely amazing — clean, cozy, and beautifully set up. The host was incredibly responsive and helpful, always quick to reply whenever we needed any information. A lovely personal touch was the cookies and muffins she left for us — such a thoughtful gesture! The lighting at night created a warm and inviting atmosphere, and the heated pool was just perfect for relaxing and having fun.

4.9 out of 5 average rating, 29 reviews

Home in Kingsville

Modern lake-town cottage

ErinRating, 5 stars1 month ago

Great spot very convenient and walkable to town, nice open space, and I liked that it had workout equipment too in the basement. Check in and check out was extremely easy.

5 out of 5 average rating, 5 reviews

Luxurious South Windsor Oasis with private pool

AndreasRating, 5 stars1 month ago

We had a family of 7 adults and 3 little children. While the house does have echoes it was the right size, bedrooms good and plentiful. The outside porch was great and though too cool for swimming the pool looked nice(have to guard the little ones). Wonder house for our family reunion.

5 out of 5 average rating, 4 reviews

Spacious Family Getaway w/ Pool -Sleeps 12 - 2 TVs

Da SungRating, 5 stars7 months ago

The place was absolutely gorgeous! also the neighborhood was quiet that it was a nice change of pace for us to rest after working at a noisy environment. Felt like home 🏡