Vacation rentals with a pool in Essex County

4.82 out of 5 average rating, 170 reviews

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

NancyRating, 5 stars3 weeks ago

This was a great place to stay! It was spacious and well stocked with everything you’d need for a comfortable stay. It was immaculate upon our arrival. Since our 5 night stay was during some of the coldest days in Windsor this winter, it was nice to enjoy the warmth and cozy atmosphere of the gas fireplace in the downstairs living room. The house is located on a nice, quiet street. While the VIA train passes by a few times a day it becomes barely noticeable. It’s an easily walkable neighborhood and there’s a park close by that was nice to take our dog to. It’s close to restaurants, grocery stores and other shopping which made it very convenient for our stay. It’s very easy to get to any part of the city. The host was very responsive to any questions we had. He was extremely helpful and pleasant in all communications we had! We would definitely stay at this property when returning to Windsor in the future!

4.92 out of 5 average rating, 118 reviews

Guest suite in Windsor

Covid Clean 2 bdrm Entire Lower Level Sport Themed

FaithRating, 5 stars5 months ago

My friends and I really enjoyed staying at Franco’s place. We spent a few days in Windsor, also visited Niagara Falls one of the days, and really loved being able to come back at the end of the day to relax around the pool. Definitely check out Cafe Amor & Art in Windsor. They had some really amazing chilequeles and flan. And we’re from chicago, so we know good Mexican food! We are jealous this place is so far away from us, so definitely go enjoy it when you can! We’ll definitely stay here again!

4.9 out of 5 average rating, 70 reviews

Home in Amherstburg

Cottage Escape by the Water

MarcinRating, 5 stars2 weeks ago

Very good and peaceful stay. Beds are very comfortable and nice bedrooms especially the master. The couch is great to sit around and relax with your family. If we have another figure skating competition in LaSalle we would consider renting again, has very convenient location. Two good sized washrooms. Relaxing even during winter, must be fun in warmer months with the swimming pool and a cute patio area.

4.95 out of 5 average rating, 78 reviews

Home in Kingsville

Sunny Days Estate ✦ Large Saltwater Pool ✦ Hot Tub

JonathanRating, 5 stars4 months ago

I would stay with Vik anywhere he chooses to have a rental. It was a pleasure to connect with such a pleasant host. The kingsville area could keep us coming back for years. The wineries are world class and the restaurants know how to make you feel like a king, while also have a small town vibe. Highest of recommendations

4.87 out of 5 average rating, 103 reviews

Cabin in Lakeshore

Resort- # 500 - midnight Blue * Prime Location *

RicoRating, 5 stars4 months ago

Enjoyed our stay very clean a lot of necessities for us more than expected you really don’t need to bring anything but food they had everything you could think of there to use for cooking supplies… was also was very easy to find and the neighbors around us were nice also would definitely recommend…

Vacation rentals for every style

Get the amount of space that is right for you

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

4.74 out of 5 average rating, 66 reviews

Cheerful 5 bedroom home | Heated Indoor Pool!

RobertRating, 5 stars1 month ago

It was a great time. The kids loved the pool. The house accommodated 8 people without any difficulty.

4.73 out of 5 average rating, 22 reviews

Memories to Remember/free parking/upper unit

ShefalyRating, 5 stars1 month ago

We stayed here for one night, and it was absolutely fabulous! The place was spotless, well-maintained, and looked exactly as it does in the photos. Ali was incredibly friendly and highly responsive, making our stay even more enjoyable. I highly recommend this place to anyone visiting Windsor!

4.29 out of 5 average rating, 17 reviews

Luxury at its finest (Windsor) Swimming Pool

SheenaRating, 5 stars7 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, 3 reviews

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

Da SungRating, 5 stars3 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 🏡

4.75 out of 5 average rating, 12 reviews

Luxury Modern smart home for vacation

Da SungRating, 5 stars4 months ago

Second time visiting and as always she is very responsive and helpful. She is very welcoming and also caring too!

5 out of 5 average rating, 5 reviews

Home in Ruscom Station

Lakeshore Weekend Getaway

CookyRating, 5 stars1 month ago

Great host, communicative, house was big and spacious! Would love to come back again in the summer!

4.87 out of 5 average rating, 23 reviews

Home in Kingsville

Modern Oasis: Private Poolside Escape

LisaRating, 5 stars5 months ago

Had a fantastic stay at Sue's place. House was located in a very quiet, peaceful and private location. Pool was an added bonus and was warm and large. Beds were very comfortable and the kitchen was well laid out and well equipped. Close proximity to Pelee Winery, grocery store and many other stores. We hated to leave and will definitely be back!