Vacation rentals with a pool in Windsor

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Windsor

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

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Superhost

Home in Windsor, Canada

4.84 out of 5 average rating, 135 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!

Mar. 25 – Apr. 1

$265 CAD per night

Guest favourite

Barn in Tilbury, Canada

4.93 out of 5 average rating, 44 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.

Oct. 23 – 30

$153 CAD per night

Guest favourite

Apartment in Tecumseh, Canada

4.94 out of 5 average rating, 82 reviews

Sunsets on Shawnee - Executive Apt w/ Heated Pool

January 2023 : Wednesday nights are discounted an extra 20+% Minutes from Windsor / Detroit, this spacious Tecumseh apartment is for couples, executives and small families looking to escape to a quiet location. It is fully equipped, with high speed internet, work space, complete kitchen, dining room, bathroom with shower and its own laundry facilities. Our heated salt water pool (in season) and backyard are accessible to our registered guests. This Includes use of our large BBQ on request.

Jan. 6 – 13

$160 CAD per night

Guest favourite

Cottage in Belle River, Canada

4.91 out of 5 average rating, 23 reviews

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!!

Jun. 21 – 28

$239 CAD per night

Guest favourite

Condo in Royal Oak, Michigan, US

4.93 out of 5 average rating, 107 reviews

*Zen* Entire King suite w rooftop spa, @MicroLux

MicroLux micro hotel Center of it all Walk to downtown restaurants nightlife all around Walk to a park or 2 or the Detroit zoo! Included with your stay: ✅️Stunning upper terrace with private hot tub ✅️Bathrobe/slippers ✅️Hot massage stones ✅️Tranquility fountain ✅️Heated tile ✅️Full luxury kitchen ✅️King bed with new memory foam mattress ✅️Queen sleeper sofa ✅️Shared patio access ✅️Fireplace ✅️Netflix/HBO ✅️Premium water and tea ✅️Mood lighting ✅️Coffee and breakfast ✅️Gym use Experience Zen

May 5 – 12

$238 CAD per night

Guest favourite

Guest suite in Windsor, Canada

4.92 out of 5 average rating, 105 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

Sep. 1 – 8

$104 CAD per night

Guest favourite

Barn in Kingsville, Canada

4.98 out of 5 average rating, 43 reviews

Wilderness Retreat with Pool, Sauna & Games

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!

Jan. 26 – Feb. 2

$442 CAD per night

Superhost

Home in Amherstburg, Canada

4.87 out of 5 average rating, 38 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.

Sep. 14 – 21

$373 CAD per night

Guest favourite

Bungalow in Royal Oak, Michigan, US

5.0 out of 5 average rating, 86 reviews

Fenced Yard with King * blocks from Main St+Parks

"The Dotte" 7 blocks to downtown Royal Oak & minutes to local favorites like the Zoo and Farmers Market. *Fully stocked kitchen *King in the Primary+ TV *Queen in the upstairs + TV *Hulu, Netflix and Disney Plus *Special reading nook upstairs with books and toys. *Pet Friendly home with fenced yard , room to run and pet amenities like bowls, pet gate, dog bags & more *WFH desk & fast WiFi *Lots of local bars, restaurants & parks Fenced Yard with King * blocks from Main St+Parks

Sep. 7 – 14

$282 CAD per night

Guest favourite

Cottage in Lakeshore, Canada

4.95 out of 5 average rating, 43 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."

Oct. 7 – 14

$249 CAD per night

Guest favourite

Guest suite in Windsor, Canada

4.92 out of 5 average rating, 309 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.

Oct. 1 – 8

$190 CAD per night

Guest favourite

Cottage in Lakeshore, Canada

4.88 out of 5 average rating, 72 reviews

Rochester Place Golf Club& Resort #715 (#16) WIFI

Beautiful modern cottage for rent located between the 16th and 17th holes and steps away from canal to Lake St Clair. (boating slips available) The modern clean cottage is open concept with 2 bedrooms; sleeps 6 including a sofa bed . There is something for everyone whether it's boating, relaxing by the pool, entertaining the family or a day of golfing. If you are not in the mood to cook/BBQ you can treat yourself to 5 star restaurant overlooking the golf course.

May 26 – Jun. 2

$261 CAD per night