Vacation rentals with a pool in Woolwich

4.96 out of 5 average rating, 155 reviews

Guest suite in Kitchener

The Oasis

Enjoy the bright, spacious, homey cottage vibes with a fully private saltwater pool **(Open until October 17th) hot tub **(Open until Nov 15th), luscious green yard, fire pit area, and several walking trails out the back gate. Retreat to the spacious walk out basement suite with 70” TV home theater, elliptical trainer, desk space and plenty of windows open to the forest view behind the house. Beautiful Doon neighbourhood within minutes of the 401. Plenty of shopping and eating choices close by.

LocationFamilyHiking

4.95 out of 5 average rating, 217 reviews

A welcoming porch features a blue exterior with white trim, adorned by potted plants and lush greenery. Rocking chairs are positioned on the porch, providing a comfortable space to relax. The pathway is lined with stones, leading from the driveway to the entrance.

Apartment in Ariss

Rural Retreat, near to Elora

A peaceful , rural, retreat in Ariss. Hot tub, great bird watching. Well situated between Elora, Fergus, St Jacobs and Guelph. Visit Cox Creek Winery, Kissing Bridge, G2G & Cotton Tail hiking/biking trail, snowshoeing, snowmobile trails & Chicopee Ski Resort. Two dogs on the property. Walkout basement, king bed, portable crib (on request) shower, kitchenette, seating area, natural light. Large backyard, firepit, barbeque, outdoor eating area. Keyless, separate, private entry, free parking.

LocationValuePool

4.88 out of 5 average rating, 137 reviews

A serene view of the villa is captured from the edge of the natural spring-fed pond, showcasing its spacious, multi-level design. Surrounding greenery, including trees and landscaped gardens, adds to the tranquility of the setting. Fluffy clouds drift across a bright blue sky.

Villa in Cambridge

Luxury Villa for Accommodation

★★★ SUPERHOST for 6+ years ★★★ Escape to this stunning, secluded villa for exquisite accommodation or hosting memorable events. ✔ Secluded villa on 8.8-acre lot ✔ Private 17 ft deep natural spring-fed pond + hot tub ✔ 4000 sqft living space ✔ Full access ✔ 4 bedrooms, 7 beds ✔ High-end finishes: Offers comfort & elegance. ✔ BBQ ✔ Next to Whistle Bear Golf Club & Langdon Hall (Relais & Châteaux, 5 Diamond dining), Cambridge Mill, walking trails, scenic Blair Creek. ✔ 401 easy access

FamilyValueAccess

4.99 out of 5 average rating, 116 reviews

Apartment in Waterloo

Charming Hideaway: 1-bedroom Apartment

Whether you’re in town for sports, work, or family, you'll love how the apartment is: Fully Furnished: from kitchen to bedroom, we’ve got you covered. Cozy: Gas fireplace and a queen air mattress for extra guests. Private Entrance: Your own smart lock access. Outdoor Space: Your own private deck with a BBQ. Heated Pool: SHARED pool available mid May to September. Entertainment: Stay connected with WIFI and enjoy Netflix, Prime, and Disney on the Smart Parking: No worries about finding a spot

ValueLocationQuiet

Guest suite in Elora-Salem

Private Basement Suite with Pool & Hot Tub

Welcome to The Salem Hideaway, a private basement suite nestled among the trees in the quiet village of Salem, just minutes from historic Elora. Enjoy your own private entrance, heated pool, hot tub, fire pit, and peaceful surroundings. We live upstairs, so you may occasionally hear normal household sounds, but we do our best to keep things quiet and ensure you have a relaxing stay. Minutes from Elora, you’ll be close to shops, restaurants, hiking trails, and everything the area has to offer

LocationFamilyHospitality

4.98 out of 5 average rating, 51 reviews

4.96 out of 5 average rating, 135 reviews

The exterior of the house features a combination of stone and wooden siding, with a pronounced roofline. A welcoming pathway leads to a spacious front deck, surrounded by manicured greenery and landscaping. Large windows and a colorful door enhance the inviting appearance.

Home in Alton

Cozy Fall Escape | HotTub + Fire Pit + River

Escape to the countryside this fall! Unwind in the hot tub under the stars, gather around the fire, and wake up beside the Credit River. Just under an hour from Toronto! Perfect for a relaxing getaway, girls weekend, or quiet work-from-home retreat. • Sleeps up to 8 guests comfortably • 3 cozy bedrooms (2 with private decks!) • 1.5 bathrooms • Fully equipped kitchen + BBQ patio for year-round grilling • Stylish living room with fireplace & smart TV • Fast Wi-Fi, workspace-friendly

LocationValuePool

4.88 out of 5 average rating, 113 reviews

A spacious living room is highlighted by tall wooden ceilings and large windows that invite ample natural light. Two comfortable sofas face each other over a coffee table, with a patterned area rug underfoot. A small fireplace and colorful stained glass add character to the warm design.

Barn in Milton

Five Star Hayloft Suite

This open space home is in the top level of a century-old bank barn. Witness the beautiful architecture while enjoying modern amenities like an open-concept kitchen, projector & movie lounge, and more! Enjoy 180 degree views from the bay window in the living room during your stay. Five Star Ranch offers a year-round getaway in a beautiful country setting. Situated on a working farm, and surrounded by gardens, animals and beautiful forest, it is a perfect destination for seclusion and peace.

LocationValueAmenities

4.97 out of 5 average rating, 37 reviews

A vibrant, triangular-shaped house is surrounded by greenery, reflecting in a clear, inviting swimming pool. A shaded seating area with lounge chairs can be seen beside the pool, and large glass doors allow natural light to fill the interior space.

Home in Elora-Salem

Riverside Retreat w Hot Tub, Pool & Sauna in Elora

Are you looking for a Fall Getaway in Elora? Althea Crystal Retreat, located in picturesque Elora, Ontario, has everything you need. For this September 2026: Get 4 nights at 20% off Unwind in one of our unique crystal rooms. Relax by the hot tub, and warm up in the sauna and by the indoor or outdoor fireplace. Go swimming in the beautiful heated pool (closes end of September). Get cozy by our fireplace while you watch TV. Look out to the breathtaking views of the river nearby.

LocationFamilyGrill

Guest suite in Orangeville

This inviting bedroom features a spacious bed adorned with soft linens and a textured throw. A large armoire stands alongside, complemented by decorative plants and soft lighting. Natural light is welcomed through an adjacent glass door leading to a private entrance.

Headwaters Retreat - Private Hot Tub & Fireplace

Escape to our modern and rustic Queen Suite, with private hot tub right at your door. Relax by the pool, or unwind by the fireplace & enjoy Netflix & Amazon TV. This cozy retreat features a private entrance, ensuite bathroom, and a second bedroom with twin beds. Steps from scenic hiking trails, minutes from the town center, your stay is ideal for outdoor adventures, wine tours, weddings, work trips or a quiet escape away. Book now for your ultimate getaway in comfort and nature!

LocationValueCheckout

4.92 out of 5 average rating, 896 reviews

4.97 out of 5 average rating, 228 reviews

Guesthouse in Breslau

House on the Hill

What makes The House unique? How about: - a year-round heated indoor pool & sauna - private 2-bedroom + loft guesthouse with private entrance - fully-equipped kitchen - homey living area with electric fireplace - 27 gorgeous acres with 2 ponds - private patio & BBQ There's so much more! Come join your hosts Frances & Rod and experience a country retreat in the middle of the city... all this within 5km to Waterloo Int'nl Airport & 15 min to tri-cities & 401.

ValueFamilyLaundry

4.76 out of 5 average rating, 119 reviews

A comfortable sleeping area is furnished with a queen bed, dressed in a patterned blue and white blanket. A cozy sofa is positioned nearby. Warm lighting is provided by a wall-mounted fixture, and a piece of artwork featuring a tree is displayed above the bed.

Home in Milton

Spacious, Pet Friendly Basement Apartment

Quiet, pet-friendly private basement suite designed for comfort and easy stays. Features a queen bed, sofa bed, fully equipped kitchen, dining area, in-suite laundry, free Wi-Fi, and complimentary coffee & tea. Guests enjoy a shared backyard with a seasonal pool and barbecue in summer. Loved for its privacy and comfort while being steps from a park, grocery store, pharmacy, bank, and nearby restaurants—perfect for short or extended stays.

ValueLocationIndoor spaces

4.99 out of 5 average rating, 204 reviews

The exterior of a cabin is depicted, featuring wooden siding and a stone base. A small wreath decorates the entrance, which is flanked by a snow-covered landscape. Tall trees stand in the background, hinting at the surrounding nature.

Cabin in Hamilton

The Fox's Retreat - A Cozy Cabin for Two

Escape to this open concept cabin in Flamborough, Ontairo. Get to Flamborough Downs Casino and Racetrack, McMaster University, African Lion Safari, Valens and Christie's Conversation Areas, Westfield Heritage Village, and Dundas Waterfalls and multiple Golf Courses in under 15 minutes. Modern amenities provide all the comforts necessary for a relaxing stay, quiet remote work, or a unique space to get wedding ready.

LocationFamilyComfort

Popular amenities for Woolwich rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5.0 out of 5 average rating, 29 reviews

A spacious outdoor area features a heated pool surrounded by a tiled deck. Comfortable seating is arranged under large umbrellas, alongside a dining set and a barbecue grill. Lush greenery and potted plants enhance the relaxing atmosphere of the space.

Home in Cambridge

Under the Whispering Pines

FamilyLocationAccuracy

4.76 out of 5 average rating, 34 reviews

Home in Erin

Indoor Pool • Hot Tub • Heated Dome • 40 min GTA

LocationFamilyAmenities

4.94 out of 5 average rating, 18 reviews

Home in Hamilton

City Meets Forest Year Round Tree House Retreat

LocationFamilyLayout

4.96 out of 5 average rating, 25 reviews

Home in Cheltenham

Indoor Pool & Hot Tub Villa | Sleeps 14

LocationFamilyGetting around

4.93 out of 5 average rating, 82 reviews

A spacious living area features a stone fireplace with a wooden mantel as its focal point. Comfortable seating, including a sectional sofa and armchairs, surrounds a glass coffee table. Natural light filters through large windows, complemented by warm wooden accents on the ceiling.

Home in Kitchener

Chalet by hiking trail and ski hill

LocationFamilyPets

4.9 out of 5 average rating, 82 reviews

Home in Hamilton

The Bayfront - Harbour Views + Private Pool!

LocationFamilyQuiet

4.92 out of 5 average rating, 102 reviews

The entrance of a renovated stone home is framed by lush greenery and colorful flower beds. A wide, paved pathway leads to the front door, flanked by stone steps, while large windows allow natural light to fill the interior, showcasing the property's unique architectural features.

Home in Elora-Salem

Estate, Secluded On the Grand River.

LocationFamilyPets

5.0 out of 5 average rating, 9 reviews

Home in Puslinch

Forest Edge Luxury Estate

FamilyLocationCheck-in

Condo rentals with a pool

5.0 out of 5 average rating, 38 reviews

Modern High-Rise Condo w City Views & Balcony

LocationValuePool

A modern living area showcases a dark sectional sofa, complemented by a round coffee table atop a light rug. Large glass doors provide access to a balcony, while a television stands on a white media console adorned with decorative items and potted plants.

4.87 out of 5 average rating, 45 reviews

Lux Condo by Downtown Kitchener

LocationValueGetting around

4.67 out of 5 average rating, 6 reviews

City Views & Private Balcony | Pool, Gym & Bowling

ViewCleanlinessHot tub

4.85 out of 5 average rating, 34 reviews

LuxCondo in the downtown kitchener uptown waterloo

LocationFamilyLong stay

A modern open-concept space features a well-equipped kitchen on the left and a cozy seating area with a sofa and television. Large glass doors lead to a private balcony, allowing natural light to fill the room. Light wood flooring adds warmth to the environment.

4.7 out of 5 average rating, 47 reviews

*Modern* 1 Bed Condo Station Park

ValueLocationWifi

4.69 out of 5 average rating, 58 reviews

Luxe Suite With Home Cinema - Gym, Bowling, Pool

ValueLocationCheck-in

4.46 out of 5 average rating, 13 reviews

City Views | Pool, Gym, Bowling, Games Room & More

ValueLocationHot tub

@ Kitchener ON | 1 bed 1 bath | 5 * Condo apt !

LocationSleep qualityView

New place to stay

Other vacation rentals with a pool

4.96 out of 5 average rating, 28 reviews

Townhouse in Elora-Salem

The Wynford Dreamy Capri Suite

FamilyLocationKitchen

4.92 out of 5 average rating, 12 reviews

Apartment in Kitchener

City Views at Station Park + Swim Spa + Hot Tub

FamilyLocationPool

4.86 out of 5 average rating, 65 reviews

The living area features a modern sofa with colorful accent pillows, a glass coffee table, and a flat-screen TV. A dining table is positioned by the large floor-to-ceiling windows, which provide ample natural light and showcase vibrant city views.

Apartment in Kitchener

High Rise 1BR Building with Gorgeous Views

ValueFamilyComfort

5.0 out of 5 average rating, 35 reviews

Guesthouse in Guelph

Private Pool House near UoG

LocationAccessOutdoor spaces

4.89 out of 5 average rating, 37 reviews

A spacious farmhouse with a stone exterior is surrounded by greenery. A large deck extends from the house, with a hot tub situated below it. A tall tree stands in the foreground, partially obscuring the view of the property.

Farm stay in Puslinch

KJ's Farmhouse w/SwimSpa Retreat

ValueLocationHot tub

4.88 out of 5 average rating, 98 reviews

A modern living area features a white media console with a speaker and decorative elements, accompanied by a flat-screen TV displaying the word 'WELCOME.' Natural light enhances the space, while a potted plant is nestled in a woven basket beside the console.

Apartment in Kitchener

21st- floor Luxury & City Views

ValueLocationParking

5.0 out of 5 average rating, 19 reviews

Guesthouse in Cambridge

Historic Blair Road Coach House

LocationFamilyCheck-in