Airbnb your place

Holiday rentals with a pool in Wellington County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Wellington County

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

%{current} / %{total}1 / 1
Superhost
A private backyard space features a swimming pool with steps leading in. Comfortable lounge chairs sit nearby on the concrete patio, while vibrant green trees and a well-maintained lawn surround the area. A shaded seating area can be seen in the background.
Home in Waterloo
4.84 out of 5 average rating, 167 reviews

Entire Guest Unit+Free Parking by Glenbridge Plaza

Located in a prime location in Waterloo, one of the most desirable safe and quiet neighborhoods of Lincoln Heights, this unique place perfectly blends privacy and comfort. Just minutes away from University of Waterloo, Wilfrid Laurier University, Conestoga College, highways (7/8),2 minute walk to Glenbridge Plaza, Zehrs Market (Grocery), CIBC Bank, A&W, Canadian Pizza, pharmacies, etc. It is an 8-minute drive to the St. Jacobs Farmers Market and only a 5-minute drive fromWalmart.Busstop is here

Top Guest favourite
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.
Guest suite in Orangeville
4.93 out of 5 average rating, 854 reviews

Headwaters HotTub & Fireplace-Cozy Spring Retreat

Escape to our rustik-modern queen suite, perfect for your getaway. Relax in the private hot tub right outside your door, 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 just quiet escape away. Book now for your ultimate getaway in comfort and nature!

Top Guest favourite
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
4.95 out of 5 average rating, 195 reviews

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.

Top Guest favourite
Apartment in Waterloo
4.99 out of 5 average rating, 101 reviews

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

Guest favourite
The image showcases a spacious swimming pool surrounded by lush greenery. The calm, clear water reflects the bright blue sky and is complemented by a two-story house in the background, featuring an inviting outdoor seating area and rustic stone details.
Home in Mono
4.9 out of 5 average rating, 48 reviews

Mono Springs - Dream Country Escape w pool/hot tub

Welcome to Mono Springs! Our straight-out-of-a-storybook family retreat, located in the heart of Mono. Lovingly renovated with all new furnishings, this dream country escape with rustic finishes sits on 10 acres of gorgeous landscape and fields with pre-made trails ready to explore giving wholesome Cottage-Vibes. Plenty of space for everyone with lots of quiet sitting areas, both inside and outside, private hot tub and heated pool. Ideal setting for family get togethers and nature enthusiasts

Top Guest favourite
A charming two-story cabin is nestled among lush greenery, with a pathway leading to the entrance. Tall trees and well-maintained hedges surround the home, creating a sense of privacy. Soft sunlight illuminates the cabin, enhancing its rustic appeal.
Cabin in Mono
4.95 out of 5 average rating, 340 reviews

The Trails Retreat (Private Cabin)

Beautifully renovated 2-story private hilltop cabin for romantic getaway, family stay or friends' retreat, experience a taste of the country together. Backed by forest and trails and set away from our family home, minutes to the Bruce Trail, Hockley Ski & Golf Resort, Mansfield Ski Club and charming Orangeville. Enjoy total guest privacy & spectacular sunrises. Guests are welcome to share our heated pool in season:) Add a playful Yoga/Functional Movement class or chef's dinner to your stay!

Superhost
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
4.9 out of 5 average rating, 101 reviews

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.

Superhost
The living area features modern furniture with a blue sofa and a wooden coffee table. A piece of wall art depicting floral arrangements is displayed above the sofa. Large windows allow ample natural light and showcase city views.
Condo in Kitchener
4.91 out of 5 average rating, 135 reviews

Luxury Resort-Style Condo| HotTub, Sauna & Bowling

**Hydro spa hot tubs are open! **Fully licensed Airbnb - no hassle during your stay! **Stunning Interior decor, guests'' unique experience **Unmatched amenities in town! you must check out the amenities' pictures **Corner unit with stunning city views ** Location! Heart of Kitchener, centrally located to grocery stores, hip restaurants/bars, cute local shops, parks & happening city life ** 3 mins walk GO Station. 126 Weber St. W **Across Goo-gle Head office w/ LRT rail at doorsteps

Top Guest favourite
A refreshing saltwater pool features an elegant waterfall edge, with water cascading gently into the pool below. Two lounge chairs are positioned under a bright umbrella, surrounded by lush greenery, providing a tranquil space for relaxation.
Guest suite in Centre Wellington
5 out of 5 average rating, 32 reviews

Cozy Private Suite with Year-Round Hot Tub

Welcome to The Salem Hideaway – your private, peaceful retreat tucked among the trees in the quiet village of Salem, just moments from historic Elora. Surrounded by forest and just steps from Irvin Creek, this cozy getaway is perfect for relaxing in nature. Enjoy the peaceful setting as you soak in the hot tub or swim in the pool, take a walk through the woods with a warm drink, or unwind by the fire pit while listening to the creek nearby. minutes from downtown Elora

Top Guest favourite
Guesthouse in Breslau
4.97 out of 5 average rating, 199 reviews

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.

Guest favourite
A cozy sitting area is presented with a blue checkered sofa and a striped armchair, adorned with nautical-themed cushions. Light is provided by two lamps on either side, illuminating the artwork and rustic wooden beams above.
Guesthouse in Erin
4.96 out of 5 average rating, 146 reviews

The Captain's Cottage at Willow Pond

You will have your own private one bedroom cottage on our 17 acre property. Your countryside getaway can be as quiet or as busy as you make it. You will have access to our tennis court, swimming pool, hot tub, gazebo, pond, garden and woodland trails. Adults are welcome to use the exercise studio. There is a flock of heritage chickens, guinea hens and quail who lay beautiful eggs for your breakfast. We also have bees who produce delicious honey for our guests.

Guest favourite
The exterior of a two-story house showcases a blend of stone and dark wood siding, with a spacious deck accessible from the upper floor. Lush green grass and neatly arranged flower beds surround the home, while a gray sky sets a calm backdrop.
Home in Alton
4.97 out of 5 average rating, 119 reviews

Cozy Country Spring Getaway | HotTub + Fire Pit

Escape to the countryside this spring 🌸 Unwind in the hot tub, enjoy cozy fires under the stars, and soak in the peaceful charm of Alton. 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

Popular amenities for Wellington County rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

A modern kitchen features dark wood cabinetry and a stainless steel gas range. Countertops are adorned with cooking essentials, including a coffee maker and a selection of kitchenware. The design is complemented by neutral tile flooring and overhead lighting to illuminate the workspace.
Home in Orangeville

House Near Osprey Valley Golf

Home in Saint Clements
New place to stay

St. Clement’s Vacation AIR BnB

An aerial view of a fully renovated raised bungalow is displayed, showcasing its modern blue exterior. Lush greenery surrounds the home, with a well-maintained lawn and a driveway visible. The large pool and outdoor event tent are positioned in the backyard, enhancing the inviting atmosphere.
Home in Erin

Walk in basement with huge pool

Superhost
A round wood sauna features wooden benches arranged alongside a central heater. The outdoor deck displays a swim spa surrounded by lounge chairs, with a view of the spacious backyard. An indoor living area showcases a stone fireplace and modern furnishings, while a well-equipped kitchen includes a central island.
Home in Mono
4.66 out of 5 average rating, 38 reviews

Luxury Hockley Estate Spa

Superhost
An outdoor area is visible with a private pool surrounded by a spacious patio. Red seating is arranged near the pool, along with a shaded area under an umbrella. The cottage, characterized by a combination of brick and wood siding, is set against a backdrop of lush trees.
Home in Orangeville
4.82 out of 5 average rating, 45 reviews

Private cottage heated pool/HotTub/Games 20 Acre

Guest favourite
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 Centre Wellington
4.93 out of 5 average rating, 96 reviews

Estate, Secluded On the Grand River.

Home in Alton
4.43 out of 5 average rating, 7 reviews

Spectacular Estate Pristine 100 Acres Private Lake

A sparkling pool reflects the blue sky, surrounded by lush greenery and colorful flowers. A potted plant with vibrant pink blooms sits in the foreground, adding a touch of color to the tranquil outdoor space.
Home in Waterloo

Retreat with Luxury in this 4-bed, 4-bath home

Condo rentals with a pool

Guest favourite
Condo in Kitchener
5 out of 5 average rating, 10 reviews

Stylish Downtown Suite with Patio & City Views

Superhost
A modern living area features a sleek kitchen with stainless steel appliances, a stylish couch, and a flat-screen TV mounted on the wall. Large glass doors open to a balcony, allowing natural light to fill the space. A small dining table is set for two beside the kitchen.
Condo in Kitchener
4.82 out of 5 average rating, 28 reviews

LuxCondo in the downtown kitchener uptown waterloo

Condo in Kitchener
4.84 out of 5 average rating, 49 reviews

Luxe Suite With Home Cinema - Gym, Bowling, Pool

Superhost
Condo in Kitchener
New place to stay

Platform 19 | City View at Station Park

Superhost
A stylish living area is presented with a green sofa and two textured chairs surrounding a light wood coffee table. A large television is mounted on the wall, and vibrant tropical wallpaper adds a splash of color. Ample natural light enters through two large windows.
Condo in Waterloo
4.92 out of 5 average rating, 39 reviews

The Laundry Rooms, Waterloo - Two Bedroom Suite

Superhost
The living area features a modern design with a blue sofa, two soft armchairs, and a coffee table. A desk is positioned nearby, and a large artwork adds a touch of color to the wall. Natural light streams through the glass doors leading to a balcony.
Condo in Kitchener
4.65 out of 5 average rating, 49 reviews

Perfectly Located in Kitchener

Guest favourite
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.
Condo in Kitchener
4.96 out of 5 average rating, 26 reviews

Lux Condo by Downtown Kitchener

Guest favourite
Condo in Kitchener
5 out of 5 average rating, 17 reviews

Modern High-Rise Condo w City Views & Balcony

Other holiday rentals with a pool

Superhost
Apartment in Kitchener
New place to stay

Contemporary Condo in DTK | Gym, Pool, & More

Guest favourite
A shaded outdoor seating area is furnished with dark wicker chairs and a coffee table, featuring decorative candles. In the background, a sparkling saltwater pool is surrounded by lounge chairs and sun umbrellas, framed by lush greenery and a small shed.
Guest suite in Halton Hills
5 out of 5 average rating, 17 reviews

Backyard Oasis with pool in the countryside

The exterior of the Rakes Chalet is shown, featuring a stone facade and a well-maintained front yard. Lush trees provide shade around the property, while colorful leaves hint at the changing seasons. The nearby building is visible, indicating additional space for guests.
Farm stay in Puslinch
4.76 out of 5 average rating, 68 reviews

Luxury 1800s Farmhouse: Private Pool & Hot Tub

Superhost
A stunning sunset reveals vibrant red and orange hues across the sky, reflecting beautifully in the calm waters of a pond. Silhouettes of trees can be seen in the background, alongside a unique white structure that stands adjacent to the water's edge.
Campervan/RV in Saint Agatha

40@50 Glamping in this 2 Bedrm 1 Bath Destination.

Apartment in Kitchener
New place to stay

Luxurious High Rise Condo - Pool/Gym/Sauna

An aerial view of a spacious luxury estate is presented, showcasing a well-maintained outdoor pool surrounded by a patio area. Lush greenery and trees fill the manicured lawns, complementing the home's large deck with seating. Two ponds are visible in the background, enhancing the serene landscape.
Bungalow in Erin
4.63 out of 5 average rating, 40 reviews

36 Acres Luxury Estate - Family & Weekend Getaways

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
4.78 out of 5 average rating, 41 reviews

High Rise 1BR Building with Gorgeous Views

Villa in Cambridge

Beaverdale Play and Stay By The Green | pool

Destinations to explore

  1. Airbnb
  2. Canada
  3. Ontario
  4. Wellington County
  5. Rentals with pools