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.

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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, 206 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.

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Guest favourite

A private pool is framed by a spacious patio and surrounded by well-maintained greenery. The villa stands nearby, featuring large windows that overlook the serene outdoor area. A natural stone sits on the patio, adding to the tranquil ambiance.

Guesthouse in Fergus

4.82 out of 5 average rating, 33 reviews

Country Villa Fergus Elora

Come escape to the country! This beautifully villa offers a memorable STAYCATION! Step into this stylishly designed oasis and feel yourself unwind. The open concept villa with king bed, sitting area, fireplace and full kitchen seamlessly flows into the outdoor space, where you’ll find plenty of room to unwind and dine al fresco. The private pool is yours to enjoy. Enjoy morning coffee, soak up some rays and as the sun sets, enjoy the propane fire pit for a cozy evening. Minutes away from Elora

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Top Guest favourite

Apartment in Waterloo

4.99 out of 5 average rating, 111 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

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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, 350 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!

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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

4.88 out of 5 average rating, 108 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.

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Top Guest favourite

A charming wooden structure is set against a backdrop of lush greenery. A bright red door serves as a focal point, complemented by a large deck with outdoor seating. Flowering plants and trees enhance the serene environment, creating a welcoming arrival space.

Apartment in Mono

4.96 out of 5 average rating, 75 reviews

Guest Suite in Hockley Valley

Escape to our charming separate unit nestled in the heart of a serene forested area, just off Hockley Valley Road. Perfect for nature lovers and those seeking tranquility, this cozy retreat offers a unique blend of comfort and outdoor adventure. Outdoor Activities Explore nearby hiking trails, enjoy birdwatching, or simply relax in the peaceful surroundings. In winter, take advantage of nearby ski hills. Book your stay today and experience the beauty of nature right at your doorstep!

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Top Guest favourite

Guest suite in Orangeville

4.92 out of 5 average rating, 884 reviews

Private HotTub & Pool - Headwaters Retreat

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!

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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

4.96 out of 5 average rating, 128 reviews

Cozy Country Spring Getaway | HotTub + Fire Pit

Escape to the countryside this spring 🌸 Unwind in the hot tub or pool, 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

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Top Guest favourite

Guesthouse in Breslau

4.97 out of 5 average rating, 222 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.

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Top 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, 152 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.

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Top Guest favourite

A stone farmhouse is set against a clear blue sky, with a saltwater pool in the foreground. The pool area is bordered by lush greenery and features lounge chairs arranged on a flagstone patio. The reflection of the house is visible on the pool's surface.

Farm stay in Guelph/Eramosa

4.98 out of 5 average rating, 80 reviews

Luxe B&B - Pool, Firepit, Hot Tub & Farm Animals

Escape to *Livingstone Farm 1860*, a peaceful luxury farm B&B with a private hot tub, friendly animals, and wide-open countryside. This charming farmhouse retreat combines rustic & modern comforts, including breakfast items to start your day. Unwind in tranquil surroundings, explore local hiking trails, or simply enjoy the farm’s serene landscape. Perfect for girl’s trips & friends seeking a restful getaway immersed in nature’s beauty.

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Guest favourite

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

4.92 out of 5 average rating, 147 reviews

Resort Condo with Bowling and Spa Hot Tub

Stunning 2BR/2BA corner suite in the heart of Kitchener, directly across from Google Kitchener Downtown. Enjoy city views, a fully equipped space for up to 7 guests, and amazing amenities like a hot tub, bowling alley, sauna, rooftop patio & gym. Includes free parking. This fully licensed Airbnb offers a seamless, worry-free stay in a vibrant, walkable neighborhood with easy access to the LRT and GO Station.

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