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Vacation rentals with a pool in Dufferin County

Find and book unique homes with a pool on Airbnb

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Vacation rentals for every style

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Popular amenities for Dufferin County rentals with a pool

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

House rentals with a pool

Guest favorite
The charming cabin exterior features a red façade with a welcoming front porch. Two rocking chairs and a bench are arranged on the porch, complemented by lush greenery. Steps lead up to the entrance, inviting visitors to enjoy the serene surroundings.
Home in Shelburne
4.84 out of 5 average rating, 31 reviews

Primrose Park

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

A two-story house is shown, surrounded by a blanket of snow. The exterior features a combination of brick and dark siding, with a bright red front door providing a pop of color. A driveway leads to a garage, and a wooden fence complements the entrance.
Home in Caledon

House with a pool In Caledon

The cottage’s exterior is showcased with a blend of brick and modern architecture. A driveway leads to the entrance, flanked by landscaped areas. Large windows allow natural light to illuminate the interior, while a chimney adds a cozy touch to the design.
Home in Mono
4.92 out of 5 average rating, 12 reviews

Mono Hills - Your Perfect Country Getaway!

Superhost
A spacious living area features a contemporary stone fireplace as a focal point. A large television is mounted above it, while a comfortable sectional couch and two wooden tables provide seating. Glass doors open to a private outdoor deck surrounded by greenery.
Home in Mono
4.78 out of 5 average rating, 18 reviews

Custom home that feels like the Spa

A serene pond is surrounded by lush greenery, reflecting the clear blue sky above. A wooden dock extends over the water, inviting relaxation. The house is visible in the background, framed by trees, providing a tranquil backdrop for outdoor activities.
Home in Mulmur
5 out of 5 average rating, 14 reviews

Private Pool/Pond/River in Secluded 14Acres Estate

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Other vacation rentals with a pool

Top guest favorite
A spacious heated pool is surrounded by lush greenery and colorful flowers. Lounge chairs provide seating options, while a vibrant umbrella offers shade. The pool area includes a patio, decorative plants, and a fenced perimeter, creating a serene outdoor retreat.
Home in Mono
4.98 out of 5 average rating, 45 reviews

Country Family Getaway with Pool and Trails

Guest favorite
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
4.92 out of 5 average rating, 774 reviews

HotTub & Pool Getaway - Headwaters Retreat

Guest favorite
A newly renovated pool is surrounded by a spacious stone deck, complemented by a shaded cabana in the background. Lush greenery and tall trees frame the area, creating a serene outdoor setting ideal for relaxation.
Home in Orangeville
5 out of 5 average rating, 8 reviews

Hockley Valley - Jazzy Pines - 4 BR with Pool

Top guest favorite
A clear view of the heated swimming pool is presented, surrounded by a well-manicured lawn. Two lounge chairs are positioned beside the pool, offering a relaxing space. Lush greenery and trees create a natural backdrop, enhancing the serene atmosphere of the outdoor area.
Cabin in Mono
4.95 out of 5 average rating, 318 reviews

The Trails Retreat (Private Cabin)

Top guest favorite
The kitchen area is spacious and features a large island with seating for four in stylish black chairs. Modern appliances are visible, alongside a large refrigerator and sleek cabinetry. Colorful artwork adorns the walls, and large windows allow natural light to brighten the space.
Place to stay in Laurel
5 out of 5 average rating, 26 reviews

Countryside Gem

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
4.57 out of 5 average rating, 23 reviews

Luxury Hockley Estate Spa

Guest favorite
A clear swimming pool is surrounded by a concrete patio. A small shed is visible in the background, accompanied by green plants and a watering can. Lounge chairs are placed along the edge of the pool, creating a welcoming outdoor space.
Guest suite in Orangeville
4.96 out of 5 average rating, 165 reviews

Your Peaceful Santuary in Nature

Guest favorite
An outdoor pool area features a surrounding deck with wooden steps leading up to it. Bright blue water reflects the sky, and vibrant green grass borders the patio. Two red Adirondack chairs are placed nearby, complemented by lush trees and a distant green landscape.
Guesthouse in Orangeville
4.95 out of 5 average rating, 366 reviews

Sunny Pines Farm Studio Tennis Court/Bruce Trail

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