Holiday rentals with a pool in Durham Region

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Top-rated rentals with a pool in Durham Region

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

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Guest favourite
A spacious living room features comfortable seating arrangements, including a large sectional sofa and plush armchairs. A stone fireplace serves as a focal point, accompanied by a mounted artwork depicting a horse. A large television is positioned across from the seating area.
Home in Port Perry
5 out of 5 average rating, 10 reviews

Horse Farm Luxury Estate

Unwind in this serene, stylish retreat nestled within a stunning 100-acre horse farm.Property boasts a park-like ambiance and is situated on a secluded section behind a gate. Guests can enjoy picturesque views of horses grazing in the distance. The house features a spacious event/lounge room, perfect for gatherings. The fully renovated basement offers a pool table, multiple TVs, and a bar for your entertainment. The entire house is equipped with a 'Sonos' sound system for an audio experience.

Guest favourite
A modern kitchen area is presented with sleek white cabinetry and black appliances, complemented by a textured backsplash. A dining table with two black chairs sits invitingly, while greenery is introduced by a potted plant in the corner, enhancing the clean and contemporary design.
Home in Toronto
4.95 out of 5 average rating, 122 reviews

Cozy Modern Suite•Heated Flrs•Game Rm•Free Pkg

Welcome to our brand new, luxury modrn unit located in a quiet, family-friendly neighborhood only min from HWY401,407,DVP, TTC & countless amenities! Newly & lovingly modern space with luxury finishes throughout. Enjoy comfortable living quarters, brand new kitchen appliances, bright rooms, large windows, a dedicated workspace, in-unit washer/dryer, free WIFI, Netflix, Prime & free parking. This upscale oasis is truly the perfect space for business travelers, young professionals & couples alike!

Guest favourite
A spacious backyard features a large swimming pool surrounded by lush greenery. An umbrella provides shade to a seating area, while trees encircle the space, enhancing privacy. A fenced perimeter ensures safety, and the pool is inviting under dappled sunlight.
Guest suite in Toronto
4.9 out of 5 average rating, 105 reviews

Prestigious Bluffs Private Guest Suite

Enjoy this beautiful, private, sun-filled suite with a large secluded yard and pool in a safe, upscale and serene forested neighborhood where deer and other wildlife are often spotted. A short walk to public transit (TTC, GO Trains), shopping, restaurants, parks and scenic trails to the top of the Bluffs with breathtaking views of Lake Ontario. Hike down to the waterfront trail to Bluffers Park Beach and Marina. Fast Fibre Internet. Parking for multiple vehicles and an EV charger (Tesla/J1772).

Guest favourite
A tree house is nestled among tall trees, featuring a wooden structure with a balcony and staircase. Soft sunlight filters through the branches, highlighting the natural wood finish and the serene forest surroundings.
Treehouse in Port Perry
4.98 out of 5 average rating, 556 reviews

Treehouse on private, isolated forest (300 acres)

You will feel like you're a thousand miles from Toronto. Your own private space with several ponds for swimming, gazebo, fire pits, running water, hot shower, mtn bike and hiking trails. With 300 acres at your door step, you can choose not to see another soul during your stay or venture to a nearby winery, restaurants, shopping, horse farms, golf courses or ski hills! We are just 1 hour from Toronto with easy access off the 407. We also have an amazing log cabin for rent on the same 300 acres.

Guest favourite
An aerial view captures the expansive property featuring multiple structures, a large swimming pool surrounded by a grassy area, and well-maintained landscaping. The clear separation of different outdoor spaces is evident, along with a trampoline and several trees dotting the landscape.
Farm stay in Kawartha Lakes
4.88 out of 5 average rating, 127 reviews

Luxury, One-of-a-kind Pool and Zen with Horses

Luxury spaces for the whole family, YEAR ROUND Zen with horses in our heated barn, magnificent views. Private suite, Fire Pit, Hiking Trail, outdoor kitchen and BBQ. Billiards, shuffleboard, trampoline, table tennis, basketball and more. Book an archery tag or axe throwing game! Search horse experiences Sky Haven Equestrian in Bethany. Kids Stay Free! When booking enter number of adults only. Wutai Shan Bhuddist Garden is 4 min. away. Great for entertaining. Inquire about our event space.

Superhost
An outdoor seating area is presented with a glass-top table surrounded by four red cushioned chairs. A large red umbrella provides shade, while a grill is positioned nearby. The space is bordered by trees, creating a private and relaxed atmosphere.
Bungalow in Whitby
4.88 out of 5 average rating, 16 reviews

2 BHK home 5 min from Go Train

7 min walk from Whitby train and Lake, this is a 2 BR house that offers accommodation with a 2 private parkings The self contained apartment is located in a brightly lit lower floor features, a separate entrance, a living room, and a fully equipped kitchen & laundry room. Guests can enjoy sun bathing in the garden or a barbque grill with your family. The backyard is shared however the guests have a private entrance. The pool is opens in june until September For monthly discounts contact us

Guest favourite
An inground pool is set within a serene forest backdrop, surrounded by a spacious patio area. Comfortable seating is arranged with bright red chairs and a matching umbrella. Soft lighting is provided by strings of lights overhead, enhancing the outdoor space.
Guest suite in Kawartha Lakes
4.93 out of 5 average rating, 153 reviews

Hidden Acres - a Stay and Play Retreat!

Are you looking for some nature therapy? You'll be nestled in several acres of forest, where you can hear the birds and enjoy the private backyard. The hot tub and campfire* beckon in all seasons, and the heated inground pool is open from mid-June to Labour Day each year. We are dog friendly, but cannot accept other pets due to allergies. Please be sure to read our house rules before booking. **We are excited to share that we now offer a Level 2 EV outlet!** Licence number STR2025-344

Top Guest favourite
A private hot tub is positioned on a wooden deck beneath a lattice covering, allowing for relaxed soaking. Lounge chairs are arranged nearby, and vibrant greenery and decorative flowers provide a natural backdrop. A swimming pool can be seen in the distance, enhancing the outdoor ambiance.
Home in Port Perry
4.94 out of 5 average rating, 232 reviews

Home away from home with a hot tub and pool

This spacious home is a short walk to downtown Port Perry. Enjoy your time around the pool or hot tub, relaxing by the outdoor fireplace, lounging at the bar or just spending your time under a large covered deck ( rain or sunshine, uv ray protection). Port Perry offers shopping, fun at the lake (fishing and boating), skiing, hiking, local brewery, many restaurant choices and easy access to the Blue Heron casino. Check local web site for the many events going on around town.

Top Guest favourite
The serene backyard features a heated saltwater pool surrounded by a stone deck, bordered by lush greenery and blooming trees. A patio area includes outdoor seating and a grill, while large windows overlook the pool, enhancing natural light in the adjacent indoor space.
Home in Toronto
4.99 out of 5 average rating, 161 reviews

Year-Round Heated Pool & Hot Tub Family Oasis

Enjoy a private, year-round heated pool and spa only steps from the lake. Kayak, volleyball, tennis and basketball gear all ready for you-plus skates and ski trails when snow falls. Inside you'll find a gourmet kitchen, wood-burning fireplace and four comfy bedrooms that sleeps the whole crew. Pool & hot tub heated to 87-102 F, 365 days. Winter rink, summer pickle-ball courts. Please respect quiet hour 11pm-7am so everyone can relax.

Guest favourite
The exterior view of the two-story house is framed by lush trees, showcasing large windows that allow natural light to filter inside. A balcony extends from the second floor, providing outdoor space. The structure features a blend of wood and siding materials.
Home in Uxbridge
4.85 out of 5 average rating, 96 reviews

The Ridge Roost - Uxbridge Township

Two floors of large two bedroom house (no access to walk out basement) located in beautiful Uxbridge Township, Canada's trail capital. Minutes by car from either skiing, golfing or hiking, this beautiful property is only an hour from Toronto and is the perfect escape from the city. 10-15 minutes by car to town, either Uxbridge or Port Perry, puts you in easy reach for grocery shopping when planning your meals.

Top Guest favourite
The interior features rustic log walls complemented by wooden beams. A dining area is set with a white tablecloth and dark chairs, while a vintage dresser holds decorative items. A minimalist wall art piece depicting a deer adds character to the warm space.
Guest suite in Uxbridge
4.95 out of 5 average rating, 232 reviews

Mackenzie Cottage

Historic Log home in a country oasis. Nestled in the forest with a large pool just outside the back door, and quick access to some of the most beautiful and exciting trails in southern Ontario. Inside, surround yourself with the warmth of a log cabin circa 1815, as well as the soaring ceilings of the newer post and beam structure. Visit us on Insta @allbrightlane

Guest favourite
The modern condo building features a multi-story design with balconies and large windows. Soft greenery lines the ground level, enhancing the urban landscape. A clear blue sky provides a bright backdrop, while the street is lined with manicured trees, creating an inviting atmosphere for residents and visitors.
Condo in Markham
4.91 out of 5 average rating, 123 reviews

Downtown Markham Unionville

Newer Condo, 2 bedroom entire unit, fully furnished with everything you need as if you were at home; steps to Historic Unionville, Cineplex with VIP Cinema,, Famous Ruth's Steak House, Good Catch Creole Seafood Place; Japanese Restaurant, Go-for-Tea Fusion, Historic Rouge Valley, Great Dining, Pubs, theatre, shopping Malls

Popular amenities for Durham Region rentals with a pool

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