Vacation rentals with a pool in Durham Region

Find and book unique homes with a pool on Airbnb

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 favorite

The heated pool is enclosed by a metal fence and features a playful inflatable float. Sun loungers are placed under colorful umbrellas, while a grassy area and trees provide a natural backdrop. A distant view of blue buildings and a hillside completes the scene.

Guesthouse in Uxbridge

5 out of 5 average rating, 38 reviews

Redwood Haven East: Your Dream Getaway in Uxbridge

Welcome to Redwood Haven, your lavish Uxbridge retreat! 2 bedrooms await, comfortably accommodating 4 guests. Be captivated by breathtaking views, immerse yourself in luxury, taking a dip in the inviting heated pool (shared by attached East and West units residents and guests). Embark on thrilling equestrian adventures for an extra touch of excitement. With ample parking, heating, and AC, ensuring the ultimate comfort throughout your stay. Unleash unforgettable memories in this enchanting haven.

Guest favorite

The outdoor area features a large in-ground swimming pool surrounded by a stone patio, with bright yellow chairs positioned nearby for relaxation. Lush greenery and wooden fencing provide privacy, creating a tranquil space ideal for outdoor enjoyment.

Home in Toronto

4.96 out of 5 average rating, 115 reviews

Modern Custom Home w/ Pool, Games & Parking

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 favorite

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

4.89 out of 5 average rating, 101 reviews

Prestigious Bluffs Private Guest Suite

Beautiful, private, sun-filled guest suite with a large private yard and pool in a safe, upscale, tranquil, forested neighbourhood. Deer and other wildlife. Short walk to public transport (TTC, GO Trains), shopping, restaurants, parks and trails to the top of the Bluffs with breathtaking views of Lake Ontario and also down to the waterfront trail to nearby Bluffers Park Beach and Marina. Parking for 6 vehicles and boat trailer. Fast Fibre Internet. EV Charger (Tesla/J1772). No parties or events.

Top guest favorite

An aerial view captures the log home nestled among greenery, with a pool surrounded by manicured grass and landscaping. A deck with patio furniture is visible, providing a space for outdoor lounging. The roof features multiple skylights, enhancing the home's natural light.

Home in Fraserville

4.98 out of 5 average rating, 52 reviews

Kawarthas storybook cottage, hot tub & heated pool

Relax and rejuvenate in the serenity of Robin’s Nest - a storybook loghome where comforts abound. Enjoy the day lounging poolside, exploring local shops or hiking the beautiful Ganaraska trails nearby. At meal time, choose the well-equipped gourmet kitchen complete with huge granite island and bar stools - or dine alfresco and BBQ on the new deck. Watch the sun set and star-gaze from the hot tub, or relax by the wood-burning fireplace with a game, movie or good book and a glass of wine.

Guest favorite

A serene pond is visible, with a person kayaking on calm waters. A wooden dock is in the foreground, featuring two white lounge chairs and a blue float. Lush greenery surrounds the pond, complementing the tranquil atmosphere.

Treehouse in Port Perry

4.98 out of 5 average rating, 555 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 favorite

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, 126 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.

Top guest favorite

A serene inground pool is surrounded by a sunlit patio, featuring lounge chairs for relaxation. Soft lighting hangs overhead, creating an inviting ambiance. The house, set against a backdrop of lush greenery, showcases multiple outdoor seating areas for comfort.

Guest suite in Kawartha Lakes

4.93 out of 5 average rating, 145 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

Guest favorite

A spacious backyard is displayed, featuring a large salt-water pool surrounded by stone edging. Several lounge chairs are positioned on the grassy area, along with a red patio umbrella. A hammock hangs between two posts, inviting relaxation amid greenery and the backdrop of a modern home.

Home in Hampton

5 out of 5 average rating, 10 reviews

Enniskillen Vacation Home Retreat!

Located in a sought after community, this attractive modern home is situated on 3/4 acre surrounded by farmland and estate homes. Explore the area with tons to do! Conveniently 5min from 407, an hour east of Toronto, 10min from Canadian Tire Motorsport Park, 5min from Cedar Park (waterpark) 20min to Brimacombe Ski Hill & Ganaraska Forest, with many ATV, snowmobile, mountain biking and walking trails close. “Pack your bags and get ready for a memorable, stress-free stay at our retreat”

Guest favorite

A modern living area features a sleek kitchen equipped with stainless steel appliances, including a microwave and oven. A comfortable sofa is positioned beside a large window, offering natural light. A breakfast bar with stools enhances the inviting space, which includes a neutral-toned area rug.

Condo in Markham

4.9 out of 5 average rating, 31 reviews

Modern Downtown Unionville Stay

Cozy 1+Den Condo in Downtown Unionville Stay in our modern condo with 11-foot ceilings, two beds, a fully equipped kitchen, and a 4K TV. Enjoy access to the building’s pool and gym for your convenience. Located just 5 minutes from Unionville GO, 30 minutes to downtown Toronto or Pearson Airport, and close to the Markham Pan Am Centre. With restaurants, gyms, and VIP theaters nearby, it’s the perfect base for work or leisure. Book your stay today to experience the best of Unionville!

Top guest favorite

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, 151 reviews

Heated Pool-tub Open 365 Days

Welcome to the Toronto Beach. We are right next to the lake and have a HEATED private pool and spa that are both open year round. Explore local shops on the high street and swim, kayak (provided), volleyball, basketball and tennis courts right beside us. In winter, an outdoor ice rink (skates provided), cross-country ski trails, and lots of walking to be had. We decorate for the holidays, and the house has a real wood burning fireplace. **note quiet hours are 11:00 pm to 7:00AM

Top guest favorite

An outdoor pool is surrounded by a stone patio, featuring landscaping elements including flower beds and a small bush. Seating options are provided by chairs placed around the pool area, and a decorative birdbath is visible nearby.

Home in Port Perry

4.93 out of 5 average rating, 228 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.

Guest favorite

The backyard features a spacious pool surrounded by lush greenery. A stone patio is visible, with several lounge chairs and a dining area nearby. The home, with a dark exterior, has large windows and a deck that connects to the serene forest backdrop.

Guest suite in Uxbridge

4.96 out of 5 average rating, 217 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