Vacation rentals with a pool in Regional Municipality of Durham

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Top-rated rentals with a pool in Regional Municipality of Durham

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

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Top guest favorite

A private heated pool is framed by stone tiles and lush greenery, reflecting sunlight. Large glass doors lead into the home, enhancing the outdoor connection. Seating areas are available nearby, surrounded by natural landscaping and elevated steps leading to the indoor space.

Home in Toronto

4.99 out of 5 average rating, 142 reviews

Heated Pool-tub Open 365 Days

** Ask about MID WEEK Specials. 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 (bring your own equipment) and lots of walking to be had. We decorate for for holidays, and the house has a real wood burning fireplace.

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

A serene backyard pool area is framed by lush greenery and vibrant flowers. A blue umbrella provides shade over a dining table, while a pool features a protective cover. Lounge chairs are positioned beside the water, creating a space for relaxation and enjoyment.

Bungalow in Kawartha Lakes

4.92 out of 5 average rating, 60 reviews

The Perfect Retreat-Heated salt water pool

HST in-Pool open May long weekend to Oct 1. Very quiet area. Beautiful modern space, full main floor. Enjoy the spa atmosphere and backyard oasis. Granite countertops, hardwood floors, CAC, stainless steel appliances, convection oven, 3 TV 's. Perfect for families. Kawartha Lakes offers beautiful lakes, parks, trails, and small town shops. Kids will love Logie Park playground and water park..it's free. (owners sometimes stay in basement separate entrance) Municipal License STR2024-177

Top 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

4.89 out of 5 average rating, 122 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, Covered patio, Hiking Trail, outdoor kitchen and BBQ. Billiards, shuffleboard, trampoline, table tennis, basketball, badminton, bocce ball. Something for everyone! 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.

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, 130 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!** * except during bans, April

Guest favorite

Home in Oakwood

4.98 out of 5 average rating, 44 reviews

All Season Indoor Pool Escape

This stunning property has completed a full renovation to offer you the ultimate in luxury living. Our estate property features 4 newly renovated large bedrooms, each with an ensuite bathroom. The indoor pool with floor-to-ceiling windows will be the perfect spot for family fun and relaxation, and the basketball pad and outdoor space backing onto a wheat field will provide plenty of opportunities for outdoor activities. Even when it's cold and raining, the indoor pool is a perfect escape!

Guest favorite

The backyard features a spacious saltwater pool with a shallow end, surrounded by a stone patio. Several lounge chairs are positioned nearby, and colorful flowers decorate the wooden support posts of the house. The property has multiple covered balconies and steps leading up to the house.

Home in Hampton

5 out of 5 average rating, 7 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

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, 218 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

A covered porch area features a glass-top table with four chairs. Beyond, the pool is visible alongside the lake, offering serene water views framed by trees. The setting captures a peaceful outdoor space ideal for relaxation and family gatherings.

Home in Kawartha Lakes

4.95 out of 5 average rating, 20 reviews

Charming 3-Bedroom Lake Front Cottage with Pool

Escape to a cozy, family-friendly retreat at our charming 3-bedroom cottage on beautiful Sturgeon Lake! Enjoy the peaceful surroundings, refreshing pool (seasonal), and comfortable accommodations, all within easy reach of local attractions. Whether you're looking to relax by the pool, explore the local attractions, or enjoy the natural beauty of the area, this cottage is the perfect getaway for families or small groups. Book your stay today and make unforgettable memories!

Superhost

Home in Pickering

4.85 out of 5 average rating, 46 reviews

Toronto Vacation DecemberPromotion/Park/Zoo/Casino

Welcome to our newly renovated 4-bedroom home. This spacious and stylish accommodation offers both a living room and a family room for your comfort and convenience. Dive into relaxation with access to our private heated pool. We take pride in upholding high cleanliness standers to ensure your stay is comfortable and enjoyable. Whether you’re here for a family getaway or a group retreat, our home provides the perfect blend of comfort and convenience.

Guest favorite

Home in Toronto

4.91 out of 5 average rating, 68 reviews

Toronto Pool Retreat

Experience prestige and privacy in our spacious, well-maintained family home. Enjoy resort-like living with a private yard featuring an inviting pool, hot tub, and large deck. Plus, indulge in additional entertainment options like air hockey and ping pong. Perfect for entertaining! Steps away from ravines, parks, and nature trails, plus easy access to amenities and transportation. Your ideal Toronto getaway awaits!

Superhost

An aerial view captures the bungalow surrounded by a spacious interlocked patio, featuring a large private pool. The deck, furnished with seating, provides a relaxing area. Soft lighting outlines the backyard, enhancing the outdoor space for evening enjoyment.

Home in Ajax

4.87 out of 5 average rating, 15 reviews

Luxurious house with private Pool

Enjoy Luxury Living in detached bungalow with 3 bedroom 1.5 washroom. Sitting on a Massive 50 Ft. Wide Lot with Fully Interlocked Resort Style Backyard Featuring Huge private Pool(closed mid September- end of May)along with Deck Prime Neighborhood of Ajax, 1.5km from Serene Ajax Lakefront 800 Mts from grocery store, convinience stores and restaurants 500 mts from Lush Parks and 4.5 km from Ajax Go Station

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What guests are saying

The Happy Camper @ Cedar Park Resort

4.78 out of 5 average rating, 45 reviews8 months ago

Stayed there with my 3 kids (11, 12, and 14) and they had a blast. The camper is away from the public area, so even though it got quite busy at the pool during the day, things cleared out by the afternoon, and it was quiet at night. The kids could safely explore, and they loved the water park, slides and pool. Huge playground as well. The Tuck shop was a bonus, it took debit, and it was a great way to be lazy in terms of cooking lunch/dinner! Plus ice-cream. :) There are picnic tables and muskoka chairs for the camp fire, we didn't lack for anything, mattresses were comfy. We're used to tent camping, so this was a luxury for us. We'll be back!

Camper/RV in Haydon

What guests are saying

Contemporary A Frame on Scugog Island with Pool

4.95 out of 5 average rating, 21 reviews8 months ago

This was our second time staying at the property and it was just as beautiful as the first time. Our family enjoyed the pool and all the amenities offered by the house made us feel very comfortable and right at home. Would recommend for families looking to enjoy some relaxation in peaceful surroundings with all the comforts of home. Thank you for your wonderful hospitality!

Vacation home in Port Perry

What guests are saying

Waterfront Sunrise bungalow with Swimming Pool

4.85 out of 5 average rating, 75 reviews2 months ago

We had a wonderful stay! The place has a beautiful view, and while we visited during a winter storm and couldn’t fully enjoy the lake, we’ll definitely keep an eye out for a summer visit. The host was extremely helpful. When we asked if they had a snow blower, they brought everything we needed before check-in. They were also very responsive whenever we called or messaged. The place was spotless and well-maintained. Highly recommend!

Bungalow in Little Britain

What guests are saying

The Birch Cottage

4.71 out of 5 average rating, 14 reviews8 months ago

Exactly as advertised and perfectly suited to time away from the hustle and bustle of the city. Lots of amenities and steps from the dock which overlooks Sturgeon Lake.. You'll appreciate the beautiful sunsets and great walking options. A short drive to restaurants and shopping. Kayleigh was a great host and makes this destination an absolutely easy place to want to come back to.

Home in Kawartha Lakes

What guests are saying

Scenic cottages (2bdrm) south shore Sturgeon Lake

4.71 out of 5 average rating, 21 reviews9 months ago

We had a great time Gord’s place!The cabin is spacious, cozy, and functional with a fully equipped kitchen and two full bathrooms. Great location with easy access to the pool and a beautiful view of the lake where you can enjoy stunning sunsets right from the deck. The grounds are meticulously maintained with beautiful flowerbeds and ample lakeshore space, very quiet,creating a peaceful and tranquil atmosphere. Gord and his family are exceptional hosts—friendly, respectful, accommodating, and quick to respond to any questions we had. Gord even offered a flexible check-in time and provided two heaters for a couple of chilly nights. His local recommendations for nearby attractions were also greatly appreciated. Additionally, their thoughtful gesture of providing a play kitchen structure with toys made our toddler incredibly happy. We highly recommend Gord’s place to anyone seeking a peaceful retreat surrounded by nature. Thank you for a memorable stay—we look forward to returning!

Cottage in Kawartha Lakes

What guests are saying

Stunning Beach 3 bedroom home with swim spa

5 out of 5 average rating, 11 reviews9 months ago

We stayed at Jody's place with a group of friends and really enjoyed it. The house was large and roomy, and was ideal for a group to spend the weekend in Toronto. Jody was really communicative and helpful and made the visit a breeze. The space is nice with plenty of nice outdoor spaces to enjoy, including the cozy backyard with the spa pool which we really enjoyed. This is the family's home, so there were some personal effects in the space, so we were conscious of not disturbing any of their belongings – and this also meant there were some things that needed to be tidied a bit and moved out of the way in the house & yard, so just worth noting FYI. The neighborhood was awesome, and we were really glad we ended up staying over this way. It was really close to the beach and to several great spots coffee, food & drinks. We'd recommend for a group visit!

Home in Toronto

What guests are saying

Tranquil Getaway with Pool

4.93 out of 5 average rating, 46 reviews7 months ago

Staying Jun's place was a great experience. He was very responsive and friendly from the start and had clear instructions on how to use/maintain amenities such as the pool and hot tub. The house was spacious and clean, with everything you need in an organized manner. Overall a fantastic place to stay with family.

Villa in Kawartha Lakes

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