Vacation rentals with a pool in Durham Region

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!

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.

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.

Whole Family, 3 Generations, 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.

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

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

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.

Year-Round Heated Pool & Hot Tub Family Oasis

Enjoy your own private, year-round heated pool and spa just steps from the lake. Kayaks, volleyball, tennis, and basketball gear are ready for you whenever adventure calls - and when winter arrives, lace up your skates or explore nearby ski trails. Inside, a gourmet kitchen, wood-burning fireplace, and four inviting bedrooms offer a cozy retreat for your entire group. The pool and hot tub are heated to a comfortable 87–102°F, every single day of the year.

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.

Pool/ King Bed/Wifi/Toronto LakeView/Free Parking

The Shopping & Dining Retreat Shop, dine, and relax in style. This chic 1-bedroom condo features high-end décor, a queen pull-out sofa, and a full kitchen. 🛍️ Just steps from a vibrant mall and countless restaurants. 🚆 Toronto is only 23 minutes away via GO. Perfect for weekend getaways, foodie trips, or retail therapy. Secure your dates now and enjoy the ultimate mix of comfort and city convenience!

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

Thunderbird Farm - Luxury Farm Stay

Our farmhouse offers more than just a place to stay—it’s an experience. With luxurious accommodations, scenic views, a private pool and hot tub, and hands-on farm activities, your group will enjoy an exclusive retreat designed for those who value tranquility and natural beauty. Perfect for family reunions, group getaways, or a peaceful escape from city life.