Vacation rentals with a pool in Durham

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.

Family · Location · Check-in

One-of-a-kind pool, Farm Stay, Learn about 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.

Family · Location · Condition

5-Acre Waterfront Cottage w/sauna，Pool & Hot Tub

Welcome to "the Easy Time", an escape to unforgettable luxury at our waterfront cottage on Lake Scugog, less than 1 hour drive from Toronto. The property includes 5 acres of wooded land, 280ft of waterfront, 2700sq. ft. four season main cottage, an A-framed Bunkie, and a domed tent. The cottage is open and spacious, providing a generous living area with stunning views of the water all around with multi-level decks, outdoor sauna, swimming pool, hot tub, shower, firepit, and extra long dock.

Value · Location · Bathroom

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 STR2026-149

Family · Value · Nearby

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!

Location · Family · Kitchen

1BR Bluffs | Pool + Yard | Pets Ok | EV Charger

Enjoy this beautiful, sun-filled, private suite with a large pool and secluded, fenced yard in a safe, upscale and serene forested neighbourhood 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. EV Charger.

Location · Value · Getting around

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.

Family · Location · Backyard

Luxury 4BR: 365 Days Open- Heated Pool & Hot Tub

A Private Luxury Getaway in Toronto’s Most Coveted Neighbourhood Escape to an extraordinary 4-bedroom luxury home in Toronto’s iconic Beaches, where sophisticated design meets relaxed lakeside living. This top 1% rated Airbnb property offers an unforgettable weekend experience—perfect for families, couples, or a curated group of friends seeking both comfort and wow-factor. A year round private heated pool and hot tub are yours to enjoy !

Location · Family · Backyard

Toronto Pool Retreat

Spacious and private family home with 5 bedrooms, sleeping up to 10 guests. Enjoy a seasonal pool open May to September (not heated), an all-season hot tub, large backyard, and games area with ping pong, air hockey, and foosball. Includes a fully equipped kitchen, multiple living spaces, and 3.5 bathrooms. Conveniently near Hwy 401, DVP/404, shopping, and supermarkets. Respectful family and group stays only — no parties.

Location · Family · Shared spaces

New Custom-Built | Marble Pool + BBQ | Toronto

Welcome to our brand-new, custom-built luxury suite in a quiet, family-friendly neighbourhood. Enjoy a cozy boutique-style retreat with radiant heated floors, luxury finishes, a seasonal heated marble pool (Apr–Oct), private game room, BBQ, fire table, workspace, high-speed Wi-Fi, Smart TV, in-suite laundry, and 24/7 self check-in. Minutes to Hwy 401, DVP, TTC, and the Crosstown LRT with easy access to downtown Toronto.

Family · Location · Amenities

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.

Value · Family · Heating

Big Luxury Detach House For Short And Long Stay

It’s a big Stunning Luxury, beautiful detach house located in the prime,quiet location of Whitby.Master bed with attach bath,spa tub on main floor,.2 bed upstairs with common bath,21 “feet ceiling,gorgeous kitchen and breakfast bar,heated inground pool. 2 free parking spots,No parties,loud music,yelling.Screaming inside or outside or any extra guests not allowed at any time of the day or night

Family · Location · Pets