Vacation rentals with a pool in Oshawa

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.

Private Home + PS4 + Foosball: 5 Bedrooms, 3 Baths

Welcome to our spacious 5 bedroom / 3 bathroom bungalow with 3 queen beds, 2 king beds, 2 kitchens, 2 dining areas, and 2 cozy living rooms. With 3 bathrooms and plenty of space, it's ideal for families or groups. Conveniently located near shopping, HWY 401, and just a 45-minute drive to Toronto. IMPORTANT: Pool not available in Mid Sept to May. Outdoor Backyard is unavailable during quiet hours 11 PM to 7 AM daily. Zero tolerance for parties, loud noises. Quiet, family-friendly neighborhood.

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.

Modern Custom Built Walkout to Marble Pool Game RM

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!

Oasis by the Lake

Relax in this newly constructed 2-bedroom apartment, just a 3-minute walk to the Ajax waterfront, Rotary Park, and the Waterfront Trail. Enjoy nearby biking, hiking, and water sports with a kayak & canoe launch minutes away. Inside, you'll find a bright space with natural light, brand-new stainless steel appliances, in-suite laundry, and central heating and cooling. Outside, unwind in your private backyard with inground pool, hammock, and sun chairs surrounded by mature trees for full privacy.

Modern Luxury Retreat~Pool-Gym & Designer Finishes

✨ Modern country retreat surrounded by rolling farmland — minutes from trails, spas & attractions. Your peaceful escape just 1 hour east of Toronto. Explore the area with tons to do! Conveniently close to Thermea Spa, Canadian Tire Motorsport Park, Cedar Park, 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

Private Walkout Suite | 3 PM Checkout | 1.5G Wifi

Travel on your own terms with early check-in and a rare 3 PM late checkout. Located at the Finch/Dixie junction, this 600sqft executive suite offers 1.5G Fiber, a King Bed, and a private walkout for the discerning modern traveler. Relax by the fireplace, utilize the equipped office desk, and enjoy a full kitchen with total indoor privacy. (Laundry and the landscaped yard with a seasonal pool access are shared spaces)

Waterfront community ideally for long stays

Furnished 4 bedroom, 2.5 bathroom Executive townhouse located in upscale neighborhood in Bowmanville waterfront community. Close the Hwy 401 and all shopping center. Bowmanville Hospital and the Go bus service. Easy access to nice restaurants and many more amenities. It is bright, spacious, with many beautiful features. All inclusive (parking, tv and internet included) The basement will be rented separately.

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.

Forest Retreat | Winter Sanctuary in the Woods

Private hilltop retreat on 22 acres with panoramic winter views, just 2 minutes from Lake Ridge Ski Resort. Cozy 1-bedroom with a flexible living room that converts to a second bedroom. Enjoy peaceful privacy, snow-covered forests, stunning sunrises and sunsets, and direct access to Glen Major Forest for winter hikes and snowshoeing. Perfect for couples, families, and outdoor lovers seeking comfort and nature.

2 Bedroom Modern Basement Apartment

In addition to the heated pool (currently closed for winter season), hot-tub (open year-round), and barbecue grill, your family will be close to everything you need to enjoy your stay at this centrally-located place. Places like Cedar Park resort, Port Darlington East Beach park, Freshco, banks, Shoppers Drugmart, hospital, Home Depot, Dollarama amongst others are just few mins away.

Ravine Paradise ! heated pool and hot tub!

Ravine Paradise in the city of toronto! 3 bedrooms with 3 queen size beds ! Come relax and enjoy yourself backing on to the twin rivers ravine. very private property close to the Toronto zoo within minutes. downtown Toronto within 20 minutes. very big pool heated and hot tub as well!