Holiday rentals with a pool in Oshawa

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.

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.

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

Executive Suite: King Bed | Office Desk Fast Wi-Fi

This quiet walkout suite is designed for high-performance work days and high-quality rest. Enjoy 1.5 Gbps Fiber internet and a King-size bed, with the added luxury of seasonal pool access during the summer months. Designed for productivity and premium comfort. Whether you are a traveling executive or a digital nomad, this walkout suite offers a high-performance workspace and hotel-standard amenities. Enjoy a private entrance, ultra-fast fiber internet, and a "No Cleaning Fee" stay.

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

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.

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!

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.

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

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!