Vacation 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

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

Welcome to Gather House - Luxury Courtice Stay

Escape to this executive-style Courtice home featuring 4 bedrooms, including 2 in the finished basement- ideal for families or groups. Enjoy the private backyard oasis with sparkling pool, spacious deck and barbeque for outdoor dining. Inside, a modern kitchen, open living spaces and stylish decor offer comfort and elegance. Close to parks, shops, and highway 401, it's the perfect mix of luxury, relaxation and convenience.

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.

Spacious 1 bedroom Walkout Basement Apt

✅ Key Features • 🛏 1 Bedroom (king size bed) + Sofa Bed (sleeps 2) • 🍽 Fully equipped kitchenette: stove, fridge, microwave, Keurig, toaster, cookware & more • 🛋 Dining area, comfy seating, 65” Smart TV • 💻 1.5 Gbps high-speed fiber internet • 🚗 Up to 2 parking spots • ☀️ Private Walkout entrance • 🏊‍♂️ Shared seasonal pool access (with rules/hours) • 🤖 Robot Vacuum

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!

Airbnb King & Queen/Wifi/ near Toronto & Casino

Indulge in a stay that’s equal parts style and convenience. This beautifully furnished condo is located next to a bustling mall and countless restaurants. Shop, dine, and explore by day, then retreat to your modern condo oasis by night.