
Holiday rentals with a pool in Oshawa
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Oshawa
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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.

Bluffs Private Suite | World Cup 2026 | Pets Ok
Enjoy this beautiful, private, sun-filled suite with a large secluded yard and pool 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 and an EV charger (Tesla/J1772).

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.

Gorgeous 2BR Suite | Swim Pool | Fire Table | BBQ
Welcome to our brand new, luxury modern suite located in a quiet, family-friendly neighbourhood. Mins to HWY401/DVP, TTC. Featuring: ✓ Luxury Finishes Throughout ✓ Heated Swimming Pool (seasonal April - Oct) ✓ Dedicated Workspace ✓ Washer/Dryer ✓ High-Speed WIFI ✓ Smart TV with Netflix, Prime & sound system ✓ Keyless Entry (24/7 Self Check-In) ✓ Outdoor BBQ, seating and fire table This upscale oasis is truly the perfect space for business travellers, young professionals & couples alike!

Executive Suite | 1.5G Fiber | Late 3PM Checkout
Purpose-built for remote workers and business travellers: 1.5Gbps dedicated fiber, 24” monitor, ergonomic chair, and a private walkout entrance so your workday starts the moment you arrive. Travel on your own terms with early check-in and a rare 3 PM late checkout. Located minutes from Pickering GO Station (downtown Toronto in ~45 min), this 600sqft executive suite offers a King bed, sofa bed, and full kitchen with total indoor privacy. Wind down by the gas fireplace after a long day.

“Modern 3BR Condo w/ Free Parking | 1 Min to 401”
Welcome to your home away from home! Enjoy this fully independent, beautifully maintained 3-bedroom condo located just 1 minute from Scarborough Town Centre and right off Highway 401 — perfect for families, business travelers, and vacation guests. 🏡 The Space ✔️ Entire private apartment ✔️ 3 spacious bedrooms with comfortable beds ✔️ Bright living & dining area ✔️ Fully equipped kitchen ✔️ Clean, modern bathrooms ✔️ High-speed WiFi ✔️ Smart TV ✔️ In-unit laundry ✔️ Free parking

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.

Luxury High Rise Living Parking, Gym, Pool, View
Experience upscale high-rise living in this stylish 2-bed, 2-bath Scarborough condo. Perfect for 4+ guests, it features a modern design, a private balcony with stunning forest views, and a dedicated workspace. Enjoy premium amenities like an indoor pool, gym, and free parking. Located in the heart of Scarborough, you're steps from shopping, dining, and transit. Your perfect urban retreat awaits!

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.

Private Pool Lakeview House
Enjoy a memorable visit when you stay in this unique place. Absolutely stunning waterfront cozy home near the Toronto bluffs beach. This is a gorgeous place in a classy neighbourhood with everything you need. Private pool and spacious yard with extraordinary views. Walking distance to the beach, Go transit, restaurants, grocery, pharmacy and more. You'll love it!
Popular amenities for Oshawa rentals with a pool
House rentals with a pool

Modern home away from home in Courtice

Ultimate Privacy In The City | 4 Bdrms 4 Washrooms

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

Farm house - Cottage get away

Cozy Winter Retreat In Toronto w/ Fireplace

Welcome to Gather House - Luxury Courtice Stay

Entire Modern Home | Spacious | Near Lake & Park

Hearth & Haven | Warm Cozy Home Retreat
Apartment rentals with a pool

“Modern 3BR Condo w/ Free Parking | 1 Min to 401”

Luxury High Rise Living Parking, Gym, Pool, View

Spacious 1 Bedroom Scarborough Condo (STC) Area

Lovely 1 bedroom unit with balcony. Sleeps 1-4
Other holiday rentals with a pool

Pickering King & Queen/Wifi/ near Toronto & Casino

Guesthouse on Horse Farm

Dee’s palace

Escapeto ourcharming studiostyle retreat in Whitby

Private Oasis – next to Toronto- Wifi / Lake View
Quick stats about holiday rentals with a pool in Oshawa

Total holiday rentals
Explore 10 holiday rentals in Oshawa

Nightly prices starting at
Oshawa holiday rentals start at £22 per night before taxes and fees

Verified guest reviews
Over 330 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Wifi availability
10 of Oshawa holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Oshawa rentals

4.8 Average rating
Oshawa stays are highly rated by guests – averaging 4.8 out of 5!
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- Rogers Centre
- CN Tower
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