
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.

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.

3 BR Getaway w/ Heated Pool 40 min to Toronto
Modern & Stylish 3-Bedroom Retreat, Perfect for Families or Groups Escape to this contemporary home featuring a heated outdoor pool, BBQ area, and plenty of space to relax after a day of exploring. Enjoy all the comforts of home with Fast Wi-Fi, A fully equipped kitchen Free parking and in-suite laundry Close proximity to local shops, scenic trails Your stay includes exclusive access to the private main unit—no shared spaces. Book your getaway today & experience comfort in a perfect location!

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.

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

Modern home away from home in Courtice
A luxurious home with a salt water pool including 3 bedrooms, 3.5 washrooms, a full finished basement, a full equipped kitchen, BBQ grill, and an office space. This spacious home can accommodate any occasion and setting to host families and friends! Located right off the highway at Harmony Rd and less than 45 minutes away from Toronto.
Popular amenities for Oshawa rentals with a pool
House rentals with a pool

Ultimate Privacy In The City | 4 Bdrms 4 Washrooms

Escapeto ourcharming studiostyle retreat in Whitby

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

Country close to city

Farm house - Cottage get away

Cozy Winter Retreat In Toronto w/ Fireplace

Cozy 1BR w/ Sauna, Pool & Private Entrance

Welcome to Gather House - Luxury Courtice Stay
Other holiday rentals with a pool

Executive Suite | 1.5G Fiber | Late 3PM Checkout

Beautiful Cottage in Ajax

Horse Farm Luxury Estate

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

Ravine Paradise ! heated pool and hot tub!

The Ridge Roost - Uxbridge Township

2 Bedroom Modern Basement Apartment

Private Suite with Pool Access
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
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