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.

0 of 0 items showing

1 of 3 pages

Guest favourite

Home in Port Perry

5 out of 5 average rating, 10 reviews

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.

Guest favourite

Home in Port Union

4.98 out of 5 average rating, 62 reviews

Ultimate Privacy In The City | 4 Bdrms 4 Washrooms

Surrounded By Nature,This East-End Toronto Gem Features A Heated 4Ft Deep Pool(Open May-Oct),Pergola w/Ample Seating+BBQ On An Over-Sized Deck.The HGTV Inspired Renos Will Make Your Stay Extra Special.A True Get-Away Where Lasting Memories Will Be Made! ✔ 5-7 Min to PanAM Centre, Toronto Zoo, Rouge Beach &Train Station ✔ 10 Min To Pickering Casino ✔ 35 Min to CNtower ✔ 35 Min To YYZ airport ✔ 5 Min Walk to TTC bus stop ✔ 5 Min To Groceries ✔ 5 Min To Highland Creek Village ✔ 10 Min To The Guild

Superhost

Home in McLaughlin

4.8 out of 5 average rating, 49 reviews

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.

Superhost

Bungalow in Whitby

4.88 out of 5 average rating, 16 reviews

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

Guest favourite

Home in Hampton

5 out of 5 average rating, 10 reviews

Enniskillen Vacation Home Retreat!

Located in a sought after community, this attractive modern home is situated on 3/4 acre surrounded by farmland and estate homes. Explore the area with tons to do! Conveniently 5min from 407, an hour east of Toronto, 10min from Canadian Tire Motorsport Park, 5min from Cedar Park (waterpark) 20min to 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”

Superhost

Home in Whitby

4.8 out of 5 average rating, 10 reviews

Luxe 4BR Retreat w/ Heated Pool, Hot Tub & BBQ

Welcome to your ultimate getaway – a beautifully maintained, spacious 4-bedroom, 2.5-bath family home designed for relaxation, entertainment, and comfort. Whether you're planning a weekend escape, a family vacation, or a longer stay near Toronto, this home has everything you need for a memorable experience. Step into your own backyard paradise! Enjoy a refreshing swim in the private heated pool, soak your cares away in the hot tub, or fire up the BBQ grill for a delicious outdoor meal.

Superhost

Guest suite in Uxbridge

4.78 out of 5 average rating, 18 reviews

Forest Retreat | Pool, BBQ & Fall Colors

Hilltop retreat on 22 acres with panoramic views, just 2 min from Lake Ridge Ski Resort. Perfect for a cozy fall escape. Features: 1 bedroom + living room (convertible to 2nd bedroom) Pool still open for refreshing swims BBQ for outdoor dining under the trees Direct access to Glen Major Forest hiking & biking trails Peaceful privacy with sunrise & sunset views Vibrant fall colors and crisp country air Ideal for couples, families & adventurers seeking both comfort and nature.

Superhost

Flat in Pickering

4.67 out of 5 average rating, 3 reviews

Private Oasis, HUGE KING Bed, book now !

The Family Mini-Getaway Comfort and fun for everyone. This modern 1-bedroom condo includes a queen pull-out sofa, full kitchen, and stylish furnishings — ideal for small families. 🎡 Steps to casino events, restaurants, and shopping. 🚆 Quick GO access gets you to Toronto in just 23 minutes for museums, sports, and city fun. The perfect family mini-getaway or staycation. Reserve your dates now before they’re gone!

Guest favourite

Home in Uxbridge

4.85 out of 5 average rating, 95 reviews

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.

Guest favourite

Guest suite in Bowmanville

4.77 out of 5 average rating, 53 reviews

2 Bedroom Modern Basement Apartment

In addition to the heated pool (closed 2nd week of October), 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.

Guest favourite

Guest suite in Uxbridge

4.95 out of 5 average rating, 222 reviews

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

Home in Whitby

4.63 out of 5 average rating, 19 reviews

3 BR Getaway w/ Heated Pool 40 min to Toronto

Modern & stylish 3-bed home—perfect for families or groups. Relax outside in the heated pool, fire up the BBQ and unwind after exploring Toronto (just 40 min). Fast Wi-Fi + dedicated workspace Fully stocked kitchen & baking sheets Free parking and in-suite laundry Minutes to shops, trails and wineries. Book your getaway today! Private main unit only for guests