Vacation 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.

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Top guest favorite

A heated swimming pool surrounded by lush greenery reflects the clear sky above. The pool is framed by a glass fence and features colorful pool toys floating on the surface. A pergola provides shaded seating along the spacious deck, inviting outdoor relaxation.

Home in Scarborough

4.98 out of 5 average rating, 52 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

A serene pool reflects the clouds above, with vibrant turquoise water inviting relaxation. A furnished gazebo is visible in the background, accompanied by red Adirondack chairs positioned nearby, surrounded by lush greenery and a fenced area.

Guest suite in Uxbridge

4.69 out of 5 average rating, 13 reviews

Hilltop Getaway|Scenic Views| Pool | Back toTrails

Escape to this stunning hilltop 2-bedroom Airbnb, nestled on 22 acres of beautiful woodland just 2 minutes from Lake Ridge Ski Resort.Enjoy breathtaking panoramic views of the mountains from your private retreat, perfect for those seeking both relaxation and adventure This cozy unit is ideal for hikers, with direct access to Glen Major Forest and scenic trails right at your doorstep There is no living room, you will have 2 bed rms, 1 washroom and a kitchen This unit is a portion of main cottage

Superhost

The exterior of a two-story home is presented, featuring a stone façade and a welcoming porch. Four outdoor chairs are arranged at the front, with a well-maintained lawn and shrubs visible on the side. Tree foliage adds a touch of greenery to the serene setting.

Home in Ajax

4.75 out of 5 average rating, 4 reviews

Rustic Charm: A Tranquil Getaway

Welcome to our charming rustic getaway, featuring three cozy bedrooms and 1.5 bathrooms. Nestled in a serene neighborhood, this home offers a perfect blend of comfort and tranquility. The large backyard is a true highlight, offering ample space for outdoor activities. It's a perfect spot for both kids and adults to play and enjoy the fresh air. Located just a short drive from local attractions, shopping centers, and dining options, our rustic retreat is the ideal base for your next getaway.

Guest favorite

The backyard features a spacious saltwater pool with a shallow end, surrounded by a stone patio. Several lounge chairs are positioned nearby, and colorful flowers decorate the wooden support posts of the house. The property has multiple covered balconies and steps leading up to the house.

Home in Hampton

5 out of 5 average rating, 9 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

The garden area features a fenced backyard with a pool surrounded by lounge chairs and umbrellas. Colorful flowers and greenery add to the landscape. Visible are shaded seating areas, inviting for relaxation and enjoyment.

Bungalow in Whitby

4.87 out of 5 average rating, 15 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 closed until June 2025 For monthly discounts contact us

Superhost

An outdoor swimming pool occupies the center of a spacious backyard, surrounded by neatly arranged seating. Lush trees and greenery provide natural shade, while a wooden bench sits near the poolside, creating a serene environment for relaxation.

Home in Oshawa

4.74 out of 5 average rating, 35 reviews

Private Pool + BBQ + PS4: 5 Bedooms, 3 Bathrooms!

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: Outdoor Backyard is unavailable during quiet hours 11 PM to 7 AM daily. Zero tolerance for parties, loud noises. Quiet, family-friendly neighborhood.

Superhost

Home in Pickering

4.85 out of 5 average rating, 52 reviews

Toronto Vacation Pool/Park/Zoo/Casino

Welcome to our newly renovated 4-bedroom home. This spacious and stylish accommodation offers both a living room and a family room for your comfort and convenience. Dive into relaxation with access to our private heated pool. We take pride in upholding high cleanliness standers to ensure your stay is comfortable and enjoyable. Whether you’re here for a family getaway or a group retreat, our home provides the perfect blend of comfort and convenience.

Superhost

Two blue Adirondack chairs are positioned facing a large swimming pool under a clear blue sky. The pool area is equipped with slides and features shaded sections nearby, inviting relaxation and enjoyment.

Camper/RV in Haydon

4.78 out of 5 average rating, 45 reviews

The Happy Camper @ Cedar Park Resort

No trailer? No problem! Camping at this family fun waterpark is for trailers only. Accomodation in a pop up camper with all amenities to make for a comfortable 'glamping' experience. 1 queen and 1 double bed with upgraded mattresses. additional children can sleep on the dinette which converts to a single bed. Bring your own bedding. kitchen is all inclusive except kitchen cloths. must bring your own pillows and blankets and sheets

Guest favorite

A serene outdoor area features a passive-solar heated pool surrounded by lush greenery and tall trees. The pool deck, partially visible, includes a slide and seating areas, offering a tranquil retreat in a natural setting.

Home in Uxbridge

4.85 out of 5 average rating, 92 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 favorite

The backyard features a spacious pool surrounded by lush greenery. A stone patio is visible, with several lounge chairs and a dining area nearby. The home, with a dark exterior, has large windows and a deck that connects to the serene forest backdrop.

Guest suite in Uxbridge

4.96 out of 5 average rating, 211 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

Superhost

A bright sunroom is showcased with a glass ceiling and walls, providing expansive views of the surrounding nature. A glass dining table is surrounded by black chairs, resting on a soft area rug. The space offers a connection to the outdoors while remaining sheltered.

Home in Scarborough

4.92 out of 5 average rating, 77 reviews

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!