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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Guest favorite

A spacious living room features comfortable seating arrangements, including a large sectional sofa and plush armchairs. A stone fireplace serves as a focal point, accompanied by a mounted artwork depicting a horse. A large television is positioned across from the seating area.

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.

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, 59 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

Guest favorite

The heated pool is enclosed by a metal fence and features a playful inflatable float. Sun loungers are placed under colorful umbrellas, while a grassy area and trees provide a natural backdrop. A distant view of blue buildings and a hillside completes the scene.

Guesthouse in Uxbridge

5 out of 5 average rating, 38 reviews

Redwood Haven East: Your Dream Getaway in Uxbridge

Welcome to Redwood Haven, your lavish Uxbridge retreat! 2 bedrooms await, comfortably accommodating 4 guests. Be captivated by breathtaking views, immerse yourself in luxury, taking a dip in the inviting heated pool (shared by attached East and West units residents and guests). Embark on thrilling equestrian adventures for an extra touch of excitement. With ample parking, heating, and AC, ensuring the ultimate comfort throughout your stay. Unleash unforgettable memories in this enchanting haven.

Guest favorite

The outdoor area features a large in-ground swimming pool surrounded by a stone patio, with bright yellow chairs positioned nearby for relaxation. Lush greenery and wooden fencing provide privacy, creating a tranquil space ideal for outdoor enjoyment.

Home in Scarborough

4.96 out of 5 average rating, 112 reviews

Modern Custom Home w/ Pool, Games & Parking

Welcome to our brand new, luxury modrn unit located in a quiet, family-friendly neighborhood only min from HWY401,407,DVP, TTC & countless amenities! Newly & lovingly modern space with luxury finishes throughout. Enjoy comfortable living quarters, brand new kitchen appliances, bright rooms, large windows, a dedicated workspace, in-unit washer/dryer, free WIFI, Netflix, Prime & free parking. This upscale oasis is truly the perfect space for business travelers, young professionals & couples alike!

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

4.71 out of 5 average rating, 14 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

Guest favorite

A spacious backyard is displayed, featuring a large salt-water pool surrounded by stone edging. Several lounge chairs are positioned on the grassy area, along with a red patio umbrella. A hammock hangs between two posts, inviting relaxation amid greenery and the backdrop of a modern home.

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

A private outdoor space features a large above-ground pool and a luxury hot tub. Surrounding the pool, lounge chairs and a covered seating area provide comfort and shade. The wooden deck is complemented by greenery along the perimeter, creating a relaxing atmosphere for outdoor enjoyment.

Home in Whitby

New place to stay

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

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

4.88 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 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

4.79 out of 5 average rating, 43 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

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

4.74 out of 5 average rating, 47 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

Superhost

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, 216 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