Holiday rentals with a pool in Oshawa

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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 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, 63 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/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! ✔7 Min to PanAM Centre, Toronto Zoo &Train Station ✔10 Min To Pickering Casino ✔35 Min to CN Tower ✔35 Min To YYZ airport ✔5 Min Walk TTC bus stop ✔5 Min To Groceries ✔5 Min To Highland Creek Village ✔10 Min To The Guild ✔ 20 Min To Thermea Spa Whitby

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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.

Guest favourite

Home in Scarborough

4.95 out of 5 average rating, 121 reviews

Modern Designer Home w/ Pool Open Game Rm/Fire Pit

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!

Guest favourite

Guest suite in Scarborough Village

4.89 out of 5 average rating, 104 reviews

Prestigious Bluffs Private Guest Suite

Beautiful, private, sun-filled guest suite with a large private yard and pool in a safe, upscale, tranquil, forested neighbourhood. Deer and other wildlife. Short walk to public transport (TTC, GO Trains), shopping, restaurants, parks and trails to the top of the Bluffs with breathtaking views of Lake Ontario and also down to the waterfront trail to nearby Bluffers Park Beach and Marina. Parking for 6 vehicles and boat trailer. Fast Fibre Internet. EV Charger (Tesla/J1772). No parties or events.

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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

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.

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Condo in Unionville

4.86 out of 5 average rating, 35 reviews

Modern Downtown Unionville Stay

Cozy 1+Den Condo in Downtown Unionville Stay in our modern condo with 11-foot ceilings, two beds, a fully equipped kitchen, and a 4K TV. Enjoy access to the building’s pool and gym for your convenience. Located just 5 minutes from Unionville GO, 30 minutes to downtown Toronto or Pearson Airport, and close to the Markham Pan Am Centre. With restaurants, gyms, and VIP theaters nearby, it’s the perfect base for work or leisure. Book your stay today to experience the best of Unionville!

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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.

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 Uxbridge

4.95 out of 5 average rating, 224 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

Guest favourite

Condo in Unionville

4.91 out of 5 average rating, 123 reviews

Downtown Markham Unionville

Newer Condo, 2 bedroom entire unit, fully furnished with everything you need as if you were at home; steps to Historic Unionville, Cineplex with VIP Cinema,, Famous Ruth's Steak House, Good Catch Creole Seafood Place; Japanese Restaurant, Go-for-Tea Fusion, Historic Rouge Valley, Great Dining, Pubs, theatre, shopping Malls