
Vacation 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.

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.

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

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.

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!

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.

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

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”

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.

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

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!

KING & QUEEN, Royal Design, near Casino
Indulge in a stay that’s equal parts style and convenience. This beautifully furnished condo is located next to a bustling mall and countless restaurants. Shop, dine, and explore by day, then retreat to your modern condo oasis by night.
Popular amenities for Oshawa rentals with a pool
House rentals with a pool

Luxury home 4BR, Pool, & 5 Mins to 401

Cozy 1BR w/ Sauna, Pool & Private Entrance

Welcome to Gather House - Luxury Courtice Stay

The Ridge Roost - Uxbridge Township

Cozy 1 bedroom studio apartment in oshawa

Entire Modern Home | Spacious | Near Lake & Park

Home away from home

Luxe 4BR Retreat w/ Heated Pool, Hot Tub & BBQ
Other vacation rentals with a pool

Elite Penthouse, Stunning Views & Private Balcony

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

Mackenzie Cottage

Escape – Escape to your own Private Oasis

Private Oasis, 5 Star KING Bed, book now !

2 Bedroom Modern Basement Apartment

KING & QUEEN, Royal Design, near Casino

Guesthouse on Horse Farm
Quick stats about vacation rentals with a pool in Oshawa
Total rentals
20 properties
Nightly prices starting at
R348 ZAR before taxes and fees
Total number of reviews
310 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
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- Rogers Centre
- CN Tower
- Scotiabank Arena
- University of Toronto
- Budweiser Stage
- Exhibition Place
- Distillery District
- Port Credit
- Metro Toronto Convention Centre
- The Danforth Music Hall
- Toronto Zoo
- Harbourfront Centre
- Financial District
- CF Toronto Eaton Centre
- BMO Field
- Trinity Bellwoods Park
- Massey Hall
- Casa Loma
- Dufferin Grove Park
- Rouge National Urban Park
- Royal Ontario Museum
- Toronto City Hall
- Jackson-Triggs Niagara Estate
- Christie Pits Park