Mansion holiday rentals in Oshawa

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Top-rated mansion rentals in Oshawa

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Guest favourite

A spacious back deck features a hot tub and seating area, surrounded by greenery. Large glass doors provide a view into the living room, while a cooking area and dining table are positioned outdoors. A metal container holds beverages, inviting relaxation.

Home in Ajax

4.93 out of 5 average rating, 102 reviews

Luxury Kitchen/King Beds/Hot Tub Table+Beds for 24

Bring your family or team together in this luxurious home! Beautifully refurnished in 2022, including a new hot tub and new hotel-quality mattresses & linens, this 4000 sq. ft house is ideally suited for large families or athletic teams. Featuring a remodeled kitchen w/ gas stove, 7 new beds (3 king), gym, office, smart TVs, 4 parking spaces & fast Wi-Fi. Only 5 minutes from the 401 & Ajax Go Train station, accessing the city is a breeze. Tennis + playground 50 meters away. *3 extra beds avail

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Guest favourite

Aerial view of a spacious bungalow set in a large green landscape. The property is surrounded by trees and open fields, with a long driveway leading to the entrance. Nearby structures and a natural setting contribute to a serene atmosphere.

Cottage in Hampton

4.86 out of 5 average rating, 147 reviews

Serene 5-BR Bungalow, 3 Full + 2 Half Baths

Stay at our tranquil Bowmanville bungalow! Free parking, Wi-Fi, fire pit, BBQ. 5 bedrooms for 16 guests. 4000 sqft,3 full baths,2 half baths,kitchen,living room Ideal for family/friends Near Cedar Park Resort Note Beds for 16 guests Truck parked in front 5 extra folding beds available on request at no extra cost Maximum capacity: 20 guests Inform us in advance if bringing additional visitors or hosting an event. No underage/teen parties allowed. Violation may result in booking cancellation

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Superhost

The exterior of a retro-executive home features a red brick façade and a welcoming front porch. A sloped roof with skylights is visible, while greenery frames the porch area, enhancing the connection with nature. The spacious yard offers a well-maintained appearance.

Home in Leskard

4.92 out of 5 average rating, 135 reviews

The Hive - Exclusive Full House, Nestled in Nature

The Hive Stay offers exclusive use of a retro-executive home for up to 15 people. The house features 6 bedrooms (13 beds); an expansive kitchen, large gathering area, sheltered deck & front porch, BBQ, fire pit & forested property surrounded by a nature reserve. Great for families, friends & colleagues. We are on the Greenbelt Cycling Path and very close to Ganaraska Forest Centre, Canadian Tire Motorsport Park, Brimacombe Ski Resort, Trail Tours, Tyrone Mills, Orono Park, Antiques + more.

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Superhost

The modern three-story residence features a mix of stone and siding, characterized by large windows that allow natural light to fill the interior. A rooftop terrace is visible, providing a perfect spot for outdoor relaxation, alongside two garages located at the ground level.

Villa in Bowmanville

4.89 out of 5 average rating, 168 reviews

Grand Waterfront Retreat – Under 1hr from Toronto

Experience the ultimate in refinement and relaxation on the north shore of beautiful Lake Ontario. Luxurious waterfront 5000 sq ft modern house with an incredible 180 degree view of Lake Ontario. Just 5 minutes walks to Port Darlington Marina & beach. This brand-new house with modern high-end furnishings and decor in the prestigious Lakebreeze community is something you don't want to miss. Enjoy sunrise and sunsets directly from the house. All this is only 40 minutes away from Toronto!

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Guest favourite

A modern living area features a spacious gray sectional sofa and a minimalist coffee table. The walls are adorned with a gallery of framed artwork. A large window brings in natural light, while greenery adds a fresh touch to the room's bright yellow accent wall.

Townhouse in Whitby

4.94 out of 5 average rating, 116 reviews

EXQUISITELY DECORATED, 4 Bdrm Townhome W/ Parking!

Welcome to your home away from home!!! A Clean, Cozy and Exceptionally Decorated Luxury Home located just outside of Downtown Whitby and minutes to Hwy 401 & 407. This Trendy Townhome boasts tons of eye catching decor and is filled with every amenity your heart could desire. Equipped with 2 King beds, 2 Queen Beds and 2 full couches this Modern Townhome is perfect for a medium to large sized family or a handful of friends or associates looking for the perfect short or long term stay.

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Home in Oshawa

4.89 out of 5 average rating, 9 reviews

Luxury 4BR | 2 Ensuites | 77" OLED TV | EV Charger

Welcome to Oshawa's most impressive rental — a brand-new, 3,000+ sq ft designer home in the sought-after Kedron community. Soaring 10-ft ceilings, a gas fireplace, 77" OLED TV, premium Bluetooth ceiling speakers, a chef's gas kitchen with oversized cooktop, EV charging and fast 850 Mbps WiFi. With 4 bedrooms, 3.5 baths, two private en-suites, and a dedicated office, this home is built for groups who refuse to compromise on space, style or the details that make a stay unforgettable.

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Guest favourite

A well-lit bedroom features a spacious bed dressed in a plaid blanket, with large windows providing natural light and access to a walk-out balcony. The modern townhouse exterior showcases a blend of brick and siding, framed by neatly landscaped areas.

Townhouse in Pickering

4.88 out of 5 average rating, 102 reviews

Modern 4beds+Office: Whole house with 4/5 parking

Welcome to our charming retreat nestled in the heart of Pickering. This cozy 4-bed house offers a serene escape from the busy Toronto city while staying conveniently close to all its attractions. Step inside to a state-of-the-art furnished living space. Modern kitchen and vibrant dining. 4 bedrooms 2.5 baths 1 dedicated office 2 balconies for patio space 2 free driveway parking Ideal for families, friends and working professionals seeking comfort and urban living at its finest.

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Top guest favourite

The living room features a large sectional sofa and a coffee table with a decorative plant. A modern gas fireplace is situated beneath a wall-mounted television displaying a streaming service. Sunlight fills the space through multiple windows, creating a bright and cozy atmosphere.

Home in Pickering

4.99 out of 5 average rating, 162 reviews

Toronto [45 mins] Sleep 8| Free Parking | Backyard

Why you will love your stay here: - ***ENTIRE HOME*** No one will be on the property but those on the booking. This is a DETACHED house. No connecting houses. - Open concept on the main floor so you can connect and create memories - Dedicated work from home spaces . Cat 6 ports -The 2nd floor has 4 different rooms where you can unwind and take a much deserved break - 10ft ceilings on a corner lot with lots of sunlight - Central Hub to Toronto (45 min drive)

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Guest favourite

The modern exterior of the house showcases a blend of stone and brick materials. Sunlight reflects off the upper windows, highlighting the clean lines and architectural features. A spacious driveway leads to the garage, complemented by neatly manicured grass.

Home in Bowmanville

4.92 out of 5 average rating, 261 reviews

Cozy Lakeside Modern House 4Br - Steps To The Lake

Great place to get away to the lakeside, family get together, relax, enjoy downtime. Tons of space for everyone in this 2,800 Square ft brand new modern home in the waterfront community in Bowmanville. Just a few steps to the walking trails, biking trails, beaches, playground & splash pad. Enjoy your stay with a walk when sunset or sunrise on the trails. Come and relax with a coffee by the fireplace on chilly days, or outside by the porch on warm summer days.

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Guest favourite

A spacious living area features a large sectional sofa facing a modern fireplace. Light wood flooring complements the warm color palette. An open floor plan is highlighted, with a view of the kitchen in the background, which includes sleek cabinetry and a large island.

Home in Oshawa

4.89 out of 5 average rating, 132 reviews

Modern 4BR Home in North Oshawa

Welcome to your modern 4BR, 3.5BA retreat in North Oshawa near Harmony & Collins. Perfect for families or professionals, this spacious home offers comfort and style with a bright open layout. Just 15 mins to malls, groceries & fine dining, with quick access to Hwy 401/407. Explore Lakeview Park, Parkwood Estate & Tribute Communities Centre nearby. Exterior security cameras ensure peace of mind. Early check-in/late check-out available!

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Guest favourite

The modern townhome exterior features a clean brick facade and large windows providing ample natural light. A set of steps leads to the main entrance, framed by black railings on either side. A small potted plant sits at the base of the steps.

Townhouse in Pickering

4.9 out of 5 average rating, 105 reviews

The Cyberspace (No cleaning fees, Private Hot Tub)

Private hot tub! No cleaning fees! This stylish modern townhome is the perfect place to stay for you and your family. Two car garage, 4 parking spots, 4 bedrooms, 4 bathrooms, pool & ping pong table, arcade game, Occulus, BBQ, exercise equipment, hot tub, walk to: store, pizza, and Cannabis shop. Fibreoptic internet for working from home/streaming. Local and trusted ride services available at competitive rates. USA friendly!

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Guest favourite

A private outdoor space features a hot tub positioned beside a blue swimming pool. Surrounding amenities include a charcoal grill, dining table, and lounge chairs set on a wooden deck, with trees providing natural shade and decorative lighting enhancing the evening atmosphere.

Home in Toronto

4.86 out of 5 average rating, 106 reviews

Toronto Pool Retreat

Spacious and private family home with 5 bedrooms, sleeping up to 10 guests. Enjoy a seasonal pool open May to September (not heated), an all-season hot tub, large backyard, and games area with ping pong, air hockey, and foosball. Includes a fully equipped kitchen, multiple living spaces, and 3.5 bathrooms. Conveniently near Hwy 401, DVP/404, shopping, and supermarkets. Respectful family and group stays only — no parties.

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