Mansion holiday rentals in Oshawa

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Top-rated mansion rentals in Oshawa

Guests agree: These mansions are highly rated for location, cleanliness and more.

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Superhost
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 980 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. STR# RHSTR2026006

Top Guest favourite
The exterior of a two-story home showcases a brick façade with a blue garage door. A welcoming front porch features seating, while a neatly landscaped pathway leads to the entrance. Ample windows allow natural light to brighten the space.
Home in Whitby
4.87 out of 5 average rating, 214 reviews

Cheerful 4-bedroom home with huge patio

This bright and airy 4 bedroom 3 bathroom home is perfect for a family or a friends getaway. High speed internet and full amenities. Minutes from Deercreek Golf Course, the NEW Thermëa spa, top rated restaurants, supermarkets, and shopping. Easily accessible by highway 401 or 407/412. 45-min drive to downtown Toronto. 10-min drive to Whitby GO Train station. Perfect for families, business trip or a weekend getaway, your stay here is sure to be convenient and effortless. Long-term stays welcome.

Superhost
Home in Whitby
4.83 out of 5 average rating, 71 reviews

Stylish 4BR Townhouse (TV in every room, GameRoom)

Relax in this stylish 4-bedroom townhouse just minutes from downtown Whitby. Perfect for families or groups, it features a fully equipped kitchen, cozy living spaces, and a private game room with a pool table. Enjoy nearby parks, restaurants, and local attractions while staying in a quiet, family-friendly neighborhood. Whether you’re here to unwind or explore, this space offers the perfect mix of comfort, fun, and convenience. Reserve your stay today and experience Whitby like never before.

Guest favourite
A modern two-story brick home is featured, showcasing large windows and a welcoming front porch. The well-maintained lawn is bordered by a paved driveway leading to a garage. Neighbors’ homes are visible in the background, highlighting a friendly residential setting.
Home in Bowmanville
4.89 out of 5 average rating, 36 reviews

The Bliss

Welcome to The Bliss located in the heart of Bowmanville ! Whether you're here for a relaxing getaway or an adventurous trip, this space is perfect for couples/families/groups. Enjoy cozy comforts with modern amenities, spacious rooms, and a beautifully designed home. Whether you're here for relaxation or adventure, we’re sure you’ll feel right at home!" With easy access to the 401 highway and historic Bowmanville Downtown, you're sure to have a memorable stay. We can't wait to host you!

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
4.9 out of 5 average rating, 162 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!

Superhost
Home in Oshawa
5 out of 5 average rating, 4 reviews

Luxury 4BR | Jacuzzi | 2 Ensuites | Gas Fireplace

Welcome to 3,165 square feet of luxury in Oshawa's sought-after Taunton community near Durham College and Ontario Tech University — a home that earns the word rather than just claiming it. A Jacuzzi ensuite, gas fireplace, two separate living rooms, two private en-suites, chef's kitchen, 2-car garage and a perfect 5-star guest rating. Four bedrooms, 3.5 bathrooms, and everything a group of eight could possibly require. Ideal for families, professionals, workers, or business travellers.

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, 115 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.

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, 101 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.

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, 160 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)

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, 259 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.

Guest favourite
A modern living area is highlighted by a large black sectional sofa adorned with colorful throw pillows. A light wood coffee table sits atop a soft area rug, with a potted plant nearby. Light streams through large windows dressed with stylish shades, creating a bright and inviting space.
Townhouse in Oshawa
4.94 out of 5 average rating, 62 reviews

Brand New Luxurious 4B Townhouse

Experience Luxury & Cozy Living at Our Place - Book Now Before Spots Fill Up! ★ Spacious Brand New Townhome ★ Fully equipped with luxurious furnishings throughout ★ Multiple Queen-sized beds with premium mattresses for ultimate comfort ★ High-speed internet up to 1GB for seamless connectivity ★ Smart TV in the living area for your entertainment ★ Open-concept design with a fully stocked kitchen for all your culinary needs ★ And MANY more amenities

Superhost
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, 130 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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