Condo holiday rentals in Oakville

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Top-rated condo rentals in Oakville

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

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Guest favourite
The living area presents a spacious layout, featuring a white sofa and a glass coffee table. A large television is mounted on the wall. Decorative glass vases in teal shades are placed nearby. Natural light filters through the open space, creating a welcoming ambiance.
Condo in Oakville
4.92 out of 5 average rating, 106 reviews

LUXURY CONDO, GREAT DECOR, WHEELCHAIR FRIENDLY!!!

NEW GORGEOUS LUXURY CONDO WHEELCHAIR ACCESIBLE. *** NEW BED in 2nd!*** PRIME BEDROOM has a queen size memory foam mattress & a desk. SECOND BEDROOM has a brand new bed with double mattress medium/firm and a working desk, now accessible to guests. 2 FULL BATHROOMS: The en-suite has has a step up shower and a Bidet. SECOND: Has a tub & shower, very spacious. *OPEN CONCEPT LIV. AREA. *OPEN BALCONY. TASTEFULLY FURNISHED, SOFT AND CLEAN COLORS HARDWOOD FLOORS THROUGHOUT EXTRA WIDE HALLS AND DOORS

Guest favourite
A modern living area features a gray sofa adorned with blue cushions. A wooden coffee table sits on a patterned rug, with a large flat-screen TV mounted on the wall displaying content. The kitchen area is visible in the background, equipped with sleek appliances.
Condo in Churchill Meadows
4.92 out of 5 average rating, 127 reviews

Entire Condo - 20min from Toronto Airport

This cozy one bedroom, 500 sq. ft., condo is located in the desirable Churchill Meadows area. It’s conveniently located across the street from Erin Mills Mall and within walking distance to all major amenities. You’ll find highway access to be a breeze; HWY 403 is only 1 minute away and the 401 under 10 minutes. Toronto Pearson Airport is a 15 minute drive, and you’ll find yourself downtown Toronto within 25 minutes. My place is perfect for business travelers, solo adventurers and couples.

Top Guest favourite
A balcony view captures the iconic CN Tower alongside a modern building structure. The expansive glass windows reflect the urban skyline and lake in the distance, evoking a sense of openness and connection to the city.
Condo in Entertainment District
4.83 out of 5 average rating, 179 reviews

Toronto CN Tower 2 Bed 2 B w Master King w Parking

Luxury newly furnished home away from home in central downtown 300 Front Street with balcony CN Tower view. 2 Bedroom 2 Bath, Comfortable King bed TV en suit, Double bed TV w blackout curtains Enjoy in building Gym, Steam room, Outdoor pool with 360 degree view of the city, Whirlpool, and BBQ. Steps away from CN Tower, Rogers Centre, Aquarium, Metro Convention Centre, short walk to Scotiabank Arena, the lake, Bell Lightbox, Billy Bishop Airport, Union Station, Entertainment District and more

Guest favourite
The image displays the CN Tower from different angles, showcasing its height against a sunset and nighttime sky. The left view highlights the tower with the Rogers Centre below, while the right view features the illuminated tower amidst the city lights, emphasizing the vibrant colors at night.
Condo in Harbourfront
4.95 out of 5 average rating, 615 reviews

Stunning Lake/CN Tower View: 2BR+2BA, Free Parking

Cozy 2 bedrooms + 2 full baths condo in the heart of downtown tourist hotspot; unobstructed CN tower view; 1 free dedicated parking. Perfect for business or vacation stay! WALKING DISTANCE to: • Supermarket & LCBO: 1 min • Scotiabank Arena: 3 min • Union Station: 3 min • Convention Center: 3 min • Ripley's Aquarium: 3 min • UPX Train: 5 min • Harborfront: 5 min • CN Tower: 5 min • Rogers Center: 7 min • Roy Thompson Hall: 9 min • Royal Alexander Theater: 12 min • St. Lawrence's Market: 18 min

Top Guest favourite
A bright and airy living space features large corner windows that offer expansive views of the city. A modern sectional couch is paired with a light rug, while a flat-screen television is mounted on the wall. Lush green plants add a touch of nature to the inviting décor.
Condo in Yorkdale
5 out of 5 average rating, 129 reviews

The Penty: Luxurious Penthouse with Pool, Hot Tub

Welcome to our modern & luxurious corner penthouse! Stylishly designed with lush greenery and upscale touches, this bright space offers comfort, elegance, and a relaxed tropical vibe. Take in stunning panoramic city views and unwind with premium amenities including an outdoor pool, hot tub, and steam room sauna. Just a 15-min drive to downtown. Public transit at the doorstep. 10-min drive to Rogers Stadium. Perfect for discerning guests seeking an elevated stay in Toronto’s vibrant urban core

Top Guest favourite
A modern kitchen area features stainless steel appliances and sleek cabinetry, complemented by a glass dining table with two chairs. Wooden flooring adds warmth to the space, while a glass partition allows views of the adjoining bedroom.
Condo in Harbourfront
4.92 out of 5 average rating, 273 reviews

Luxury Downtown Waterfront Condo + Free Parking

Luxury 1BR downtown condo, steps to Scotiabank Arena, Rogers Centre & Harbourfront. Ideal for business trips, couples & Toronto getaways. Located in Toronto’s Entertainment & Financial District, this modern waterfront condo puts you near top attractions, transit, restaurants, and nightlife. Enjoy 5-star building amenities, a spotless, well-designed space, and a comfortable hotel-style stay. Perfect for business travelers, couples, and tourists looking for a central downtown Toronto stay.

Guest favourite
Condo in Mississauga
4.9 out of 5 average rating, 147 reviews

Beautiful & Cozy 2Bed 2Bath Condo Steps to Square1

Welcome to this exquisite 2-bedroom 2 bathroom condo, a blend of modern sophistication and breathtaking views. Nestled in the heart of downtown Mississauga this private-corner unit is everything you’re looking for. Everything in this unit is brand new. Cleanliness and providing a 5 star stay is our priority. All necessities are provided to make you feel at home. Amenities are available to all guests including a gym, pool, hot-tub, sauna, yoga room, music room, game room and much more.

Guest favourite
A stylish living space features an eye-catching geometric wallpaper, complemented by a contemporary wooden sideboard and a gray sectional sofa. A small round table and a two-person bar table are positioned near large windows that offer expansive city views.
Condo in Yorkville
4.93 out of 5 average rating, 203 reviews

Beautiful 1 Bedroom Yorkville Condo (IG-hotspot)

Pamper yourself with everything Yorkville has to offer with this professionally decorated, NYC inspired condo at the heart of Toronto's most exclusive address with complimentary valet parking. Queen size bed, sofa bed in living room, 2 person bar table, work station and a 55" Smart TV to accommodate all your needs. Contemporary art by local artist throughout with high end furniture and Miele appliances. South facing lake/city views through expansive floor to ceiling windows.

Guest favourite
A modern living space features a spacious seating area with a gray sofa and a bright orange accent chair. A dining table with plants stands nearby. Natural light floods the room through a glass sliding door leading to a balcony, offering views of the city skyline.
Condo in North Toronto
4.86 out of 5 average rating, 132 reviews

1Brm 2beds 5*Cozy, Hot tub, Midtown, Subway 5mins

1,Welcome to my home in the heart of midtown Toronto in the Yonge & Eglinton area! It sleeps three guests comfortably and is an excellent base for your Toronto adventures! 2,With excellent access to public transportation, you can be in downtown within 15 minutes; you are a 5-minute walk from Eglinton Subway Station, 2 mins from TTC, and within walking distance to tons of shops and restaurants. 3,Loblaws (grocery) & LCBO (liquor) on the main floor of the building.

Superhost
Condo in Mississauga
4.94 out of 5 average rating, 155 reviews

Luxury 2BR • Steps to Sq1 & Celebration Sq • View

Luxury high-floor 2BR in the heart of Mississauga Steps to Square One & Celebration Square Perfect for families, business stays & events Fully renovated with modern finishes, bright open layout. Lake & skyline views 🌆 • 2 queen beds (sleeps 4–5) • Fast WiFi + smart TV • Fully equipped kitchen • Private balcony + free parking Walk to top restaurants, shopping & events Clean, stylish & professionally managed for a seamless stay ✨

Top Guest favourite
A simple black background features the text 'Gallery Suite' in a bold, modern font. Below it, the words 'Stay a While' are presented in a smaller, complementary style, creating a welcoming and contemporary graphic. The overall design is minimalistic and elegant.
Condo in Kirkendall North
4.97 out of 5 average rating, 140 reviews

Gallery Suite

The Gallery Suite near Locke St. and McMaster is ideal for business or leisure stays. This bright, open-concept suite with a separate bedroom features unique artwork by Guelph artist Ryan Price. Located above a quiet RMT clinic, you'll enjoy a peaceful and private stay. Walking distance to trendy shops and cafes. Free parking is included for your convenience. Book now to experience a blend of comfort, art, and convenience!

Superhost
A cozy sleeping area is furnished with a spacious bed adorned with a patterned blanket. On both sides of the bed, bedside tables hold stylish lamps. Above the bed, a decorative wall art piece spells 'HOME,' enhancing the simple decor of the room.
Condo in Brampton
4.9 out of 5 average rating, 230 reviews

Cozy Condo-Apartment/Suite in Brampton

Welcome to our beautiful, Pristine & Spacious 1-queen Bed, well decorated Condo Studio-Apartment/Suite in Brampton west, the apartment is a minute walk to Mount Pleasant Go Station which connects you to anywhere in Greater Toronto Area, and some few steps to shops, parks. Close access to Airport, Hwy 410, 401, 407 & Mount pleasant village. Providing the experience to see the nice beauty of Mount pleasant /Brampton west.

Popular amenities for Oakville condo rentals

When is the best time to visit Oakville?

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Quick stats about condo rentals in Oakville

  • Total holiday rentals

    Explore 50 holiday rentals in Oakville

  • Nightly prices starting at

    Oakville holiday rentals start at $34 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,140 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Oakville holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Oakville rentals

  • 4.8 Average rating

    Oakville stays are highly rated by guests—averaging 4.8 out of 5!

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