Condo holiday rentals in Greater Toronto and Hamilton Area

4.91 out of 5 average rating, 141 reviews

Bright, cozy downtown condo near King/Queen West

Bright, quiet, cozy bachelor condo in the heart of downtown, 10 min walking distance to the CN tower, Scotiabank Arena (go Leafs go!), Rogers Centre, & Queen/King St West. Restaurants, bars, night life, & late night food literally steps away. Within 2 min walk of public transit (TTC - streetcars and subway). Full condo including loft bed (double bed), couch, & 60 inch TV with Prime, YouTube, and Chromecast. Condo gym available. My quaint home with endless adventures right outside the front door.

5 out of 5 average rating, 242 reviews

A stylish living area features deep green walls adorned with framed artwork. A plush velvet sofa and leather armchair provide cozy seating around a wooden dining table. A vintage chandelier hangs from the ceiling, while a decorative fireplace adds character to the space.

Condo in Port Hope

The Wilf Jones – Heritage Loft, Downtown & Hot Tub

The Wilf Jones, the most central airbnb in Port Hope! This main street stay is the optimal location for a morning walk to the coffee shop, unique eateries, and evening cocktails. To see more, visit: @thewilfjones PLEASE NOTE There are two stair cases from street level to the apartment. Expect some noise transfer from other travellers at times. While the hot tub itself is only available to you, the patio has a shared privacy wall with the neighbouring unit (there is a second fully private patio).

A glass table is set on a balcony, featuring an ice bucket holding a bottle of sparkling wine, accompanied by two elegant glasses. Soft string lights provide gentle illumination, enhancing the cozy atmosphere. A potted plant adds a touch of greenery.

5 out of 5 average rating, 215 reviews

Fire & Ice Spa w/ Private Sauna!

Welcome to the most unique suite at Friday Harbour Resort! Relax, refresh and unwind in your very own private spa experience which includes large infrared sauna, 3 indoor fireplaces and outdoor fire table. Kiss those winter blues away while you warm up in the most cozy suite, perfect for a romantic getaway. Every stay includes a bottle of bubbly to toast with the one who is most important to you! Make Fire & Ice your next vacation destination and reconnect in a most romantic, relaxing suite!

4.93 out of 5 average rating, 181 reviews

A spacious living area is furnished with a comfortable sectional sofa and a coffee table, complemented by an area rug. Natural light floods in from a large window, illuminating the modern kitchen with wood cabinetry and bar seating in the background.

Condo in Elora

Riverview...A Gorgeous Condo on the Grand

This limestone gem has been meticulously restored with loads of charm & character. Has the lure of historic downtown Elora & the majestic Grand River captured your imagination? Enjoy mystical morning sunrise views or evening night caps from the private balcony overlooking the Grand. Located steps from the Elora Mill, quaint shops, galleries, pubs, restaurants & LCBO. Walk to Gorge park, Quarry, access hiking/biking trails & enjoy all that mother nature has bestowed on this beautiful village.

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.

5 out of 5 average rating, 140 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

The city skyline is illuminated at night, featuring the CN Tower prominently lit in red. A mix of modern skyscrapers reflects various colors, with a clear sky and moon visible in the background, highlighting the vibrant atmosphere of Toronto.

4.98 out of 5 average rating, 163 reviews

Amazing Views, King Bed, Easy Access to World Cup!

Easy access for those going to FIFA World Cup events! Enjoy views from the large balcony with great views of the CN Tower, Lake Ontario and Toronto skyline! King size bed. Ideal for couples, solo guests, friends or those in town for work. Steps from Union Station with instant access to all major transit. Short walk to CN Tower, The Harbourfront, sports/concert venues, the Entertainment District, restaurants and shopping. No additional guests permitted. Please read the rules section in full!

A modern living area features a spacious sectional sofa complemented by decorative pillows and a large coffee table. Natural light floods in through expansive glass windows, revealing a view of the private patio. Minimalist decor includes a geometric wall design and a stylish light fixture.

4.94 out of 5 average rating, 131 reviews

Exceptional 2+1 ground floor condo @Friday Harbour

Enjoy early check in and extra late check out in an exceptional 2+1 condo on the ground floor of the desired Aquarius building at Friday Harbour resort. Professionally designed for comfort and style. Aquarius building offers an outdoor pool, BBQ and sitting area. Friday Harbour is an all-season resort, 1 hour north of Toronto, that offers fine dining, LCBO, Starbucks and grocery store within walking distance. Enjoy seasonal activities & events all year round, water sports, live music & more!

4.98 out of 5 average rating, 107 reviews

Stunning 1BR w Pool ~ Free Parking & Self Check-In

Embark on a journey of unparalleled luxury as you discover our exquisite suite, crafted to offer an escape that transcends the ordinary and leaves you refreshed. Experience opulent design, a full bedroom, a spacious living area with TV, high-speed WiFi, fully stocked kitchen, and a stunning balcony . Enjoy the breeze by the sun, and BBQ on our new electric grill. Access our outdoor pool and hot tub, no fees or reservations required. Additional fees may apply for 30 nights and more.

Superhost

An open-concept kitchen features sleek white cabinetry and a black granite island with three modern bar stools. Natural light fills the space through large glass doors, which lead to a balcony. A minimalistic design with potted plants enhances the welcoming atmosphere.

4.87 out of 5 average rating, 181 reviews

Friday Harbor Upscale 1Bed+Sofabed+Pool Option

Experience the allure of Friday Harbour! Stay in this gorgeously furnished 1-bedroom condo, complete with a pullout sofa bed. Enjoy the stunning outdoor relaxation area that overlooks the courtyard pool. The condo features a spacious bedroom with a closet and a large bathroom. Its layout is perfect for both relaxation and entertainment, with an open concept living area and a kitchen featuring an island. Embrace the ultimate indoor and outdoor living experience at Friday Harbour!

A glass table is positioned near large windows, offering an unobstructed view of the city skyline. Two modern chairs are placed around the table, with a small potted plant and a decorative item enhancing the scene. The background features tall buildings and hints of greenery.

4.89 out of 5 average rating, 173 reviews

Steps to Four Seasons Hotel Yorkville Condo

Unobstructed panoramic view in the heart of upscale Yorkville. Minute walk to Bay subway station, Whole Foods, ROM and U of T and high-end restaurants. Easy parking @ 74 Yorkville for $20 (daytime). Around the corner from Toronto's main luxury shopping hub, Yonge + Bloor. *Upscale neighborhood *Highspeed WIFI *Walk score of 96 *Transit score of 93 *Bike score of 98 (rentable Bixi bikes nearby) *Fully equipped kitchen *Full-sized washer/dryer *Gym in building

An open living area features a deep green sofa, a round coffee table, and a warm rug on light wood flooring. Natural light floods through large glass doors adorned with teal curtains, framed by plants and decorative wall art, creating a cozy and vibrant atmosphere.

4.99 out of 5 average rating, 112 reviews

Bohemian Luxury at Friday Harbour Resort Simcoe

Welcome to a Bohemian Paradise in the Heart of Friday Harbour. Treat yourself to a relaxing experience only 1hr from Toronto. This beautifully designed condo was designed to make your experience at Friday Harbour the best it can be. **Convenience** One of the few condos with direct walkout to the courtyard’s Firepit and BBQs. Steps away from Restaurants, Nature Trails, Beach & Boardwalk, Golfing, Live Music Events every Weekend.

A modern living area features a spacious, cozy sectional sofa with decorative pillows. A large window offers views of the city skyline and access to a balcony adorned with patio furniture. Natural light fills the room, complementing the contemporary decor and wooden flooring.