
Condo vacation rentals in Caledon
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Top-rated condo rentals in Caledon
Guests agree: these condos are highly rated for location, cleanliness, and more.

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.

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

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!

Upscale Spa Getaway w/ Private Sauna
Welcome to our most Dramatic & Romantic Penthouse Spa Getaway Suite! Reconnect with your loved one or celebrate that special milestone in our professionally designed to play with all your senses spa suite, this escape will leave you feeling refreshed and rejuvenated! Cozy up to any of 3 fire elements and then cleanse and detox in your own private in-suite Infrared Sauna! Cook up a gourmet meal in our fully equipped chef's dream kitchen and year round Weber BBQ for grilling!

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.

*HotTub*Pool*FirePit*King Bed*
The perfect getaway an hour away from Toronto! Modern and bright fully stocked condo with a year-round hot tub, outdoor pool, fireplace, and an outdoor fire pit. Outside you are surrounded by 200 acres of nature preserve, with trails for walking and biking, golf, kayak, canoe, boat, etc. → Beach access → Underground Parking for 1 vehicle → Fully equipped + stocked kitchen → Year Round Hot Tub → Outdoor Swimming Pool

🔥Charming 1 BR Condo🔥 Steps To Square One!👌
This beautiful sunfilled condo is newly furnished and well cared for, equipped with everything you need to make you feel right at home! Free Wifi included with Netflix access and underground parking. Amenitites in the building include a swimming pool and gym. Located very conveniently in the heart of Mississauga, steps to Square one, Hwy 403, Pearson Airport and only a short drive to Downtown Toronto.

Boho by the Bay
BlogTO writes: " Friday Harbour Resort is a vibrant, upscale destination...That's perfect for a quick getaway..., with plenty of cool restaurants and shops, a waterfront pedestrian village, and year-round recreational activities." I encourage you to search eventsatfridayharbour to see what is seasonally available. if after searching, you still have questions or need clarification, please ask!

Liberty Village Luxurious 1 Bed + Free Parking
STR-2307-HDGHHW Welcome to Toronto! Enjoy a cozy 1-bedroom suite in vibrant Liberty Village. With free parking, it's perfect for solo travelers or couples. Explore nearby restaurants, bars, and shops, or take a short walk to the Entertainment District for more fun. Relax in comfort in this thoughtfully designed space. Can't wait to host you and make your Toronto stay memorable!

Lovely Open Concept Friday Harbor Resort Condo
This is a perfect getaway! Just bring a suitcase and enjoy! Only an hour from Toronto and minutes to Barrie with a resort feel. This condo has a great location with a short walk to grocery store, restaurants, marina etc. → Approx. 700ft² / 65m² of space → Highspeed WIFI! → Beach access → Parking for 1 vehicle → In-unit washer + dryer → Fully equipped kitchen

Bright & Stylish 1 Bedroom Condo in King West
My condo is at the heart of Toronto’s Entertainment/Fashion Districts and has everything you need for fantastic stay. The city’s trendiest restaurants and bars, theatres and sporting venues are steps away. Whether enjoying a short vacation or staying for an extended time, you’ll have all the comforts of home and access to the best Toronto has to offer. Welcome!

Luxury 2 Bdrm, CNTower/Lake View +Parking+Pool+Gym
We are back! A Luxury 2-bedroom overlooking the city. Open concept living space with a modern flare and stainless steel appliances, encompassing the city life. Bedrooms have comfy queen beds and loads of closet space. Stunning views of the CN Tower and lake. Parking, Pool, Spa, Sauna, and gym access.
Popular amenities for Caledon condo rentals
Weekly condo rentals

Modern Studio @ Downtown | Clean & Convenient

Beautifully Upgraded One Bedroom and Den + Balcony

LuxCondo in the downtown kitchener uptown waterloo

Stunning 1+Den Condo by the Lake

Sunny, peaceful by the River

Elevated Living at the heart of Toronto

studio sanctuary - private apt in DT, wifi, pool

Lux Condo by Downtown Kitchener
Pet-friendly condo rentals

Modern Eclectic Condo in King West Area

Humber Bay Family Friendly condo w Terrace&Parking

Admire City Views from Bed at this Chic Apartment

Designer Condo with beautiful harbour view.

The Beaches pied-á-terre (Woodbine Beach)

Stylish Apartment in Toronto - Long term available

Resort Condo in Friday Harbour

Vibrant downtown place
Condo rentals with a pool

Lovely 2-bedroom at Friday Harbour

Luxury 2.5Br-2Bath 1 Prk Condo SQ1 Striking Views

Gorgeous 2 bedroom Penthouse

Lux Waterfront Condo Pool Hot Tub Free Parking

Walkout to Courtyard w/ Pool, Hot Tub and Fire Pit

Elegant & Modern Condo

One Bedroom Condo In Downtown

Exceptional 2+1 ground floor condo @Friday Harbour
Quick stats about condo rentals in Caledon

Total vacation rentals
Explore 20 vacation rentals in Caledon

Nightly prices starting at
Caledon vacation rentals start at G$4,182 GYD per night before taxes and fees

Verified guest reviews
Over 340 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Caledon vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Caledon rentals

4.6 Average rating
Caledon stays receive an average rating of 4.6 out of 5 from guests

Nearby attractions
Caledon's top spots, include SilverCity Brampton Cinemas, Landmark Cinemas 7 Bolton, and Uptown Theatre
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- Rogers Centre
- CN Tower
- Scotiabank Arena
- Union Station
- Blue Mountain Village
- University of Toronto
- Metro Toronto Convention Centre
- Distillery District
- Port Credit
- The Danforth Music Hall
- Nike Square One Shopping Centre
- BMO Field
- Harbourfront Centre
- Exhibition Place
- Toronto Eaton Centre
- Toronto Zoo
- Trinity Bellwoods Park
- Financial District
- Massey Hall
- Snow Valley Ski Resort
- Casa Loma
- Dufferin Grove Park
- Wasaga Beach Area
- Lakeridge Ski Resort




