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

Luxurious Condo Apartment 1BR-1BA-1Den, w. parking
"Thanks for stopping by! A lovely space to unwind and relax. Indulge in the comfort and tranquility of this contemporary space. Amazing location! Whether your visit is for business or pleasure - this is a perfect space with all the comforts of home. Enjoy great views and morning sun on the 90 SF balcony. Walking distance to restaurants, shopping and parks. Close access to Airport, hwy410, 401, 407 & Mount pleasant GO Station. Come and see why Brampton is rated one of the best cities in Canada."

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!

Open concept w/ city views
Welcome to our open concept highrise with city views in the heart of Kitchener-Waterloo, where style and comfort meet to create a truly memorable stay. This 1-bedroom open concept unit thoughtfully designed to accommodate up to 4 guests, making it perfect for couples, small families, or solo travelers looking for a modern and cozy retreat. ✔ Fully Equipped Kitchen ✔ Comfortable Bedroom w/ Queen bed ✔ Open Concept Living Area ✔ High-Speed Wi-Fi ✔ Free Parking ✔️Access to gym Learn more below!

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 Friday Flat | Sunny Escape by the Marina
Enjoy access to all of Friday Harbour's world-class amenities, including a golf course and sandy beach. Take a dip in the outdoor pool and explore the kilometres of scenic walking trails that wind through the Nature Preserve Located just a short drive from Toronto, Friday Harbour offers the perfect escape from city life. Spend your days exploring the shops and restaurants of the promenade, or venture out onto the lake Come experience the ultimate waterfront getaway at Friday Harbour

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.

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.

Resort Condo in Friday Harbour
Exquisite 1 Bedroom condo with separate pull out couch. Get ready to relax and unwind. Only 45 minutes from Toronto. Great getaway for couples, singles, work travelers and those just wanting to relax or some adventure. Enjoy the marina, boardwalk, shops, restaurants, nature trails, golf course and much more. Visit: friday harbour .com for complete list of activities and explore all that FH has to offer. Owner only restrictions apply.

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.

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!

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.

Gorgeous & Modern 2Bed 2Bath Sq1 Condo Corner unit
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 well equippedand gym and games room. Located very conveniently in the heart of Mississauga, steps to Square one, Hwy 403, Pearson Airport and only a short drive to Downtown Toronto
Popular amenities for Caledon condo rentals
Weekly condo rentals

Entire DT Condo • Parking • Msg me 4 discount

Super Luxury Condominium in Brampton

Nature trail views with cozy patio and firetable!

The Calm House | 5 mins Walk to Square One Mall

Entire Unit | Walk Everywhere

Cedar Hill Hideaway

Charming 2 Bed/2 Bath at Friday Harbour Resort

Toronto Skyline view | Walk Everywhere
Pet-friendly condo rentals

Luxury and Spacious 1BR + Den - Financial District

Beautiful suite in Downtown Toronto

Beautiful Penthouse with Breathtaking View

Humber Bay Family Friendly condo w Terrace&Parking

Pet friendly 2 BR with a private terrace at FH

Designer Condo with beautiful harbour view.

Modern 1BR Toronto Downtown Condo, King size bed

Beautiful Lake View Studio Condo + 1 free Parking
Condo rentals with a pool

Golf, Spa & Spring Vibes Getaway at Friday Harbour

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

Downtown Markham Unionville

1 Bedroom + Den (Office/Bidet/Balcony) near Rogers

FIFA Fan Zone Pool-Hottub-Free Parking Walk to BMO

Hidden gem in Humber bay shores Toronto w/ parking

Closest condo to Rogers Centre/CN tower in Toronto

Luxury Downtown Condo For 6 (CN Tower View)
Quick stats about condo rentals in Caledon

Total vacation rentals
Explore 10 vacation rentals in Caledon

Nightly prices starting at
Caledon vacation rentals start at $69Â CAD per night before taxes and fees

Verified guest reviews
Over 350 verified reviews to help you choose

Wifi availability
10 of Caledon vacation rentals include wifi access

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

4.8 Average rating
Caledon stays are highly rated by guests—averaging 4.8 out of 5!

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
- University of Toronto
- Enercare Centre
- Blue Mountain Village
- Metro Toronto Convention Centre
- BMO Field
- The Danforth Music Hall
- Harbourfront Centre
- Distillery District
- Nike Square One Shopping Centre
- Toronto Eaton Centre
- Exhibition Place
- Toronto Zoo
- Trinity Bellwoods Park
- Downsview Park
- Snow Valley Ski Resort
- Financial District
- Wilfrid Laurier University
- Massey Hall
- Casa Loma
- Dufferin Grove Park





