
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

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.

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

Resort Condo with Bowling and Spa Hot Tub
Stunning 2BR/2BA corner suite in the heart of Kitchener, directly across from Google Kitchener Downtown. Enjoy city views, a fully equipped space for up to 7 guests, and amazing amenities like a hot tub, bowling alley, sauna, rooftop patio & gym. Includes free parking. This fully licensed Airbnb offers a seamless, worry-free stay in a vibrant, walkable neighborhood with easy access to the LRT and GO Station.

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!

(E) Elora Riverside Nook
Welcome to Elora’s Riverside Nook, a bright and cozy one‑bedroom retreat perfectly positioned for guests who want to experience Elora on foot. With zero stairs, a private entrance, and a location just moments from Downtown Elora, The Elora Mill, and the Grand River, this suite is ideal for wedding guests, weekend explorers, and anyone seeking a peaceful, walkable stay.
Popular amenities for Caledon condo rentals
Weekly condo rentals

Our cozy casa

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

Luxurious Friday Harbour Winter Wellness Escape

Mississauga Square One Condo

Entire Unit | Walk Everywhere

Charming 2 Bed/2 Bath at Friday Harbour Resort

Toronto Skyline view | Walk Everywhere

Serene Stays - Oakville (3 Bed, 2 Bath, 1 Parking)
Pet-friendly condo rentals

Luxury and Spacious 1BR + Den - Financial District

Stylish Yorkville Studio: Near U of T & ROM

Humber Bay Family Friendly condo w Terrace&Parking

Admire City Views from Bed at this Chic Apartment

Designer Condo with beautiful harbour view.

Beautiful Lake View Studio Condo + 1 free Parking

3 Bed Downtown Toronto CN Tower Financial District

Trendy & Cozy 1BD Condo in the Heart of Toronto
Condo rentals with a pool

Golf, Spa & Spring Vibes Getaway at Friday Harbour

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

Beautiful Condo Across CN Tower and MTCC

Modern 1+Den condo steps away from CN Tower & Lake

Large & Bright 2BR+Den in Midtown w/ Free Parking

Luxury Downtown Condo For 4 (CN Tower Views)

Artsy and Comfy Home with a View

Closest condo to Rogers Centre/CN tower in Toronto
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 ﺩ.ﺇ184 per night before taxes and fees

Verified guest reviews
Over 350 verified reviews to help you choose

Wi-Fi availability
10 of Caledon vacation rentals include wi-fi 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
Destinations to explore
- Greater Toronto and Hamilton Area Vacation rentals
- Greater Toronto Area Vacation rentals
- Mississauga Vacation rentals
- Pocono Mountains Vacation rentals
- Grand River Vacation rentals
- Northeast Ohio Vacation rentals
- St. Catharines Vacation rentals
- Pittsburgh Vacation rentals
- Niagara Falls Vacation rentals
- Erie Canal Vacation rentals
- Detroit Vacation rentals
- Cleveland Vacation rentals
- Rentals with a patio Caledon
- Smoking-friendly rentals Caledon
- Rentals with pools Caledon
- Waterfront rentals Caledon
- House rentals Caledon
- Rentals with a fireplace Caledon
- Guesthouse rentals Caledon
- Fitness-friendly rentals Caledon
- Private suite rentals Caledon
- Pet-friendly rentals Caledon
- Rentals with outdoor seating Caledon
- Rentals with an EV charger Caledon
- Apartment rentals Caledon
- Rentals with breakfast Caledon
- Rentals with a washer and dryer Caledon
- Rentals with a fire pit Caledon
- Rentals with a hot tub Caledon
- Family-friendly rentals Caledon
- Rentals with lake access Caledon
- Townhouse rentals Caledon
- Bed and breakfasts Caledon
- Condo rentals Peel
- Condo rentals Ontario
- Condo rentals Canada
- 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





