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.

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Guest favorite
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
4.91 out of 5 average rating, 116 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.

Guest favorite
A modern living area is highlighted by large windows allowing natural light. A sleek black sectional couch faces a glass coffee table, while a light-colored armchair adds comfort. A wall-mounted TV is positioned for viewing, contributing to a relaxed atmosphere.
Condo in Entertainment District
4.95 out of 5 average rating, 155 reviews

Spacious 1 Bed + Den + Downtown + Free Parking

Spacious 1 bed+den modern condo located in the heart of downtown. Steps from the lake, parks, recreation centers. Short walk to CN Tower, Union Station, Rogers Center, Convention Center. → FAST WIFI Perfect for WFH, video calls, & streaming → Approx size 620ft² / 57m² → Dedicated Working space → 60" QLED TV → *NEW 2024* Fully equipped kitchen w/ set of cookware → Walking distance to dining & night life option → Minutes away from grocery, liquor stores, & city transit network (94 Transit Score)

Top guest favorite
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, 120 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

Guest favorite
The living area features modern furniture with a blue sofa and a wooden coffee table. A piece of wall art depicting floral arrangements is displayed above the sofa. Large windows allow ample natural light and showcase city views.
Condo in Kitchener
4.96 out of 5 average rating, 116 reviews

Hydropool Spa HotTub/Bowling Alley/Patio/BBQ/Games

**Hydro spa hot tubs are open! **Fully licensed Airbnb - no hassle during your stay! **Stunning Interior decor, guests'' unique experience **Unmatched amenities in town! you must check out the amenities' pictures **Corner unit with stunning city views ** Location! Heart of Kitchener, centrally located to grocery stores, hip restaurants/bars, cute local shops, parks & happening city life ** 3 mins walk GO Station. 126 Weber St. W **Across Goo-gle Head office w/ LRT rail at doorsteps

Guest favorite
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.
Condo in Innisfil
4.99 out of 5 average rating, 173 reviews

Fire & Ice Spa w/ Private Sauna!

Welcome to the most unique suite at Friday Harbour Resort! Relax, refresh, unwind and rejuvenate in your very own 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! We know you will enjoy your stay and love the outdoor elements AND the indoor ones too!

Top guest favorite
A modern living space is highlighted by large windows offering panoramic city views. A deep red area rug anchors the room, complementing the sleek furniture. Two barstools and a compact table are positioned near the kitchen, providing a functional dining space.
Condo in North Toronto
4.94 out of 5 average rating, 291 reviews

SpectacularPenthouse VIEWS/ POOL /free Parking

Sparkling clean, lovely Penthouse Unit with panoramic city view. Lots of amenities, great neighbourhood. The building is 2 mins from subway-which leads you to Downtown Toronto- in ten minutes. Lots of amazing restaurants and pubs in the area for your enjoyment and entertainment. There is a gym, salt water pool and sauna on the 4th floor and 24 hour security; a secured parking garage with a spot for guests to park free; and there is additional paid public parking in the underground.

Guest favorite
A modern living area features a stylish black sofa and a glass coffee table, complemented by a round dining table with four wooden chairs. Large windows allow ample natural light, enhancing the clean lines of the space. A decorative mirror adds depth to the room.
Condo in Entertainment District
4.85 out of 5 average rating, 122 reviews

Trendy & Cozy 1BD Condo in the Heart of Toronto

Enjoy a trendy and cozy experience at this centrally located condo. This 1 bedroom, 1 bathroom unit is located in the heart of the city within walking distance to many of Toronto's most popular restaurants, bars and tourist destinations. Steps away from King street, The Well and walking distance from the CN Tower, Rogers Centre, Ripley' s Aquarium and much more. The unit is equipped with high speed Wi-Fi with unlimited internet. You can also enjoy the gym and studio room.

Top guest favorite
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 Strathcona
4.98 out of 5 average rating, 107 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!

Guest favorite
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
4.89 out of 5 average rating, 206 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.

Guest favorite
A light-toned living space is showcased with a soft, upholstered couch featuring neutral cushions. Above, two abstract artworks adorn the wall. A decorative table holds a small framed item resembling a house and soft foliage. Natural light streams through a large window.
Condo in Glen Abbey
4.9 out of 5 average rating, 107 reviews

Cozy Oakville Oasis | Modern & Peaceful Stay

Enjoy a peaceful stay in this stylish apartment near Saw Whet Golf Club and beautiful Bronte Creek Provincial Park. 3 min from the QEW, Bright, open-concept living space, full kitchen, private balcony, high-speed WiFi, and free parking. Just a short drive to Bronte Village with its waterfront trails, cafes, and shops. Ideal for couples, solo travelers, or business guests seeking comfort and convenience in Oakville.

Guest favorite
A spacious living area features a modern light fixture and a comfortable sofa with decorative pillows. A coffee table rests on a patterned rug. Behind the seating area, an open kitchen is visible, showcasing dark cabinetry and contemporary bar stools.
Condo in Mississauga
4.86 out of 5 average rating, 236 reviews

🔥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.

Top guest favorite
A colorful seating area features a bright, multi-colored sofa alongside a contemporary black shelf. A mirror is positioned above the shelf, which holds decorative items and books. Natural light enters through large windows, illuminating the warm wood flooring.
Condo in Innisfil
4.99 out of 5 average rating, 254 reviews

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!

Popular amenities for Caledon condo rentals

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$10,443 GYD per night before taxes and fees

  • Verified guest reviews

    Over 250 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

    10 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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