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.

0 of 0 items showing

1 of 3 pages

Guest favourite

Condo in Elora, Canada

4.87 out of 5 average rating, 504 reviews

Elora Gingersnap

The Gingerbread House would like you to say hello to its little friend. Welcome to the Gingersnap. It's a one bedroom apartment with zero stairs your own entrance and a 60 second walk to the Mills wedding venues. Upon entering the room you will find yourself in a retro modern oasis. With a king sized bed, inground heat in both the bedroom and the bathroom. Also you will have a retro kitchenette which is somewhat groovy. The bathroom has a large walk-in shower and all the amenities you need.

Feb. 4 – 11

$162 CAD per night

Guest favourite

Condo in Fergus

4.96 out of 5 average rating, 189 reviews

Cozy Fireplace & Loft - Stone Mill Retreat

Escape to our modern and rustic 1860 open-stone, three-floor townhome in the heart of Fergus. Our cozy retreat features our queen suite, loft, kitchen, sunroom, and indoor fireplace. Centrally located in historic Fergus, just minutes from Elora and the Grand River. Enjoy nearby hiking trails along the Grand River and many annual festivals, such as the Fergus Highland Games, Riverfest music festival and many culinary adventures. Relax and unwind at this getaway retreat in the heart of it all!

Nov. 25 – Dec. 2

$186 CAD per night

Guest favourite

Condo in Innisfil

4.97 out of 5 average rating, 111 reviews

•#TheFridayFlat Luxury Poolside Retreat for Summer

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!

Oct. 5 – 12

$156 CAD per night

Guest favourite

Condo in Innisfil

4.84 out of 5 average rating, 171 reviews

Marina view at Friday Harbor 2bdm/2bth Pool option

Friday Harbour is a brand new all season resort just 1 hour and 15 minutes from Toronto. A perfect getaway without the long drive. Airbnb guests can now purchase a pass for the beach club pool! This Airbnb is an eight hundred square foot condo all newly furnished with king bed in master bedroom with ensuite bathroom, Queen bed in guest bedroom. Enjoy 65” Samsung Smart TV or sitting on the huge deck overlooking the marina and island homes. Board walk to beach, this place is amazing!

Apr. 15 – 22

$162 CAD per night

Superhost

Condo in Innisfil

4.88 out of 5 average rating, 107 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!

Jul. 21 – 28

$152 CAD per night

Guest favourite

Condo in The Blue Mountains, Canada

4.88 out of 5 average rating, 142 reviews

Sweet Retreat - Private Patio / Community Pool

Sweet Retreat is located in North Creek Resort at the North Base of Blue Mountain. Ideal location for those seeking easy access to the ski hills and hiking trails but still within minutes to Blue Mountain Village. North Creek resort offers a free shuttle service to Blue Mountain Village, an outdoor swimming pool open in the summer months, two hot tub year round, tennis courts with night lights, charcoal grills and community picnic tables that you can use during your stay.

Jun. 4 – 11

$169 CAD per night

Guest favourite

Condo in The Blue Mountains

4.89 out of 5 average rating, 350 reviews

Base of Blue Mountain, Modern Updated Studio

This gorgeous studio chalet is absolutely perfect for two, or a couple with small children! Newly renovated with a custom kitchen and fireplace. Located right at the base of the ski hill, our cozy chalet is a lovely fully furnished 1 bedroom, 1 bath. Blue Mountain Village only 1Km away, as well as the Scandinavia Spa , Northwinds Beach and restaurants. Our chalet is ski in ski out and located right at the North Chair. Come and enjoy all that Blue Mountain has to offer!

Sep. 30 – Oct. 7

$214 CAD per night

Guest favourite

Condo in Brampton

4.91 out of 5 average rating, 103 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.

Jul. 22 – 29

$123 CAD per night

Guest favourite

Condo in Innisfil

4.83 out of 5 average rating, 389 reviews

Lovely 2-bedroom at Friday Harbour

Friday Harbour Resort welcomes you to the start of something extraordinary. Friday Harbour was designed to be a destination. A destination you look forward to visiting all year round, where you can unwind and truly feel relaxed. Whether you arrive to take in the peaceful serenity of the lake, spend hours in the Nature Preserve or mingle with friends over a gourmet meal, there’s no shortage of way to enjoy your days.

Oct. 21 – 28

$102 CAD per night

Superhost

Condo in Mississauga

4.82 out of 5 average rating, 221 reviews

Beautiful Cozy 1 BR Condo👌🔥 Steps to SQ1! 👍

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.

Sep. 29 – Oct. 6

$219 CAD per night

Guest favourite

Condo in Collingwood

4.94 out of 5 average rating, 591 reviews

Modern & Chic Sanctuary Suite in Collingwood

Unit located by Living Stone Golf Resort, minutes away from downtown Collingwood, and 10 mins from Blue Mountain/Scandinave Spa. Our renovated condo offers modern-chic elegance. Enjoy 625 sq ft of privacy with two bedrooms and one bathroom with tub and shower. There is also a sofa, electric fireplace, Netflix and basic cable, WIFI, en-suite washer-dryer. Outdoor terrace with garden views.

Oct. 11 – 18

$165 CAD per night

Guest favourite

Condo in Innisfil, Canada

4.94 out of 5 average rating, 111 reviews

Lake Simcoe Resort Retreat

Beautiful, fully furnished one bedroom vacation retreat in the vibrant resort community of Friday Harbour. Experience the all-season recreation including the beach, marina, nature preserve, eighteen hole golf course, sports facilities and more! Find everything you're looking for, from grocery stores and restaurants to coffee shops and the LCBO, just steps from the boardwalk.

Aug. 29 – Sep. 5

$191 CAD per night