Condo vacation rentals in Caledon

Find and book unique condos on Airbnb

Top-rated condo rentals in Caledon

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Guest favorite

Condo in Toronto

5.0 out of 5 average rating, 101 reviews

Cozy studio condo in a ♥ of downtown Toronto

Prime location for exploring the city! + Free Indoor Parking 3 min walk from the condo. You will be in the middle of all the action - the best restaurants and entertainment, just a short walk to CN Tower, Rogers center, Lake Ontario, Dundas Square, 4min walk to TIFF. There are two Subway stations conveniently located blocks away from this studio condo. The place is equipped with a smart Tv, Queen-size bed, Netflix, wifi, iron, coffee maker and a few other things for an easy comfortable stay.

May 26 – 31

G$35,967 GYD per night

Guest favorite

Condo in Elora

4.87 out of 5 average rating, 502 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 10 – 17

G$20,120 GYD per night

Guest favorite

Condo in Fergus

4.96 out of 5 average rating, 186 reviews

Cozy Fireplace & Loft - StoneMill 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!

Dec 19 – 26

G$28,157 GYD per night

Guest favorite

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 13 – 20

G$22,264 GYD per night

Guest favorite

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!

Sep 9 – 16

G$34,487 GYD per night

Guest favorite

Condo in Toronto

4.92 out of 5 average rating, 115 reviews

The Beaches pied-á-terre (Woodbine Beach)

Cozy and private retreat located in the desirable "The Beaches" neighbourhood. An ideal location to live the beach-life, while only minutes away to the downtown. Soak-up the sun on the beach, stroll the boardwalk. Steps to Queen Street East shops, streetcar, buses, bike trails, restaurants, cafes, bakeries, patios, bars, LCBO and groceries stores. Experiences: Donald D. Summerville Olympic Pool, Bike path, Beach Volleyball, Bike rentals, SUP boarding, Jazz Festival, Tommy Thompson Park,

Jun 8 – 15

G$28,977 GYD per night

Superhost

Condo in Innisfil

4.88 out of 5 average rating, 106 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!

May 10 – 17

G$16,755 GYD per night

Superhost

Condo in Innisfil

4.86 out of 5 average rating, 106 reviews

Beautiful 1 Bed/1Bath- Friday Harbour Resort

Enjoy our 4th floor modern condo to yourself! This 1 bedroom, 1 bathroom condo is located at the luxury all season, Friday Harbour Resort in Innisfil Ontario. Our fully furnished unit features a king bed, pullout couch, a large west facing balcony with barbeque and beautiful sunsets! Experience the 4 season recreation environment provided by the resort. There is a grocery store, Starbucks, LCBO, restaurants and entertainment steps away on the boardwalk! Fun for all!

Jun 21 – 28

G$21,029 GYD per night

Superhost

Condo in Innisfil

4.8 out of 5 average rating, 107 reviews

Friday Harbor Resort Getaway

Brand new, modern, bright, luxurious, fully furnished 1 bedroom condo with a large, patio-like balcony located in the beautiful Friday Harbour All Seasons Resort. Your perfect getaway features activities, golf course, nature preserve & trails, waterfront beach, boating, restaurants, and more. Queen bed, sofa bed, One Smart TVs, High Speed WiFi. Relax on furnished balcony overlooking private pool. 1 Free Parking Spot, Electric BBQ, In-Suite Laundry.

Jun 3 – 10

G$28,933 GYD per night

Guest favorite

Condo in Toronto

4.89 out of 5 average rating, 187 reviews

Cozy space in one of Toronto's best neighbourhoods

My place is a clean and quiet spot in the heart of Toronto's entertainment district. Location, location, location! Access the CN Tower, Ripley's Aquarium, The Royal Ontario Museum, The Art Gallery of Ontario and many more within a short walk or commute. The neighbourhood contains many restaurants and bars showcasing Toronto's cuisine and culture. My place is in the King West neighbourhood of downtown Toronto and is very convenient to access.

Jun 24 – 29

G$33,491 GYD per night

Guest favorite

Condo in Innisfil

4.83 out of 5 average rating, 388 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 16 – 23

G$13,738 GYD 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 1 – 8

G$28,658 GYD per night