Fitness-friendly holiday rentals in Caledon

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

Five Star Hayloft Suite

This open space home is in the top level of a century-old bank barn. Witness the beautiful architecture while enjoying modern amenities like an open-concept kitchen, projector & movie lounge, and more! Enjoy 180 degree views from the bay window in the living room during your stay. Five Star Ranch offers a year-round getaway in a beautiful country setting. Situated on a working farm, and surrounded by gardens, animals and beautiful forest, it is a perfect destination for seclusion and peace.

Basement Apartment - New Build!

Full basement apartment of a brand new home which was recently featured in Toronto Life Magazine. Fully loaded with brand new appliances, including a dishwasher and laundry. The best sound dampening we could implement - it's very quiet. Incredible home gym and foosball table. Nice outdoor dining and BBQ area. 1 parking space in the driveway included, however, street parking isn't usually an issue, although technically not allowed. Kipling station and Loblaws are close by (pics attached).

Luxury Downtown Waterfront Condo + Free Parking

Luxury 1BR downtown condo, steps to Scotiabank Arena, Rogers Centre & Harbourfront. Ideal for business trips, couples & Toronto getaways. Located in Toronto’s Entertainment & Financial District, this modern waterfront condo puts you near top attractions, transit, restaurants, and nightlife. Enjoy 5-star building amenities, a spotless, well-designed space, and a comfortable hotel-style stay. Perfect for business travelers, couples, and tourists looking for a central downtown Toronto stay.

Chic Oasis | Luxury Stay in the Heart of Hamilton

Step into a stunning modern-retro escape where bold red tones, playful pink accents, and vintage exposed red bricks create an unforgettable vibe. Perfectly located just steps from vibrant Hess Village, you're within walking distance to concerts, sports venues, art galleries, boutiques, and top-tier dining. Explore trendy Locke Street or hike the Escarpment nearby. With cozy bedrooms, chic outdoor spaces, and irresistible charm, this gem is a true city retreat.

The Captain's Cottage at Willow Pond

You will have your own private one bedroom cottage on our 17 acre property. Your countryside getaway can be as quiet or as busy as you make it. You will have access to our tennis court, swimming pool, hot tub, gazebo, pond, garden and woodland trails. Adults are welcome to use the exercise studio. There is a flock of heritage chickens, guinea hens and quail who lay beautiful eggs for your breakfast. We also have bees who produce delicious honey for our guests.

St. Jacobs Triangle House - Countryside Escape

Welcome to Triangle House, a unique double A-frame situated on a private 1.7 acre lot, fronting on the Conestogo river Only 6 minutes drive from St.Jacobs center, 1.5 hours drive from Toronto, 15 minutes drive from the University of Waterloo and 25 minutes to Elora. Bring the whole family. This 3 bed, 3 bath home comfortably sleeps 6. Soak in the countryside from the sprawling deck and grounds, while enjoying all the comforts of a modern home.

Waterfront Hillside Villa

Welcome to your stunning Hillside Villa situated on 150' of waterfront. Enjoy the peaceful surroundings and quiet Bay views from your 3 private outdoor decks & hot tub. Entertaining is easy in this gourmet kitchen, which is open to 1 of 2 fireplaces, family room & dining room with floor to ceiling views of the Bay. Breathe taking views of the Bay from your private dock. Hidden gems: gym, 2nd kitchen, foosball table, EV charging and private trail.

A NOTL Eden

Sitting on the most prestigious Niagara Blvd, walking to the waterfront, golf course, parks and Old Town. Quiet and very nicely maintained. Fully equipped. One of a kind experience that you would not want to miss. Spend your holiday here, hiking/winery/golfing you name it. we have 1 king in the master bedroom, then 2 queens in 2 guest rooms, 1 sofa bed in the den , 2 queen airbeds in the basement. License #042-2025

The Grimsby Getaway -Full Kitchen, Fire Pit, Lake

Open concept home with full kitchen, 6 windows for natural light, walking distance from lake, large backyard & firepit, office space 1000 Mbps High Speed Wi-Fi, washer & dryer with full bathroom. Great for up to 6 guests. ✓ Vineyard country ✓ 25 minutes from Clifton Hills, Niagara Falls ✓ Grimsby is full of hiking spots and the beautiful Bruce trail. ✓ Between Niagara and Toronto ✓ 6 minute walk to the waterfront

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.