Fitness-friendly holiday rentals in Pickering

Luxury Kitchen/King Beds/Hot Tub Table+Beds for 24

Bring your family or team together in this luxurious home! Beautifully refurnished in 2022, including a new hot tub and new hotel-quality mattresses & linens, this 4000 sq. ft house is ideally suited for large families or athletic teams. Featuring a remodeled kitchen w/ gas stove, 7 new beds (3 king), gym, office, smart TVs, 4 parking spaces & fast Wi-Fi. Only 5 minutes from the 401 & Ajax Go Train station, accessing the city is a breeze. Tennis + playground 50 meters away. *3 extra beds avail

Cheery 1941 Historic Home in Ajax

Relax with your loved ones in this cozy 1941 historic home. Located in a peaceful mature neighborhood, unwind in 1400 sq.ft. of living space, parking for 2 cars, large privately fenced backyard and everything close within 5-10 mins - retail stores, grocery, restaurants, banks, Go Train, hospital, Highway 401, Paradise Beach, Ajax Waterfront park/trails, 2 casinos and a large park just steps from the home. This historic home was built for a manager of Defence Industries Limited (D.I.L.) in WWII.

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

3 Bed Downtown Toronto CN Tower Financial District

Welcome to our beautiful and bright 2 bedroom 1 bathroom high ceiling condo in downtown Toronto, your home away from home! It is centrally located in the quieter and secure part of downtown, within walking distance to financial district, St Lawrence Market, St Regis Toronto, harbourfront, grocery stores, restaurants, bars & parks. Newly furnished in 2022: furniture, floor, bathroom and paint, modern design, bright, large. Perfect for 4 guests, with option for 1 more guest with the sofa bed

The Hilton BnB Adult Luxury Suite

Experience the elegance of the Hilton BnB nestled in Newmarket’s prestigious Stonehaven Estates, just 30 minutes from downtown Toronto. This beautifully decorated open concept walkout suite in a two-story home offers unparalleled comfort and amenities for 1-2 adult guests. Indulge in dining by the fireplace during winter or unwind with a poolside BBQ in the summer amidst breathtaking grounds. The suite boasts spaciousness and a uniquely designed interior that exudes luxury at every corner.

Private Family Friendly Suite - Separate Entrance

🌟 Family-Friendly 1-Bedroom Basement Private Suite in Ajax! 🌟 This spacious unit is perfect for small families, couples, or solo travelers, offering comfort and convenience in a central location. 🛋️ Key Highlights: 🛒 Walking distance to grocery stores and Shoppers Drug Mart. 🎰 10 mins to Pickering Casino & 12 mins to Thermae Spa Village. 🎿 20 mins to Lakeridge Ski Resort & 10 mins to Lake Ontario. 🚆 Easy access to Toronto Downtown via Go Train. ✈️ 40 mins drive to Toronto Airport.

Spacious Home/Gym/Movie Room/Direct Train to city

✨ Welcome to your ultimate Toronto-area retreat! Perfect for families, remote workers, and sports fans heading into the city. Enjoy a private movie theatre, mini home gym, and a beautiful backyard deck—all situated in a peaceful, family-friendly neighborhood. Save massive amounts on downtown hotel prices and expensive parking fees. With a spacious, amenity-packed 3-bedroom layout, a dedicated workspace, and an entertainment-ready lower level, this is your perfect home away from home.

Backyard Oasis | Hot Tub & Playground | Near DT

Summer in Toronto starts here — a private fenced backyard with an all-season 6-person hot tub, fire pit, BBQ, and a playground the kids won't want to leave. Four bedrooms, three full bathrooms, sleeps 9 comfortably — 15–20 minutes from downtown. Need more space? Add the basement unit for up to 15 guests total. ★ "The backyard is AMAZING!!! The house is super close to the parade and it's walking distance to so many restaurants and shops." — Devon, Caribana 2025

LOVE and Relax at Dream Catcher Retreat

Are you looking for the perfect getaway? 😊 Retreat yourself to a Luxurious, Charming and Modern Suite with a splash of glam.✨ Perfect for couples, families or business trips. Enjoy the Fireplace with a glass of Cabernet Sauvignon🍷Perhaps you would also like to partake in a game of pool on our custom pool table 🎱, or take a hot rainfall shower in a delightful Stone Spa Shower💦. But, most importantly, our place is yours to relax and unwind😊

Luxury 2BR Suite| Stylish Stay w/ 2 Free Parking

Enjoy a bright, spacious 2-bedroom basement suite in a peaceful, tree-lined neighborhood just minutes from the lake, trails, and top schools. Relax in your private backyard, cook in a fully equipped kitchen, and unwind in a cozy living space ideal for families, couples, or work trips. With plenty of natural light and a welcoming vibe, this retreat is perfect for both short getaways and extended stays.

Large Walk-out private apartment w/ parking

A walk-out basement apartment in Richmond Hill. This sunlit apartment has abundance of natural lighting streaming through the many large windows. It has a full kitchen, a full laundry room with a washer and dryer, a designated parking space for one car, and free Wi-Fi access. Perfect for couples or small families, this apartment comfortably accommodates two adults and up to two children.

Luxury Lakeview Condo • Steps to Sandy Beach

Relax in a bright, stylish condo just steps from Sandy Beach. This quiet, modern space is designed for comfort—perfect for unwinding after a day by the water. Located just 5 minutes from the GO Station and minutes from Pickering Town Centre for shopping, dining, and easy access to downtown Toronto. Ideal for couples or solo travelers seeking a calm, well-connected stay.