Fitness-friendly holiday rentals in Pickering

A spacious back deck features a hot tub and seating area, surrounded by greenery. Large glass doors provide a view into the living room, while a cooking area and dining table are positioned outdoors. A metal container holds beverages, inviting relaxation.

4.93 out of 5 average rating, 102 reviews

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

4.95 out of 5 average rating, 82 reviews

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.

5.0 out of 5 average rating, 149 reviews

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.

Apartment in Yorkdale

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

5.0 out of 5 average rating, 202 reviews

The exterior of a modern two-story home is displayed, featuring a brick and stone facade. A well-maintained driveway leads to a double garage with decorative doors. Bright flower pots are positioned near the entrance, while lush green landscaping surrounds the property.

Flat in Newmarket

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.

Superhost

A modern outdoor space features a large in-ground pool with vibrant blue water. An elegant fire pit sits in the foreground, its flames flickering above reflective glass stones. Surrounding the pool, tall wooden fences provide privacy, complemented by outdoor chairs positioned nearby.

Guest suite in Scarborough

4.93 out of 5 average rating, 139 reviews

Custom Luxury 2BR | Marble Pool | Games | Fire Pit

Welcome to our brand new, luxury modern suite located in a quiet, family-friendly neighbourhood. Mins to HWY401/DVP, TTC. Featuring: ✓ Luxury Finishes Throughout ✓ Heated Swimming Pool (seasonal April - Oct) ✓ Dedicated Workspace ✓ Washer/Dryer ✓ High-Speed WIFI ✓ Smart TV with Netflix, Prime & sound system ✓ Keyless Entry (24/7 Self Check-In) ✓ Outdoor BBQ, seating and fire table This upscale oasis is truly the perfect space for business travellers, young professionals & couples alike!

A well-lit game room features a classic pool table with a green felt surface and wooden frame. Above the table, three green lamps provide ample illumination. In the background, a sleek bar counter and seating area are visible, creating an inviting entertainment space.

5.0 out of 5 average rating, 68 reviews

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.

Superhost

4.86 out of 5 average rating, 22 reviews

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.

4.92 out of 5 average rating, 107 reviews

Home in Toronto

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

4.96 out of 5 average rating, 420 reviews

Flat in Whitby

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😊

5.0 out of 5 average rating, 11 reviews

Home in Pickering

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.

4.87 out of 5 average rating, 200 reviews

A spacious living area features a large sectional sofa arranged around a soft area rug. Light wood flooring is complemented by pale walls and columns. A mounted television and shelves are visible. A dining area is to the right, with a table and chairs.

Flat in Richmond Hill

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.