Holiday rentals with a pool in Markham

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

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.

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!

“CasaDeLeon”- Modern and cozy Lakeview guesthouse

Forget your worries in this quiet,, spacious & serene space. King+queen air/4 twin , lrg patio doors overlooking lush greenery in private backyard oasis. Enjoy in/outdoor living & access to private basketball court, trampoline. Landscaped backyard w deck, bbq, tons of board games, 4K projector (stream from G00gle chromecast) for large screen media / movies, and wine fridge, espresso bar, fridge w ice maker, full bathroom, heated flooring. IMPORTANT: You MUST read “Other Details To Note”

Toronto Vacation | ➊ The One Toronto Villa

The One is a unique luxurious private midle-century modern villa escape in the center of north Toronto. Having a stunning and spacious lawn for events and social gathering, this modern house is featured a thermostatic indoor swimming pool. Being inspired from a farmhouse building, the house offering a traditional touch on the vintage furniture and a rustic interior that gives a warm and cozy feelings. It is a great escape from the hustle and bustle of city life without going out of town.

Modern Downtown Unionville Stay

Cozy 1+Den Condo in Downtown Unionville Stay in our modern condo with 11-foot ceilings, two beds, a fully equipped kitchen, and a 4K TV. Enjoy access to the building’s pool and gym for your convenience. Located just 5 minutes from Unionville GO, 30 minutes to downtown Toronto or Pearson Airport, and close to the Markham Pan Am Centre. With restaurants, gyms, and VIP theaters nearby, it’s the perfect base for work or leisure. Book your stay today to experience the best of Unionville!

Tranquil Estate Retreat | Pool, Pond on 3 Acres

Escape to a private retreat designed for relaxation, connection, and unforgettable moments in nature. Nestled on a 3 Acre breathtaking estate surrounded by mature trees, peaceful water features, and beautifully landscaped grounds, this exclusive 5 bedroom, 4.5 bath home offers the perfect balance of elegance, comfort, and serenity. Wake up to tranquil pond views, enjoy your morning coffee on expansive sun-filled decks, and spend your days immersed in the beauty of the outdoors.

Cozy Suite in DT Markham Core

One of a kind, luxurious entire condo suite with unobstructed views located in the heart of Downtown Markham. First and only condo with underground access to Marriott Hotel amenities. Unwind with some soft bed sheets, fresh towels, toiletries, shared pool and jacuzzi. This suite includes one private parking space and an office den with high speed internet. Close to bus routes, GO Station, HWY 407 and 404. Steps to VIP Cineplex Theatre, restaurants, bars, parks and more!

Luxury High-Rise Condo in Downtown Markham

Modern high-floor condo in the heart of Markham with bright open views. Just a 3-minute walk to Whole Foods, plus restaurants, cafes, and supermarkets nearby. Minutes to Main Street Unionville for local dining and charming streets. Includes a fully equipped kitchen, comfortable bed, fast Wi-Fi, and a clean, well-maintained space. Enjoy building amenities such as a gym, indoor pool, and sauna. Easy access to Hwy 404 & 407. Perfect for business trips or short stays.

1Brm 2beds 5*Cozy, Hot tub, Midtown, Subway 5mins

1，Welcome to my home in the heart of midtown Toronto in the Yonge & Eglinton area! It sleeps three guests comfortably and is an excellent base for your Toronto adventures! 2，With excellent access to public transportation, you can be in downtown within 15 minutes; you are a 5-minute walk from Eglinton Subway Station, 2 mins from TTC, and within walking distance to tons of shops and restaurants. 3，Loblaws (grocery) & LCBO (liquor) on the main floor of the building.

FIFA: 4BR: 365 Days Open- Heated Pool & Hot Tub

A Private Luxury Getaway in Toronto’s Most Coveted Neighbourhood Escape to an extraordinary 4-bedroom luxury home in Toronto’s iconic Beaches, where sophisticated design meets relaxed lakeside living. This top 1% rated Airbnb property offers an unforgettable weekend experience—perfect for families, couples, or a curated group of friends seeking both comfort and wow-factor. A year round private heated pool and hot tub are yours to enjoy !

Toronto Pool Retreat

Spacious and private family home with 5 bedrooms, sleeping up to 10 guests. Enjoy a seasonal pool open May to September (not heated), an all-season hot tub, large backyard, and games area with ping pong, air hockey, and foosball. Includes a fully equipped kitchen, multiple living spaces, and 3.5 bathrooms. Conveniently near Hwy 401, DVP/404, shopping, and supermarkets. Respectful family and group stays only — no parties.