Family-friendly holiday rentals in Oakwood Village

Breathtaking Hot Tub Oasis 6 Guests 3BR 2WR Firepl

Relax and unwind in this downtown Toronto oasis. Trendy St. Clair West is a short 7 minute walk from your doorstep, and offers a wide range of excellent restaurants, bars, cafes, bespoke grocery stores, health food stores and shopping to suit every taste. On Saturdays, make your way to the bustling Wychwood Barns farmer's market for fresh goodies. Need a nature fix? A five minute walk brings you to Cedarvale Park, one of the city's best kept nature preserves. Bus stop located right outside.

Cozy 1-bdm suite filled with amenities & parking

A whimsically decorated basement apartment with a separate entrance that welcomes all. The exposed brick gives it a unique character and the location means you're not too far from downtown, close to public transportation and away from congestion. Enjoy amenities such as a kitchenette with all the fixings for a continental breakfast, plentiful snacks and refreshments. The kitchen offers an induction cooktop & toaster oven instead of a stove. Guests can enjoy Netflix, Wifi, and free parking.

Modern Private Suite By Subway w Free Parking

An entire floor is yours to use privately. Newly renovated with modern amenities, includes a 55" Smart OLED TV, Fibre Optic High-Speed WIFI, and backyard full of fun activities for couples and families. Next to public transit, a quick walk away, is TTC Eglinton W station. Centrally located, quick access to downtown or any neighbouring city (Vaughan, Markham, Brampton, Mississauga). Situated on a quiet street and walking distance from grocery stores, pharmacies, coffee shops, and eating places.

CHARMING 3 BEDROOM HOME IN THE CITY W FREE PARKING

Welcome to our clean, cozy 3 bedroom country style bungalow situated in the middle of the city. Close to anywhere you wish to go, but just far enough from all the hustle and bustle. Entire property with 3 bedrooms (1 King and 2 Queen size beds). - Free parking on a private lot for multiple vehicles - 2 televisions - Wifi - Netflix - Kitchen - 2 washrooms - Enclosed private patio and a backyard - Steps to TTC bus stop and 10 min walk to Oakwood Subway - High speed internet and working space

Bright west end 1-bedroom basement suite

A beautiful newly renovated basement suite, with 8ft ceilings, large windows, a glass rainfall shower & 2 comfy Queen sized beds (one is a fold-out sofa bed in the main living space). It's conveniently located close to the UP Express & TTC stations for traveling around the city. The house upstairs has a small child & there will be a certain amount of noise :) Please message me with any questions & I would be happy to answer you. Thanks for stopping by! registration # STR-2207-GGZRVF

Welcome to Greenhills, a Charming Home w/ Parking

Clean Open Concept, Sun-Filled 2 Bedroom main floor home with PARKING; Can sleep up to 4 people. Featuring simple modern décor, queen size beds, big beautiful windows with room darkening curtains, closet storage. Dedicated office desks in bedrooms Full kitchen, with oil, seasoning spices, toaster, hot water kettle, Keurig Coffee Machine and complimentary coffee+tea. Clean bathroom with shampoo+conditioner+body wash+lotion SMART TV 60” Fast internet Wifi Check-In: 3PM Check-Out: 11AM

Spacious Mid Century w/Patio

Adorable Historic Home with Private Patio & BBQ. ♡ 3 bedroom & 1.5 bath (1 King & 2 Queens) ♡ Hotel Inspired Home with Super Fast WIFI ♡ Automated Check in & Check Out ♡ Steps from St. Clair transit line / connects to Subway ♡ 90/100 Walk Score ♡ 100/100 Transit Score ♡ Walking distance to Casa Loma | Rated #1 by BlogTO of Places to Visit in Toronto ♡ Flexible Check in Check out - Message for Details ♡ A/C ♡ Laundry ♡ BBQ & Fully Equipped Kitchen ❤ Book today!

Cozy and Modern Lower-Level Suite in Corso Italia

Welcome to your home away from home! This newly updated, bright and cozy suite is nestled in Toronto’s buzzing Corso Italia neighbourhood. This apartment offers the perfect blend of comfort, privacy, and convenience. Whether you're here for a short stay or a longer getaway, you'll enjoy a comfortable retreat in this recently renovated and thoughtfully designed space. You will have access to the entire apartment accessible via a separate entrance located in the backyard.

Private 3BR Whole Home for Groups Near Subway

A newly built, private 3-bedroom, 3-bath home on a quiet laneway in Toronto’s Annex West, just a 3-minute walk to the subway. Bright, modern, and thoughtfully laid out, this entire home is ideal for families or groups traveling together who want to stay in one shared space. Enjoy a full kitchen, heated floors, unlimited hot water, and fast Wi-Fi. Steps from restaurants, parks, and shops, yet calm and private inside. Best suited for guests with confirmed travel plans.

Spacious & Vibrant

Stay comfortably in this spacious 2-apartment in vibrant Corso Italia, perfect for couples, friends or small groups of friends. Enjoy a bright and private second-floor unit with plenty of space to relax after exploring Toronto. Step outside to enjoy your private patio, or take advantage of convenient parking. With transit just steps away, you’ll have easy access to downtown, Toronto’s attractions, restaurants, and entertainment. Parking included.

Mid Town MidMod | Private 1BR Unit

Bright, clean and spacious lower-level guest suite located in Mid-Town's trendy St. Clair West neighbourhood. Our suite is best suited for adults exploring the city, business travelers seeking privacy and a comfortable workspace, or families visiting relatives. Our private 1-bedroom suite features a queen bed, separate futon, full kitchen, and all the amenities you need for a comfortable stay. Walk to great restaurants, cafés, shops, and transit.

Luxury 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 !