Vacation rentals in The Annex, Old Toronto

Luxury Yorkville Escape | Condo in Prime Location

Discover refined living in this beautifully furnished apartment in Yorkville Toronto’s most glamorous & exclusive neighborhood. With new furniture & modern appliances, this space blends comfort with sophistication. Step outside and find yourself surrounded by luxury boutiques, acclaimed restaurants, chic cafes, & world-class art galleries. With Bay subway station just a 3 minute walk away, the entire city is at your fingertips. Elevate your lifestyle in a place where elegance meets convenience.

Value · Family · Kitchen

Cute Private Apartment near University of Toronto

This cozy main floor apartment with private walk out patio, located on a quiet street in the beautiful Annex neighbourhood. Free parking Laundry in building Shared backyard 5 minute walk to subway (Christie Station) 5 minute walk to Bloor Street, the restaurants and bars of Korea Town, and historic Christie Pits Park. Walking distance to University of Toronto and George Brown College Casa Loma campus. There are a lot of great restaurants, bars and local grocery stores within a short walk.

Location · Value · Amenities

Chic Yorkville Pied-à-Terre | Stylish Retreat

Kick back and relax in this calm, stylish 'pied-a-terre' just outside Toronto's ritzy Yorkville area. This lower level of a townhouse condo has its own private entrance accessed from the sidewalk descending to a lower private garden terrace equipped with outdoor dining set. Beautifully designed in authentic and vibrant travel art, it comes equipped with a workspace, kitchenette, dining area, full bathroom, tv, and a living room/bedroom combo with an efficient and comfortable queen Murphy bed.

Location · Value · Checkout

Luxurious Annex/Yorkville 1300 Sq Ft & Parking

Beautifully appointed, top quality furnishings & amenities , spacious Yorkville/Annex rental. Full 1300 sq foot. apartment located within a Heritage Victorian Brownstone! Exceptionally located, walking distance to subway, restaurants and all the sights! Walk to Casa Loma, Royal Ontario Museum & Yorkville. Parking, Wifi, Chromcast, Fibe TV, Local High Def TV included. Fully equipped gourmet kitchen. Air Conditioned. Digital safe for valuables. Treat yourself to pantry snacks, coffee & tea.

Value · Family · Wifi

Luxury-Modern Home in Annex/Casa Loma ·3BR+Parking

Luxury-modern 3BR home in Toronto’s historic Annex/Casa Loma, ideal for families, professionals, and longer stays. Private main and second floors with open kitchen and living area. King primary bedroom with ensuite, Queen bedroom, and Twin bedroom with work desk. Sleeps up to 6. Upstairs laundry, PlayStation for kids, high chair on request, lane parking with EV charger. Walk to popular cafes and restaurants, Yorkville, subway, parks, and near the University of Toronto. No parties or smoking.

Location · Family · Checkout

Private 2BR Home Sleeps 6 Near Subway

Welcome to The Laneway Suite! A 1000 sq ft, 2 storey, detached laneway house. Private entrances, Smart Lock, full kitchen with island and all amenities, 1.5 bathrooms, washer/dryer, 2 Queen bedrooms with 32” Smart TV, a living room with a comfy Queen size pull-out couch and 65” Smart TV, a dining room, and a private backyard patio. Whether you’re travelling with your family, your friends, by yourself or on a business trip, this is your perfect getaway! Also suitable for long term stays!

Location · Value · Parks

Cozy 1 Bedroom Unit in the Annex, Free Parking

Welcome! This cozy unit is a great place to stay if you want to be in the city without feeling like you're in a concrete jungle. Located in the Annex, it's a food haven for those that are interested in exploring different places to eat. It's also a 5 min walk away from the Bloor/Spadina subway station (or Bathurst station in the other direction), so it's great for commuting around to different areas of Toronto. Yorkville, the ROM, and Casa Loma are also under 10 mins drive from here.

Location · Family · Wifi

Annex Haven: 1 Bedroom plus Den

This centrally located private space is newly updated with new flooring, furniture, and bathroom. It includes a separate entrance with its own kitchen and laundry. Very quiet residential neighbourhood with old growth trees. Walking distance to Christie subway station or Dupont subway station. Be downtown within 20 minutes. Close to Koreatown and many great restaurants on Bloor Street. 5 min walk to 4 grocery stores and LCBO. Basement space not suitable for people over 6 feet tall.

Value · Location · Getting around

Cozy 1BR+den in the Annex | Steps to subway

Discover the charm of the Annex in our bright 1BR+Den, steps from Bathurst Station. This quiet retreat features high ceilings, a balcony with stunning city views, and sleeps 4 comfortably. The den is a perfect home office or dining nook. You’re surrounded by Toronto’s best cafes and independent boutiques, blending historic vibes with modern comfort. Whether you’re here for work or a city getaway, enjoy a peaceful, stylish home base in the heart of it all! STR-2507-FKFFBP

Family · Location · View

The One in Yorkville-Previously Four Seasons Hotel

Our apartment in the heart of Yorkville is within a five-minutes-walk to ROM and Gardener museums, University of Toronto, libraries, theatre, bookstore, parks, subway stations, church, Whole Foods, and all retail stores, from Chanel, Dior, Holt Renfrew, to COS, Sephora, and Winners. Nestled among Park Hyatt and Hazelton Hotel, our building was previously the historic Four Seasons Hotel, and the upscale area around it is bustling with cafes, restaurants and art galleries.

Value · Location · Condition

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.

Value · Location · Check-in

Spacious 1 Bed w/ Patio Walk up by Subway

Stay in one of Toronto's most sought-after neighborhoods. This 1-bedroom suite with a spacious private patio offers the perfect balance of comfort, convenience, and location. Just steps from Bathurst & Bloor Subway Station, you'll be minutes from downtown, U of T, Kensington Market, Yorkville, Queen Street West, and Toronto's top restaurants, cafés, and nightlife.

Location · Value · Parking