Holiday houses in Rosedale, Old Toronto

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Top-rated holiday rentals in Rosedale, Old Toronto

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Apartment in Downtown Toronto

4.96 out of 5 average rating, 45 reviews

Ambient Vibe Downtown | CN Tower + Lake View Condo

The most exclusive condo where you can set the vibe by changing all the lights to your favourite colour. The perfect getaway and a home away from home. Immerse yourself in this two bedroom, two washroom Airbnb, with the perfect view of the CN Tower, lake and city skyline from the private balcony. Enjoy one of the only rooftop pools/terrace with unparalleled views of the city and cabanas/sun beds available to all guests, with everything you need to make your stay exceptional. Best location in TO

Top Guest favourite

Home in The Beaches

4.99 out of 5 average rating, 143 reviews

Heated Pool-tub Open 365 Days

** Ask about MID WEEK Specials. Welcome to the Toronto Beach. We are right next to the lake and have a HEATED private pool and spa that are both open year round. Explore local shops on the high street and swim, kayak (provided), volleyball, basketball and tennis courts right beside us. In winter, an outdoor ice rink (skates provided), cross-country ski trails (bring your own equipment) and lots of walking to be had. We decorate for for holidays, and the house has a real wood burning fireplace.

Guest favourite

Home in Churchill Meadows

4.9 out of 5 average rating, 41 reviews

Holiday retreat in Toronto

Make memories at this one-of-a-kind, family-friendly haven. With 5 bedrooms and 3.5 baths, it offers ample space. Only 2 kms from RIDGEWAY PLAZA and Meadowvale Town Centre. On a quiet street yet only 2 kms from the largest restaurant cluster in entire Toronto. An experience not comparable to anything in entire Canada. The fully equipped kitchen and the high-end mattresses ensure restful sleep. The tasteful decor adds a special touch. House is professionally cleaned between bookings.

Superhost

Apartment in Downtown Toronto

4.93 out of 5 average rating, 15 reviews

Beautiful 1BR Condo Coveted Yorkville!

Welcome to our stylish and luxurious Yorkville condo! Immerse yourself in the heart of Toronto's most upscale neighbourhood, surrounded by top-rated shopping, renowned restaurants, and cultural attractions. This chic retreat offers modern amenities, elegant design and a prime location for an unforgettable stay in a newly-constructed building. ➜ Approx. 500ft² / 56m² of space ➜ Highspeed WIFI ➜ In-unit washer & dryer ➜ Fully equipped kitchen ➜ Steps to Bay & Museum subway stations

Superhost

Villa in Burlington

4.66 out of 5 average rating, 38 reviews

Grand Villa Estate

Embrace Spring in style on this 25 acre of land with indoor heated swimming pool!! Located Centrally between Toronto & Niagara Falls. Downtown Toronto Easy Accessible Via Go Train From Appleby Station. Spacious 5 Bed Rooms, 4 Full Baths Seasonal HEATED INDOOR SWIMMING POOL. Free Parking, Grand Villa Offer HUGE FOYER W/ 5 Skylights. WIFI, NETFLIX, No PARTY CLOSE TO: PLENTY OF RESTAURANTS, CAFE, PUBS, GROCERY GOLFING, TRAILS, NIAGARA ESCARPMENT AND TO ALL MAJOR HIWAYS

Guest favourite

Home in Whitchurch-Stouffville

5 out of 5 average rating, 14 reviews

Amazing Swan Lake Villa/Private Lake/20+guests

About 4acres Manor with lake and farm. Nearby famous Emerald Hill Golf Club. 5Bedrooms, sleeps up to 16 guests. 4Queen Beds, 2Single beds & 1 Sofa-bed. Air-mattress available 2Living rooms. Smart TV with movable set. 2Kitchens and 3Dining areas. 10+ free parkings. This exceptional cottage offers a luxury and comfort space. The stunning interior and meticulous attention to detail is accompanied by a spectacular view. The property offers great outdoor space & private lake.

Guest favourite

Apartment in The Beaches

4.92 out of 5 average rating, 117 reviews

One bedroom vacation rental at The Beaches

Welcome to Our Cozy Retreat! Escape to our relaxing, perfectly situated in a prime location at the Beaches, a few minute walk to the: - Beautiful beaches - The vibrant waterfront boardwalk - Bike path and parks - A variety of delicious restaurants, pubs and shops Local Amenities including such as: - Spa and wellness services - Nail and hair salons - Flower, gift, and clothing shops - Grocery stores - Yoga studio - History Toronto (concert venue) - Theatre

Guest favourite

Cottage in Burlington

4.85 out of 5 average rating, 97 reviews

The Pearl Lodge

Almost 1 acre of land for you and your family to enjoy Free parking on premises Beautiful 4 bedroom cottage Comfortably sleeps 10 people Enjoy mini golf, pool table, and table tennis Open concept lounge and sitting area BBQ and firepit available for your use Walkout to deck with beautiful view of massive backyard Covered patio Soccer/Volley ball available upon request Located within minutes to trails, Lake Ontario, shopping and much more.

Guest favourite

Home in Brampton

4.93 out of 5 average rating, 55 reviews

Modern Lakefront Cottage In The City With Hot Tub

Experience ultimate luxury at our Lakefront Mansion, a modern marvel with 4 bedrooms, 3.5 baths, and a wealth of amenities. From access to the beach at Professor's Lake Recreation Centre, to the entertainment haven with games and a bar, every moment promises excitement. Unwind in the hot tub, savor morning treats from the Nespresso machine, and marvel at the architectural grandeur. Perfect for family staycations and unforgettable events.

Guest favourite

Townhouse in Downtown Toronto

4.91 out of 5 average rating, 11 reviews

TIFF, Scotiabank Arena, Rogers & Convention Centre

Experience Toronto like a local in this rare 18th-century townhome, perfectly located near TIFF, Rogers Centre, Scotiabank Arena, and the Metro Toronto Convention Centre. Surrounded by world-class dining and culture, this spacious heritage stay blends timeless character with modern ease. Ideal for travelers who value comfort, access, and atmosphere. Availability is limited—reserve your stay today.

Superhost

Apartment in Downtown Toronto

4.84 out of 5 average rating, 43 reviews

Jungle Made of Concrete: Free Parking & City View

Want to save on your booking? Just send me a message to book directly! Concrete jungle where dreams are made of.. My sister & I are DIY lovers, we are always looking for creative ways to dress our homes & create a one of a kind experience for our guests. Hence, the exact song that through our mind when we designed this jungle industrial themed villa.

Superhost

Home in Pickering

4.77 out of 5 average rating, 79 reviews

Beach House: First Floor

Have fun with the whole family at this stylish place. It's a beach side custom made luxury house where you can enjoy sunrise and sun set view with Bar, Restaurant, Park, Public transport, Shopping Mall and many other amenities are just one step away. Its bright, specious and peaceful accommodation.