Luxury rentals in Greater Toronto and Hamilton Area

JeremyRating, 5 stars6 months ago

Beautiful Luxury Urban Retreat in Leslieville

6 of us stayed here for a reconnect weekend. The house was so cozy and perfect, we only left a few times. Otherwise, we were all hanging together in the kitchen or living space like it was our own home. A great location, walkable to cafes and lunch spots and a wine shop a quick 5 min walk away. Hosts were very communicative and accommodating.

Villa in Georgina

RichieRating, 5 stars4 weeks ago

Georgina Waterfront Villa

Hands down the best cottage we've ever stayed at! Alex's place exceeded all expectations — it's even more stunning in person than in the photos. The cottage is spacious, beautifully designed, and packed with thoughtful touches. The basement is a game-lover’s dream, and the beds are incredibly comfortable. They’ve truly thought of everything to make your stay perfect. The hot tub at night was a highlight, and the outdoor barrel sauna was such a unique and relaxing experience. The location is perfect — very private and peaceful, yet just a short walk to Jackson’s Point for ice cream, cute shops, and great restaurants. So much to love about this spot — we can’t wait to come back!

5 out of 5 average rating, 8 reviews

Ultra-Modern 5BDR Home with Pool, Gym & Theatre

LauraRating, 5 stars1 week ago

This Airbnb was absolutely beautiful, as stunning as it shows in the photos (if not even more beautiful in person!). With the owner and property manager's permission, we rented the space for my clients to host their little ones' birthday bash. Julie, the property manager was very responsive, helpful, and flexible with making the booking and check-in process as smooth as possible. The cleaning crew also did an impeccable job, ensuring the house was in tip top shape (the pool was spotless and everything was vacuumed/steamed cleaned!) All the guests absolutely had a blast at this wonderful Airbnb!

Place to stay in Caledon

Peak House

Hills and valleys stretch for 100 acres around this design-forward hilltop home in the Ontario countryside. A pool and hot tub sit mid-lawn, and a firepit anchors a covered outdoor seating area. Glass walls contrast moody rooms splashed with dark stone and wood paneling. It’s a few minutes to the village of Caledon and less than an hour to dining, shopping, and entertainment in downtown Toronto. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Master: King size bed, Ensuite bathroom with standalone shower and bathtub • Bedroom 2: Queen size bed • Bedroom 3: Twin size bed, Shared access to hallway bathroom, • Bedroom 4: 2 Twin over bunk beds, Ensuite bathroom with standalone shower • Bedroom 5: Queen size bed, Shared access to hallway bathroom, STAFF & SERVICES Extra Cost (advance notice may be required): • Activities and excursions • More under “Add-on services” below

Home in Nobleton

King Vista

This Scandinavian inspired vacation home is the perfect escape from the city. Located just 40 km north of Toronto, you will feel like you're a million miles away but within an hour's drive. This brand new sustainably built home invites you to come and enjoy the nature of the 50 acre estate while minimizing your carbon footprint. With endless nearby hiking trails, a heated saltwater pool and hot tub, everything is here for your enjoyment! Copyright © Luxury Retreats. All rights reserved.

Apartment in Toronto

5 Star SoHo Hotel 2BR (No Cleaning Fees)

No Cleaning Fees! A spacious 916 sqft luxury suite in a four star boutique hotel located in downtown Toronto's most walkable neighborhood. Suite features two king size beds, fully equipped open concept kitchen, a separate living area filled with natural light and cozy dining space. With two restaurants and 24 hour concierge services enjoy hotel luxury. Walk out to Union Station, Metro Toronto Convention Centre, CN Tower , the Rogers Centre or The Well for shopping across the street.

A space that's all yours, with room for everyone

Place to stay in Toronto

5 Star SoHo Hotel 1BR (No Cleaning Fees)

No Extra Cleaning Fees! A spacious 800-square-foot luxury suite in a four star boutique hotel located in downtown Toronto across from Roger Centre. Suite features a king size bed, fully equipped open concept kitchen, separate living area filled with natural light and cozy dining space. Enjoy the privacy of a separate bedroom and a well-appointed bathroom. This is the perfect place for extended stays, close to Union Station, Metro Toronto Convention Centre, and CN Tower.

Holiday rentals for every style

Get the amount of space that is right for you

Houses

Bungalows

Intimate homes, inviting architecture

Villas

Luxurious estates for the ultimate escape

Popular amenities for Greater Toronto and Hamilton Area luxury holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great luxury holiday rentals in Greater Toronto and Hamilton Area

5 out of 5 average rating, 24 reviews

Villa in Innisfil

Luxury Waterfront Cottage

Chantal Rating, 5 stars3 weeks ago

We had a fabulous 4 days with our family at this beautiful place. It rained 80% of the time, but the house was so lovely that it didn’t matter. There was enough to do for everyone from 4 yrs old to 84! I would highly recommend staying here.👍

Villa in Georgina

RichieRating, 5 stars4 weeks ago

Georgina Waterfront Villa

Hands down the best cottage we've ever stayed at! Alex's place exceeded all expectations — it's even more stunning in person than in the photos. The cottage is spacious, beautifully designed, and packed with thoughtful touches. The basement is a game-lover’s dream, and the beds are incredibly comfortable. They’ve truly thought of everything to make your stay perfect. The hot tub at night was a highlight, and the outdoor barrel sauna was such a unique and relaxing experience. The location is perfect — very private and peaceful, yet just a short walk to Jackson’s Point for ice cream, cute shops, and great restaurants. So much to love about this spot — we can’t wait to come back!

JeremyRating, 5 stars6 months ago

Beautiful Luxury Urban Retreat in Leslieville

6 of us stayed here for a reconnect weekend. The house was so cozy and perfect, we only left a few times. Otherwise, we were all hanging together in the kitchen or living space like it was our own home. A great location, walkable to cafes and lunch spots and a wine shop a quick 5 min walk away. Hosts were very communicative and accommodating.

5 out of 5 average rating, 8 reviews

Ultra-Modern 5BDR Home with Pool, Gym & Theatre

LauraRating, 5 stars1 week ago

This Airbnb was absolutely beautiful, as stunning as it shows in the photos (if not even more beautiful in person!). With the owner and property manager's permission, we rented the space for my clients to host their little ones' birthday bash. Julie, the property manager was very responsive, helpful, and flexible with making the booking and check-in process as smooth as possible. The cleaning crew also did an impeccable job, ensuring the house was in tip top shape (the pool was spotless and everything was vacuumed/steamed cleaned!) All the guests absolutely had a blast at this wonderful Airbnb!

IbbyRating, 5 stars10 months ago

Villa in Burlington

Lavish Luxury Experience

Big and modern luxurious house with everything you need in it. Very private and surrounded by nature. The place looks amazing on Airbnb but it even looks better in person! Gina was very friendly, responsive and helpful. Highly recommended and I look forward to staying here again in the future.

Apartment in Toronto

5 Star SoHo Hotel 2BR (No Cleaning Fees)

Home in Georgina

Malibu-Style Lake House