Holiday rentals in Simcoe Island

River Ledge Hideaway

New construction home designed specifically with the thought of guests in mind overlooking the Saint Lawrence River. Enjoy a memorable fall or holiday getaway to this waterfront oasis. Highlighting this home is a large master bedroom overlooking numerous islands speckled throughout the expansive water view. Outdoor fire pit and grilling area will be set up for the fall season. Walk down our path to your own private waterfront. Great place for couples, small families or friends getting together

City Retreat With Board Games

Welcome to our newly renovated detached home! The fully stocked kitchen, smart TV, board games and patio offer convenience and entertainment. Unwind on the patio with high end patio furniture and a barbecue. Enjoy our central location in Kingston for a memorable stay. This property has a garden suite on the back of the property with a separate entrance and backyard space. We look forward to hosting you! Fully licensed for short term rentals with the City of Kingston - License #LCRL20250000092

The Urban Cottage on Earl

The Urban Cottage on Earl is located in the heart of Kingston's historic Sydenham Ward and is within 2-3 blocks of KGH, Hotel Dieu, Queen's University, Lake Ontario and Kingston's vibrant downtown. Whether you are coming to Kingston for work or play, The Urban Cottage has all the conveniences of a downtown city home coupled with a relaxed cottage feel. After a long day, enjoy the fully enclosed, private backyard oasis complete with hot tub and water feature. LCRL20230000005

Newly renovated downtown suite!

Downtown Sydenham Ward… Location… Location… Location! Stay with Whit and enjoy a newly renovated private suite in a 1930’s downtown Sydenham Ward home. Enjoy your own private entrance to a spectacular lower level suite. One luxurious queen bed with top-of-the-line bedding, upgraded double pull-out sofa, three-piece bath, electric fireplace, large screen TV (Netflix, etc.), and kitchenette. This property is perfect if you’re looking for a quiet escape, parking included!

Off-Grid Tree Canopy Retreat

Escape to this private off-grid retreat, nestled high in the trees overlooking the natural beauty of the Moira River. This elevated nature shelter provides a cozy, rustic space for guests seeking solitude, adventure, or a peaceful getaway. This is a multi-use nature retreat designed to provide shelter and relaxation in a secluded setting. Guests are welcome to rest and recharge in the space, enjoying the warmth of the wood stove while taking in the peaceful surroundings

Spacious and brightly furnished lower unit

Bright, clean and cozy - we are a respectful family of 3, and welcome you for your stay. This area is ideal for those who like to keep to themselves, with a private bedroom, kitchen, and living room. It can be entered directly from outside. Included with two stylish pull-out couches (can be turned into beds), an open kitchen provided with cooking utensils and equipment, protected with outdoor security cameras, as well as a washing machine to take care of dirty laundry.

Cosy Downtown Apartment With Parking!

Discover a charming downtown Kingston apartment, occupying the main floor of a townhome. Enjoy a well-furnished bedroom with a Queen bed and a couch in the living room that converts into a double bed. The fully-equipped kitchen makes cooking easy! A 5-minute stroll to historic Princess Street. Conveniently, there's parking available behind the house, perfect for your ideal getaway! Licensed for short term rental with the City of Kingston - License #LCRL20230000551

The Sweet Suite

- This bright, peaceful and quiet private apartment has an abundance of amenities at your home away from home. Enjoy this space and explore what Kingston has to offer from its convenient central location. - Separate exterior entrance. - Sound treated ceilings and walls. - Beautiful wooded area, park, and walking paths behind the property. - Two tobogganing hills -Complimentary snacks. -Linens washed after each stay with o3 commercial grade laundry system

Private Suite near Skeleton Park

Sunny private suite 700 m from the downtown hub with separate entrance & 3-piece bath overlooking back courtyard. Entire space & amenities in ONE ROOM. FREE 2nd guest FREE high-speed wifi FREE coffee & teas FREE filtered water FREE (shared) parking No special cleaning by guests. Walk to hospitals & grocery or take-out. Sit in the private sunny courtyard & train chickadees to eat from your hand. No house access. City STR license # LCRL20210000518

Victorian Boutique Apartment-Steps from Lakeshore!

Enjoy the elegance of a by-gone era while staying in this stunning Victorian loft, located on a quiet leafy boulevard in the heart of Kingston’s most historic and architecturally eclectic neighborhood! Beautifully decorated and featuring a bright vaulted grand living room with a tin clad mezzanine supported on original exposed beam, exposed brick, period furniture, and a stunningly unique black-and-white tiled bathroom.

The Crows Nest Cozy River Cottage in Kingston

Welcome to The Crows Nest, our cozy waterfront cottage with your own private swimming dock. Here you’ll find the simplicity of river life. It’s a real birders paradise and a great place for spotting wildlife like deer.Enjoy the cozy living space, private deck to enjoy magnificent sunrises and sunsets, and the special calm that is the St. Lawrence River in the heart of The 1000 Islands. License number LCRL20210000964.

The Carriage House - Unit 1

Welcome to the newly restored 18th century Carriage House. At one time, the home belonged to a wealthy merchant and his noble stead’s. Today, it has been transformed into a beautiful loft maintaining its historic charm with modern day amenities. It is perfect for a romantic getaway for two or a quiet retreat for one - just minutes from downtown Kingston and everything this beautiful City has to offer!