Holiday rentals in Simcoe Island

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Top-rated holiday rentals in Simcoe Island

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Top guest favourite
A master bedroom features a queen-size bed with a textured white coverlet. Large windows and sliding glass doors allow for natural light and offer views of the waterfront. A small table is positioned near the window for additional functionality.
Cottage in Hammond
4.97 out of 5 average rating, 148 reviews

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

Top guest favourite
A charming guesthouse is set in a vibrant garden, featuring a spacious deck overlooking the landscape. Lush greenery and flowers surround the building, enhancing the natural environment. A tree provides shade, and clear blue skies add to the serene atmosphere.
Guest house in Township Of Frontenac Islands
4.98 out of 5 average rating, 142 reviews

Wolfe Island Oasis

Welcome to our cozy country retreat. Our guesthouse offers everything you need to unplug from the hustle of the city. Whether its enjoying a coffee on the lounge chair while watching the sunrise; stargazing on the patio; sitting around a warm campfire; or falling asleep under our son's handcrafted cedar strip canoe: this retreat was designed to maximize a unique experience. The building is completely separate from our family hobby-farm and offers a secluded space for our guests.

Top guest favourite
A comfortable living area features two brown armchairs and a spacious light-colored sectional. A mounted flat-screen television remains positioned above a wooden media console. A round mirror is displayed above a fireplace, contributing to the cozy ambiance of the space.
Home in Kingston
5 out of 5 average rating, 163 reviews

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

Top guest favourite
The suite features a dark sofa adorned with decorative pillows, accompanied by a round wooden coffee table with a potted plant on top. A luxurious queen bed is visible in the background, with the bathroom area partially seen to the right.
Guest suite in Kingston
5 out of 5 average rating, 121 reviews

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!

Top guest favourite
A well-maintained front yard features a variety of colorful flowers including vibrant red begonias surrounded by white blooms. A large tree provides shade, while the neatly trimmed grass complements the garden. The house, with a gray exterior, is partially visible in the background.
Guest suite in Kingston
4.93 out of 5 average rating, 228 reviews

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.

Top guest favourite
A light grey sectional sofa features striped throw pillows and extends into a spacious seating area. A rustic wooden coffee table is centered on a patterned area rug, providing a warm contrast to the neutral tones of the furniture.
Guest suite in Kingston
4.97 out of 5 average rating, 297 reviews

Bright, cozy basement apartment with fireplace!

Welcome to our bright, cozy, and licensed basement apartment in Kingston's west end. Enjoy fresh, locally-roasted, coffee each morning and spend the evening beside the gas fireplace. With parking for one vehicle, you'll find yourself under 10 minutes away from the mall, local restaurants, and the Invista Centre—and a quick 18-minute drive to downtown. Whether you're here with a purpose or just looking to wander, we've got you covered. License #: LCRL20210000493

Top guest favourite
The bedroom features a queen size bed with a tufted headboard, complemented by two bedside tables, each with a decorative lamp. A soft, neutral blanket covers the foot of the bed, and subtle artwork adorns the wall above the headboard.
Flat in Kingston
4.98 out of 5 average rating, 153 reviews

Spacious Downtown Loft

This spacious downtown 2 level loft is the perfect location to enjoy everything that Kingston has to offer. Walking distance to the Grand theatre, Slush Puppie Place, restaurants, universities, ferry, and Fort Henry. The perfect location for an evening or weekend getaway to explore Kingston, visit family or just unwind and relax. No parking available with the property (see more detail under Location - Getting Around) City of Kingston License #LCRL20220000211

Guest favourite
A private apartment is set amidst lush greenery, characterized by well-maintained grass and various shrubs. The exterior features a vibrant purple facade, complemented by large windows. Two parked vehicles can be seen nearby, adding convenience for guests.
Flat in Kingston
4.91 out of 5 average rating, 225 reviews

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

Guest favourite
A modern open-concept living area features a comfortable grey sofa adjacent to a wall-mounted TV. A small dining table with two chairs offers seating near the kitchen, which is equipped with stainless steel appliances and bright white cabinetry. Natural light is provided by multiple windows.
Townhouse in Kingston
4.91 out of 5 average rating, 330 reviews

Downtown Haven: Roomy Home with Parking

This newly renovated home is located in downtown Kingston, minutes walking distance to major amenities such as the K-Rock Centre, waterfront, restaurants, bars, and shopping on Princess Street. The unit, which encompasses the entire first floor of a townhouse, consists of a large open concept living space along with one bedroom and a bathroom. Fully licensed for short term rentals with the City of Kingston - License #LCRL20230000420

Guest favourite
A cozy bedroom features a double bed with a decorative blanket, accompanied by bedside tables. Natural light enters through the window, illuminating the room. A door leads to the outside, enhancing the space's brightness.
Flat in Kingston
4.83 out of 5 average rating, 171 reviews

Bachelor Apt close to Queen's/Downtown Kingston

This third-floor apartment is VERY close to Queen’s University as well as Lake Ontario and historic downtown Kingston. It has its own private entrance at the back of the house up a set of outdoor, narrow, metal stairs (the original fire escape). It also has air conditioning. The homeowners live on the first two floors, making this the ideal space for someone looking for a quiet space close to Queen's and downtown Kingston.

Top guest favourite
An elegant historic brick facade is presented, showcasing multiple gabled roofs and large arched windows. A detailed front porch with decorative woodwork invites entry, while a mix of mature trees and landscaping frames the exterior.
Guest suite in Kingston
4.98 out of 5 average rating, 162 reviews

Hotel Room Bela in downtown Kingston

A small and cozy hotel room accommodation with a private entrance to your own space and free parking until check out, located in downtown Kingston's Sydenham Ward. You are steps away from the heart of downtown shopping, restaurants, Hotel Dieu Hospital and 3 blocks from Queen's University and KGH. Our space is small at 175 sq ft, but you’ll have everything you need for a comfortable stay. Licence: LCRL20230000508

Top guest favourite
Two neatly rolled white towels are placed on a bed with soft linens. A decorative pillow with a subtle pattern rests against the headboard. A warm ambient light is emitted from a pendant lamp, enhancing the calming atmosphere.
Flat in Kingston
4.99 out of 5 average rating, 131 reviews

KingstonStays | Historic Downtown Hideaway

Your historic hideaway awaits you with a calming, cozy luxury. It is in the heart of downtown Kingston within easy walking distance to Market Square, the Wolfe Island ferry, the Leon's Center, Fort Henry, Confederation Park and City Hall, both Hotel Dieu and Kingston General Hospitals, Queens University, RMC as well as all of the restaurants, cafés, bars and shops the beautiful Canada's first capital has to offer.

Popular amenities for Simcoe Island holiday rentals