Vacation rentals in Simcoe Island

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Top-rated vacation rentals in Simcoe Island

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Top guest favorite
A dining area is depicted with a round wooden table set for four. Light gray chairs surround the table, complemented by decorative placemats. A woven light fixture hangs above, and a door with a window allows natural light to enter. A small closet and a wall-mounted plant holder are visible.
Home in Kingston
4.98 out of 5 average rating, 152 reviews

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

Guest favorite
A cozy living space features a black armchair and a dining area with a table and chairs. A new gas fireplace is integrated into a brick wall, providing warmth. The kitchen area with modern appliances is visible on one side, while natural light comes from a nearby door.
Home in Kingston
4.88 out of 5 average rating, 444 reviews

Bagot Street Hidden Cottage

Offering a 2 bedroom fully furnished, fully detached home once owned by Gord Downie of the Tragically Hip. This cottage has character! It is in the heart of downtown Kingston. A private and unique setting will surprise you as it is hidden from the eye behind the facade of Bagot street in the historic and affluent  Sydenham Ward. This private house offers walking access to the core of downtown, Hospitals & Queen's University,  KGH Hospital. Our free Parking is away from street. LCRL20210000877

Guest favorite
A modern kitchen is displayed, featuring stainless steel appliances and a stylish backsplash. High ceilings are complemented by exposed beams, while windows with soft curtains allow natural light to filter in. The open layout creates a seamless connection to the adjoining living space.
Apartment in Kingston
4.8 out of 5 average rating, 828 reviews

Waterfront suite over looking Lake Ontario

Additional upgrades such as large granite counter tops, brand new furniture, stainless steel appliances, high ceiling. Fine finishes show the care that have gone into the history of this limestone suite located in one of the best locations in the heart of downtown Kingston. Please note: Our place does not have an elevator and is located on the third floor. Guests will need to climb two flights of stairs to access the unit. This may be challenging for seniors or guests with limited mobility.

Top guest favorite
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, 180 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 favorite
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, 134 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!

Guest favorite
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.
Apartment in Kingston
4.82 out of 5 average rating, 179 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. The private, third-floor entrance is at the back of the house and at the top of two flights of outdoor, narrow, metal stairs (the original fire escape). 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. No parking provided. It has air conditioning.

Guest favorite
The spacious living area showcases two sofas and an ottoman, complemented by a wooden dining table surrounded by four chairs. A large window allows natural light, illuminating a 50-inch Smart TV on a media console against the wall.
Apartment in Kingston
4.91 out of 5 average rating, 249 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 favorite
A cozy sleeping area is highlighted by a spacious bed covered with a light blue blanket. Natural light enters through large windows adorned with tied-back curtains, revealing a view of a green outdoor space. A piece of contemporary wall art adds a colorful touch.
Guest suite in Kingston
4.81 out of 5 average rating, 245 reviews

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

Top guest favorite
Four white Adirondack chairs are arranged in a grassy area, each with a colorful pillow. A small fire pit surrounded by stacked firewood is nearby, complemented by vibrant flowers and greenery in the background. The cottage is visible, featuring a grey exterior with dark windows.
Cottage in Kingston
4.94 out of 5 average rating, 359 reviews

The Crows Nest Cozy River Cottage in Kingston

Welcome to The Crows Nest, our cozy waterfront cottage with your own private swimming dock (5 mins to Kingston!). 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.

Guest favorite
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, 348 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

Top guest favorite
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, 166 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 for one vehicle until check out. You are steps away from the heart of downtown shopping, restaurants, Hotel Dieu Hospital and 3 blocks from Queen's University and Kingston General Hospital. Our space is small at 175 sq ft, but you will have everything you need for a comfortable stay. Licence: LCRL20230000508

Top guest favorite
Cottage in Kingston
4.97 out of 5 average rating, 268 reviews

Waterfront cottage close to downtown Kingston.

We welcome our guests to our cozy and pet friendly waterfront cottage, Rube's Retreat. Enjoy the beauty of cottage living, very close to City Hall, downtown Kingston. Rube's Retreat is a great place to be, whether it's with your family, friends or a business trip, we have everything you need to make your getaway a most memorable experience.

Popular amenities for Simcoe Island vacation rentals

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  2. Canada
  3. Ontario
  4. Frontenac County
  5. Frontenac Islands
  6. Simcoe Island