Vacation rentals in Simcoe Island

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Top-rated vacation rentals in Simcoe Island

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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, 480 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, 909 reviews

Charming Suite with Views of 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 welcoming single-story house features a stone facade and a well-maintained front yard. A pathway lined with decorative lighting leads to the entrance, which is adorned with a dark green door. Lush greenery surrounds the home, adding to its inviting presence.
Home in Kingston
4.95 out of 5 average rating, 168 reviews

Sunny House- Steps to terminal- Great Value

Welcome to our sunny house! Our unique, beautiful, and newly remodeled home is the perfect place to escape and enjoy a peaceful getaway. Located on a quiet street in the heart of the city, it offers easy access to shopping, restaurants, and local attractions. Whether you're looking for a romantic weekend, business trip, or a family retreat, our house awaits you! Off the 401 hwy Walking distance to the Coach Bus Terminal 5 mins to Via Rail Station 10 mins to downtown and 1000 Islands Cruises

Top guest favorite
An aerial view captures a spacious waterfront area featuring a gray concrete patio. Bright red outdoor chairs surround a fire pit on the grass, while a sauna is positioned nearby. The cozy retreat is nestled among trees, with direct access to the water.
Home in Bath
4.93 out of 5 average rating, 107 reviews

Lakefront with Sauna & Trails

Escape to our serene Lake Ontario retreat, nestled on a gated property with westward views. Enjoy a sauna, indoor fireplace, and outdoor fire pit. Features three bedrooms, two bathrooms, a fully-equipped kitchen with modern appliances, high-speed FIBE internet, and a 50" TV. Located at the quiet end of a cul-de-sac, just 15 minutes from Kingston and steps from walking trails. Ideal for a romantic getaway or a family vacation, sleeps up to 8 with plenty of parking. Your lakeside oasis awaits!

Top guest favorite
Apartment in Kingston
4.93 out of 5 average rating, 104 reviews

Waterfront Coach House

Experience all downtown Kingston has to offer in this historic limestone guest house. Steps to Lake Ontario, a few minutes walk to Queen’s University and downtown Kingston. This guest house has many amenities: kitchen (no dishwasher) living area, full bathroom, two bedrooms with Queen size beds and parking for up to three cars. The guest house is located across the street from City Park, which offers a splash pad and play structures, and MacDonald Park waterfront trail and swimming beach.

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
5.0 out of 5 average rating, 228 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 open-plan living and dining area features a wooden dining table with caned chairs, facing a cozy seating arrangement. A gas fireplace is centered on the wall, accompanied by large windows that allow ample natural light, and decorative plants are positioned around the space.
Home in Kingston
4.96 out of 5 average rating, 207 reviews

Spacious 6BR+3.5BA •Peaceful, By Shops •For Groups

Spacious bungalow ideal for 𝐫𝐞𝐮𝐧𝐢𝐨𝐧𝐬, teams or wedding groups ● 𝟔 large bedrooms (4 in basement), 8 beds and 𝟑.𝟓 bathrooms. ● 𝐁𝐢𝐠 𝐋𝐢𝐯𝐢𝐧𝐠 𝐬𝐩𝐚𝐜𝐞 with two 𝟑-seater sofas. 𝐋𝐚𝐫𝐠𝐞 dining table for 𝟏𝟎. well stocked kitchen. ● 𝐒𝐮𝐧𝐫𝐨𝐨𝐦 seats 5, 𝐝𝐞𝐜𝐤 & 𝐁𝐁𝐐, 𝐟𝐞𝐧𝐜𝐞𝐝 𝐛𝐚𝐜𝐤𝐲𝐚𝐫𝐝 for 𝐩𝐞𝐭𝐬. ● Parking for 𝟒 𝐜𝐚𝐫𝐬. Quiet residential street, walking to Costco & Tim Hortons, short drive to Downtown, Queen’s & INVISTA.

Top guest favorite
Home in Kingston
4.94 out of 5 average rating, 113 reviews

Tanyas_Place_ygk

Clean and comfortable, fully equipped three bedroom home on a quiet cul-de-sac in Kingston. Conveniently located only 5 minutes to the 401, Via Rail train station, and Coach Canada bus station. Several grocery stores, restaurants, movie theater and Norm's indoor golf are close by. Ten minutes from downtown Kingston. Licenced by the City of Kingston since 2024-02-26 Short-Term Rental Licence # LCRL20240000005 Effective until 2027-02-26.

Top guest favorite
Cottage in Kingston
4.95 out of 5 average rating, 421 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
The main entrance is located on the sidewalk and features a modern black door framed by stone and wood accents. Large windows provide natural light, while vibrant plants and flowers add a touch of color to the exterior. Steps lead to additional entrances above.
Apartment in Kingston
4.91 out of 5 average rating, 126 reviews

Heritage loft downtown Kingston

An historic gem located just steps from Kingston’s vibrant and bustling downtown. Located at Queen & Montreal, this large bachelor boasts stylish steam-punk finishes, fully furnished kitchen, 4-piece bathroom, and a spacious living room equipped with smart TV. Relax in the comfy queen-sized bed after a day of exploring. The bedroom can be enclosed by massive sliding barnwood doors, adding a touch of rustic charm to your stay.

Top guest favorite
A spacious dining area is showcased, featuring a long wooden table with intricate carvings. A chandelier hangs from a green ceiling above. The room is illuminated by natural light from large windows, revealing exposed brick walls and a cozy seating area in the background.
Home in Kingston
4.91 out of 5 average rating, 214 reviews

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.

Guest favorite
The charming exterior of a converted church is presented, showcasing a striking red brick facade and a steeply pitched roof. Tall trees and lush greenery surround the building, adding to the serene setting. A welcoming entrance with a dark door and steps leads to the front.
Home in Prince Edward County
4.96 out of 5 average rating, 312 reviews

The Prince Edward County Church, A Unique Escape

Stunning 1888 converted church in Prince Edward County on a private 2.3-acre waterfront property backing onto the Bay of Quinte. This one-of-a-kind stay blends soaring ceilings and historic charm with modern luxury. Sleeps 8 adults with 4 bedrooms, lake views, direct waterfront access, high-speed WiFi, Sonos, fireplaces, kayaks, and more. Featured in Forbes, House & Home & Cottage Life with over 300 guest reviews.

Popular amenities for Simcoe Island vacation rentals