
Vacation rentals in Simcoe Island
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Simcoe Island
Guests agree: these stays are highly rated for location, cleanliness, and more.

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
4.88 out of 5 average rating, 486 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.
4.8 out of 5 average rating, 912 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!
4.93 out of 5 average rating, 109 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.
4.93 out of 5 average rating, 105 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
5.0 out of 5 average rating, 228 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.
4.96 out of 5 average rating, 208 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.
4.94 out of 5 average rating, 114 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.
4.95 out of 5 average rating, 424 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.
4.91 out of 5 average rating, 129 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.
4.91 out of 5 average rating, 215 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.
4.96 out of 5 average rating, 314 reviews
Private and Perfectly Positioned home.
Large open concept family home. Great for business travellers, couples or families. Very quiet home in residential area. 3.8 kms to market square in downtown and to the K-Rock Centre, 4.4 kms to Queens University, 2 kms to the Memorial Centre, 2.2 kms to the 401. I am offering 3 bedrooms to stay in. Room for 3 cars to park in driveway. Apple TV (with Netflix) hooked up to televisions.
4.98 out of 5 average rating, 322 reviewsPopular amenities for Simcoe Island vacation rentals
Other great vacation rentals in Simcoe Island

Shopkeeper's Apartment Waterfront 1186B Main st.
4.92 out of 5 average rating, 120 reviews
Historic Bela in downtown Kingston
4.98 out of 5 average rating, 182 reviews
Ella's House
4.99 out of 5 average rating, 103 reviews
DWELL Aparthotels - Craftsman House 2 (2 Bedroom)
4.98 out of 5 average rating, 112 reviews
Your Home Away From Home! Entire house!
4.96 out of 5 average rating, 618 reviews
Sandra's Wee House on Simcoe Island
4.94 out of 5 average rating, 18 reviews
Stunning Simcoe Island Retreat with Sauna
5.0 out of 5 average rating, 36 reviews
Waterfront Oasis on Wolfe Island with sunset views
4.97 out of 5 average rating, 73 reviewsDestinations to explore
- New York Vacation rentals
- Montreal Vacation rentals
- Philadelphia Vacation rentals
- Niagara Falls Vacation rentals
- Jersey City Vacation rentals
- Mississauga Vacation rentals
- Newark Vacation rentals
- Mont-Tremblant Vacation rentals
- Buffalo Vacation rentals
- Brampton Vacation rentals
- Niagara Falls Vacation rentals
- Cambridge Vacation rentals
- Sandbanks Provincial Park
- Thousand Islands National Park
- Thousand Islands
- Pike Lake
- Sandbanks Dunes Beach
- Kingston 1000 Islands Cruises
- Lemoine Point Conservation Area
- Rosehall Run Vineyards Inc
- Charleston Lake Provincial Park
- Black Bear Ridge Golf Course
- Grange of Prince Edward Vineyards and Estate Winery
- Closson Chase Vineyards
- Lake on the Mtn Provincial Park
- Frontenac Provincial Park
- Thousand Islands Winery
- Sandy Island Beach State Park
- Boldt Castle & Yacht House
- Bay of Quinte
- Hinterland Wine Company
- Clayton Island Tours
- Lake Ontario Park
- Casa-Dea Winery & Banquet Hall
- Shorelines Casino-Belleville





