Holiday rentals in Simcoe Island

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Top-rated holiday rentals in Simcoe Island

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Top guest favourite
A spacious outdoor patio features cozy seating arranged around a fire pit, with gentle lighting from strung bulbs. A view of the lake and sunset is visible in the background, framed by trees. Comfortable seating options encourage relaxation and enjoyment of the setting.
Cottage in Prince Edward
4.98 out of 5 average rating, 109 reviews

Waterfront Casa in wine County w/SAUNA and HOT TUB

Escape to this beautifully updated lakefront home on 170ft of private shoreline in beautiful Prince Edward County. Enjoy our new panoramic view sauna, hot tub and outdoor shower. This relaxing getaway is located on the Bay of Quinte, just 2hrs east of Toronto. A 30 min drive to Sandbanks, 20 mins to Picton/Wellington. Close to many wineries and breweries. Large yard space makes this an ideal home for groups, couples and families looking for postcard views and private spa amenities. ST-2023-0002

Guest favourite
The cabin is situated on a gently sloping green lawn surrounded by trees. A spacious deck is visible, complemented by outdoor furniture. A landscaped area with stone walls and plants can be seen in the foreground, enhancing the natural setting.
Cottage in Leeds and the Thousand Islands
4.92 out of 5 average rating, 238 reviews

Smugglers Getaway on the St. Lawrence River

Enjoy your privacy in this waterfront cabin in the historic Smugglers Cove on the St. Lawrence River in the heart of the 1000 Islands. You'll have use of the entire cabin with fantastic River views from your own patio. Conveniently located off of the 1000 Islands Parkway, one of the most beautiful scenic drives in North America, guests may enjoy walking, hiking and cycling the paved and scenic 37 km Waterfront Trail. You're welcome to arrive by boat or car; private entrance to your cabin.

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, 152 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.

Guest favourite
Dome in Plainfield
4.81 out of 5 average rating, 191 reviews

From quiet rivers to starlit skies,

Experiencing forest bathing while you are also enjoying the comfort of our bubble, Escape the hustle of the modern lifestyle and re-balance your Self with the rythme of nature. Inside, there is a Queen-size bed and wood stove will keep you toasted. No running water; you will find an outhouse a few steps away from the dome. Cook outside on the BBQ, relax in the hamac and explore nature on our trail or in a kayaks or paddle board. A unique way to enhance your experience? Rent a sauna!

Top guest favourite
A stylish bedroom features a spacious bed with soft linens and decorative pillows, set against a light brick wall. Two bedside tables with lamps provide ambient lighting, while a cozy throw blanket is draped over the bed, creating a comfortable and inviting space.
Flat in Kingston
4.99 out of 5 average rating, 100 reviews

Earl View Place - downtown gem!

Enjoy a stylish experience at this centrally located gem, professionally designed and renovated. Compact, elegant and comfortable. The location is amazing, nestled in the historic Sydenham Ward district midway between the downtown area and Queen's University, only a block from Lake Ontario. Earl View Place provides a perfect blend of convenience, comfort and location - get a great night's sleep before heading off to the nearby university, hospitals, or Kingston's many attractions.

Top guest favourite
Home in Adams Center
4.86 out of 5 average rating, 191 reviews

The Hideaway Cabin

Welcome to the Hideaway Cabin, where you can unwind in the embrace of nature. Here, you can sizzle your favorites on the grill, lounge in the Adirondack chairs on the balcony, or simply relax indoors. Come evening, gather by the firepit on the porch to watch the fireflies dance or relax in the hot tub on the back porch. It's the ideal blend of natural serenity and homely comfort. In the winter, cozy up by the woodstove in the living room and catch up on your favorite TV shows.

Guest favourite
The geodome is situated on a wooden deck overlooking Varty Lake. Soft clouds are visible in the expansive sky, while trees frame the serene view. Large windows of the dome reflect the natural light, inviting the beauty of the landscape indoors.
Dome in Yarker
4.93 out of 5 average rating, 144 reviews

Sky Geo Dome on the Lake

Our beautiful geodome offers a unique glamping experience with breathtaking lake views. Perfect for romantic getaways, celebrations or family vacations. Enjoy stunning sunrises, stargaze, roast marshmallows by firepit, BBQ, play air hockey/pool/axe throwing, enjoy a night sky projector -indulge in peace & serenity. Varty Lake is ideal for fishing, kayaking & canoeing. Just 15 min from amenities & 30 min from alpaca farms, wineries, 1000 Islands, & stargazing in Stone Mills.

Top guest favourite
A wooden treehouse is nestled among lush trees and overlooks a gentle stream. Large windows allow natural light to fill the space, and a staircase leads to the entrance. Stones and moss line the streambank, contributing to the tranquil natural setting.
Treehouse in Tweed
4.95 out of 5 average rating, 268 reviews

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

Top guest favourite
A bright red door is framed by black trim, standing out against a backdrop of exposed red brick. A clear glass panel in the center allows light to filter through, and overhead, the structure features wooden beams. An outdoor light fixture is mounted beside the door.
Guest suite in Kingston
4.98 out of 5 average rating, 184 reviews

Hotel Room Bela in downtown Kingston

Welcome to Hotel Room Bela, in the heart of downtown Kingston. Our space is a small and cozy hotel room accommodation with your own private entrance and everything you need for a comfortable stay. We are steps away from unique local stores, restaurants, Queen's University and Hotel Dieu Hospital. Our prime location includes free parking for 1 vehicle. Discounted rate for bookings any day, Sept 25-27, 2026 due to unavailable parking. Licence: LCRL20230000508

Top guest favourite
Tiny home in Perth
4.93 out of 5 average rating, 352 reviews

Off-grid A-frame cabin, come relax in the forest!

Welcome to “The Hemlock” cabin One of two unique cabins on the property. A unique stay situated minutes from historic Perth, Ontario. The Hemlock sits on 160+ acres of private, natural forest. Enjoy 3 season lake access for kayaking & canoe. Year round trails for hiking, snow shoeing, exploring etc. Beautiful scenery and wildlife in a peaceful, private setting, relax and unwind by the fire! We look forward to having you!

Guest favourite
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
4.9 out of 5 average rating, 186 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 favourite
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
4.97 out of 5 average rating, 304 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 holiday rentals

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