Vacation rentals in Simcoe Island

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Top-rated vacation rentals in Simcoe Island

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Top guest favorite
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
4.96 out of 5 average rating, 201 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 favorite
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.
Guesthouse in Township Of Frontenac Islands
4.98 out of 5 average rating, 156 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 favorite
A modern two-storey home features a sleek design with large glass windows and balconies. The outdoor area includes a spacious deck with seating arrangements, while a decorative neon sign reads 'Water's Edge' against a textured green wall, enhancing the contemporary aesthetic.
Home in Belleville
4.95 out of 5 average rating, 218 reviews

Spectacular Waterfront Home in PEC

Situated on the edge of the beautiful Bay of Quinte, this brand new modern build is sure to steal your breath. Built in 2023, this stunning two-storey waterfront oasis, Water’s Edge, is located just over the Bay Bridge in spectacular Prince Edward County. Featuring two kayaks, fishing gear, outdoor propane fire table, and an upper and lower deck with front row seats to the most unforgettable sunsets. Water’s Edge is conveniently located to both Belleville and all that PEC has to offer.

Top guest favorite
An evening view of the cabin's entrance is lit by soft outdoor lighting. A welcoming porch features a wooden railing and decorative elements, while plants surround the steps. The structure has large glass windows, allowing a glimpse of the interior ambiance.
Farm stay in Newburgh
5 out of 5 average rating, 126 reviews

Escape Goat Hideaway at Barking Goat Farms

“Glamping” at its best. Come experience an off grid all season cabin, tucked away in a very private location at Barking Goat Farms, between Toronto and Ottawa. Enjoy your morning coffee on the lovely screened in porch and spend you evenings around the campfire star gazing amid the peaceful surroundings. Many local attractions to visit or just unplug and relax. Perfect for a couples romantic escape or a fun girls getaway. Enjoy a complimentary meet and greet with our goats and donkeys

Guest favorite
Dome in Plainfield
4.81 out of 5 average rating, 193 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 favorite
A charming cottage is shown at sunset, featuring a metal roof and expansive porch. The structure faces a vibrant sky filled with pink and purple hues. Outdoor seating is arranged on the porch, providing a serene space to enjoy the natural surroundings.
Cottage in Wolfe Island
5 out of 5 average rating, 28 reviews

Stunning Retreat with Sauna and Spectacular Views

A peaceful country retreat with all the little luxuries. Enjoy stunning river views, watching local wildlife and taking in the serenity of the surroundings. Wander the boardwalk to the 60-foot floating dock. Relax in your private sauna or soaker tub overlooking 28 acres of farmland. This craftsman-built cottage is filled with thoughtful details including herringbone tile, reclaimed doors, and custom millwork. Combined with modern comforts, this property is a little piece of paradise.

Top guest favorite
The guest room features two twin beds made with rustic log frames, accented by patterned throws. Light wood paneling covers the walls, and a ceiling fan hangs above. A small nightstand is placed beside one bed, with a lamp and decorative items displayed.
Guesthouse in Chaumont
4.99 out of 5 average rating, 132 reviews

Peaceful Getaway

Kick back and relax in this peaceful space. Guest house has two twin beds, private bathroom, microwave, toaster, Keurig, small refrigerator. WiFi access, outdoor grill with outdoor dining and seating area all under a 16x24 pavilion. This property offers incredible views, fish jumping and canoe and kayak access. End your incredible day fishing off the dock with s’mores at the fire pit. Hunters and fishermen welcome. Plenty of parking so bring your motorized toys! See you soon!

Guest favorite
A green door with three vertical windows stands at the entrance, framed by white siding. A hanging basket filled with colorful flowers is positioned nearby, and a small white mailbox is mounted to the right of the door.
Apartment in Kingston
4.8 out of 5 average rating, 262 reviews

Steps to Portsmouth Harbour & Kingston Penn Tour!

Wonderfully located facing Portsmouth Olympic Harbour and Aberdeen Park in Portsmouth Village, now part of central Kingston. Lots of windows, great views, wood floors, antique furniture. Tea, coffee and a fully equipped kitchen. Covered parking. The park has picnic benches and BBQs. Walking distance to Ontario's oldest pub and five restaurants and eateries. There is a waterfront pathway of 8 kilometers/5 miles only 2 blocks away. One half block from 2 different bus stops.

Top guest favorite
A treehouse sits elevated beside a gently flowing river, surrounded by lush greenery. Stairs lead to the entrance, while the water's smooth surface reflects the vibrant hues of the trees above, creating a serene atmosphere within nature.
Treehouse in Tweed
4.95 out of 5 average rating, 276 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

Guest favorite
A cottage is nestled among tall grass and wildflowers under a vast sky, reflecting warm tones from the setting sun. The surrounding greenery complements the serene landscape, with trees visible in the distance, enhancing the tranquil atmosphere of the countryside.
Cottage in Wolfe Island
4.94 out of 5 average rating, 18 reviews

Sandra's Wee House on Simcoe Island

Cycle or drive to this charming cottage on Simcoe Island for tranquillity, stunning sunsets, birdwatching, solitude, cycling, kayaking, swimming in clear water. Huge sky. Amazing views. Close to historic Kingston and Wolfe Island. ⭐ Panoramic vistas of Lake Ontario ⭐ 200 feet of private limestone shoreline ⭐ Fresh linens, towels and essentials ⭐ Family-owned and treasured, and managed with care ⭐ Outfitted for remote work with high-speed internet, desk and printer

Top guest favorite
Apartment in Kingston
4.98 out of 5 average rating, 182 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

Top guest favorite
Tiny home in Perth
4.93 out of 5 average rating, 354 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!

Popular amenities for Simcoe Island vacation rentals

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