Vacation rentals in Simcoe Island

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Top-rated vacation rentals in Simcoe Island

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Top guest favorite

A charming houseboat is illuminated softly at night, featuring large windows that reveal a cozy interior. The surrounding trees create a natural privacy barrier, while a wooden walkway leads to the entrance. The starry sky adds a touch of magic to the scene.

Houseboat in Yarker

5 out of 5 average rating, 211 reviews

4 season cabin in the woods -A romantic Riverboat!

You won’t forget this memorable experience! A 1974 River Boat has been lovingly transformed in to a whimsical all season cabin. Come for the fantasy then bask in the comfort and romance of it. Luxurious amenities include everything but the kitchen sink..literally! A perk to no running water is that I do your dishes at my place while you relax! The houseboat is tucked in to the trees and just across the road from a lakefront park. Plus...a Playshed full of seasonal outdoor equipment is included!

Guest favorite

A vibrant green sofa is adorned with decorative pillows and positioned near a window. Light filters through sheer curtains, illuminating woven wall hangings and leafy plants that add texture to the space.

Home in Kingston

4.89 out of 5 average rating, 142 reviews

Stay & Shop The Boho Room Entire 3 Bed, 1 Bath

Private entrance to a spacious 3 bedroom, 1 bath with kitchenette & small living room. One Parking Spot. 4 minute drive from Airport & 15 minute drive to downtown core. Kingston has always been a makers town where arts culture runs deep; visit the limestone city while occupying one half of a makers house. The Boho Room is a textile & handcrafted goods company that has grown into an Airbnb experience. Filled with woven wall hangings & nostalgic art prints, you are always welcome to stay & shop.

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

4.97 out of 5 average rating, 133 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, 126 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

An inviting dining area features a round wooden table surrounded by black chairs, setting a comfortable atmosphere for meals. A stylish chandelier hangs above, providing soft lighting. Light from large windows brightens the space, highlighting the warm tones of the wooden flooring.

Home in Kingston

4.99 out of 5 average rating, 451 reviews

Capitan Burn's House on Wellington

Superb location in historic downtown Kingston, 3 blocks from princess street, walking distance to Queens, waterfront, City park, both hospitals, and the K-Rock center. Short drive to RMC and Fort Henry. Fully outfitted kitchen and beautiful courtyard. Fully renovated 175 year old Historic limestone building, with a cozy gas fireplace for the winter. If you need more space or the dates booked, please check out our other listing! airbnb.com/h/kingstonloft Licence #: LCRL20210000899

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, 101 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!

Top guest favorite

A spacious deck features red Adirondack chairs positioned for lake views, overlooking calm waters at sunset. The horizon captures warm tones, while the reflection on the water creates a serene ambiance. Clear railing allows uninterrupted sightlines of the scenic surroundings.

Cottage in Prince Edward

4.97 out of 5 average rating, 157 reviews

Picton Bay Hideaway

Picton Bay Hideaway is a family owned and operated licensed waterfront bungalow with 2 bedrooms and a walk out basement that can comfortably sleep up to 4 adults plus 2 children. This getaway is ideal for those wanting to slow down, relax and spend quality time with loved ones or for those who are looking for a quiet and peaceful workspace retreat. Whether you are a wine, food, fishing, or a beach goer, there is something for everyone in Prince Edward County (PEC)!

Superhost

A modern living room features a comfortable gray couch adorned with light-colored throw pillows. A round coffee table sits in front, complemented by two framed wall art pieces. Natural light enters through a nearby window, illuminating the warm wooden flooring.

Townhouse in Kingston

4.82 out of 5 average rating, 264 reviews

Cosy Downtown Apartment With Parking!

Discover a charming downtown Kingston apartment, occupying the main floor of a townhome. Enjoy a well-furnished bedroom with a Queen bed and a couch in the living room that converts into a double bed. The fully-equipped kitchen makes cooking easy! A 5-minute stroll to historic Princess Street. Conveniently, there's parking available behind the house, perfect for your ideal getaway! Licensed for short term rental with the City of Kingston - License #LCRL20230000551

Top guest favorite

The bedroom features a queen size bed with a tufted headboard, complemented by two bedside tables, each with a decorative lamp. A soft, neutral blanket covers the foot of the bed, and subtle artwork adorns the wall above the headboard.

Apartment in Kingston

4.98 out of 5 average rating, 136 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

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

4.83 out of 5 average rating, 162 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. It has its own private entrance at the back of the house up a set of outdoor, narrow, metal stairs (the original fire escape). It also has air conditioning. 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.

Superhost

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, 148 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.

Top guest favorite

A cozy living area features a rustic wood stove, complemented by two stylish chairs and a vibrant area rug. Large windows frame the serene view of Lake Ontario, enhancing the space's inviting ambiance.

Guesthouse in Prince Edward

4.98 out of 5 average rating, 261 reviews

Little Ben Prince Edward County

Located ten feet from Lake Ontario, in the heart of beautiful Wellington, Little Ben is a fully renovated 1 bedroom cottage in the centre of wine country. Little Ben offers a fully equipped kitchen, a dining area and a comfy living area with a wood stove. The true glory of Little Ben exists outside its walls--you are just a mere ten steps down to your own limestone beach on Lake Ontario! Licence Number ST-2019-0358