Waterfront vacation rentals in Keswick

A glass table is set on a balcony, featuring an ice bucket holding a bottle of sparkling wine, accompanied by two elegant glasses. Soft string lights provide gentle illumination, enhancing the cozy atmosphere. A potted plant adds a touch of greenery.

4.99 out of 5 average rating, 173 reviews

Fire & Ice Spa w/ Private Sauna!

Welcome to the most unique suite at Friday Harbour Resort! Relax, refresh and unwind in your very own private spa experience which includes large infrared sauna, 3 indoor fireplaces and outdoor fire table. Kiss those winter blues away while you warm up in the most cozy suite, perfect for a romantic getaway. Every stay includes a bottle of bubbly to toast with the one who is most important to you! Make Fire & Ice your next vacation destination and reconnect in a most romantic, relaxing suite!

4.87 out of 5 average rating, 166 reviews

Cottage in Keswick

Waterfront Cottage-Sauna, Dock, 4-bed, 4 Parking

Bright and airy waterfront cottage in one of Lake Simcoe’s most desirable areas. The open-concept layout and unique lot design offer stunning lake views from almost every room. Enjoy custom furnishings, stylish decor, and a fully equipped kitchen—perfect for relaxing getaways or extended stays. Whether you're here for a peaceful retreat or lakeside fun, this cottage provides comfort, beauty, and convenience in a serene upscale setting. Ask us about fun activities that Lake Simcoe offers.

Cabin in Whitchurch-Stouffville

A charming cabin is nestled among tall evergreen trees, surrounded by well-maintained landscaping. Stone steps lead to the entrance, illuminated softly by exterior lights. The lush green lawn flows gently, creating a serene outdoor setting.

4.99 out of 5 average rating, 116 reviews

Lakefront getaway for two on Musselman's Lake

An amazing getaway space for two and your dog on beautiful Musselman's Lake, close to Toronto but feels like you're in the Muskokas. This rustic designer one-bedroom cabin is the original attached cottage that our house grew from. Sit at the dock or on your patio to watch the spectacular sunsets. Have a coffee in the backyard and watch the sunrise over 160 acres of trails out your back door. This is your retreat with high-speed internet, full-size kitchen & dining area to enjoy cottage life.

4.95 out of 5 average rating, 121 reviews

A spacious living area features a high vaulted ceiling and large windows that provide sweeping views of the lake. A stone fireplace and a modern TV complement the cozy seating arrangement, which is paired with a stylish dining area, ensuring a comfortable gathering space.

Cottage in Georgina

Resort-Style Luxury Waterfront Cottage

Experience luxury at our 5-star, Superhost-rated waterfront cottage on Lake Simcoe, just 80 KM from Toronto! A guest favorite, it offers breathtaking sunsets and sunrises from the living room and loft. Relax on the sandy beach with waist-deep waters, and enjoy the patio, BBQ, bar, lounge, kayaking, and fishing. With a fully equipped kitchen, 3 bedrooms, and 2 bathrooms, it comfortably accommodates up to 8 guests. Book your dream getaway today for the perfect blend of relaxation and adventure!

4.96 out of 5 average rating, 135 reviews

A peaceful beach scene captures the soft sand shoreline leading to the water's edge. Gentle waves lap at the shore, and the sky is filled with warm sunset hues. A cottage is visible in the background, nestled among trees, enhancing the serene atmosphere.

Cottage in Tiny

Ultimate Georgian Bay Vacation Getaway

Come and stay at our beautifully renovated *all-season* beachfront cottage and enjoy a breathtaking panoramic view of Georgian Bay! You'll discover the cottage sitting atop a sand dune, right on one of the most stunning freshwater beaches in the world. This rare location hosts a private covered deck hovering over the white sand, in a beach house closer to the bay than anywhere else around! Summer guests also enjoy use of a heated salt water pool and large resort deck created by Paul Lafrance.

4.82 out of 5 average rating, 103 reviews

A backyard view features a grassy area with stone pathway leading to a dark exterior cottage. Outdoor furniture, including a dining table and chairs, is situated nearby. Large windows offer glimpses of the serene environment, with a barbecue grill positioned to the side.

Bungalow in Georgina

Lake Simcoe Retreat

Holiday retreat on Lake Simcoe with Sunset view. Front bedrooms and kitchen facing the river and Living room, Dining room, other rooms and open kitchen facing the Lake. You can enjoy the views from every part of the house. Totally renovated interior. High speed internet, a work space, Close to many world class family activities including Fishing, Hunting, Ice Fishing, Snowmobiling. Conveniently located an hour from Toronto, closest small town 5 minutes drive and Sutton town 12 minutes drive.

Home in Nestleton Station

4.99 out of 5 average rating, 147 reviews

Retreat 82

Located just a little over an hour from Toronto, this cozy and unique lakefront cottage is the perfect place for a relaxing couples getaway. Offering private access to Lake Scugog with an oversized dock for you to take advantage of water activities, enjoy your morning coffee and watch some of the best sunsets on the lake. The cottage sits only 15 min. from the quaint town of Port Perry where you can go to enjoy its brewery, incredible cuisine, farmers markets, and picturesque Main Street.

4.99 out of 5 average rating, 168 reviews

A serene lake view captures twilight colors reflected on the calm surface of the water. Soft pastel hues of pink, purple, and orange fill the sky, while the silhouette of trees frames the horizon, adding to the peaceful ambiance of the lakefront.

Cottage in Keswick

Granny's Cottage

Granny’s Cottage is located on Lake Drive East across the road from Lake Simcoe. Our private lakefront is yours to enjoy. Our lakehouse equipped with mini fridge and chairs while looking out over beautiful Lake Simcoe. Lakehouse is available late spring to early fall. This cozy cottage is newly renovated with all the comforts for a much needed getaway. Available for your use is a badminton net, 2 kayaks and a large canoe (seasonal). There is also a secure lock up for you bicycles.

4.97 out of 5 average rating, 179 reviews

A spacious living area is equipped with a large sectional sofa and a rounded ottoman. A flat-screen television is mounted on the wall, while a mirror reflects natural light from the sliding glass doors leading to an outdoor patio. Plants are arranged to enhance the decor.

Cabin in Orangeville

Hockley Valley Cozy Cottage

Take it easy at this unique and tranquil setting where the entire property is yours! Freshly renovated cottage only 600M from Hockley Valley Resort and also close to restaurants and hiking trails. This cottage sleeps 4 comfortably with separate bedroom. Picturesque setting directly on Nottawasaga river with mature gardens and plenty of outdoor space. Morning coffee or afternoon drinks under the covered gazebo at the waters edge or relax in the hammocks, this place truly has it all.

4.98 out of 5 average rating, 120 reviews

The exterior of a modern home is highlighted at sunset, showcasing large windows that reflect warm interior lighting. A spacious backyard features green grass, a dining area under a gazebo, and a hot tub on the deck, creating an inviting outdoor space.

Home in Barrie

Waterfront home, city/sunset view & steps to beach

Waterfront w/ private dock. Renovated upscale home + new hot tub, full city bay views w/summer sunsets+sunrise. Steps to Minet's Point beach & park. 4 proper bdrms & 2 pull out couches(Queen & Twin) 3 full bthrms + sauna, over 2400+sqft. Prking for 3 cars, additnal prking available via lot beside. Gas BBQ, fire pit, 2x gas FP, fast Wifi & 77" TV, wshr/dryr. 48amp EV pwr. Minuts to Marina for Seadoo/boat rentals. Wlking distnce to fine dining/pubs & stores. Kite surf & ice fishing

4.95 out of 5 average rating, 131 reviews

A relaxing outdoor space features a circular fire pit surrounded by four red Adirondack chairs. A stack of firewood sits nearby. Behind the seating area, a glimmering glass geodesic dome is surrounded by lush greenery and open sky.

Dome in Zephyr

Glass Dome - Sleep Under The Stars- Free Sundays

Discover this new, stunning 22ft Glass Geodesic Dome nestled in the heart of Uxbridge. Imagine waking up surrounded by 360-degree panoramic views of the natural landscape Please note... its FULL WEEKEND STAYS ONLY - BOOK FRIDAY AND SATURDAY-SUNDAY IS FREE. This allows guests to fully enjoy their Sunday without feeling rushed to check out at 11am. Enjoy all day Sunday with option of staying the evening. 8X12 BUNKIE NOW AVAIL. SLEEPS 4 $100/NIGHT ( 2 bunk beds)

4.96 out of 5 average rating, 108 reviews

The exterior of a two-story log cabin is illuminated at night, showcasing its natural wood finish and gabled roof. A welcoming entryway features a wooden staircase leading to the front door. Surrounding green grass provides an open space, enhancing the rustic charm.

Cottage in Gilford

Lake simcoe Waterfront Log Cabin near Toronto

*Great for ice fishing on lake Simcoe* Some of the best ice fishing in Ontario, lots of Jumbo Perch, trout, whitefish etc Relax with the whole family at this peaceful place to stay. This two story, modern cottage built entirely of logs and situated on Lake Simcoe is the perfect getaway. Whether you are in the mood for entertainment, adventure, or simple relaxation, this cabin can provide you a comfortable and picturesque stay throughout your visit.

Popular amenities for Keswick waterfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

4.78 out of 5 average rating, 40 reviews

A spacious living room showcases a comfortable gray sofa facing a wall-mounted TV. A coffee table is centered on a light area rug, and a desk with a chair is positioned in the corner. The kitchen area is visible in the background, featuring modern appliances and a dining table.

Apartment in Pickering

Cozy Entire Apt - Quietness & Privacy

4.84 out of 5 average rating, 64 reviews

The living room features a comfortable leather reclining sofa and a simple grey couch, complemented by a coffee table and a media stand with a television. Natural light filters through the large windows adorned with light curtains, creating a bright and welcoming atmosphere.

Apartment in Alliston

Stunning 1 Bedroom unit

A wooden ladder-style shelf displays decorative items against a soft gray wall. A bright yellow 'Smile' sign sits above a framed print titled 'DREAM' on a small easel. A lantern and a decorative floral arrangement complete the scene.

4.89 out of 5 average rating, 35 reviews

Luxury Serene Escape @ Friday Harbour Resort

An outdoor seating area is furnished with a large sectional sofa and a table, providing a comfortable space for relaxation. The balcony overlooks a pool surrounded by greenery and modern buildings, offering a serene view of the outdoor amenities.

4.97 out of 5 average rating, 37 reviews

Modern Luxury Delight with a Pool and Hot Tub

A modern living area features a gray sofa adorned with decorative pillows, accompanied by a glass coffee table and a patterned area rug. Wall shelves display decorative items and potted plants, adding a fresh touch to the muted backdrop.

4.98 out of 5 average rating, 42 reviews

Trendy 1 Bdrm w/Pool & Hot Tub View

5 out of 5 average rating, 12 reviews

A modern home showcases a spacious balcony with outdoor seating, surrounded by potted plants and garden features. Below, a well-maintained driveway leads to a two-car garage. The architecture reflects a blend of contemporary design and outdoor living spaces, enhancing the overall aesthetic of the property.

Apartment in Ajax

Lake Breeze Apartment, EV Charging & Free Parking

4.89 out of 5 average rating, 9 reviews

2 Bedroom Luxury Suite @ Friday Harbour Resort

A contemporary living space features a spacious sofa with cozy blue pillows set against large windows. A round coffee table rests on a patterned rug, and stylish dining chairs surround a kitchen island in the open-concept design.

4.96 out of 5 average rating, 51 reviews

NEW Luxurious Corner Unit at Friday Harbour Resort

Waterfront house rentals

Two black Muskoka chairs are positioned on a wooden dock, facing a serene lake. The sky is filled with soft clouds, casting gentle reflections on the water's surface, creating a peaceful atmosphere for relaxation.

5 out of 5 average rating, 38 reviews

Blu Lake House | Waterfront August Special

4.93 out of 5 average rating, 27 reviews

The image captures a private lakeside setting during sunrise. Adirondack chairs surround a fire bowl on a circular stone area. A private dock extends into the calm lake, reflecting the soft hues of morning light. Lush greenery frames the scene, enhancing the tranquility.

Home in Kawartha Lakes

Lakefront Bungalow "Sunrise Bay" Kawartha Lakes

5 out of 5 average rating, 16 reviews

Home in Egbert

Underhill Riverside Retreat-Nature Preserve

4.92 out of 5 average rating, 86 reviews

A spacious private room is visible, featuring a comfortable couch and a wooden coffee table on a soft area rug. A double bed is positioned along one wall, with natural light streaming in through patio doors that open to the outside deck.

Home in Washago

Waterfront Muskoka guest suite near Casino Rama

The cottage presents a charming exterior, showcasing a white facade with decorative trim. A neatly paved driveway leads up to the entrance, framed by vibrant yellow flowers and lush greenery. A clear view of Lake Simcoe is visible in the background under a bright blue sky.

4.82 out of 5 average rating, 74 reviews

Beautiful lakefront Cottage on Lake Simcoe.

4.77 out of 5 average rating, 106 reviews

A three-story luxury house is shown, featuring a stone facade and large front steps. Lush greenery surrounds the property, and the well-maintained street leads towards the nearby beach. Clear blue skies create a bright and inviting atmosphere.

Home in Pickering

Beach House: First Floor

A charming brick house is surrounded by well-maintained gardens and lush green grass. The exterior features a inviting walkway and multiple windows. Mature trees provide shade, contributing to a serene outdoor environment. A small shed and fence are visible in the background.

4.77 out of 5 average rating, 52 reviews

Sunrise Villa on the Lake

A spacious lakefront property is surrounded by lush greenery and trees. The area features a sandy beach leading to the water, with a wooden dock extending over the lake. Several outdoor chairs are positioned on the lawn, offering a relaxing view of the serene environment.

5 out of 5 average rating, 58 reviews

Luxurious Lake House for Family Stays

Waterfront condo rentals

A modern living area features a light-colored sofa adorned with decorative pillows, positioned next to a wooden coffee table. A striped area rug lies beneath, while a kitchen island with bar stools and stainless steel appliances is visible in the background.

4.97 out of 5 average rating, 101 reviews

Cozy Stays – Your Fall Getaway at Friday Harbour

An aerial view captures Friday Harbour Resort, highlighting its serene waterways and lush green landscapes. The sprawling development showcases a variety of buildings alongside the water, with a beach club pool visible in the foreground. The scene is framed by trees and the horizon over Lake Simcoe.

4.86 out of 5 average rating, 237 reviews

2BR Getaway at Friday Harbour All Season Resort

A stylish living area features a cozy dark sofa beside a circular coffee table. A large flat-screen TV is mounted against a striped wood accent wall. Soft natural light filters through sheer and blackout window treatments.

4.98 out of 5 average rating, 86 reviews

Stunning 1BR w Pool ~ Free Parking & Self Check-In

A comfortable outdoor balcony area features two lounge chairs and a glass-top table. Planters with various plants are positioned around the space, enhancing the natural ambiance. A textured rug adds warmth, completing the inviting outdoor setting.

4.94 out of 5 average rating, 178 reviews

Stylish getaway condo, resort living

A wide wooden boardwalk is shown alongside a marina, with modern buildings lining the waterfront. Soft sunlight reflects off the water and the boats docked. Comfortable blue chairs are placed on the green lawn, inviting relaxation while enjoying the serene harbor view.

4.94 out of 5 average rating, 233 reviews

Designer Condo with beautiful harbour view.

The living room features a comfortable sofa adorned with decorative pillows. A Smart TV is positioned on the wall opposite a glass dining table set for four. Natural light floods the space through large glass doors, offering views of the private patio.

4.91 out of 5 average rating, 151 reviews

Beautiful Condo, 2 Bedrooms and a Den in a Resort!

A bright living area is showcased with a red sofa and a glass coffee table positioned on a patterned rug. Large glass doors open to a balcony. A colorful wall art piece features a scenic landscape, adding a vibrant touch to the space.

4.94 out of 5 average rating, 131 reviews

Friday Harbour Luxury Condo Escape, Sleeps 4

An open-concept living space features modern furnishings and sleek cabinetry. A spacious grey sofa and an accent chair are set around a coffee table. The kitchen area includes stainless steel appliances and a breakfast bar with four stools, creating a warm and functional atmosphere.