House vacation rentals in Keswick, Georgina

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Top-rated house rentals in Keswick, Georgina

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Guest favorite

An A-frame house featuring a white exterior and a steep roof stands beside a serene lake. A gravel driveway leads to the entrance, surrounded by greenery. Large windows allow ample natural light, providing views of the lake and trees in the background.

Home in Little Lake

4.88 out of 5 average rating, 111 reviews

Lakefront detached house on the little lake

♥️an unique, lovely elf house in front of the little lake. Here you’ll find a unique hideaway in the middle of the city Barrie with gorgeous lake views as far as the eye can see. ♥️ Only one hour drive from Toronto. Walking distance to everywhere (shoppers,restaurants, cinemas….) ♥️This home including new furniture, microwave, coffee maker, washing machine and all other appliances ! Walk out the back door and be greeted by our updated dock where you can fish for pike, perch, pickerel and bass.

Guest favorite

A fire pit area is surrounded by multiple Muskoka chairs, with a vibrant fire burning in the center. The expansive lawn is meticulously landscaped, framed by lush greenery and a view of the lake house's covered porch, illuminated by soft evening light.

Home in Georgina

5 out of 5 average rating, 6 reviews

Royal Beach Lake House & Spa w/ Hot Tub & Sauna

Royal Beach Lakehouse & Spa is your perfect experience of lakeside luxury! Sink your toes into the sand as you relax with your loved ones, our luxury retreat boasts panoramic views of Lake Simcoe! Wake up feeling refreshed after enjoying your private infrared sauna and fun water toys and activities. End your days with a spectacular sunset from your lakeside hot tub & firepit! Our chef's dream kitchen also awaits! This fully equipped lake house is sure to become your next vacation destination!

Guest favorite

A well-maintained backyard features a circular fire pit surrounded by lush green grass. A fenced area provides privacy, while a tranquil pond is visible in the background, framed by tall reeds. A gazebo offers additional outdoor seating options.

Home in Holland Landing

4.96 out of 5 average rating, 25 reviews

Private river access with pool, canoes, kayak

Cozy, homely and peaceful cottage-like getaway conveniently located close to Toronto and modern conveniences while also a short distance away from nature. Perfect for young families or small groups. Guests have exclusive use of the entire 2nd floor, which is like a spacious, fully stocked apartment unit (see below for details) with separate entry Please note: -the owners live on the first floor with friendly dogs (separate entrance for guest) -air conditioning is not available but fans are

Top guest favorite

A modern kitchen area is presented with white cabinets and stainless steel appliances. A glass dining table, set with blue dishware and decorative candles, sits centrally, surrounded by sleek grey chairs. Soft lighting creates an inviting space for meals and gatherings.

Home in Oak Ridges

4.96 out of 5 average rating, 113 reviews

Place You Want To Stay at With Tons of Options ! !

Brand New, Modern & Open Concept Basement Unit With 9 ft Ceilings & Brand New LG Appliances, Located at Bathurst & King Street In Richmond Hill. Beautifully Decorated & Fully Furnished For Your convenience, Making it a Comfortable Stay - Min walk to Community Park With Playground For The Kids - Min Drive From Lake Wilcox & Bond Lake + Many Other Trails - Tons of Different Variety Of Restaurants - Grocery Stores - Multiple Gyms Close By - Coffee Shops - Public Transportation and Much More

Top guest favorite

A calm lake scene is visible, featuring a wooden dock extending into the water. Two chairs are positioned on the dock, inviting relaxation. Lush greenery surrounds the area, with trees framing the view, and gentle ripples on the lake reflect the clear sky.

Home in Nestleton Station

4.99 out of 5 average rating, 127 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.

Guest favorite

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

4.97 out of 5 average rating, 108 reviews

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

Guest favorite

A spacious living area is presented with comfortable seating arrangements and modern decor. A pool table is positioned in the background, while large windows allow natural light to fill the space. A fireplace serves as a focal point, enhancing the welcoming environment of the room.

Home in Georgina

4.96 out of 5 average rating, 28 reviews

PoolTable 8MinsToLake PingPong Foosball King Beds

Welcome to Simcoe Sanctuary, a stunning 7-bedroom, 5.5-bath retreat just 8 minutes from the shores of Lake Simcoe. Perfect for families and groups, this modern getaway offers sleek design, spacious living areas, and endless entertainment, including a ping pong table, pool table, and foosball table. Whether you’re exploring the lake, relaxing in style, or enjoying game nights, Simcoe Sanctuary delivers the ultimate escape with a perfect balance of comfort, fun, and convenience.

Superhost

An inviting outdoor pool is surrounded by a wooden deck, offering views of the lush green landscape. A tranquil pond is visible in the distance, accompanied by a charming boathouse and mature trees, enhancing the serene atmosphere of the retreat.

Home in Keswick

4.78 out of 5 average rating, 36 reviews

Beautiful Waterfront Cottage with Pool&HomeTheater

🌲Lake Simcoe Getaway Escape to our rustic-chic Lake Simcoe retreat—perfect for families and friends! Enjoy a private swimming pool, sunny backyard with BBQ, cozy pool table, and a premium home theater for unforgettable movie nights. Just minutes from the lake, this farmhouse-style cottage blends relaxation and fun. Whether you're exploring scenic trails or relaxing by the pool, it's the perfect spot to unwind and create lasting memories. Book your getaway today! 🌞🌲

Top guest favorite

A cozy living area is filled with soft lighting and modern decor. A blue sofa is complemented by accent pillows, while a stylish chair in warm tones sits nearby. A round coffee table is placed atop a decorative rug, with a floor lamp enhancing the inviting ambiance.

Home in Georgina

4.88 out of 5 average rating, 16 reviews

Luxury 4BR Retreat ~ By Lake Simcoe ~ Full Privacy

Welcome to our Newly Furnished and Professionally Cleaned home in Georgina - minutes drive to Lake Simcoe! ✓ 4 BR, 3.5 WR - 100% Private & Spotless ✓ Just 5 Minutes to Keswick Beach ✓ Fully equipped kitchen for preparing meals ✓ Cozy Family & Living Rooms ✓ High-quality Linens. Comfy Beds ✓ 70" Smart TV, High-speed WiFi ✓ Laundry washer & dryer ✓ Private Backyard ✓ Free parking! ✓ Safe neighbourhood Book your stay with confidence and make unforgettable memories!

Guest favorite

The living area features a grey couch adorned with assorted cushions and a vibrant throw blanket. A coffee table is centrally positioned, holding decorative items and a floral centerpiece. Natural light filters through large windows, highlighting the artwork on the walls and the soft rug beneath.

Home in Holland Landing

4.87 out of 5 average rating, 23 reviews

Bright & Clean One Bdrm Aprt

Enjoy a stylish experience at this beautiful one bedroom apartment with all the amenities you need ! Located in beautiful Holland landing Neighbourhood, minutes from upper Canada Mall,Costco, Cineplex movie Theatre, 4004 and 400, Go Train and Southlake Hospital. Feel cozy on the couch or in the bed with Smart TV or access to a Fully equipped kitchen with all the tools necessary for you needs. Backyard access with a patio furniture the summer to enjoy outside!

Guest favorite

A living space features a light-colored sofa with orange accent pillows, positioned beside a subtle stone fireplace. A coffee table is centered on a light area rug. Natural light enters through large windows, illuminating the room, while a dining area with wooden chairs and potted plants is visible.

Home in Newmarket

5 out of 5 average rating, 6 reviews

Urban Oasis Guest house

Your family will be close to everything when you stay at this centrally located place! 🏠 - 13 minutes walk from Newmarket bus terminal 🚶‍♀️ - 11 minutes walk to Upper Canada Mall 🛍️ - 4 minutes drive to grocery and Shoppers Drug Mart 🛒 - 8 minutes drive from South Lake Hospital 🏥 - 9 minutes drive to Fairy lake and downtown Newmarket 🌳 - Close to all grocery stores and different restaurants 🍕 - Easy access to highway 404 and highway 400 🛣️

Superhost

A spacious living room features a large sectional couch and a round coffee table. Natural light floods the space through multiple windows, illuminating a cozy bay window seating area. A decorative plant and a mounted flat-screen TV add to the welcoming ambiance.

Home in Barrie

4.86 out of 5 average rating, 118 reviews

King Bed Farmhouse- w/ Fire-pit, 75" TV, Ping Pong

Great location- 7 min to Waterfront, 18 min to Horseshoe Resort and Snow Valley Ski Resort, 18 min to Vetta Spa. Entire Private and Cozy 4 Bedroom 2 bath Home - Fully Equipped Kitchen! - Media Room w/ 75" Smart TV, Ping Pong & Foosball table!! - Outdoor Patio with Fire-pit area! - Fast Wifi and Parking for 4 Cars!! - 5 Beds and a Sofa Bed. - Park Across the Street... - Comfy Bay Window Seating!!!