Vacation rentals in Keswick, Georgina

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Top-rated vacation rentals in Keswick, Georgina

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

A rooftop terrace features an expansive seating area with grey wicker furniture arranged around a central table. Lush greenery outlines the space, providing a vista of the city skyline under a partly cloudy sky.

Apartment in Downtown Toronto

4.96 out of 5 average rating, 45 reviews

Ambient Vibe Downtown | CN Tower + Lake View Condo

The most exclusive condo where you can set the vibe by changing all the lights to your favourite colour. The perfect getaway and a home away from home. Immerse yourself in this two bedroom, two washroom Airbnb, with the perfect view of the CN Tower, lake and city skyline from the private balcony. Enjoy one of the only rooftop pools/terrace with unparalleled views of the city and cabanas/sun beds available to all guests, with everything you need to make your stay exceptional. Best location in TO

Guest favorite

An open-concept living area features large windows allowing natural light to fill the space. A modern dining table with eight chairs sits adjacent to a sleek kitchen island. A comfortable seating area is positioned near a stone fireplace, creating a warm ambiance.

Home in Stayner

5 out of 5 average rating, 8 reviews

The Vault

Nestled in a serene location, you’ll feel close to everything yet far from everyone. • Prime Location: Just meters away from ATV and snowmobiling trails. • Outdoor Adventures: Near Blue Mountain for skiing in the winter and Georgian Bay for swimming in the summer. • Plenty of space at the front to park ATVs, snowmobiles, or any gear you bring—space for everything! Whether you’re seeking adventure or relaxation, this property is the ideal base for your next trip. Book now and make memories.

Superhost

Home in Tiny

4.68 out of 5 average rating, 224 reviews

Private log cottage on 2 acres

Spectacular 4,500 sq ft Scandinavian scribed white pine log cottage on 2 acres lot, walking distance - 5 minutes to Georgian Bay (Balm Beach) white sand, short drive to shopping, ski hills and Golf Courses, Go-carts, mini golf; year-round vacation cottage. Sauna (extra $) For winter lovers, just imagine having a glass of wine in front of a wood fireplace when it is lots of snow outside....2 minutes away from an open skating rink. Pool Table, foosball table, pingpong table, Netflix, HD, Wi-fi.

Guest favorite

A spacious outdoor deck is surrounded by lush greenery, providing a serene atmosphere. Comfortable seating arrangements, including a dining set, invite al fresco meals and gatherings. The natural light filters through the trees, enhancing the tranquil outdoor experience.

Cottage in Innisfil

4.95 out of 5 average rating, 101 reviews

Innisfil retreat: Hot Tub, Sauna, Game room

Welcome to our serene Lakeside Retreat in Innisfil, a haven of relaxation and fun. This getaway features a rejuvenating sauna and hot tub, perfect for unwinding after a day of adventure. Entertain with family and friends in our game room, which includes a pool table, air hockey table, and dartboard. The large outdoor deck is ideal for BBQs, complemented by a cozy fire pit for evening relaxation. The house offers five beautifully appointed bedrooms, ensuring comfort for everyone. Water softener.

Guest favorite

A modern courtyard features sleek glass walls and a patio area. Comfortable gray seating surrounds a white coffee table, complemented by soft landscaping with a small tree. Natural light fills the space, creating an inviting atmosphere for relaxation.

Condo in Innisfil

4.88 out of 5 average rating, 25 reviews

The Boathouse: *pools*courtyard lounge*firepit*

Immerse in maritime charm at our nautical Airbnb. Sea-inspired decor, pool view, and cozy comfort await. Enjoy some welcome snacks and grill up some food while taking in the balcony view. Head down to the pools to catch some sun on the comfy patio furniture. After a long day, sink into the Endy mattress for a sleep experience you will not forget. Simply pull out the couch to reveal a second full bed to provide a good night's rest. Bring the kids or gather some friends and sail into relaxation.

Guest favorite

Cottage in Wasaga Beach

4.94 out of 5 average rating, 233 reviews

Charming riverside cottage, walk to beach

Charming riverside cottage available on Wasaga Beach. Just a 4-minute stroll from a pristine sand beach. Immerse yourself in nature's beauty while enjoying modern amenities, including a private hot tub for relaxation. Unwind with a friendly round of mini-golf or gather around the fire pit for cozy evenings under the stars.Create lasting memories at this perfect oasis that combines riverside tranquility, mini-golf fun, hot tub relaxation, and the warmth of a fire pit. Your dream getaway awaits!

Superhost

Condo in Innisfil

5 out of 5 average rating, 4 reviews

Luxurious 2-Bed, 2-Bath Furnished - 5 Star Resort

Spectacular view of marine and lake view! Abundant natural light. Opening to a spacious atmosphere. 1,010.00 sf, luxurious living space. 2 bedrooms equipped, 2 upgraded bathrooms. Fully furnished, all brand new furniture. Hot top available all season. Kitchen includes Island, microwave oven, toaster, kettle (all new). Dining table seats four. 65 inch Sony smart TV. Washer & dryer. Over 15 days+ require to pay utilities. Underground parking. Wifi included. long term rental available.

Guest favorite

A wooden dock extends into clear water, featuring vibrant red lounge chairs positioned for relaxation. The shoreline is bordered by smooth stones and gentle waves, with lush greenery in the background enhancing the natural setting.

Cottage in Kawartha Lakes

4.95 out of 5 average rating, 165 reviews

Balsam Brilliance, Modern Lake Home.

Picturesque lakehouse nestled on 370ft of prime sandy waterfront on pristine Balsam lake at the top of the Trent canal. EVERY room has breathtaking views of the water. 4 bedrooms, 2 bathrooms and large, fully stocked open-concept kitchen with upscale appliances – perfect for any large group. Excellent internet Large docks to park your boat or rent from Balsam RPM Only 1.5 hours from Toronto 5 minutes to Coboconk Note that during July and August only Friday to Friday bookings are accepted.

Top guest favorite

An inviting living area features a cozy sofa adorned with an orange throw blanket. A round coffee table sits on a soft rug, while a wall-mounted TV is positioned above a stylish wood-paneled accent wall. A bright kitchen is in the background, enhancing the open space.

Condo in Innisfil

4.98 out of 5 average rating, 59 reviews

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

Embark on a journey of unparalleled luxury as you discover our exquisite suite, crafted to offer an escape that transcends the ordinary and leaves you refreshed. Experience opulent design, a full bedroom, a spacious living area with TV, high-speed WiFi, fully stocked kitchen, and a stunning balcony . Enjoy the breeze by the sun, and BBQ on our new electric grill. Access our outdoor pool and hot tub, no fees or reservations required. Additional fees may apply for 30 nights and more.

Guest favorite

A cozy outdoor seating area features comfortable gray wicker furniture arranged around a wooden deck, with decorative flower boxes enhancing the backdrop. Surrounding greenery provides a serene atmosphere, complemented by clear blue skies and a nearby heating element for cooler evenings.

Apartment in The Beaches

4.92 out of 5 average rating, 116 reviews

One bedroom vacation rental at The Beaches

Welcome to Our Cozy Retreat! Escape to our relaxing, perfectly situated in a prime location at the Beaches, a few minute walk to the: - Beautiful beaches - The vibrant waterfront boardwalk - Bike path and parks - A variety of delicious restaurants, pubs and shops Local Amenities including such as: - Spa and wellness services - Nail and hair salons - Flower, gift, and clothing shops - Grocery stores - Yoga studio - History Toronto (concert venue) - Theatre

Top guest favorite

An open-concept living area showcases a spacious island with a wine rack, surrounded by wooden cabinetry and granite countertops. A large dining table is visible in the background, along with a comfortable seating area featuring grey couches. Soft lighting enhances the inviting atmosphere.

Home in Wasaga Beach

4.92 out of 5 average rating, 12 reviews

Hot March Deal at The Perfect Getaway

Welcome to Your Serene Georgian Bay Retreat! Just a two-minute walk from the beautiful Wasaga Beach, this cozy home is perfect for family getaways. With 8 bedrooms(5 queen beds and 3 bunk beds) and 2 full bathrooms. Enjoy stunning sunsets, spacious living and a fantastic size backyard for endless fun. Comfort and Convenience Close to shops, parks, and ice cream parlour’s, with Collingwood nearby for more adventures. Book Your Family Escape Today

Guest favorite

Villa in Tiny

4.9 out of 5 average rating, 146 reviews

Beautiful Getaway Location - Cuddles Cove

Enjoy a all year round getaway either personal or corporate retreat at this spacious, well equipped Bungalow located short minutes walk from beautiful sand beach access. This newly built cottage is approx 5,000 Sqft with an additional 1,000 Sqft covered balcony offering accommodations of 6 queen beds, 1 Luxury full kitchen, 1 BBQ and lots of entertainment! Enjoy a nice Quiet getaway in the lovely community of Tiny! STRTT-2025-152

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What guests are saying

Luxurious 4BDRM-King Bed-Barrie-near Snow Resorts

4.92 out of 5 average rating, 90 reviews4 days ago

We had a wonderful stay in this beautiful house. We booked it for a small get-together with our friends. The house is spacious and beautifully decorated. Jerry made sure everything was set up to make our stay comfortable. Although the pool wasn’t open during our visit, it’s definitely something we’re looking forward to next time. We are glad we chose this place. Thanks again for hosting us!

Home in Barrie

What guests are saying

Lakeside Retreat: Viva La Vida

4.87 out of 5 average rating, 68 reviews1 week ago

We stayed here for a weekend and had such a great time! The place is cute, clean, and located in a quiet neighborhood with the most beautiful view. It was the perfect spot to relax and unwind. The host was also super accommodating and made sure we had everything we needed. Would definitely recommend this place to anyone looking for a peaceful getaway!

Home in Bowmanville

What guests are saying

The Hideaway Balm Beach Cottage

5 out of 5 average rating, 41 reviews1 month ago

For my birthday last weekend, I was looking for a cottage to getaway for work and to celebrate, and I immediately fell in love with this cozy little house when I saw it. It has everything I could ask for to create a warm and welcoming atmosphere, just like home. I spent my birthday here, and I couldn't have asked for a better place. The Scandinavian interior style is my absolute favorite, and every detail of the decor and soft furnishings was perfectly chosen. It’s clear that the owner, Lina, put a lot of thought and care into making this space feel like a true home for visitors. Each room was spotless, and everything I needed for a comfortable stay was provided. Lina is incredibly understanding and accommodating. We all had an amazing time and are so grateful for this experience. Five stars aren’t enough to express how much we enjoyed our stay and how this beautiful house made our birthday weekend so memorable. Highly recommend!

Cottage in Tiny

What guests are saying

Little slice of heaven!

5 out of 5 average rating, 9 reviews1 month ago

Cozy, cute, clean and comfortable! Very quiet and peaceful surroundings which is just what we needed. Good location, felt private and tucked away but it’s only 15 minutes or so from Orillia if you need more restaurant/coffee shop options. Sharon and Rob were attentive hosts and very friendly. We would stay here again

Apartment in Washago

What guests are saying

Teddy Bear Cottage

4.76 out of 5 average rating, 79 reviews2 days ago

We stayed at the Teddy Bear cottage over the long weekend in Spring with two families and 3 children ages 8-13. The cottage is spacious and beautifully laid out for both rainy and sunny days. We found the set up to be very family friendly and the kids had a blast playing outside on the trampoline, the small playground and exploring the lake & large lawn. The beds were very comfortable and the cottage is very bright and full of light. The large dinner table allowed us to gather together to eat and have social time for games & crafts. The city of Orillia and all the highlights it has to offer is a quick 10 minute drive away. We went to bakeries, shopping and had a lovely lunch at Brewery Bay pub. Highly recommend this location for families looking to make beautiful memories and relax.

Home in Orillia

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