Vacation rentals in Head Lake

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Head Lake

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

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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.

Superhost

Apartment in Wasaga Beach

4.82 out of 5 average rating, 11 reviews

Double Waterside Beach Oasis

Stay in this newly renovated brand new listing and enjoy sunsets at the worlds largest fresh water beach. Two waterside patios!🌊🏖️ -Sea Doo rentals steps away-Tiki bar boat rentals steps away-Clubs and bars 2 min walk including the world famous Bananas Beach Club overlooking the beach-Skull Island Mini putt 2 min walk-Fishing out your back door-Shops, arcade and MUCH more right outside your front door or 2 min walk. -Blue Mountain a short drive-Go carts and batting cages only 10 min away!

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.

Superhost

A serene waterfront view showcases a cozy cottage surrounded by lush greenery. The grassy area features multiple seating options, including colorful chairs. A wooden dock extends into the water, with a canoe and kayak resting nearby, inviting outdoor activities.

Cottage in Peterborough

4.81 out of 5 average rating, 162 reviews

Hot Tub+Games Room | Waterfront Cottage, Kawarthas

Relax and enjoy some well deserved time in our private and newly furnished 4 season cottage. Located just a 5 min drive to the charming town of Lakefield, Kawartha Lakes, you will find our cozy cottage right on the water. • Private Waterfront • Hot Tub (open year round) • Games room • High Speed Fibre Wifi • Gas Fireplace • Office workspace • Pet friendly *Please note that we only accept bookings from those who have positive reviews from prior Airbnb stays on their profile

Top guest favorite

Chalet in Coldwater

4.95 out of 5 average rating, 456 reviews

OakRidge Retreat-HOT TUB 100s of acres WIFI

The cottage provides a serene space to share with fiends and family surrounded by nature. Enjoy beaver ponds along the trails, indoor/outdoor games, wood burning stove, sauna, hot tub, firepit, wifi, jetted tub 75" & 55" smart tv's and streaming services. Fully equipped kitchen, double oven, granite counter. In winter, snowshoes and snow saucers. At Christmas the house is decorated and boasts a 15 ft tree. 20-25 minutes from Mount St. Louis ski hill and several beaches.

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

Superhost

A serene view of a marina features multiple boats docked on calm waters, surrounded by lush greenery. Red adirondack chairs are positioned around a picnic table, creating an inviting outdoor space. The clear blue sky enhances the tranquil atmosphere of the waterfront.

Cottage in Harcourt

4.92 out of 5 average rating, 60 reviews

Modern Yellow Cottage Harbourtown Marina

Newly renovated year round cottage over looking beautiful Stoney Lake at McCracken's Landing. Steps from Hobart's restaurant, water rentals and general store. A cozy upscale modern furniture and decor. Includes private patio, screen porch, air conditioning, WIFI and satellite flat screen TV. It doesn't get any better that this! Boats and boat slips available upon request.

Guest favorite

Condo in Haliburton

5 out of 5 average rating, 12 reviews

Haliburton Heights - 1 Bedroom for 4 - On the Lake

From couples looking to escape, to families in search of a unique vacation, everyone will find something to love at this four-season resort. Kayak on the serene lake, escape to a nearby winery or art gallery, or stay in and unwind in the comforts of your 1 bedroom condo.

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What guests are saying

Rustic and Spacious Lakefront Oasis in Nature.

4.84 out of 5 average rating, 55 reviews6 months ago

Perfect peaceful cottage on the lake. So many beds available but the spaces don’t feel crowded even with many people in the house. Cozy and truly authentic cottage feel. My son felt like the bunkie was his own piece of heaven. We appreciated the outdoor amenities such as kayaks and canoe. Even on the crisp late October days we visited we enjoyed the lake, and the wood stove kept us snug in the evening. Nathan was incredibly responsive and helpful. Just a wonderful visit overall.

Cottage in Algonquin Highlands

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

Perfect Comfort 2 Bed ~ BBQ ~ Parking ~ Resort

5 out of 5 average rating, 9 reviews1 month ago

Franco and his team are lovely to deal with. They are extremely communicative and in a timely manner. The apartment is exactly “like” the pictures shown, warm, cozy and overall a very welcoming home. In addition, to having such a wonderful place to stay in, they have thought of every kitchen tool you may need during your stay, it’s great to have access to all these accessories. Thank you for the great stay, I would definitely recommend your place to anyone staying in the area.

Condo in Innisfil

What guests are saying

Rustic Cozy Cottage|Waterfront, HotTub, Wood Stove

4.98 out of 5 average rating, 63 reviews1 month ago

This place was absolutely beautiful the second we walked in. It felt so cozy and homey. I believe it was even nicer in person than in the photos. Personally cleanliness is at the top for me and the place was spotless, and smelled so wonderful. You can tell they thoughtfully chose their cleaning products and body care products - which amplifies the stay making it almost feel spa like along with staying at a cute cottage! Brought along a young daughter, and she adored it here! Dmitry was so responsive too to our questions before hand and gave us so much added information to help us plan for our trip. They even surprised us with a special treat for celebrating my birthday while we were staying there. We hope to rebook many more times!

Cottage in Hastings

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

Secluded Lakefront Private beach W/Kayak Fish.boat

4.92 out of 5 average rating, 86 reviews7 months ago

It’s my second time staying at Ludmila’s cottage and it does not disappoint! The cottage is spacious with a stunning waterfront with incredible privacy. Ludmila is very easy to communicate with and provided clear instructions. Would stay again and highly recommend this cottage!

Cottage in Muskoka

What guests are saying

Hillside Haven: Serene Studio Retreat for 4

4.86 out of 5 average rating, 87 reviews3 weeks ago

Vlad was a great host and provided detailed, easy-to-follow instructions to access the property. It was very clean and a peaceful vacation located near the Vetta spa which is amazing. Unfortunately, our stay was during a storm which caused us to lose power however, Vlad was understanding that we were unable to complete all the tasks when checking out (we lost prior the day prior). Overall it was a fantastic experience and I would stay here again!

Condo in Oro