Waterfront vacation rentals in Simcoe County

The host is very friendly and understandable, and the place is very nice. I will recommend booking this place to everyone.

Just what I was looking for. A peaceful stay close to nature. The train tracks right beside us was powerful. Caused me to stop and take it in. My wife said it was a reminder to stay present in the moment when a train passed. A lot of fun!

We had a lovely stay at Wendy’s place! Beautiful location right next to a river with a gorgeous back yard. It was a short drive to excellent hiking on the Bruce trail. The apartment had all the amenities we needed (including lots of coffee!), was very clean and super cozy. Wendy was very responsive and helpful. I’d highly recommend if you’re looking for a peaceful and pretty spot for a quiet getaway!

Friday Harbor was a beautiful location with extremely pretty walking trails. The house felt at home with everything available at your service. Our Airbnb Manager Ana was the sweetest person you could meet. She also gave us a welcome hamper! Definitely recommend to visit this place for a peaceful, home away from home kinda stay :)

We had a wonderful stay with Catherine and Tom. The place was spotless and stocked with all the essentials for cooking, making it easy to feel at home. The location was perfect - just a short walk to the town dock and everything else we needed. Catherine and Tom were incredibly flexible and went out of their way to help us during some unexpected situations. They were generous, thoughtful, and always responsive to messages. Their local knowledge was invaluable, and they truly went above and beyond to ensure our comfort. We would highly recommend staying here! 10 out of 10!!

Amazing stay, well kept, convenient and comfortable. Joanne is very responsive and flexible.

Olga’s home was beyond my expectations! The place looks exactly like the pictures, everything is spotless and very clean! There is a great attention to detail to making the home feel cozy! Olga was also very helpful throughout the trip and very responsive. It’s located very close to the restaurants and the underground garage parking was great! Overall 5/5, would highly recommend to others and will be coming back in the summer!

Sandra’s place is just like the pictures super cute, clean and private. The place has everything you need for a great stay. She’s very responsive to messages. It was our 2nd time enjoying her place and we’d look forward to booking with her again!

Would recommend Nadia’s home to anyone visiting the area, the house is located on the lake with amazing scenery within a few seconds walking distance from the house! The house was beautiful so clean and spacious, everything was labelled and well laid out for us and Nadia was just fantastic to communicate with and super helpful with any requests we had! There was a lovely homely touch when we arrived to receive a welcome basket and a note from Nadia. I would highly recommend this property to anyone and we will for sure be back to visit during the summer months.

First cottage trip with friends this summer. Stayed 3 nights and had a blast. Clint was responsive and gave us great recommendations for activities/food around the area. We were able to have a great time cooking meals with the already provided cookware, utensils, bonfire (s’mores) etc. Utilized the big TV for movies, Nintendo Switch games, and music. If you’re interested in a clean mix between cottage vibes and homey this is the right place to pick. Would come back again. Aside from staying in we visited Friday Harbour: okay boardwalk (not much to do but to walk around), trail was nice.

We had a wonderful stay at the cottage. The best part was the spectacular view of Georgian Bay. The view of the sunrise over the lake was stunning. We enjoyed relaxing on the deck, watching the swans and other birds. We also enjoyed a fire at the waterside fire pit. Not far from the beach or the slopes in winter.

We went to this cottage for a beautiful romantic weekend getaway and we were happy we got that. The owner of the cottage Necker was very kind and helpful, absolutely loved the place and there was plenty of water activities to do. It was easy to check in, communicate and plenty of peaceful vibes. Recommended 100%, please go visit this cottage it is very well worth it. P.S: we loved the character of the cottage with little artpieces and wall art from all over the globe 🌎.

We stayed at Dylan’s place for the weekend with 13 adults and 4 kids. There was enough rooms and beds for all of us with adequate bedding and space. The house was clean and well equipped for our weekend! Before the stay we had lots of questions and Dylan was very responsive and answered everything in a timely manner and with lots of details. He was always following up during the weekend as well. The dock is beautiful and amazing! It was a bit buggy but that’s expected near the waters. We used the kayaks and boat and had a wonderful time!

What a dream location for our family to spend a week of relaxation and fun! The home was as beautiful in person as it was in the photos, and Paola was a lovely host. l Every last detail was thought of and truly made for such a memorable stay. We hope to return in the future!

we had a wonderful stay. squeaky clean,stylish host was very accommodating .defiinetly would stay again.

Beautiful, spacious and very comfortable. One of the most amazing views I've ever had at a cottage. So many windows that can open to let the beautiful sunshine and breeze in. Fans, AC and heat allowed for perfect temperature control.

We recently had the pleasure of staying at a fantastic condo in Friday Harbour, and we can’t recommend it highly enough! From the moment we arrived, we were greeted with warm hospitality and a stunning view that took our breath away. The condo itself was a perfect blend of luxury and comfort. It was impeccably clean, stylishly decorated, and equipped with all the amenities one could wish for. One of the highlights of our stay was the private balcony, where we spent many mornings sipping coffee and evenings watching the sunset over the harbor. The location of the condo is unbeatable. Just a short walk to charming local shops, restaurants, and the marina, it offered the perfect mix of relaxation and convenience. Overall, our stay at this condo in Friday Harbour was exceptional. It’s clear that the owners have put a lot of thought and care into creating a perfect retreat. If you’re looking for a memorable getaway, this place should be at the top of your list!

The condo was absolutely immaculate and we will 100% be coming back and staying at one of Jack's units and would love to have people come back with us! The amenities however at Friday Harbor were disappointing because the pool, hot tub and nature preserve were all closed. All of these things were the main reason we booked at Friday Harbor because we knew the water in Lake Simcoe would be freezing and having the pool and hot tub would make up for that. But, that is no fault of Jack's so he is still getting a 5 star rating ! The short walk to all the shops and restaurants was amazing and the Dirty Oar food and service was incredible. We would love to come back when everything is open! Thank you for being an amazing host !

Stephanie was wonderful and the space she has is so perfect! Love that there is main floor back door access and super easy to get in and out of the parking garage as she’s on the main floor. Will definitely stay again!

We had amazing time! Tiana goes above and beyond. The outside patio was so nice and relaxing. Recommend to everyone. Thank you!

We had a great stay at this stylish comfortable condo in a nice neighbourhood. The condo itself is very clean and has everything,and more,than you need. The brita filter is a big plus ! Comfortable beds, luxurious linnen and a good washer an dryer made us not wanting to leave... Thank you Ron (and Anna)

Very beautiful place and surroundings. Host was very helpful with giving us advice and answering any questions we had

My kids & I had a fantastic experience at this Airbnb. The space was exactly as described—clean, comfortable, and well-equipped with everything I needed. The host was incredibly responsive and helpful, providing clear check-in instructions and great local recommendations. The location was perfect—close to everything, but quiet enough to relax. I would definitely stay here again and highly recommend it to anyone visiting the area!

My boyfriend and I stayed the weekend, it was a great location, Joe was very responsive and friendly! We had only 1 concern with the bbq that was not clean, but it has been handled with effectively. Overall space was very clean, it was easy to find kitchen supplies, and other items in the house! A great location with stores, restaurants at a walking distance, and other attractions within a 30 minute drive