Waterfront holiday rentals in Simcoe County

I stayed for the weekend and had an amazing experience. The space is exactly as listed—clean, comfortable, and beautifully maintained. The host was incredibly responsive and made everything easy. It’s the perfect spot for a relaxing getaway. Highly recommend!

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!

The gardens and creek were just lovely…the apartment was clean & pretty much had all I needed. In particular the bed was excellent- had a great sleep. Would stay here again, if needed. Wendy was easy to communicate with & prompt with her replies & very accommodating to my schedule. Thank you, Wendy!

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!!

Clean, spacious unit. Just like the photos. Had all the basics (towels, linens, cutlery, dishes). Wonderful ravine view, newer building, walkable to all the Friday Harbour amenities and Promenade. Andrew was a responsive host. We would not hesitate to book again next time we're visiting Friday Harbour.

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!

The place was beautiful and we had a lovely time. We would recommend 🙂

Thank you so much Jennifer and Blaine for hosting us! We had a fantastic time. The cottage was adorable and the surroundings were beautiful. Jennifer and Blaine were very responsive and even helped us when we had some car trouble. We loved attending the Vetta Spa which was close by. Highly recommend staying at this cottage! 10/10

Our stay here was fantastic. The house is big with plenty of rooms for a big group. It was clean and orderly. There is a beautiful dock with a canoe, kayak and life jackets. Our host Fred was very kind and accommodating. I would recommend this to anyone looking a cottage getaway.

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!

We had an absolutely wonderful time here! Beautiful house, very clean, peaceful location, and stunning views. We were a group of 8 (5 adults, 3 kids) and had plenty of space. The house had everything we needed and more and Paola was incredibly responsive throughout the week. We used the house as a base to explore the area and go into Toronto a few times, which was all easily accessible. We also just enjoyed downtime at the house, with a few nearby areas the kids could play outside. Highly recommend!

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

it was a great stay, great property and Ivan was extremely polite and helpful.

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!

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 such a peaceful long weekend stay at Ana's! The location was perfect and exactly described; overlooks right into the marina, amazing restaurants just right down the steps and extremely quiet! We didn't hear a single sound from any of neighbours around us. The space looked even more beautiful than the pictures. My husband and I were shocked to see just how incredibly clean the apartment was; not a single speckle anywhere! We were welcomed by a lovely snack basket (which my husband devoured on the first night) and a bottle of wine. Even included amenities in the bathroom which was wonderful since I forgot our toothbrush. The bathroom was so cozy and such a lovely surprise to have a tub. We will definitely be coming back!

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)

Jack was an amazing host!! Extremely friendly, responsive and helpful throughout the entire process, before & during the stay, and morning of check out. Provided us with very clear instructions including a map if we needed, as well as linked us to the local events / dining page for the resort. The place was spotless! Matched the listing page. Would definitely recommend reserving one of Jack's listings after the great experience we had.

Condo was beautiful, relaxing and everything was walkable. Will definitely be back!

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!