Waterfront holiday rentals in Grey Highlands

Find and book unique waterfront rentals on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for waterfront rentals in Grey Highlands

Waterfront apartment rentals

Superhost
Flat in Innisfil
5 out of 5 average rating, 7 reviews

PS5 * Pool * Hot Tub * FirePit

NazaninRating, 5 stars2 weeks ago
The host is very friendly and understandable, and the place is very nice. I will recommend booking this place to everyone.
Guest favourite
Flat in Alliston
4.87 out of 5 average rating, 53 reviews

Stunning 1 Bedroom unit

SydRating, 5 stars2 weeks ago
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!
Superhost
Flat in Innisfil
4.88 out of 5 average rating, 33 reviews

Luxury Serene Escape @ Friday Harbour Resort

BalajiRating, 5 stars13 months ago
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 :)
Top guest favourite
Flat in Penetanguishene
4.88 out of 5 average rating, 85 reviews

Quiet & Pristine Georgian Bay Escape near trails

LouiseRating, 5 stars4 weeks ago
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!!
Guest favourite
Flat in Innisfil
4.96 out of 5 average rating, 27 reviews

Modern Luxury Delight with a Pool and Hot Tub

TerenceRating, 5 stars9 months ago
Amazing stay, well kept, convenient and comfortable. Joanne is very responsive and flexible.
Guest favourite
Flat in Innisfil
4.97 out of 5 average rating, 38 reviews

NEW Luxurious Corner Unit at Friday Harbour Resort

AndreaRating, 5 stars3 weeks ago
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!
Top guest favourite
Flat in Innisfil
4.92 out of 5 average rating, 13 reviews

FH Suite Getaway!

KaylaRating, 5 stars4 months ago
Beautiful place definitely will be returning in the summer friday harbour is a must visit !!
Guest favourite
Flat in Port McNicoll
4.97 out of 5 average rating, 35 reviews

Welcome to waterfront paradise on Georgian Bay

AniketRating, 5 stars9 months ago
We had a fantastic weekend staying at Gerard’s place! It was just as described from the pics and Gerard provided very clear instructions which made checking in seamless. The place was very clean, spacious, and right on the water! There was also a ton of things to do including kayaking, stand up paddle boarding, board games, a gym with weights as well as a fully stocked kitchen. We had a great time and would definitely come back again in the future!

Waterfront house rentals

Guest favourite
Home in Flesherton
4.94 out of 5 average rating, 34 reviews

Cottage Escape on Lake Eugenia

AmandaRating, 5 stars1 week ago
My family and I stayed at this wonderful cottage for 4 days. It was everything I wanted- cozy, clean, and right on the water. We really enjoyed fishing and sitting outside. The water is really clear and clean. We loved exploring the small towns. The cottage is fully stocked with everything you need for your stay. I am really looking forward to returning in the future!
Top guest favourite
Home in Wiarton
4.92 out of 5 average rating, 102 reviews

Island View Cottage

MahejabeenRating, 5 stars1 week ago
A Perfect Waterfront Getaway: Cozy, Clean, and Family-Friendly with an Exceptional Host! Our stay at this Airbnb was absolutely wonderful! From the moment we arrived, we were struck by the waterfront location, offering serene views and a truly relaxing atmosphere. The home itself was very clean, which is always a top priority, and it was evident that great care is taken to maintain a spotless environment for guests. The helpful host truly made our experience exceptional. Communication was prompt and clear, and they went above and beyond to ensure we had everything we needed, whenever required. This level of hospitality significantly enhanced our stay. The well-equipped kitchen was a dream for preparing meals. It had everything one could possibly need, from essential cookware and utensils to a good range of appliances. We particularly valued how child friendly We highly recommend this place for anyone seeking a clean, comfortable, and welcoming waterfront escape with excellent amen
Guest favourite
Home in Durham
4.9 out of 5 average rating, 165 reviews

Heron's Perch

SergioRating, 5 stars10 months ago
This was our second year at Carrie and Dan's cottage and once again my family and I had a fantastic time. The house is perfectly situated on the river with a nice beach and it has all of the amenities needed. Dan communicated regularly and checked in with us to ensure we had everything we needed. This is a beautiful property which anyone would have fun at.
Guest favourite
Home in Coldwater
4.98 out of 5 average rating, 110 reviews

Luxury Guest House with Private Hot Tub and Trails

FadilRating, 5 stars1 month ago
We had a lovely stay. The place was even nicer than we expected. This is the best air bnb we’ve ever had. It was really private and really clean, which was exactly what we were looking for. They provided so many little things which just added to the overall experience. Its the small things that go a long way. The place was really open concept and just really well furnished. Gave a fantastic vibe. The hot stub was clean, private and lovely. You wont be disappointed whatsoever here. Thank you for being a fantastic host Rebecca.
Guest favourite
Home in Wiarton
4.95 out of 5 average rating, 156 reviews

Mallory Beach Loft On the Water - Near Bruce Trail

AngieRating, 5 stars1 month ago
We had an amazing stay at Jane and Steve’s place! They were very warm and were always accommodating and ensuring our stay was going well. Jane even ensured we got to our trail start and end one day. Everything about the “loft” was comfortable, the banana bread was amazing and it felt like we were visiting old friends. Thanks so much for helping to make a rainy cold weekend enjoyable!
Guest favourite
Home in Keswick
4.91 out of 5 average rating, 273 reviews

Beach House-S/W Exposure! Hot Tub, Sandy Water!

JennyRating, 5 stars3 days ago
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!
Guest favourite
Home in Collingwood
4.93 out of 5 average rating, 28 reviews

Happy Valley Ski Golf Spa Relax

AndyRating, 5 stars2 weeks ago
A lovely place to stay! Very clean and conveniently located. Would not hesitate to stay here again next time we're in the area!
Superhost
Home in Barrie
4.86 out of 5 average rating, 116 reviews

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

BradRating, 5 stars2 weeks ago
Thank you for being a great Host to our group.

Waterfront apartment rentals

Superhost
Apartment in Innisfil
4.87 out of 5 average rating, 227 reviews

2BR Getaway at Friday Harbour All Season Resort

BryannaRating, 5 stars3 weeks ago
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!
Top guest favourite
Apartment in Innisfil
5 out of 5 average rating, 33 reviews

Friday Harbour Ground Floor w/ Large Terrance

AshleyRating, 5 stars3 days ago
We had amazing time! Tiana goes above and beyond. The outside patio was so nice and relaxing. Recommend to everyone. Thank you!
Guest favourite
Apartment in Innisfil
4.96 out of 5 average rating, 166 reviews

Stylish getaway condo, resort living

DebbyRating, 5 stars1 month ago
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)
Guest favourite
Apartment in Innisfil
4.93 out of 5 average rating, 211 reviews

Designer Condo with beautiful harbour view.

EdwardRating, 5 stars1 month ago
Very beautiful place and surroundings. Host was very helpful with giving us advice and answering any questions we had
Superhost
Apartment in Innisfil
4.91 out of 5 average rating, 142 reviews

Beautiful Condo, 2 Bedrooms and a Den in a Resort!

AnisaRating, 5 stars1 month ago
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!
Superhost
Apartment in Wasaga Beach
4.86 out of 5 average rating, 80 reviews

Wasaga Beach/WaterFront BeachHouse/ BBQ/AC/parking

RukshanRating, 5 stars5 months ago
We had a wonderful and pleasant stay! The host was very responsive and made sure we had everything we needed. The place was clean, comfortable, and welcoming. We’re already planning to come back again. Highly recommend!
Guest favourite
Apartment in Innisfil
4.94 out of 5 average rating, 115 reviews

Friday Harbour Luxury Condo Escape, Sleeps 4

SoniaRating, 5 stars8 months ago
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
Guest favourite
Apartment in Innisfil
4.84 out of 5 average rating, 180 reviews

Marina view at Friday Harbour 2bd/2bth Pool option

Joanna LRating, 5 stars12 months ago
Immaculately clean, spacious, and Beautiful condo. It had everything we need and a few steps to the marina. Easy instructions to get inside and parked. I highly recommend!

Quick stats about waterfront rentals in Grey Highlands

  • Total rentals

    100 properties

  • Nightly prices starting at

    ₹3,454 before taxes and fees

  • Total number of reviews

    2.6K reviews

  • Family-friendly rentals

    80 properties are a good fit for families

  • Pet-friendly rentals

    50 properties allow pets

  • Rentals with a pool

    30 properties have a pool

Destinations to explore

  1. Airbnb
  2. Canada
  3. Ontario
  4. Grey County
  5. Grey Highlands
  6. Waterfront rentals