Beachfront vacation rentals in Grey Highlands

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Popular amenities for Grey Highlands beachfront rentals

Pet-friendly beachfront home rentals

Superhost

Cabin in Innisfil

4.89 out of 5 average rating, 359 reviews

Lake Simcoe Cottage & Hot Tub

FarhadRating, 5 stars5 days ago
we really enjoyed our stay here host was friendly and responsive.
Guest favorite

Bungalow in Orillia

4.87 out of 5 average rating, 232 reviews

Luxury, Waterfront, 4 bdrm Bungalow in Sth Muskoka

IgorRating, 5 stars2 months ago
We had a rest on the lake shore in the off-season - at the end of October. Reality exceeded expectations. Very cozy place - both the house and the lot near the water. Privacy, the lot is almost completely fenced. Quiet and calm, we spent a lot of time by the fire in the famous comfortable Canadian chairs. There is a kayak and a catamaran, so in the summer it is definitely even better here. The house has everything you need, even bathroom accessories and shampoos. A beautiful living room with a very comfortable soft sofa for a large company. We walked for several hours along the famous Trans-Canada Trail, which is 8 minutes from the cottage. Very beautiful autumn forest, life-giving air. We stayed in the cottage with our dog and the cottage is a very friendly place for our pet. Comfortable beds in four bedrooms and pillows too. Definitely recommend.
Guest favorite

Guest suite in Innisfil

4.85 out of 5 average rating, 130 reviews

Open tiny king suite with semi-private waterfront

AdamRating, 5 stars1 month ago
Great space and thoughtful hosts. The unit is very comfortable, quiet and peaceful. Great value and location. Highly recommend staying at the King Suite.
Superhost

Cottage in Washago

4.88 out of 5 average rating, 121 reviews

Vintage Farmhouse Lakeview and Golfers Cottage

BenRating, 5 stars1 month ago
We stayed here for a long weekend in November and it was lovely. The cottage is spacious, clean, and well appointed. We loved the firepit outside (front yard and back) and the easy to use fireplace inside. The kitchen is great, and overall it's a great place to spend some time. Sandra was very helpful and responsive. I didn't want to leave!
Guest favorite

Cabin in Erin

4.97 out of 5 average rating, 131 reviews

Rustic Beach House on Private Pond

AdamRating, 5 stars1 month ago
Its a beautiful little rustic cabin i really enjoyed it would make an excellent getaway for the summer months. Only downside was the wife didn’t like the outhouse even though it was clean and a non issue for me i would definitely recommend
Guest favorite

Home in Durham

4.9 out of 5 average rating, 165 reviews

Heron's Perch

SergioRating, 5 stars4 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 favorite

Cottage in Georgina

4.88 out of 5 average rating, 119 reviews

Modern 4-bedroom Lakefront Cottage with Sauna

PrachiRating, 5 stars2 weeks ago
What a beautiful location! Elena was very responsive since the day we booked the place. It was easy to find and private. The view of lake was great! We enjoyed using Sauna as well. The place was clean and we made sure to leave as clean as it was given to us. We had great time with our friends here and made memories. Thank you Elena! will surely book again in summer.
Guest favorite

Cabin in Lion's Head

4.91 out of 5 average rating, 199 reviews

Little Lake Lookout: Sauna, Beach, Dock, Dogs!

AndreaRating, 5 stars4 weeks ago
Our home away from home. Never a dull moment at Little Lake Look Out. We stayed during the offseason, but man is it underrated. Being cozied up with our fur babies was such a treat. We took advantage of hiking Lion Heads trail and wow, what a breathless experience…not only did we humans love it, but our furry family of 5 ABSOLUTELY enjoyed it. This wasn’t our first visit and it definitely won’t be our last. Last but not least, we appreciate these incredible hosts!!! Thank you for always making our experience seamless and worthwhile!

Beachfront home rentals with a pool

Guest favorite

Condo in Innisfil

5 out of 5 average rating, 40 reviews

Lake/Marina Front, Luxury 2 Storie 1500 Sqft At FH

ElenaRating, 5 stars3 months ago
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!
Guest favorite

Condo in Innisfil

5 out of 5 average rating, 54 reviews

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

DamithRating, 5 stars2 weeks ago
Amazing place and perfect for a gateway! It was just like the pictures. The snacks & games were great. Eshan was very responsive and helpful. Highly recommend this stay!
Guest favorite

Cottage in Victoria Harbour

4.96 out of 5 average rating, 50 reviews

Gorgeous Winfield Chalet Cottage

MariéRating, 5 stars3 months ago
Tony's place was very spacious, clean and a convenient location. We really enjoyed to proximity to the waterfront and spending time in the pool. Great for a family or friends get together!
Guest favorite

Cottage in Tiny

4.95 out of 5 average rating, 42 reviews

Fran’s Beachfront Paradise Georgian Bay Beach Club

AgnesRating, 5 stars4 months ago
Lovely lovely place. Sitting on the deck watching over the blue waters of the bay - dreamy! Kids had fun at the beach and in the pool. Highly recommend.
Guest favorite

Condo in Innisfil

4.94 out of 5 average rating, 63 reviews

Luxury Beach Spa w/ Hot Tub & Sauna!

CayleyRating, 5 stars1 week ago
Michelle was an amazing host - the place looks as great as the photos! Fire features and sauna were perfect! Holiday Market was so much fun and overall it was a perfect weekend for what we had in mind.
Guest favorite

Bungalow in Lafontaine Beach

4.9 out of 5 average rating, 50 reviews

Sweet Memories of Georgian Bay

FionaRating, 5 stars3 months ago
Idyllic gem on Georgian bay. Perfect for a small family getaway by the lake. The resort pool is a big plus for the kids. Beautiful surroundings and stunning sunsets. Jefferson is a great host. Very friendly and responsive. He kindly accommodated our request.
Guest favorite

Condo in Innisfil

4.94 out of 5 average rating, 115 reviews

Friday Harbour Luxury Condo, Sleeps 4

SoniaRating, 5 stars3 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 favorite

Apartment in Innisfil

4.9 out of 5 average rating, 10 reviews

FH Suite Getaway!

LoriRating, 5 stars3 months ago
Very tidy and lovely. Well equipped with everything you would need and would love to go back.

Private beachfront home rentals

Guest favorite

Cottage in Howdenvale

4.89 out of 5 average rating, 44 reviews

Beautiful Private Cottage on 10 Acres and a view!

RavenRating, 5 stars2 months ago
We had an amazing stay! It was our second time staying and everything was perfect. It’s a cozy cottage with an at-home feel. Set the pilot light in the gas fireplace for us and let me know in advance, and offered to come pick up chairs after a windstorm the night before our stay. Very lovely host with a very speedy response time and a wonderful property!
Guest favorite

Cottage in Wiarton

4.91 out of 5 average rating, 35 reviews

Zeta's Beachfront Cottage on Georgian Bay

CarleyRating, 5 stars1 month ago
We stayed here for the weekend and photos really don’t do the place justice! It’s absolutely stunning inside and out! All the bedrooms were really nice and clean. The living room and kitchen were absolutely stunning we spent our whole stay there. Lots of games and things to do in the house they really did think of absolutely everything. The outdoor space is private and has lots of space. The water was absolutely beautiful and made for such a peaceful walk! It was an amazing winter getaway!
Guest favorite

Cottage in Port Severn

5 out of 5 average rating, 14 reviews

Sunset Lodge, Honey Harbour

AmandaRating, 5 stars3 months ago
Shauna and Ken were great hosts. Their cottage was beautifully updated and the lakefront was exactly as described and photographed. We brought our three children with us and they enjoyed themselves on the shallow shore entry into the water. Shauna and Ken had paddle boards and a canoe onsite for use during our stay. They were very responsive with any questions we had.
Guest favorite

Cottage in Gilford

4.86 out of 5 average rating, 50 reviews

Lake Side Manor With Games Room

JennRating, 5 stars3 months ago
I can highly recommend this property. Our family of 6 adults and a busy 3 1/2 yr old thoroughly enjoyed our stay. We spend most of our time at the waters edge playing with the trove of toys and water craft. Inside, we found everything exactly as described and in the photos. We all found the beds comfortable with quality bedding and pillows. We did check out the massive downstairs games room. Again as described and in the photos. We had spectacular weather and spent 95% of time outside. It would have been a great rain day refuge. We thoroughly enjoyed our 10 days and would definitely stay there again.
Guest favorite

Home in Wiarton

4.98 out of 5 average rating, 47 reviews

Waterfront Executive Home

CarlyRating, 5 stars2 months ago
The home was spacious and comfortable. The added amenities were so wonderful and it was fully stocked with towels and shampoo/ conditioner as well as body wash. All the beds were great and each person from our family slept great. The kids loved the play room and shooting hoops. The views were scenic and stunning. Soaking in the hot tub while overlooking the lake and seeing sailboats in the distance was very peaceful. What a great find. The host Marisa was kind, thoughtful and even left us some goodies! We would highly recommend this rental location to anyone.
Guest favorite

Cottage in Tiny

4.96 out of 5 average rating, 25 reviews

Just Loafin, Georgian Bay Cottage

YorkieRating, 5 stars2 months ago
Frank is very responsive and helpful! Just Loafin is beautiful, clean, and spacious! Not just my teenage kids, even my wife and myself enjoyed so much using the trampoline and kayak. The lakeview was amazing and the water was so clear! The tennis court is very well maintained. Roasted marshmallows in bonfire was a highlight! We felt totally ok without wifi as there were so much to do. The pictures didn't exegerate how big the living room is! It's huge! Very comfy couches to relax and lots of sitting areas for meals. We had 7 people so 2 bath and 1 powder room really helps. This cottage is in a nice and quiet area, at the same time it's close to the city for grocery, pharmacy, restaurants, and parks. We had definitely created a lot of wonderful memories here. Thank you so much!
Superhost

Home in Port Severn

4.75 out of 5 average rating, 32 reviews

Bluewater Lodge Beausoleil Bunkie #7

HaleyRating, 5 stars3 months ago
We had a great time! Lots of water toys for the kids (kayaks, paddle boards etc). Walking distance to playground and town. Fishing was fun and beautiful scenery from our front window. We can’t wait to go back :)
Guest favorite

Guest suite in Kemble

5 out of 5 average rating, 48 reviews

PARADISE AT PRESQUILE - WATERFRONT PROPERTY

ChristinaRating, 5 stars3 months ago
Jane was an amazing host with a beautiful home and peaceful, gorgeous waterfront garden. She was responsive even before we got there with local recommendations and while we were there as well. She ensured we had everything we needed and really opened up her home to us. Would definitely stay again if I was back in the region!

Quick stats about beachfront rentals in Grey Highlands

  • Total rentals

    20 properties

  • Nightly prices starting at

    $50 before taxes and fees

  • Total number of reviews

    680 reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with a pool

    10 properties have a pool

Destinations to explore

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