House vacation rentals in Grey Highlands

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Popular amenities for Grey Highlands house rentals

House rentals with a pool

Guest favorite
A pristine in-ground pool is surrounded by a well-maintained patio and grassy area. The house features a modern exterior with a sloped roof and accessible steps leading to a deck adorned with planters. Sunlight reflects off the water, creating a calming ambiance.
Home in Orillia
4.96 out of 5 average rating, 26 reviews

Cute and Cozy House

BobbiRating, 5 stars1 month ago
After being displaced from our home after damage from severe weather we were so fortunate to find this location. The house accommodated our family of 4 with pets for nearly a month without any issues. The kitchen is well equipped, bathrooms are well finished, bedrooms were comfortable and the location was very clean. The backyard is a beautiful and relatively private space hidden within a 15 minute walk to the downtown restaurants or the beach area. Anzhelika is an excellent host who was very responsive when needed, provided clear instructions and ample privacy. We would happily recommend this location to friends and family attending the area for events.
Guest favorite
A serene outdoor space features a sparkling pool surrounded by a mix of greenery, including a neatly trimmed tree and ornamental stones. A wooden fence provides privacy, while decorative white stones add a clean touch to the pool area.
Home in Barrie
4.92 out of 5 average rating, 91 reviews

Luxurious 4BDRM-King Bed-Barrie-near Snow Resorts

ShrutiRating, 5 stars1 month 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!
Superhost
Home in The Blue Mountains
4.87 out of 5 average rating, 106 reviews

4BR Family Home w/ Pool Access + Village Shuttle

AlanaRating, 5 stars3 weeks ago
We really enjoyed our stay! The home was large and very clean, and in a great location for going to the spa and into the village.
Top guest favorite
The serene backyard features a heated saltwater pool surrounded by a stone deck, bordered by lush greenery and blooming trees. A patio area includes outdoor seating and a grill, while large windows overlook the pool, enhancing natural light in the adjacent indoor space.
Home in The Beaches
4.99 out of 5 average rating, 147 reviews

Heated Pool-tub Open 365 Days

MinnieRating, 5 stars1 week ago
Miles is a fantastic host! Not only was he proactive in communicating details regarding entry and amenities, he went above and beyond with little fresh baked goods, Smart Home instructions guide, and providing literally everything you'd need to feel at home (bathrobes, teas, serving dishes+several cups, even milk and cream in the fridge!) The Hot tub was great, the place was spotlessly clean, and the balcony views were a pleasure to enjoy. This is a great house with lovely sky lights in the kitchen and beautiful location right by the boardwalk! 11/10 ✨
Superhost
The heated pool is framed by a paved patio, featuring several red lounge chairs for relaxation. Lush greenery and shaded areas are visible in the background, complemented by a clear blue sky with scattered clouds.
Home in East Gwillimbury
5 out of 5 average rating, 5 reviews

10 Acre Farmhouse with Pool + 5 Bedrooms/3 Baths

AbdulmalikRating, 5 stars2 weeks ago
This place is the perfect getaway for anyone looking to relax and enjoy quality time with family and friends. Surrounded by beautiful nature and fresh air, it offers a peaceful, private setting that’s ideal for both adventure and quiet moments. I highly recommend it to anyone seeking a refreshing escape.
Guest favorite
Home in North York
4.86 out of 5 average rating, 74 reviews

Toronto Pool Retreat

JasonRating, 5 stars1 week ago
Meysam’s place was a great fit for our large group. The location was convenient for getting around, and the house offered everything we needed for a comfortable stay. There was plenty of space to cook and hang out together, and the hot tub was a nice feature. Overall, a solid spot for a group getaway.
Guest favorite
Home in Chatsworth
4.89 out of 5 average rating, 146 reviews

Stonehaven - large country retreat, with pool*

TawnyaRating, 5 stars3 months ago
We struggled to find a place for our group of 17 and Stonehaven was an amazing find! The beds were comfortable, we loved being able to have meals all together in one spot, and there was lots of space for people to do different activities inside since it was winter. Outside, we enjoyed tobogganing, snowshoeing and cross country skiing on the property. Steve was quick to communicate and provided clear instructions and maps. We were already talking about going back so we can enjoy the property in the summer! Thank you for a memorable and fun weekend!
Guest favorite
The exterior of a Victorian-style home is framed by lush greenery. The exposed brick facade is complemented by vertical vines climbing the walls. Windows with white trim are positioned symmetrically, allowing natural light to enhance the inviting appearance of the house.
Home in Niagara
4.91 out of 5 average rating, 303 reviews

King West Victorian Studio Gem

JessieRating, 5 stars2 weeks ago
What an absolute gem of a house! I felt right at home and so relaxed with the cherry tree blooming in the back yard. Kathleen added thoughtful details and helpful instructions. The house was within walking distance of amazing restaurants, cafes and shops.

Weekly house rentals

Superhost
A modern living room is presented, featuring a large wall-mounted TV and a cozy electric fireplace. A minimalist coffee table is centrally placed on a patterned rug, with a light-colored sofa and armchair providing comfortable seating. Natural light enters through the window, illuminating the space.
Home in Barrie
4.78 out of 5 average rating, 9 reviews

King Beds with Home Gym and Large Backyard Oasis

ShaunRating, 5 stars1 month ago
Very nice place in a quiet neighbourhood.. steps away from my nature trail
Superhost
A modern two-story home is featured, showcasing a combination of wood and stone materials. The facade is accented by large windows, allowing ample natural light. A driveway leads to a garage, with a small landscaped area in front, enhancing the exterior appeal.
Home in Caledon
5 out of 5 average rating, 3 reviews

Mono Mills Home next to the County Great Getaway

SheenaRating, 5 stars1 month ago
We were displaced by a fire and lucky to find this spot to call home until we found our forever home. Trudy and Ray were both friendly and supportive. Big backyard was nice for our little guy to play in, safe and quiet spot as well. Thank you for having us!
Guest favorite
A cozy living area features warm wooden paneling and a rustic brick wall. A dark purple couch and a wooden coffee table create a welcoming setting. A wood stove is positioned near the entrance, adding a touch of warmth to the space.
Home in Wasaga Beach
4.88 out of 5 average rating, 113 reviews

2min walk to the beach & 20 min drive to Blue Mnt

TammyRating, 5 stars1 week ago
Lovely place, friendly but unobtrusive host! Great for family!
Guest favorite
A cozy living area features an orange L-shaped sofa adorned with decorative pillows, paired with a round coffee table. A 55" smart TV sits on a sleek black stand against the wall, surrounded by neutral decor and natural light from the nearby window.
Home in Barrie
4.95 out of 5 average rating, 166 reviews

4 Bedroom Fully Private Townhouse in Barrie

RyanRating, 5 stars3 weeks ago
Muhammad's place was clean,quiet and private. Muhammed was easy to get ahold of and very accommodating I recommend this stay to anyone. Thank you for you hospitality. Ryan
Superhost
A spacious wooden deck features a glass-top dining table surrounded by six chairs, set under a pergola. A gas barbecue is positioned nearby, with views of the lush greenery beyond the deck.
Home in Barrie
4.87 out of 5 average rating, 104 reviews

Entire House, Private/Clean 5bdr 6 Beds/Sleeps 12

TylerRating, 5 stars3 weeks ago
Had a great time staying here with 6 people including myself. Great location. It was close to everything we wanted. 4 mins to Tims. 13 mins to downtown. and 25 mins to Horseshoe Valley Resort. Beds were decent. Couches were very comfortable, and my back isn't the best. So that was a nice feature. Back deck was very nice. We had no issues with the neighbors, even though I was worried based on one of the other reviews. We only used 3 cars, and parked in a row on our side of the driveway. We enjoyed our stay a lot. Would definitely recommend.
Superhost
A comfortable living area is showcased, featuring two leather sofas and a coffee table. A television mounted above the fireplace displays Netflix. Natural light enters through large windows, and decorative elements include a flower vase and a colorful wall art piece.
Home in Toronto
5 out of 5 average rating, 4 reviews

3 bdr home + bsmt in Swansea/High Park

KirillRating, 5 stars1 month ago
we lived Johan's hosted house over two and half months. it's a pleasant staying. It's cozy and beautiful neighborhood , short distance to subway and almost everything in the walkable distance. Johan is such a responsible and considerate host, We do enjoy our staying.
Guest favorite
The exterior of The Nest is depicted, featuring a charming brick façade with large windows. Lush greenery and vibrant shrubs surround the entrance, which is approached by a stone pathway. The inviting porch offers a welcoming entrance to the suite.
Home in Southampton
4.86 out of 5 average rating, 79 reviews

The Nest at Victoria Street

CharlotteRating, 5 stars1 day ago
Would definitely recommend staying at the Nest. The location is very close to the centre of town, and walkable to the beach and fairy lake. The Nest itself is very cozy and has everything you need, and Sheila is a very responsive and welcoming host!
Guest favorite
A modern living area is presented with soft white seating arranged around a central coffee table. Shelves hold decorative items, while a large window allows natural light to fill the space, offering views of greenery outside. A mounted television complements the inviting atmosphere.
Home in Richmond Hill
4.89 out of 5 average rating, 155 reviews

Luxury 5 beds, 6 Baths custom home

PaulineRating, 5 stars3 weeks ago
An amazing home meeting the needs of our multi-generational family spending a week together in the GTA to cheer on our daughter participating in a National sporting event. Listing is reflective of the gorgeous, clean home. We would definitely look to return should another opportunity present!

Private house rentals

Guest favorite
A charming single-story house is framed by lush greenery and a well-maintained garden. A wooden deck invites entry, while a shaded seating area provides a relaxing spot. The clear blue sky creates a bright backdrop, enhancing the inviting outdoor space.
Home in Port McNicoll
4.86 out of 5 average rating, 21 reviews

Cozy Cottage with Private Beach Access

OleksiiRating, 5 stars1 week ago
Thanks for having us! Lovely home, great neighborhood, huge backyard.
Superhost
The exterior of a spacious Scandinavian-style cottage is presented, featuring a red-tiled roof and wooden facade. The building is set on a lush green lawn, surrounded by tall trees. A small wooden bench and a children's play structure are visible in the yard.
Home in Tiny
4.68 out of 5 average rating, 230 reviews

Private log cottage on 2 acres

KenRating, 5 stars2 weeks ago
Natalia's listing was spot on, easy to get to and very well kept. Guests are going to book her place hopefully next summer for their family. Great for all ages. I would recommend Natalia's place as a destination for AIRbnb. Ken
Top guest favorite
The exterior of the villa showcases a well-maintained brick facade complemented by a red-tiled roof. Lush greenery surrounds the property, with vibrant orange flowers blooming along the front. A manicured lawn enhances the inviting atmosphere, offering a serene setting amidst the trees.
Home in Innisfil
4.98 out of 5 average rating, 224 reviews

Luxe Villa with Sauna and Hot Tub @ Lake Simcoe

MarkRating, 5 stars6 days ago
Great stay. Private and peaceful area, but within walking distance to the vibrant Friday Harbor. We have had lovely time. Thanks Alex!
Superhost
An outdoor patio area is designed with comfortable seating arrangements, including a sectional sofa and ottomans. A pergola provides partial shade over the space, while greenery from nearby trees enhances the natural atmosphere. The wooden deck offers ample room for relaxation.
Home in Oak Ridges
4.88 out of 5 average rating, 109 reviews

Luxurious Spacious Dream Home with Parking!

MellissaRating, 5 stars4 days ago
Romalis place was Beautiful comfortable, so spacious and clean!!
Guest favorite
A well-appointed dining area features a long wooden table surrounded by chairs, complemented by a light-coloured rug. A large display showcases decorative items, with a television prominently featuring the Netflix logo. Natural light floods in through expansive windows, revealing garden views.
Home in Elora
4.91 out of 5 average rating, 11 reviews

Riverside Retreat /w Pool,Hot Tub & Sauna in Elora

ShannonRating, 5 stars6 days ago
The Crystal Retreat was really a fun vacation spot, and especially interesting as architecture buffs. The house is a custom home built in 1978 with the plans framed and on display. It is a unique and beautiful house with so much to enjoy on the property. We managed to check off everything over the course of four days, but needed at least that much time to get to all the pretty and relaxing spots throughout. From getting cozy with a movie with a tv that spins to face all the various lounging nooks, to diving in the pool, canoeing to the Elora Quarry, vegging out by the fire pit, we did it all and are thankful to Djurdjica for sharing her special home.
Top guest favorite
A welcoming living area features a light-colored sofa facing a flat-screen television. A decorative fireplace is prominent against a textured wooden wall. Natural light enters through nearby windows, illuminating the space and highlighting the warm wooden flooring.
Home in Alton
4.97 out of 5 average rating, 94 reviews

Cheerful 3 bedroom home with outdoor pool & hottub

RachelRating, 5 stars4 weeks ago
An absolutely stunning property with great amenities - the hot tub soak was super appreciated. Instructions to get to the property and check-in are super clear, and everything is clearly labelled in the house. Paige supplies everything you need at the house to cook, clean up, and keep everything running. She is super responsive and very helpful! Thank you for a lovely stay and we are already hoping to come back!
Superhost
A rustic cabin is nestled among lush greenery and trees. A set of stone steps leads to the entrance, framed by vibrant green foliage. The wooden structure features a porch and a window that allows natural light to brighten the interior.
Home in Township Of Tiny
4.8 out of 5 average rating, 5 reviews

Skyhouse - Private Beach Access

JosephRating, 5 stars10 months ago
The place we stayed at was great, and whenever there was a problem Irena found a quick solution that worked with both her and I. Great people great stay. 10/10
Guest favorite
A modern house exterior is displayed, featuring a welcoming entrance with a covered porch. The facade combines brick and siding elements. A well-maintained driveway leads to the two-car garage, complemented by a neatly trimmed lawn and neighboring homes creating a contemporary street view.
Home in Barrie
4.9 out of 5 average rating, 102 reviews

Entire Vacation Home in Barrie

DonnaRating, 5 stars1 week ago
John and Monica’s place was perfect for my family to stay after a wedding in the area. Felt right at home. It was clean and just as described. John and Monica were very responsive, allowing us to check in early. Thank you for a wonderful stay, we would highly recommend!

Quick stats about house rentals in Grey Highlands

  • Total rentals

    270 properties

  • Total number of reviews

    7.3K reviews

  • Family-friendly rentals

    240 properties are a good fit for families

  • Pet-friendly rentals

    110 properties allow pets

  • Rentals with a pool

    60 properties have a pool

  • Rentals with dedicated workspaces

    150 properties have a dedicated workspace

Destinations to explore

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