House vacation rentals in Keswick, Georgina

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Top-rated house rentals in Keswick, Georgina

Guests agree: these houses are highly rated for location, cleanliness, and more.

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Guest favorite

The entrance features double doors in a dark finish, adorned with elegant seasonal wreaths. Flanking the doors are decorative wall art pieces. A small bistro table with two chairs is positioned on a stone patio, complemented by potted snake plants and decorative pumpkins.

Home in Barrie

4.92 out of 5 average rating, 90 reviews

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

ShrutiRating, 5 stars1 week 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!

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, 143 reviews

Heated Pool-tub Open 365 Days

PatrickRating, 5 stars1 day ago

We came up for a concert for the night and it was a great experience. The pool and hot tub were a wonderful perk and very well maintained and nice. The house is beautiful and spacious. Miles was extremely accommodating, we needed to get there a little early to help with making the concert on time and it was no problem at all. He worked with us and when there was an issue with the internet. he came and fixed it in person. The location is killer too! I strongly recommend staying here, it was a wonderful experience in every way!

Superhost

The exterior of the Scandinavian log cottage features a large front porch with a rail and steps leading to the front door. The distinctive red roof complements the natural wood finish, surrounded by lush green landscaping and trees in the background.

Home in Tiny

4.68 out of 5 average rating, 225 reviews

Private log cottage on 2 acres

DanaRating, 5 stars1 week ago

We recently held our annual family birthday weekend at Natalia's place with a multi-generational crew that spanned 1.5 years to 90 years young! This incredible log cabin met all of our needs. The bedroom on the main floor meant an accessible space for our great aunt, the games room in the basement was such a fun space for our teens. The sliding doors to the wide front porch and the giant yard with fire pit, play structures and trampoline gave us lots of space to play. Plenty of fridge and freezer space and bathrooms on every level was really helpful. Natalia was very responsive and kind as a host. Balm Beach is gorgeous and walkable. There are some really cute restaurants and coffee shops close by (shout out Cawaja General Store and Balm Beach Bar & Smokehouse!) No place is perfect - I note the stairs to the basement are rather steep, and a few suggestions were shared with our awesome host, including about kitchen amenities, but this is a pretty spectacular place to stay for a group.

Superhost

A bright living area features a large sliding glass door that opens to a picturesque view of the outdoor space and water. Comfortable gray couches are arranged around a circular coffee table, while sunlight streams into the room, highlighting the warm wooden floors.

Home in Richmond Hill

4.85 out of 5 average rating, 39 reviews

Awesome Lakefront House/5Bedrooms/Private Dock

ShannonRating, 5 stars1 month ago

Our family enjoyed our stay! The house had plenty of room for all of us. Lots of natural light and a beautiful view. This would be a great place to rent in the summer! If we return to the arena in the summer we will definitely book again.

Superhost

A serene view of the water is captured at sunset, with soft hues of orange and purple reflecting on the calm surface. Silhouetted trees line the shore, while a few ducks glide across the water, enhancing the tranquil atmosphere of this lakeside setting.

Home in Wasaga Beach

4.89 out of 5 average rating, 114 reviews

Stunning Beach House

KarinRating, 5 stars9 months ago

What stunning place to stay for a few days of peace and relaxation. The house is beautiful and the location is even better. David was a generous host and we also met his house keeper equally as friendly and helpful. Sunsets were stunning and the house had all we needed. Would love to stay again!

Guest favorite

A spacious living room is presented, featuring a large sectional sofa in a neutral tone adjacent to a contemporary entertainment unit. A modern area rug lies beneath, complementing the decor. A foosball table adds an element of fun, while artwork enhances the stylish ambiance.

Home in Wasaga Beach

4.93 out of 5 average rating, 30 reviews

Cozy Luxury Lake Retreat-Wasaga Beach+Slopes+Trail

KeziaRating, 5 stars1 month ago

Our group and I had a wonderful time at Alona and Mikes place. The house was clean, cozy, and exactly as described. The location was perfect, and the host was attentive, responsive and helpful. Highly recommend this Airbnb for a comfortable and enjoyable stay!

Superhost

The exterior of a semi-detached house is displayed, showcasing a blend of stone and siding. The two-and-a-half story structure features a covered front porch with multiple steps leading to the entrance. Symmetrical windows are present on the upper levels, with a grass lawn and street visible in the foreground.

Home in Ajax

4.77 out of 5 average rating, 44 reviews

HiddenGem: home away from home

AlphonsaRating, 5 stars1 week ago

We had a great stay at this Airbnb! The place was very neat, clean, and spacious exactly as described in the listing. It had everything I needed for a comfortable stay. The host was super responsive and helpful throughout, making check-in and any communication really easy. Would definitely recommend this place to anyone looking for a hassle-free, comfortable stay!

Guest favorite

The exterior of the upscale home showcases a spacious deck with two lounge chairs and subtle turquoise lighting. A well-maintained lawn surrounds the property. The design features large glass doors, providing views into the interior. A shaded area for outdoor seating is also visible.

Home in Barrie

4.97 out of 5 average rating, 107 reviews

Waterfront home, city/sunset view & steps to beach

JimmyRating, 5 stars2 months ago

We really enjoyed our stay here. The place was exactly as described, spacious, and had a ton of amenities. Even in the winter, we could always find things to do at the home, and the location was great as it was in a nice and quiet neighbourhood but also it was easy to access activities in the surrounding areas/mountains/resorts. Also, Curtis was a very responsive and positive host; he was very clear with his instructions and quick to answer any questions we had. Great experience!

Vacation rentals for every style

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Popular amenities for Keswick, Georgina house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Guest favorite

A modern seating area features a red leather sofa centered around a glass coffee table. Two stylish armchairs with unique designs flank the sofa, while soft overhead lighting creates a warm ambiance. The walls are painted in neutral tones, enhancing the contemporary decor.

Home in Utopia

4.86 out of 5 average rating, 44 reviews

Serene Escape: A Nature Getaway

HindRating, 5 stars1 week ago

We had a lovely stay, everything was great. Kitchen was well equipped. Only issue is that there were no towels at all. Which was communicated but we were expecting at least a kitchen rag or hand towels in the washroom.

Guest favorite

An outdoor pool is surrounded by a stone patio, featuring landscaping elements including flower beds and a small bush. Seating options are provided by chairs placed around the pool area, and a decorative birdbath is visible nearby.

Home in Port Perry

4.93 out of 5 average rating, 218 reviews

Home away from home with a hot tub and pool

LornaRating, 5 stars1 week ago

Had a great time at Angie's place! Everything was very clear, clean and easy—instructions were left out and amenities were provided. The hot tub was a great bonus to the weekend. We even had a delayed car picking us up, and Angie was very accommodating and understanding about letting us stay slightly longer while waiting for its arrival.

Guest favorite

A bright and airy multifunctional room is showcased, featuring two light gray sofas positioned around a wooden coffee table. An air hockey table is visible against a white wall, while a staircase is seen in the background. Large glass doors provide access to natural light.

Home in Oakwood

4.98 out of 5 average rating, 44 reviews

All Season Indoor Pool Escape

RaviRating, 5 stars1 month ago

Loved their place super responsive It was my 40th bday and wanted to be with my friends and family pool was a big plus and the best part was the no of bathroom Including kids we were 20. But had plenty of washrooms and ample room out cots and blankets Shout out for being accommodative and I would highly recommend their place the the host Looking forward to booking it in summer again.

Guest favorite

Home in Beaverton

4.88 out of 5 average rating, 41 reviews

Luxury Family Home Indoor Pool Hot Tub Lake Access

AlyssaRating, 5 stars1 month ago

The place was beautiful and the pool was perfect for a winter get-away. They were super responsive the entire time and check-in/out was super easy.

Superhost

The spacious basement living area features a cozy seating arrangement with green chairs and a glass-top coffee table. A modern kitchen with stainless steel appliances is visible in the background, and light-colored walls contribute to a bright and airy atmosphere.

Home in East Gwillimbury

5 out of 5 average rating, 3 reviews

10 Acre Farmhouse with Pool + 5 Bedrooms/3 Baths

PaulRating, 5 stars3 months ago

This place was absolutley spotless and communication was amazing even though nothing was needed til checkout. Would love to have enjoyed pool but tough in January. Minimal amount of snow fell and they had someone come shovel and salt.

Guest favorite

Home in North York

4.91 out of 5 average rating, 68 reviews

Toronto Pool Retreat

JessicaRating, 5 stars2 weeks ago

I enjoyed my stay and looking forwarding to staying here in the future . The home is fully equipped with everything you need . Felt like I was at home ☺️☺️

Superhost

A modern living room features a gray sectional couch paired with two mustard yellow armchairs. A wooden coffee table sits at the center, displaying a decorative vase with white flowers. Soft lighting illuminates the space, complemented by light-colored walls and a decorative plant in the corner.

Home in Pickering

4.85 out of 5 average rating, 46 reviews

Toronto Vacation DecemberPromotion/Park/Zoo/Casino

Huy LongRating, 5 stars1 month ago

Great host! Great response time and services!

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, 302 reviews

King West Victorian Studio Gem

JoelRating, 5 stars6 days ago

Kathleen's place was great, exactly as advertised. I really appreciated how tidy and well stocked the suite was. A great place to stay.

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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 stars6 days ago

Very nice place in a quiet neighbourhood.. steps away from my nature trail

Superhost

A modern kitchen features sleek white cabinetry and stainless steel appliances. A central island provides additional workspace, while marble-like flooring enhances the aesthetic. Natural light enters through a window dressed with light shades, and decorative flowers add a touch of greenery to the space.

Home in North York

4.93 out of 5 average rating, 28 reviews

Rare & Spacious massive home w 7 beds

AlexisRating, 5 stars4 months ago

Quoc’s place was as described! Nice neighborhood, not too far from the city (about 30 minutes). The place was spacious, very clean and had comfortable beds. Host checked in and was responsive but not bothersome. Would stay again!

Guest favorite

A well-lit bedroom features a spacious bed adorned with a patterned duvet cover. Light curtains frame the windows, allowing natural light to illuminate the soft carpet. Two framed artworks are displayed above the bed, enhancing the room's simple elegance.

Home in Wasaga Beach

4.91 out of 5 average rating, 11 reviews

Townhouse 5 min to Wasaga Beach

VidalRating, 5 stars3 months ago

This is a beautiful home. It is very clean and perfect for anyone. We definitely recommend staying here and would come back again. The owners were extremely responsive to any of our questions.

Superhost

A wooden staircase leads to the upper floor, enhanced by detailed railings. A vintage wooden writing desk is positioned against the wall, showcasing a rich finish. Warm wooden flooring runs throughout the space, creating a cohesive and inviting entryway.

Home in Toronto

5 out of 5 average rating, 4 reviews

3 bdr home + bsmt in Swansea/High Park

KirillRating, 5 stars3 weeks 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 a charming three-story house is depicted, featuring a wooden porch with a railing. The facade combines dark brick and light grey siding, while large windows allow natural light to enter. A small garden area is visible in front, enhancing the welcoming entrance.

Home in Midtown

4.92 out of 5 average rating, 72 reviews

Luxurious 2 Bedroom in the heart of the city!

JessicaRating, 5 stars5 months ago

Throughly enjoyed our stay. Polite and welcoming host. Had everything we needed. Amazing location.

Guest favorite

The entryway features a striking chandelier composed of colorful glass, illuminating the space. A large black front door stands prominently, flanked by side windows. The polished floor reflects the subtle patterns and soft lighting, creating an inviting first impression.

Home in Richmond Hill

4.89 out of 5 average rating, 154 reviews

Luxury 5 beds, 6 Baths custom home

PeterRating, 5 stars4 days ago

Loved the place. We were a party of 10 here to celebrate a 100th bday. It met everyones needs/expectations.

Superhost

A softly lit bedroom features a spacious bed dressed in a patterned duvet, flanked by two nightstands with lamps. Light-colored walls are complemented by decorative framed artwork. A rug lies beneath the bed, completing the serene atmosphere.

Home in Pickering

5 out of 5 average rating, 6 reviews

Beautiful 2 Bedroom Home Suite

ShabnamRating, 5 stars1 month ago

Nicest day. Nice hosting. Nice people very clean, really. We enjoy our stay. I hope everyone does.And we're gonna keep everytime staying here whenever we are here

Guest favorite

A well-lit basement unit is seen, showcasing a dining area with two white chairs around a wooden table. A green sofa and a yellow bed with patterned bedding are visible in the background, complemented by light-colored flooring and a plush area rug.

Home in The Beaches

4.82 out of 5 average rating, 50 reviews

Beaches Bliss: Stylish & Cozy

MeaganRating, 5 stars1 week ago

One of the best Airbnb’s I have ever stayed, amazing host! It was near our event and so we were able to walk as it was such short distance and for what we paid for it was an amazing place! Thank you again for having us!

Show all

Private house rentals

Guest favorite

A spacious open-concept living area is displayed, featuring elegant wooden flooring. The inviting seating arrangement includes a bright sofa and a dining area with a large table surrounded by white chairs. Natural light is filtered through the large windows, enhancing the modern decor.

Home in Bowmanville

4.91 out of 5 average rating, 183 reviews

Cozy Lakeside Modern House 4Br - Steps To The Lake

LisaRating, 5 stars1 week ago

thank you for letting us check in early. beds were fabulous !!!

Guest favorite

The exterior of a brick house is displayed, featuring a double garage with doors that match the home's vibrant color. Lush greenery surrounds the property, including trees and low shrubs. A concrete pathway leads to the front entrance, with a well-maintained lawn visible.

Home in Brampton

4.92 out of 5 average rating, 26 reviews

Your Second Spacious Home

RonRating, 5 stars5 days ago

Perfect place for us. No problems, beautiful house, great neighborhood. We will definitely book here again.

Top guest favorite

A comfortable living area is visible with a cozy armchair and a sectional sofa featuring beige upholstery. Natural light streams through large windows, offering a view of greenery outside. A stylish area rug and a decorative blanket add warmth to the hardwood floor.

Home in Lindsay

5 out of 5 average rating, 24 reviews

3 Bedroom House Rental

MariaRating, 5 stars2 weeks ago

We recently booked Nicole's Airbnb for 6 of our pilots, and it was absolutely fantastic. Our group of 6 aspiring pilots were looking for a spacious and comfortable place close to the Lindsay Airport, a place to unwind after their long days of training, and Nicole's place did not disappoint.

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, 218 reviews

Luxe Villa with Sauna and Hot Tub @ Lake Simcoe

KrunaRating, 5 stars2 weeks ago

This was our 2nd stay at Alex's place for our girl's weekend getaway. We will definitely be back. Everything was as great as the first time!

Guest favorite

A bright staircase with gray flooring leads to the upper level. Natural light fills the area through a window at the top. A spacious dining area is visible in the background, featuring a wooden table and elegant chairs, situated under a decorative light fixture.

Home in Orangeville

4.86 out of 5 average rating, 42 reviews

Stunning 5 Bedroom Family Home

JeffRating, 5 stars3 months ago

House was perfect for our group of 8. Will stay again next time we’re in the area

Superhost

A spacious living area features two cream-colored tufted sofas and two navy blue armchairs, positioned around a glass coffee table. Natural light enters through large windows, highlighting the elegant decor and rich area rug that adds warmth to the room.

Home in Barrie

4.87 out of 5 average rating, 101 reviews

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

BenRating, 5 stars6 days ago

We had a good experience. A+ for the host. Check-in was easy. The home was clean and well stocked / furnished. Location is good. There is some traffic noise from the highway but it didn't disturb our sleep. I've stayed in hotel's that are much louder. I wish the mattresses were a little softer but at the same time I feel we got a good value. We wouldn't hesitate to stay here again.

Guest favorite