House vacation rentals in Keswick, Georgina

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Popular amenities for Keswick, Georgina house rentals

House rentals with a pool

Guest favorite
A modern living area is highlighted by a sleek, electric fireplace beneath a large flat-screen TV. A rustic accent wall features wooden panels and decorative art. A comfortable gray sofa and a table set for dining complete the welcoming space, complemented by blue and natural tones.
Home in Innisfil
4.92 out of 5 average rating, 51 reviews

2 Bd Boardwalk Condo Patio Oasis

KeRating, 5 stars2 days ago
We love the location and the large TV and couch! Tristan was also pretty responsive, overall a great place to stay at over the weekend away from home! Btw, I’m a fan of the pillows!
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, 96 reviews

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

DianeRating, 5 stars1 week ago
This house was perfect for our large group: for couples and a baby. Having the pool was a bonus that we really appreciated in the warm weather. The kitchen was extremely well equipped, and there were enough linens as well as pool towels for us all. There was plenty of space for everybody as the rooms were all quite large, particularly the master bedroom. The house were incredibly accommodating when we realized after checkout that we had left a couple of items behind. They were able to make arrangements for us to retrieve them several days later back in Toronto! I definitely can recommend this house.
Guest favorite
Home in North York
5 out of 5 average rating, 14 reviews

Award Winning Luxury Home with Heated Pool + Sauna

SymphoneeRating, 5 stars5 days ago
Lovely home. In close proximity to most of the things we wanted to visit. The kids loved the pool and arcade, and Ryan was very responsive if we had questions or concerns
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, 220 reviews

Home away from home with a hot tub and pool

CourtneyRating, 5 stars2 weeks ago
lovely spot for some quiet outside time. backyard is spacious and welcoming. plenty of options for seating to enjoy sun or shade. kitchen was absolutely amazing to prepare food in, well organized and nicely laid out. rooms were tidy and clean, plenty of space to sleep 6 comfortably. would highly recommend this spot
Superhost
The exterior of the two-story home is showcased, featuring large floor-to-ceiling windows that reflect the surrounding trees. A spacious deck extends from the second floor, complemented by a natural stone garage below. The manicured lawn is framed by tall trees, enhancing the rustic charm.
Home in Orangeville
5 out of 5 average rating, 3 reviews

Hockley Valley - Jazzy Pines - 4 BR with Pool

DjRating, 5 stars3 days ago
We had such a wonderful time staying at John’s place—it honestly couldn’t have been better. The home was gorgeous, spotless, and felt so warm and inviting. You can tell a lot of care went into making it a space where guests can truly unwind and feel at home. The private pool was a dream. Surrounded by trees and completely peaceful, it felt like our own hidden escape. We spent hours swimming and lounging by the water, and since it was deep enough to dive, it added that extra bit of fun we didn’t expect but absolutely loved. John was an incredible host—super responsive and kind. Any time I had a question, he got back to me right away and made sure everything went smoothly. It was so reassuring to know he was just a message away. If 10 stars were an option, we’d give them in a heartbeat. This stay set the bar so high, and we’re already talking about coming back. Huge thanks to John for making it such a memorable getaway!
Superhost
The outdoor pool is framed by a stone patio, featuring a serene environment with lush greenery surrounding it. A shaded area with an umbrella and several lounge chairs are positioned nearby, creating an inviting space for relaxation.
Home in Newmarket
4.73 out of 5 average rating, 26 reviews

"THE BIRD HOUSE" getaway!

MargotRating, 5 stars8 months ago
Megan’s house was just like the pictures. It had lots of beds which was perfect for family traveling to town for a family wedding. The pool table and heated pool were an added bonus.
Superhost
A balcony features a round table with two wicker chairs, surrounded by vibrant flowering plants in hanging baskets and pots. In the background, a sparkling blue pool is visible, nestled within a fenced backyard shaded by greenery.
Home in Newmarket
4.83 out of 5 average rating, 24 reviews

Cozy Pool house in Newmarket

SharleneRating, 5 stars3 days ago
Our family really enjoyed our stay here. We loved the pool and how at home we felt. The beds were really comfortable and there was plenty of room to relax. The house is in a great location. It was easy to find and close to all amenities. The host was very helpful and responsive. We would definitely stay here again.
Guest favorite
The heated pool is enclosed by a metal fence and features a playful inflatable float. Sun loungers are placed under colorful umbrellas, while a grassy area and trees provide a natural backdrop. A distant view of blue buildings and a hillside completes the scene.
Home in Uxbridge
5 out of 5 average rating, 34 reviews

Redwood Haven East: Your Dream Getaway in Uxbridge

SarahRating, 5 stars2 weeks ago
This is a wonderful Airbnb in a really special place away from the hustle and bustle of everyday life. You are in a quiet location within easy access of trails where you can run or walk and if you like to ride, there are plenty of equestrian places providing this facility including part of the Airbnb itself. Youssef and his family were welcoming and on hand to provide advice as needed. That said, they were never intrusive. The accommodation is spacious and homely and you certainly do not feel like rushing out but rather enjoying the facilities. There is everything that you could need for a short or extended stay. Towels were plentiful as were shampoo and lots of extras in the bathrooms and kitchen. The heated pool is a real bonus for children or adults that like a daily swim and although shared with the family, I never felt restricted in its use and loved the fact that it was heated so was comfortable regardless of the external temperature. A wonderful stay and perfect host.

Weekly house rentals

Guest favorite
A modern kitchen and dining area are showcased, featuring dark cabinetry and stainless steel appliances. A wooden dining table is set with a decorative centerpiece. Large windows provide natural light and offer views of the outdoor space, enhancing the open layout.
Home in Barrie
4.96 out of 5 average rating, 27 reviews

Cozy Home in Barrie

ShobhaRating, 5 stars1 week ago
We are extremely happy with our one week stay here while visiting family. The home was clean and well stocked, everything was exactly as described on the listing. The beds were super comfortable. Labeed was always prompt with his responses. No complaints at all about this place and we'd stay here again next time we are in Barrie!
Top guest favorite
A bright family room features a white leather sectional sofa and a glass coffee table, complemented by a decorative area rug. Natural light filters through two windows, adorned with red curtains. A television is mounted on the wall, and a small Christmas tree adds a festive touch.
Home in East Gwillimbury
5 out of 5 average rating, 19 reviews

Serenity Canyon: Up Class Business-Family Retreat!

SameerRating, 5 stars1 month ago
Very comfortable and cozy space! Alex was very kind and helpful. We will definitely be back here!
Superhost
The image captures a compact bedroom featuring a spacious bed dressed in a patterned burgundy cover. A comfortable rocking chair sits beside the bed. In the background, light filters through a window covered with sheer curtains, and wooden cabinetry offers additional storage.
Home in North York
4.83 out of 5 average rating, 6 reviews

Private Bedroom, Bathroom, Kitchen -Basement Apt

AnatRating, 5 stars1 month ago
Ana is a great host and was caring and responsive. I stayed there a couple of months and felt at home. It was really great to have a private unit all to myself and for relatively reasonable price. The location is very convenient, with public transit, grocery stores, libraries, and lots of other stores very close by. The unit is quite spacious. The kitchen is probably more suitable for light cooking or heating of food, and there’s not a ton of refrigerator space. My only discomfort during my stay was that when the weather was very cold, the heat in the room was very warm, especially at night. But it made the laundry dry quickly, which was good. All in all, I’m glad I found this place and I really enjoyed my stay.
Guest favorite
A bright living area features two comfortable sofas, one in muted brown and the other with striped fabric. A round coffee table sits centrally on a light-colored rug. Natural light filters through multiple windows adorned with modern shades, while a wall-mounted television is positioned above a sleek fireplace.
Home in Holland Landing
4.91 out of 5 average rating, 11 reviews

Sunny Haven: Brand New Retreat

RyanRating, 5 stars4 weeks ago
Aly’s quick to respond as I made a last minute booking (as my previous booking was cancelled) Aly’s place is in a lovely peaceful suburb (new area). Everything was as described and we appreciate the quality and thoughtful touches around the place to ensure our comfortable stay! Thanks for hosting Aly! Will deffo recommend
Top guest favorite
An open-concept living area features a cozy grey sofa with a textured throw blanket. A stylish rug sits beneath, complementing hardwood flooring. The modern kitchen is visible in the background, equipped with stainless steel appliances and a dining table with chairs near large sliding doors leading to the patio.
Home in Innisfil
5 out of 5 average rating, 30 reviews

Simcoe Retreat

JessicaRating, 5 stars2 weeks ago
Had a great stay here, easy check in and check out. Well stocked home and kept very clean and clear directions provided by host that answered all my questions ahead of time.
Top guest favorite
A cozy living space features a comfortable black sofa adorned with decorative cushions. A wooden table is positioned nearby, accompanied by two bottles of water and a flower bouquet. A television is placed on a stand, and natural light enters through the window above.
Home in Richmond Hill
5 out of 5 average rating, 11 reviews

Bachelor Basement and 1 Free Parking Space

JoeRating, 5 stars5 days ago
David was an excellent host, was very responsive when I needed anything. Was very accommodating when my family came to visit would definitely recommend staying here and look forward to returning when I come back for school again
Top guest favorite
A spacious backyard features a cozy fire pit surrounded by four light-colored adirondack chairs. A soft yellow blanket is draped over one chair. In the background, a wooden deck is visible, with trees providing shade in the serene outdoor setting.
Home in Innisfil
5 out of 5 average rating, 47 reviews

Modern Boho Beach Retreat

RobertoRating, 5 stars1 month ago
This was hands down the cleanest Airbnb I’ve ever stayed in, spotless from top to bottom. Everything was incredibly neat, well-organized, and thoughtfully labeled with clear instructions, which made our stay seamless and stress-free. Mary truly went above and beyond in every way. She was super responsive when we had questions about local fishing tackle shops, and her attention to detail in the home was amazing. She left us a selection of teas, snacks, travel-sized lotion and hand sanitizer, and other small touches that made the whole place feel like a cozy hotel retreat. The neighborhood was peaceful and within easy walking distance of the lake a perfect location to unwind. Would absolutely recommend this stay to anyone looking for comfort, cleanliness, and a caring host.
Top guest favorite
A cozy bedroom features a spacious bed with a blue and white plaid coverlet. A colorful area rug adds vibrancy to the room. A wooden chair and small side table are present, complemented by a wall art piece that enhances the modern design.
Home in East Gwillimbury
5 out of 5 average rating, 18 reviews

comfy basement apartment

MichaelRating, 5 stars5 months ago
Mahsa’s space was well maintained and cozy. I felt at home and she is a fantastic communicator!

Private house rentals

Guest favorite
An open-concept living space showcases vaulted ceilings with exposed beams. Light-colored walls enhance the feeling of spaciousness. Comfortable seating arrangements include a gray sofa and two armchairs, while a dining table sits nearby. A large wall-mounted screen displays images, providing entertainment options.
Home in Innisfil
4.91 out of 5 average rating, 47 reviews

Summer Deals! Modern & Cozy, 4 Season Cottage!

KylieRating, 5 stars1 month ago
First cottage trip with friends this summer. Stayed 3 nights and had a blast. Clint was responsive and gave us great recommendations for activities/food around the area. We were able to have a great time cooking meals with the already provided cookware, utensils, bonfire (s’mores) etc. Utilized the big TV for movies, Nintendo Switch games, and music. If you’re interested in a clean mix between cottage vibes and homey this is the right place to pick. Would come back again. Aside from staying in we visited Friday Harbour: okay boardwalk (not much to do but to walk around), trail was nice.
Guest favorite
A serene lakeside view features a wooden dock extending into the water, with a pedal boat tied up. Adjoining the dock, a gathering of ducks floats near the shore, where red adirondack chairs are positioned in a grassy area, accented by potted flowers.
Home in Gilford
4.86 out of 5 average rating, 14 reviews

Bayview Beach Retreat 3 bedrooms 2 full bathrooms

IlyaRating, 5 stars9 months ago
Elias' place was a wonderful getaway for our group of 3 families. We all have toddler aged children, the space is very accommodating for them, the beach is 30 seconds walk away from the home and there are children's toys and books that Elias offered for us to share in. The water is really nice, great dock access. About 2ft deep at the dock and fairly weedy, you have to swim out about 30-40m to get to deeper water for a nice swim. The paddleboard worked really well for us! Outdoor patio space is fantastic, there is a large umbrella for shade for the sectional and the outdoor dining table. BBQ, outdoor shower, swing, children swings and slide, and fire pit all made for a very pleasant experience. Hot tub was lovely and comfortably sits 4. Kitchen was lovely and fully stocked, has everything you might need to cook your meals. Bedrooms were clean and comfortable. Bathrooms were very clean. Elias was great and communicative, we look forward to our next stay!
Guest favorite
A recreational area features a classic billiards table with balls arranged on top, alongside a treadmill positioned on a light-colored area rug. The walls are a striking combination of black with vertical yellow accents, and the flooring is a warm wood tone.
Home in Caledon
4.89 out of 5 average rating, 85 reviews

Studio Apartment

MohamadRating, 5 stars5 days ago
Sahar was very helpful and nice. The place was very neat I will be back for sure, Highly recommended
Superhost
A bright living space features large windows allowing natural light to fill the room. A cozy gray sofa complements a round coffee table, which is accented by decorative items. A work desk and chair are situated nearby, alongside a contemporary lamp and potted plant.
Home in Newmarket
5 out of 5 average rating, 12 reviews

Near Downtown Newmarket | Pet-Friendly | Parking

SamuelRating, 5 stars2 months ago
Foad's house met our needs very well. It was clean and spacious. The communication was always quick. The layout of the rooms is a little unusual and there is no oven or dishwasher, but we were happy overall with our stay.
Top guest favorite
A bright living area features a spacious sofa paired with two yellow armchairs. A sleek coffee table sits on a soft area rug, while a media console holds a large TV displaying a tropical scene. Natural light streams through the windows, accented by blue drapes.
Home in Oak Ridges
4.99 out of 5 average rating, 68 reviews

Sun Filled & Modern 3 Bdrm W/ 1 Parking!

AnnRating, 5 stars2 weeks ago
The house is beautiful and clean. Check in process is easy and smooth! I would definitely recommend if you are traveling with family, is a very spacious and comfortable house to stay .
Top guest favorite
A welcoming living area is furnished with two comfortable sofas, one dark and one light grey, positioned around a central coffee table. A cozy fireplace serves as a focal point, accompanied by decorative elements on the mantel. Soft lighting enhances the inviting atmosphere.
Home in Newmarket
4.95 out of 5 average rating, 39 reviews

Feel like home 1 bedroom unit w/ King bed

TolikRating, 5 stars2 months ago
Thank you very much for the hospitality. I had fun, perfect, quiet, comfortable and nothing was missing. I highly recommend and I'm sure I'll be back again!🙂
Superhost
An open concept living space features a stylish kitchen island with bar seating, surrounded by tall windows allowing natural light. A dining area with a wooden table and colorful chairs is positioned adjacent to a cozy seating area, enhanced by decorative plants and artwork.
Home in Barrie
4.85 out of 5 average rating, 41 reviews

Stylish & Renovated 3bdr home in Barrie

EvelynRating, 5 stars1 month ago
Olha & her co-host were amazing! They were quick to reply & very accommodating. We booked this place for our wedding party to get ready at since we had our wedding in Innisfil. Their house was everything advertised & beautiful. The laundry room and garage were accessible to guests which were a bonus! The area is close to Costco & major stores + is in a new neighbourhood. Would recommend people to book this house! Its gorgeous!
Guest favorite
A spacious bedroom is featured with a queen bed adorned in a floral-patterned comforter. A bedside table holds a decorative lamp, providing soft illumination. Light-colored walls and a piece of wall art add a calming touch, while a small window allows for natural light.
Home in Aurora
4.92 out of 5 average rating, 36 reviews

Stylish Lower Level Apt, Aurora

TereasaRating, 5 stars1 week ago
Reza’s place is beautifully decorated. Quiet & private. Loved the amenities.

Quick stats about house rentals in Keswick, Georgina

  • Total rentals

    30 properties

  • Nightly prices starting at

    G$2,091 GYD before taxes and fees

  • Total number of reviews

    180 reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore

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  2. Canada
  3. Ontario
  4. Georgina
  5. Keswick
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