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Family-friendly vacation rentals in Keswick, Georgina

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Top-rated family-friendly rentals in Keswick, Georgina

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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A sandy beach extends towards clear blue waters, gently lapping at the shore. Smooth stones are visible at the water's edge, while distant land can be seen across the bay. The scene is bright and open, with minimal vegetation along the shoreline.

Cottage in Tiny

4.78 out of 5 average rating, 178 reviews

Lakefront Private Beach, Waterfront Family GBay

Our property is a PRIVATE LAKEFRONT WATERFRONT on Georgian Bay. The beach and swim bay is for your exclusive use! NOT shared with others! Our private bay is part of thousands of square miles of open freshwater, twenty steps across our private lawn is over 100 feet of private sandy shoreline for your family's exclusive use! The PRIVATE BEACH is great for swimming snorkelling and the water is ultra clean and clear! A waterfront property stay means you're at the beach all the time! STRTT-2022-041

A cozy bedroom features a wooden headboard with a herringbone pattern and decorative elements. Two bedside tables hold lamps and small plants, while a wall display includes round mirrors and framed signs. Light-colored bedding is complemented by a decorative pillow, creating a welcoming ambiance.

Loft in Midland

4.92 out of 5 average rating, 298 reviews

Perch by the Bay - Downtown Midland / Private Loft

Luxury, Comfort & Georgian Bay Style. This first class rental, "Perch By The Bay", is located in Downtown Midland. Walk everywhere, park your car (free) & enjoy what Midland has to offer. Midland's boat harbour, is only minutes by foot. Live our lifestyle, enjoy our many festivals, professional theatre, artisans, culinary cuisine, etc! It's "sister" AirBnB is "Nest By The Bay" private loft at the rear of the building. 2 night min. preferred, 1 night by request. Not suitable for ages under 6

The living area features modern sofas with decorative cushions, a sleek glass coffee table, and a mounted television. Natural light fills the space through a nearby window, while a mirror enhances the open feel. A warm wooden floor complements the neutral decor.

Bungalow in Wasaga Beach

4.88 out of 5 average rating, 123 reviews

B & B Home Away from Home

The house is only 250 meters from Beach Area # 2 and it's perfect for a family or friends gathering. A short five minutes drive to the entertainment strip, restaurants and grocery stores (Walmart and Bank). The house has a modern decor, furniture, four comfy bedrooms and has 2 fireplaces one on the main floor and one in the basement. A television in the basement hooked up to the Wi-Fi so you can enjoy Netflix. *Noise By-law 11pm *NOT suitable for parties Come, relax and enjoy Wasaga Beach.

Top guest favorite

A spacious living room features a cozy seating area with a dark brown sofa and a comfortable armchair. Natural light floods in through large windows, illuminating a rustic wooden coffee table. A television is mounted on the wall, accompanied by decorative wall art.

Bungalow in Wasaga Beach

4.93 out of 5 average rating, 123 reviews

Nice Wasaga Cottage

We welcome well traveled guests over the age of 25 and families. Perfect for 4 people. Large 2 bedroom, 4 season cottage with big living room and eat-in kitchen; in a desirable area of Wasaga Beach Area 4. Renovated kitchen and bathroom. WiFi, gas furnace, and central air conditioning. 1 block to beach area, park, and bike path. 1 block to Nottawasaga river and boat launch. 25 min to Blue Mountain Village. Hiking, Golfing, and Skiing all nearby. 1 extra guest allowed for an additional fee.

A cluster of charming cottages is arranged along a dirt pathway, framed by trees. Each cottage features light-colored siding and distinct roofs. Lush shrubs are positioned near the entrance of each cottage, contributing to the inviting appearance of the property.

Guesthouse in Wasaga Beach

4.86 out of 5 average rating, 107 reviews

2 -Sun Angel Court Couples Cabin 2

We are a group of ten unique and pretty cottages, located directly In front of Beach 2. We back onto the Nottawasaga River(excellent for fishing). We are extremely clean and have a separate washroom facility for our cottages. There is a common picnic area , overlooking the river with 2 full Bbq's available for guest use. We have a fire pit for late night hotdogs, smores and marshmallow roasting. We are a 5 min walk from the waterfront square- this is where all the special events take place.

A modern kitchen features dark wooden cabinetry alongside stainless steel appliances, including an oven and microwave. A spacious island with seating is highlighted, complemented by a sleek countertop. Natural light floods the area through large windows adorned with sheer curtains, creating a bright and inviting cooking space.

4.87 out of 5 average rating, 103 reviews

Lavish. Spotless. One's Own, 4 BR 4 BA Home!

Welcome to Maple Downtown! Live Large in a Luxury Brand New Concept Home surrounded by mature 30 ft high trees. My place has 2 stories (main & second level), 4 bedrooms, 3.5 bathrooms. Sleeps 8 in Beds (Max 8 people, confirm with the host ). Basement Apartment is not included in this listing and not occupied during your stay. MUST BE 25 or OLDER in order to BOOK. Do not book my home if you are planning on parting or gathering. Please ,note a 4% City Tax will be added to each booking.

A wide wooden boardwalk is shown alongside a marina, with modern buildings lining the waterfront. Soft sunlight reflects off the water and the boats docked. Comfortable blue chairs are placed on the green lawn, inviting relaxation while enjoying the serene harbor view.

Condo in Innisfil

4.93 out of 5 average rating, 208 reviews

Designer Condo with beautiful harbour view.

Unique top floor. Rare views where every room overlooks the harbour. Professionally designed with new stylish furnishings. Ideal for those who like a little sophistication while spending time at the lake. Enjoy going out to eat every night or make a meal and curl up and relax in the beautiful living room, or a combination of both! Friday Harbour is a resort with beautiful walking trails, cafes, and restaurants, and a perfect get-away that celebrates the seasons with exiting activities.

An inviting living area is highlighted by a cozy fireplace with a flickering flame. A mounted TV is positioned above a shelf containing various movies. Soft seating arrangements are present, complemented by a decorative sign and a window that lets in natural light.

4.87 out of 5 average rating, 128 reviews

Beachy Blue Bay Cottage - licence #STRTT-2024-195

A 2 min walk to the beach, this 4 bedroom Cottage with Circular Driveway is bright and newly renovated with an open concept main floor. Very private and surrounded by mature trees. Relax on a very large deck with gas BBQ, seating and patio table. Over looking the deck is the fire pit area with lots of room for the kids to play & roast s’mores. The basement is well equipped with pool table, dart board, air-hockey, kids toys, board games & a small TV with lots of movies to snuggle up to!

A spacious backyard is depicted, featuring a striped hammock supported by a sturdy frame. Lush green grass covers the ground, surrounded by tall trees creating a natural, serene setting. The scene conveys an inviting space for relaxation and outdoor enjoyment.

Bungalow in Innisfil

4.82 out of 5 average rating, 280 reviews

Lake Simcoe-3bdr,hot tub,sauna,swim,play,hike

NEW!!: seasonal or monthly rental available, contact me directly to get the exact pricing, thank you Our cottage is about a 800 m from the beach at family friendly Innisfil Beach Park! The kitchen is modern and bright with lots of room for lounging inside the cottage or entertaining outside in the large yard with a fire pit. Our cottage is ideal for couples and families. It is beautifully furnished. There is a BBQ, patio furniture & firepit, smart TV with Roku and Chromecast.

An open-concept living area showcases a comfortable sofa and modern furnishings on a patterned area rug. Natural light streams through large windows, illuminating the space. A wooden floating staircase leads to the upper floor, while a stylish dining space and kitchen are visible in the background.

4.89 out of 5 average rating, 191 reviews

Family Home Near St Clair W and Public Transport

Steps away from vibrant St Clair West with great dining, access to public transport and shopping. A real family home with space and amenities for everyone. Free parking for 2 cars. Open-concept living & dining, well-equipped kitchen. Sunny back deck. 3 comfortable bedrooms. Spa bathroom with heated floor. Perfect for families who are in town for reunions, weddings, birthday parties and visiting. Quiet hours after 10pm - not suitable for groups in town ‘to party’.

A tranquil waterfront view is captured, showcasing a grassy area leading to the lake. Four black Adirondack chairs are arranged facing the water, under a large tree. A wooden dock extends into the lake, with a ladder visible, inviting reflection and relaxation.

Cottage in Kawartha Lakes

4.78 out of 5 average rating, 101 reviews

Serenity by the Lake: Lake Waterfront Cottage

Welcome to our delightful 3-bedroom 4 season waterfront cottage located on the beautiful Cameron Lake in Fenelon Falls, where endless aquatic adventures await! Nestled in a serene location, this picturesque retreat offers the perfect blend of comfort and natural beauty. With its prime position by the water's edge, it's an idyllic haven for swimming, boating, and fishing enthusiasts alike. Property is located only 1.5 hrs. from the GTA & directly off of HWY 35

A sandy beach stretches out under a clear blue sky, with gentle waves lapping at the shore. A wooden pathway leads to the water, while a few people are seen walking along the beach, enjoying the serene coastal atmosphere.

4.9 out of 5 average rating, 146 reviews

Beautiful Getaway Location - Cuddles Cove

Enjoy a all year round getaway either personal or corporate retreat at this spacious, well equipped Bungalow located short minutes walk from beautiful sand beach access. This newly built cottage is approx 5,000 Sqft with an additional 1,000 Sqft covered balcony offering accommodations of 6 queen beds, 1 Luxury full kitchen, 1 BBQ and lots of entertainment! Enjoy a nice Quiet getaway in the lovely community of Tiny! STRTT-2025-152

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Stylish accommodations and amenities

Popular amenities for Keswick, Georgina family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Top guest favorite

This inviting bedroom features a spacious bed adorned with soft linens and a textured throw. A large armoire stands alongside, complemented by decorative plants and soft lighting. Natural light is welcomed through an adjacent glass door leading to a private entrance.

Guest suite in Orangeville

4.92 out of 5 average rating, 760 reviews

HotTub & Cozy Getaway - Headwaters Retreat

The bedroom features a spacious bed dressed in a mix of striped and patterned linens, complemented by matching nightstands on either side. A floral artwork adorns the wall above, and modern bedside lamps provide soft lighting, enhancing the calm ambience.

Condo in Downtown Toronto

4.97 out of 5 average rating, 320 reviews

Beautiful Condo + CN Tower View + Free Parking

The modern condo building features a multi-story design with balconies and large windows. Soft greenery lines the ground level, enhancing the urban landscape. A clear blue sky provides a bright backdrop, while the street is lined with manicured trees, creating an inviting atmosphere for residents and visitors.

Condo in Unionville

4.91 out of 5 average rating, 114 reviews

Downtown Markham Unionville

A modern bedroom is showcased with a spacious bed dressed in dark grey linens and layered with a light white blanket. Sliding glass doors offer a glimpse into the adjoining living area, where natural light filters through sheer curtains.

Condo in Downtown Toronto

4.89 out of 5 average rating, 838 reviews

1 Bedroom Suite - Downtown Core (near MTCC/Rogers)

A modern kitchen features a central island with a wooden countertop, surrounded by white bar stools. Stainless steel appliances, including a refrigerator and oven, are visible. Natural light floods the space through large windows, highlighting the sleek cabinetry and minimalist design.

Condo in Downtown Toronto

4.87 out of 5 average rating, 326 reviews

Luxury heart of downtown by CN Tower/ MTCC/Union

A colorful abstract artwork hangs above a wooden bed, featuring flowing lines in shades of blue, pink, and beige. Two exposed bulb lights are mounted on the walls beside the bed, enhancing the space's artistic expression.

Condo in Downtown Toronto

4.86 out of 5 average rating, 102 reviews

Casa Di Mama | Beautiful 2BR Downtown-Free Parking

A spacious backyard is featured, with vibrant green grass and trees providing shade. The two-story cottage includes a deck above with outdoor seating. Stairs lead from the upper deck to the grassy area below, creating an inviting space for relaxation and gatherings.

Cottage in Orillia

4.72 out of 5 average rating, 210 reviews

Waterside Haven: spacious retreat w/hot tub

A two-story house with light yellow siding and a brown roof features a welcoming front porch, adorned with potted plants and furniture. Well-kept landscaping surrounds the house, offering a bright and inviting outdoor space under a clear blue sky.

Apartment in Whitby

4.95 out of 5 average rating, 230 reviews

Serenity Suite w/Sauna-Your Entire Apt Awaits You

Family- and pet-friendly home rentals

A bungalow with a wooden deck overlooks a well-maintained lawn, surrounded by greenery and flower beds. Large windows provide views of the outdoor space. The exterior showcases a warm wooden finish and a sloped roof, enhancing the inviting appeal of the home.

Bungalow in Orillia

4.87 out of 5 average rating, 244 reviews

Luxury, Waterfront, 4 bdrm Bungalow in Sth Muskoka

A well-appointed bedroom features a spacious bed adorned with neatly arranged white towels. A decorative throw enhances the bedding, while bedside lamps provide soft illumination. An exercise bike is positioned near the bed, and a tree-like light fixture adds a unique touch to the ambiance.

Home in Roncesvalles Village

4.92 out of 5 average rating, 154 reviews

Cozy one bedroom apartment in Roncesvales village

An open-concept living space features a cozy seating area with black leather sofas, a dining table, and a fully equipped kitchen. A spacious bed is positioned against the wall, with large windows providing natural light and views of the peaceful surroundings.

Guesthouse in Schomberg

4.92 out of 5 average rating, 425 reviews

Country Cabin Escape | King Bed | Pet Friendly

Top guest favorite

The exterior of a quaint cottage features a welcoming porch area with a set of chairs and a table. Flower pots enhance the environment, while the charming purple door adds a whimsical touch. The surrounding natural landscape includes grassy areas and scattered stones.

Cottage in Kawartha Lakes

4.9 out of 5 average rating, 117 reviews

1950's Romantic & Whimsical cottage on Gull River

Top guest favorite

A cozy living room features a vintage sofa adorned with decorative pillows, complemented by a plush armchair. A large window is framed by soft drapes, allowing natural light to brighten the space. An elegant coffee table holds a decorative tray, enhancing the inviting ambiance.

Home in Toronto

4.9 out of 5 average rating, 134 reviews

Charming Century Home Close to Vibrant Shops

The kitchen is equipped with modern appliances, including a stove, microwave, and fridge. White cabinetry complements the sleek gray countertops, while a window provides natural light. A minimalist design is achieved with a stylish pendant light hanging above the sink area.

4.81 out of 5 average rating, 255 reviews

Entire House w/ Games Room- by Beaches & Downtown

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

Top guest favorite

The interior of the cabin features warm wooden walls and a cozy woodstove. Two blue lounge chairs are positioned near a rustic table. Natural light floods through a large window, illuminating the space, while a striped rug adds comfort underfoot.

Tiny home in Schomberg

4.99 out of 5 average rating, 207 reviews

SNAKE CABIN(rustic, 'off-the-grid')

Family-friendly home rentals with a pool

A charming two-story cabin is nestled among lush greenery, with a pathway leading to the entrance. Tall trees and well-maintained hedges surround the home, creating a sense of privacy. Soft sunlight illuminates the cabin, enhancing its rustic appeal.

4.95 out of 5 average rating, 304 reviews

The Trails Retreat (Private Cabin)

Condo in Downtown Toronto

4.67 out of 5 average rating, 374 reviews

Modern Condo in the heart Downtown Toronto!

A spacious living area is highlighted by a plush couch adorned with throw pillows and a soft blanket. A modern coffee table has a wooden tray atop it. Art is displayed on the walls, and a leafy plant is positioned beside a light source.

Condo in Downtown Toronto

4.97 out of 5 average rating, 239 reviews

Chic, High-Rise Apartment with CN Tower Views

An outdoor pool area features a surrounding deck with wooden steps leading up to it. Bright blue water reflects the sky, and vibrant green grass borders the patio. Two red Adirondack chairs are placed nearby, complemented by lush trees and a distant green landscape.

Guesthouse in Orangeville

4.95 out of 5 average rating, 352 reviews

Sunny Pines Farm Studio Tennis Court/Bruce Trail

A rustic log cabin is surrounded by greenery, showcasing a wooden exterior. Large glass doors provide natural light, while several windows allow for outdoor views. A wooden deck leads to the entrance, enhancing the cabin's connection with its natural setting.

Cottage in Tiny

4.85 out of 5 average rating, 87 reviews

Haven at Georgian Bay

A private pool area features a clear blue pool surrounded by lounge chairs. A covered seating area provides shade, and a decorative structure is located nearby. Lush greenery from surrounding trees enhances the tranquil environment.

Bungalow in Lafontaine Beach

4.9 out of 5 average rating, 50 reviews

Sweet Memories of Georgian Bay

An open-concept living area features hardwood floors and exposed brick walls. A spacious bed is complemented by elegant chandeliers, while a white futon is situated nearby. Decorative artwork adorns the walls, and a light-filled kitchen area is visible in the background.

Home in Niagara

4.91 out of 5 average rating, 303 reviews

King West Victorian Studio Gem

An aerial view captures the layout of Friday Harbour, featuring an expansive marina surrounded by lush greenery and residential buildings. The coastline, with a sandy beach and ample water access, provides recreational opportunities. The serene water reflects the natural beauty of the surrounding landscape.

Condo in Innisfil

4.84 out of 5 average rating, 180 reviews

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

Quick stats about vacation rentals that are family-friendly in Keswick, Georgina

Total rentals
40 properties
Nightly prices starting at
€ 9 before taxes and fees
Total number of reviews
840 reviews
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi

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