Family-friendly holiday rentals in Bradford

4.85 out of 5 average rating, 288 reviews

A spacious living area features a comfortable brown sofa positioned near a glass coffee table. Natural light pours in through large windows with blinds, illuminating a dining area with seating for four. A modern kitchen is visible in the background, equipped with sleek appliances.

Guest suite in Moonstone

RELAX @ our HOT TUB and SAUNA in the woods

PLEASE READ! Mt. St. Louis & Horseshoe Valley at doorstep! This is a bright, large and private walk-out GUEST SUITE (basement apartment). Hot tub, patio, fire pit & secluded path in the woods to enjoy nature. Kitchen is equipped with an induction cooktop and all things necessary, even wine bottle opener:) Open concept living room/kitchen/dining room with TV & Roku. Bedroom is a work of Art: dark, mysterious and romantic! Custom Queen bed made from weathered barn wood salvaged from our property.

4.93 out of 5 average rating, 233 reviews

A cozy living area features a couch facing a 55" television, placed on a low white media console. A floor lamp provides additional lighting, while a small coffee table adds functionality. Doorways can be seen in the background, leading to other areas of the suite.

Guest suite in Newmarket

2 Bed-2Bath-Kitchen | Private | Family-Couple-Work

We have an ideal place for you regardless of work, pleasure, or family time. The recently renovated suite includes: - Separate keyless entry - 2 bedrooms with closets - Living room with 55" TV - Full kitchen with storage & dining - 2 full bathrooms (1 en suite) - 2 on-premises Parking - Laundry - WiFi & more FAST EV Charger-Check for availability ($15/charge) CENTRAL LOCATION! Steps to Upper Canada Mall, Groceries, Restaurants, Trails, Parks, Golf Course, Costco, Walmart, Highway, Go, & more

Dome in Bradford West Gwillimbury

Vibrant autumn foliage displays shades of yellow and orange surrounding a geodesic dome. A pathway of stone steps leads through a lawn covered in colorful leaves, creating a serene outdoor setting amidst lush greenery.

4.96 out of 5 average rating, 423 reviews

Four season glamping dome under the stars

Whether you are looking for a romantic getaway for two, a solo remote work week in solitude surrounded by nature, or a family adventure, this 4-season geodesic dome is just the right place. Explore picturesque trails of Scanlon Creek Conservation Area, enjoy inground pool in summer, experience breathtaking sunsets over the farm fields, the starry skies by the bonfire, mesmerizing dance of fireflies in June, and let the frogs and crickets lull you to sleep in the place where time stands still...

Guest suite in East Gwillimbury

A comfortable living area features a cozy sofa with decorative pillows, positioned near a large window allowing natural light. A flat-screen TV is mounted on the wall, and a small coffee table rests on a patterned rug. A lamp and electric fireplace add to the inviting ambiance.

4.92 out of 5 average rating, 484 reviews

Stylish, Modern 2nd Floor Private Apt. Quiet Area

Located in a beautiful and quiet neighborhood, this modern apartment can make for a perfect peaceful getaway no matter the occasion. Close to Lake Simcoe, beautiful beaches for swimming & fishing, and plenty of nature trails. Highlights: Large and cozy bedroom with ample storage and work space. Beautiful open concept dining area and kitchen with everything you need. Keurig coffee, tea and some snacks provided. Comfy sofa in front of a large screen TV with Netflix. High speed internet provided.

Guest suite in East Gwillimbury

A cozy seating area is featured with a dark leather recliner sofa positioned near a modern fireplace. A large TV is mounted on the wall, displaying a serene sunset over water. Lush greenery is provided by a potted plant nearby, enhancing the inviting space.

4.98 out of 5 average rating, 189 reviews

Adorable Entire Suite,Sep. Entry,1 Parking

Enjoy easy access to stores, restaurants and entertainment from this perfect location. Only 5 min. drive to GO Train & Bus Terminal with quick, convenient transport to Downtown Toronto, Canada’s Wonderland, etc. This lower level guest suite is fully equipped with own laundry, kitchenette with mini fridge, Induction 2 burner Cook Top Stove, microwave, toaster and coffee maker. Cozy Fireplace, 60” screen HD TV and Luxurious King Size Bed Safe Neighbourhood with walking trails and parks.

4.93 out of 5 average rating, 476 reviews

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.

Guest house in Schomberg

Country Cabin Escape | King Bed | Pet Friendly

Tucked away on our peaceful family farm, this private cabin offers tranquility and comfort—while not secluded in the woods, it provides a true countryside experience. The cabin is located on the same property as our farmhouse, Country Suite, and Event Barn. Blinds are provided to enhance your privacy during your stay. The Cabin includes a full kitchen, king sized bed, propane BBQ and many other amenities, for a full list please review the "What this place offers" section of our listing.

4.86 out of 5 average rating, 162 reviews

Home in Caledon

Studio Apartment

Discover the perfect blend of comfort and convenience in this cozy studio apartment, ideally situated in the vibrant heart of Caledon. Key Features: Prime Location: Steps away from shops, cafes, and parks. Modern Amenities: Spacious living area, and stylish bathroom. Natural Light: Large windows that fill the space with warmth and brightness. Community Vibe: Enjoy the friendly neighborhood atmosphere and local events. This peaceful retreat, offers everything you need. Don't miss out!

4.77 out of 5 average rating, 159 reviews

Home in Newmarket

Cozy apartment in Newmarket

This cozy home, located at Leslie and Mulock, is within walking distance of parks, grocery stores, and restaurants. It’s a short drive to Southlake Hospital, Historic Downtown Newmarket, the GO station, and Upper Canada Mall, Walking distance to Pickering College. Guests have full access to the first floor, featuring a living room, kitchen, dining room, and a private basement apartment, with a private bathroom. Perfect for a comfortable and convenient stay.

5 out of 5 average rating, 190 reviews

A spacious bedroom area features a queen bed adorned with light bedding. A large wall-mounted TV is visible, and a cozy rug lies on the floor. Two comfortable chairs with bright yellow cushions provide seating beside the bed. Natural light streams in through a small window.

Guest suite in Barrie

Private Basement Suite in a family neighborhood

Its a clean & spacious private Basement suite in a family neighborhood with all amenities that you may require for your stay. Features a queen bed, bathroom and kitchen. Free Parking is included. Highway 400, Park Place, Walmart, Costco, Canadian Tire are within 5-7 minutes driving distance. We offer our guests complete privacy from check-in to check-out, but always available if needed. Perfect for savvy budget travelers who deserve quality stay.

Guest suite in New Tecumseth

A spacious living area features a sectional sofa and a wooden coffee table, complemented by a textured area rug. Natural light is provided by recessed lighting, and a white curtain elegantly separates the space. Nearby, a kitchen area with a dining table and modern appliances is visible.

4.85 out of 5 average rating, 325 reviews

Modern, Private and Luxurious!

Welcome to our bright and stylish lower level unit in a friendly new development! You'll enjoy all the comforts of home in this cozy space. Located near Base Borden, the Honda Plant and Baxter Labs. 5 mins from Nottawasaga Inn. 30 mins to skiing at Snow Valley Ski Resort, Hockley Valley Resort, and Mansfield Ski Club. Right around the corner is an awesome community park that features a summer splash pad and a great winter tobogganing hill.

4.86 out of 5 average rating, 134 reviews

A spacious open-concept suite features a comfortable sleeping area with a bed adorned with decorative pillows. A sleek black sofa is paired with a circular table, while a small plant adds a fresh touch. Soft lighting and a window enhance the inviting atmosphere.

Guest suite in Newmarket

The Quiet Retreat

Welcome to our cozy suite, your perfect private retreat. Soft beige walls and warm lighting create a comforting atmosphere in our open-concept space. Unwind in the sleeping area or kick back in the living and dining areas with a good book or work. Our separate entrance ensures complete privacy, allowing you to come and go as you please. Make yourself at home in our warm and inviting place, your home away from home. License #BL2023-00257

4.77 out of 5 average rating, 384 reviews

The living area features a sectional couch positioned near a small white coffee table, creating a comfortable gathering space. A doorway leads to a staircase, while a kitchenette is visible in the background. Natural light enters through a nearby window, enhancing the neutral decor.

Flat in Innisfil

1 Bedroom Hotel Style Short/Long term Available

Come stay at this brand new all-season, private & modern guest suite close to all Innisfil has to offer! 1.2 km away from Lake Simcoe, Big Cedar Golf Course & minutes away from all major Ski hills in Barrie! Enjoy summer activities such as multiple beaches, boating/marinas, golfing & fishing- all within walking range. Enjoy winter activities such as skiing, snowboarding and very special ice fishing spot at the end of the road.

Popular amenities for Bradford family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A modern living area features a light-colored sofa adorned with decorative pillows, positioned next to a wooden coffee table. A striped area rug lies beneath, while a kitchen island with bar stools and stainless steel appliances is visible in the background.

4.97 out of 5 average rating, 103 reviews

Cozy Stays – Your Fall Getaway at Friday Harbour

4.89 out of 5 average rating, 422 reviews

A cozy cottage is nestled among vibrant autumn foliage. The front features large windows and a welcoming deck, with outdoor seating visible. Surrounding trees display various shades of yellow and orange, contributing to a serene nature setting.

Cabin in Innisfil

Kempenhaus- Lake Simcoe Cottage & Spa

4.82 out of 5 average rating, 137 reviews

The living area features a comfortable sofa beside a stone fireplace, providing a cozy focal point. A light-toned armchair sits nearby, while a television is mounted on the wall. Natural light enters through the glass door, leading to an outdoor space.

Apartment in Oro

Cozy 1-Bedroom Romantic Retreat with full Kitchen

4.97 out of 5 average rating, 118 reviews

Guest suite in Innisfil

Cozy Lakeside Couples Spa Getaway *seasonal*

4.9 out of 5 average rating, 242 reviews

Cottage in Alcona

Utopia villa and spa

4.98 out of 5 average rating, 140 reviews

Home in Coldwater

Luxury Guest House with Private Hot Tub and Trails

4.87 out of 5 average rating, 148 reviews

A spacious lake house exterior is set against a cloudy sky, featuring large windows that allow natural light to enter. The surrounding yard is adorned with fallen leaves, while a deck with outdoor furniture and a hot tub enhances the outdoor space.

Cottage in Innisfil

Spacious family cottage 45 mins from GTA!

4.91 out of 5 average rating, 286 reviews

A circular patio area features a fire pit at the center, surrounded by eight colorful Muskoka chairs in red and blue. The setting overlooks a serene lake and wooden dock, with a guitar resting nearby on the lawn, framed by a clear blue sky and scattered clouds.

Home in Keswick

Lakefront Retreat w/ Hot Tub, Game Room & Beach

Family- and pet-friendly home rentals

4.9 out of 5 average rating, 462 reviews

A kitchenette area features modern cabinetry and countertop space, illuminated by recessed lighting. Decorative touches, including wall art and greenery, create a welcoming atmosphere. Appliances include a full fridge and microwave, with options for cooking, providing convenience for guests.

Home in Vaughan

Private Lower 1 BR + Sofabed Self Checkin with PKG

4.89 out of 5 average rating, 230 reviews

The room contains two spacious beds with soft linens arranged neatly. A wall-mounted smart TV is positioned near a cozy electric fireplace. Natural light enters through two windows dressed with light curtains, and a small table with dining essentials is visible in the corner.

Flat in Gilford

Lakeside Simcoe Fisher's apartment

4.87 out of 5 average rating, 472 reviews

A cozy living and dining area features a wooden dining table set with plates and glassware. Two plush sofas surround a glass coffee table in front of a television, while bright yellow flowers add a pop of color to the space. Light-colored walls enhance the inviting atmosphere.

Flat in Berczy

spaciuos 2BD 3-6 ppl homestyle BSMT豪宅精装带窗地下一层130平

4.89 out of 5 average rating, 114 reviews

A white guest suite is shown attached to the host house, featuring a separate entrance. A gazebo with a circular structure stands nearby, surrounded by lush greenery and open fields. A patio area with a table and chairs is visible, providing outdoor seating.

Flat in Egbert

Lovely one bedroom guest suite in the country

4.91 out of 5 average rating, 148 reviews

A modern living space features a cozy sleeping area with a bed adorned in neutral tones and decorative pillows. A dining table with chairs stands nearby, while two comfortable armchairs are positioned around a wooden coffee table. Small plants and wall decor add a touch of style.

Guest suite in Aurora

Fourmi- Cute And Cozy Getaway

Farm stay in Whitchurch-Stouffville

A cozy living area features two brown sofas adorned with colorful cushions. Soft lighting is provided by two lamps flanking the seating. A vibrant artwork hangs on the wall, and light-colored curtains frame the window, contributing to the welcoming atmosphere.

4.83 out of 5 average rating, 258 reviews

Orchard cottage, experience the farm in the city

4.99 out of 5 average rating, 223 reviews

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

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

4.9 out of 5 average rating, 115 reviews

A modern living space features a comfortable couch positioned in front of a wall-mounted television. A dining area with sleek white chairs is visible, along with a cozy bed beyond a sliding door. Natural light is softly illuminated by recessed lighting.

Flat in Barrie

The Chieftain Suite

Family-friendly home rentals with a pool

4.84 out of 5 average rating, 147 reviews

Guest suite in Minesing

Farmhouse GUEST SUITE; Year round hot tub

4.86 out of 5 average rating, 100 reviews

A bright and spacious living area features a comfortable white sofa paired with dark blue accent chairs. A stylish dining table is set for meals, while a gas fireplace and mounted television create a cozy atmosphere. Natural light fills the room through large windows.

Home in Shanty Bay

King Bed, Pool, Gym, Ravine View, Your Getaway!

4.91 out of 5 average rating, 117 reviews

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

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

An open-concept kitchen features sleek white cabinetry and a black granite island with three modern bar stools. Natural light fills the space through large glass doors, which lead to a balcony. A minimalistic design with potted plants enhances the welcoming atmosphere.

4.87 out of 5 average rating, 170 reviews

Friday Harbor Upscale 1Bed+Sofabed+Pool Option

The living room features a comfortable sofa adorned with decorative pillows. A Smart TV is positioned on the wall opposite a glass dining table set for four. Natural light floods the space through large glass doors, offering views of the private patio.

4.88 out of 5 average rating, 154 reviews

Beautiful Condo, 2 Bedrooms and a Den in a Resort!

4.81 out of 5 average rating, 114 reviews

An outdoor area is presented with a circular seating arrangement made of woven material, positioned around a central table. An umbrella provides shade over the seating. A heated salt-water pool reflects the surrounding greenery, surrounded by a stone patio and wooden fencing.

Flat in Barrie

Beautiful Basement apartment with swimming pool

A bright living area is showcased with a red sofa and a glass coffee table positioned on a patterned rug. Large glass doors open to a balcony. A colorful wall art piece features a scenic landscape, adding a vibrant touch to the space.

4.94 out of 5 average rating, 132 reviews

Friday Harbour Luxury Condo Escape, Sleeps 4