Family-friendly holiday rentals in Ajax

4.96 out of 5 average rating, 187 reviews

The sleeping area is defined by a cozy queen bed, featuring decorative pillows with intricate patterns. Soft lighting is provided by wall-mounted lamps on either side, against a calming blue accent wall. Minimalist artwork is displayed above the bed, enhancing the space's modern design.

Guest suite in Pickering

- Free street parking - Great pitstop for travels along the 401 (exit 399) - Open concept space with private bathroom - Queen bed, fast Wi-Fi, and mini kitchen bar - Kettle, microwave, and coffee station included - Cozy workstation for remote work or email - Convenient location near transit, shops and restaurants - Pickering Casino (10 min drive), Pickering Golf club (2 min drive), Bubble tea, Rollz Ice Cream, Good Life, Shawarma, Mexi Guac within a 4 min drive -A cozy ~200 sq ft resting place

4.93 out of 5 average rating, 387 reviews

Home in Pickering

“Elysium” Where happiness is real!

Stay connected with our fast Bell Fibe Wi-Fi, free parking and unwind with over 1000 streaming channels on our TV, including Netflix and Prime. Whether you're here to catch the game or watch an exciting fight you’ll have everything you need for a great time Our location is the perfect base for discovering all that Pickering has to offer. You’ll be just a short drive away from fantastic restaurants, lively bars, shopping spots, and even casinos—everything you need for a fun and convenient stay!

The spacious living area features a leather sectional sofa and a cozy ottoman, situated atop a soft area rug. A modern kitchen with an island and dark cabinetry is visible in the background, complemented by ambient blue lighting.

4.96 out of 5 average rating, 168 reviews

Brand New Private Luxury Suite Open Consept living

Sun filled Private Suite, cozy & modern. Entire space with separate entrance. Peaceful Ravine, walking path & Sunrise. Minutes to the 401 & Ajax GO Station. 18 min to Toronto Pan Am Sports Centre. Drive or GO to downtown Toronto. Walking distance to a wide variety of restaurants, major shopping plazas, Walmart, Costco, RCSS, Iqbal foods, Ajax Downs & Casino. Life Time Athletic, Ajax convention Centre. Minutes to Lake Ontario & Pickering Casino. 12 min to Dagmar Ski Resort & Whitby Thermëa spa.

A modern two-story house features a welcoming front porch supported by white columns. Large windows adorn the upper level, with a stone pathway leading to the entrance. The driveway accommodates two garage doors, enhancing the home's curb appeal in a suburban neighborhood.

4.78 out of 5 average rating, 202 reviews

Finished 2 BR Apartment in an Upscale Area of Ajax

Get your own private space in a newly finished basement apartment close to all amenities. Located in an upscale area, gated type community. Private separate entrance and big windows. Car parking and wifi. Private kitchen with dishwasher, bathroom and laundry. No sharing needed. Fully furnished 2 Bedrooms with Kitchen, Sofa, Fireplace, Workspace, with standing desk option. 5 min drive to Ajax Go, 10 min to waterfront. Close to Amazon facility, Shopping, conservation area, golf etc.

4.92 out of 5 average rating, 144 reviews

The kitchen area features sleek black cabinetry contrasted by white countertops, providing a modern aesthetic. A dining table with wooden chairs is positioned near the window, enhancing natural light. Essential appliances, including a microwave and coffee maker, are neatly arranged for convenience.

Apartment in Whitby

Absolutely gorgeous basement guest suite!

Legal Basement - This chic place comfortably accommodates up to 5 guests and comes fully furnished. There are 2 bedrooms, each accommodating 2 guests, along with a daybed in the living room for the 5th person. One bedroom offers a queen-size bed, while the other has a double-size bed. Also, there are 2 study tables with chairs, one in each bedroom and one in the living room. The meticulously designed kitchen boasts modern and luxurious touches. The stylish washroom features a standing shower.

4.96 out of 5 average rating, 559 reviews

Bright Private Suite w/Separate Entrance & Patio

PRIVATE Walk Out Basement Apartment W/Separate Entrance. 420 Sq.Ft space. Queen Sized Bed. Oversized Shower w/ Rainfall Shower-head. Microwave, Two Mini Fridges, Coffee/Hot Water Tea Maker. Please note: not a full kitchen. Dining/Work Table w/Benches. High Speed Wi-fi. Living Room w/ Reclining Lazy Boy Couch and 50” Smart Tv. Over 1000 Live Tv Channels and Netflix. Private Little Backyard Patio w/Table. Private Driveway ( 2 Cars). 1 Min Drive to Hwy 401. 15 Min Walk to Ajax Go Station.

A cozy living space features a modern television stand with a flat-screen TV, accentuated by a bold artwork. A gray couch with yellow cushions invites relaxation, complemented by a light rug atop wooden flooring. Large windows allow natural light to brighten the room.

4.86 out of 5 average rating, 231 reviews

Moons & Noons -Separate Unit for your Comfort

Welcome to our charming retreat in Ajax! You'll be greeted by living space adorned with carefully curated decor. The sofa beckons you to unwind, while the large windows' scenic views allow natural light to fill the room. Just take a stair down to the Basement, to be greeted by an elegant kitchenette. Enjoy a drink on the sofa while watching shows on 55' QLED. Step into a world of relaxation in our stunning bathroom designed to calm your stress. Your unforgettable stay awaits U!

A cozy bedroom features a spacious bed with elegant bedding, flanked by two nightstands. A dresser is positioned against the wall, and natural light filters through a window, illuminating the soft grey walls and light-colored flooring.

4.99 out of 5 average rating, 137 reviews

Private Sauna Suite Retreat

1 Bedroom • 1.5 Bathrooms • Private Entire Unit Newly renovated and quiet, just minutes from Hwy 401 and local restaurants. Highlights • Private self check-in • Driveway parking for 1 car • Private sauna • 55 Inch TV with Netflix Amenities Fresh towels, linens, tooth brushes & pastes, hairdryer, home essentials, shower essentials, and extra pillows/towels on request. Spotless home, quick replies, and your comfort guaranteed - book with confidence.

4.92 out of 5 average rating, 224 reviews

A cozy living area is presented with a grey sofa adorned with yellow cushions. A large TV is mounted on the wall, facing a white coffee table on a textured rug. A colorful abstract painting decorates one wall, complemented by a small indoor plant.

Apartment in Pickering

Lower Unit - Central location

Enjoy the charming touches of this cozy basement suite with a clean modern feel. Beautifully decorated featuring a spacious open concept living room/kitchen combo area with spacious island and a brightly lit bathroom with a stand-up shower. This guest suite with your very own private entrance is bright and full of warmth. Conveniently located: 5 min walk to Pickering Town Center, 10 min walk to the Pickering GO and 2 min drive to 401.

The living area features a spacious couch and two cozy blue accent chairs, positioned around a round coffee table. A large flat-screen TV is mounted on the wall, while a modern mirror reflects the open concept layout, enhancing the light from the recessed lighting.

5 out of 5 average rating, 127 reviews

Ultra-Modern Luxury Retreat! Close to Thermea SPA.

COZY and INVITING, this modern suite is in a quiet, family-friendly Ajax neighborhood. Just 10 minutes to Thermea Spa and Ajax GO Station, and a short walk to parks, shops, and groceries. Newly built with deluxe finishes, the 1,000 sq. ft. space includes in-floor heating, an electric fireplace, a spacious sofa, and smart TV with Netflix/Prime. Downtown Toronto is 35–45 mins by car, and Pearson Airport or Mississauga in about 55 mins.

A modern living space features a comfortable gray couch and two stylish lamps on side tables. A coffee table sits at the center, with a small dining area visible in the background. Natural light enters through large windows, enhancing the warm ambiance.

4.78 out of 5 average rating, 128 reviews

Adorable 1-bedroom with free parking on premises

Forget your worries in this spacious and serene space. Enjoy this cozy, modern guest suite with a private bathroom, kitchen, workspace, HD TV with alexa fire stick Amazon Prime and fast wifi. Perfect getaway, 5 minutes walk to Ajax Waterfront Park and close to Casino Ajax, Rotary Park and general hospital. Note that this is a guest suite as a part of the main house where the landlord and their family live.

4.96 out of 5 average rating, 165 reviews

Apartment in Windfields

Family Friendly | HOT TUB | Near Toronto & UOIT

Newly built 1-bedroom private basement apartment in Oshawa featuring a work/study area, and in-suite laundry. Relax in the hot tub after exploring local trails, parks, and farms. Close to Ontario Tech University, Durham College, shops, and restaurants. Easy access to Durham Transit, GO Bus/Train, and Highway 407. Ideal for couples, professionals, or small families.

Popular amenities for Ajax family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.91 out of 5 average rating, 126 reviews

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

Downtown Markham Unionville

4.86 out of 5 average rating, 202 reviews

A vibrant cityscape is illuminated by colorful fireworks, with numerous skyscrapers displaying warm lighting. A large crowd is gathered below, surrounded by modern buildings and open spaces, creating an inviting atmosphere for festivities during the evening.

Condo in Mississauga

Beautiful Penthouse with Breathtaking View

5 out of 5 average rating, 128 reviews

A bright and airy living space features large corner windows that offer expansive views of the city. A modern sectional couch is paired with a light rug, while a flat-screen television is mounted on the wall. Lush green plants add a touch of nature to the inviting décor.

Condo in Yorkdale

The Penty: Luxurious Penthouse with Pool, Hot Tub

4.99 out of 5 average rating, 170 reviews

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

Luxury 4BR Oasis Year Round Heated Pool & Hot Tub

4.95 out of 5 average rating, 142 reviews

A modern living area features a dark couch adorned with decorative pillows, positioned beside a glass coffee table. A stylish bookshelf occupies the wall, displaying plants and decorative objects. A large flat-screen TV is mounted on the wall, enhancing the entertainment options.

Condo in Fort York

Lux Waterfront Condo Pool Hot Tub Free Parking

4.99 out of 5 average rating, 135 reviews

A modern living room features a gray oversized sectional sofa adorned with various decorative pillows. A circular wooden coffee table and a potted plant enhance the space. The wall is decorated with a large, abstract artwork, and light filters through sheer curtains, creating a serene atmosphere.

Apartment in Fort York

The Fort York Flat

4.94 out of 5 average rating, 164 reviews

A modern living area features a large window with expansive views of the cityscape and surrounding landscape. A flat-screen television is mounted on the wall opposite a comfortable sofa and a coffee table, creating a welcoming space for relaxation.

Apartment in Mississauga

Luxury Stay w/phenomenal view!

4.84 out of 5 average rating, 301 reviews

A modern living area is shown with a light-colored sectional sofa featuring dark blue accent pillows. A sleek, black coffee table contrasts against the soft, patterned rug. Abstract artwork adorns the wall, complemented by an open layout that invites natural light.

Condo in Mississauga

Beautiful Cozy 1 BR Condo👌🔥 Steps to SQ1! 👍

Family- and pet-friendly home rentals

4.92 out of 5 average rating, 138 reviews

The exterior of a modern home features a stone facade, highlighted by outdoor lighting. A decorative entrance is flanked by large planters filled with vibrant flowers. The driveway leads up to a garage with contrasting colors, enhancing the inviting atmosphere of the residence.

Guest suite in Oshawa

Spacious Guest Suite near 401 with parking

Guest suite in Bowmanville

The spacious studio features a queen-sized bed with a checkered comforter and decorative pillows. A large Samsung 55-inch Smart TV is positioned on the entertainment unit, offering various streaming options. A workstation is visible in the background, providing a comfortable space for productivity.

4.97 out of 5 average rating, 111 reviews

The Cozy Cove Studio

4.93 out of 5 average rating, 41 reviews

3 bedroom bungalow in South Ajax

4.95 out of 5 average rating, 73 reviews

Cheery 1941 Historic Home in Ajax

4.96 out of 5 average rating, 162 reviews

A comfortable sofa in a neutral brown tone is positioned in the living room, complemented by a decorative blanket. In the background, a modern kitchen with bar stools and a light-colored counter is visible, along with a window allowing natural light into the space.

Apartment in Pickering

2 Plush Queen Beds + 1 Sofa-bed - Sleeps 6 - Apt

The exterior of the home features a brick façade with a prominent arched window above the entrance. A paved driveway leads to a double garage with brown doors. Well-maintained shrubs and trees frame the entrance, contributing to a tidy appearance. A light cloud cover enhances the neutral tones.

4.93 out of 5 average rating, 15 reviews

Cozy 4BR Near 401, 407 & Toronto

4.88 out of 5 average rating, 111 reviews

A spacious living area features a large sectional sofa facing a modern fireplace. Light wood flooring complements the warm color palette. An open floor plan is highlighted, with a view of the kitchen in the background, which includes sleek cabinetry and a large island.

Home in Oshawa

Modern 4BR Home in North Oshawa

4.88 out of 5 average rating, 121 reviews

A spacious living area features a large sectional sofa paired with a modern armchair. Natural light streams through the expansive windows, highlighting a round coffee table and a light-toned area rug underneath. A potted plant adds a touch of greenery to the serene space.

Home in Pickering

Serene Stays - Pickering (5Beds, 2.5Baths, 4Park)

Family-friendly home rentals with a pool

5 out of 5 average rating, 3 reviews

Guest suite in Pickering

Private Walkout Suite | 3 PM Checkout | 1.5G Wifi

4.99 out of 5 average rating, 199 reviews

The exterior of a modern two-story home is displayed, featuring a brick and stone facade. A well-maintained driveway leads to a double garage with decorative doors. Bright flower pots are positioned near the entrance, while lush green landscaping surrounds the property.

Apartment in Newmarket

The Hilton BnB Adult Luxury Suite

4.98 out of 5 average rating, 557 reviews

A tree house is nestled among tall trees, featuring a wooden structure with a balcony and staircase. Soft sunlight filters through the branches, highlighting the natural wood finish and the serene forest surroundings.

Treehouse in Port Perry

Treehouse on private, isolated forest (300 acres)

4.97 out of 5 average rating, 105 reviews

A dining table with a circular glass top and four black chairs is positioned near large windows, offering expansive views of the Toronto skyline. A small potted plant adds a touch of greenery, while natural light fills the space, enhancing the modern interior.

Apartment in Fort York

The Farmer's Cottage

4.88 out of 5 average rating, 117 reviews

A spacious bedroom features large windows, allowing natural light to fill the room. A comfortable bed is centered against a dark accent wall, complemented by minimal artwork. A round mirror hangs on the adjacent wall, and warm lighting is provided by a bedside lamp.

Apartment in Mississauga

Condo in Heart of Mississauga

Apartment in Oakwood Village

A spacious living room is presented with a neutral-colored sectional sofa adorned with yellow accent pillows. A small glass side table complements the seating area, while a patterned area rug adds texture to the floor. Natural light enters through a window placed above the sofa.

4.84 out of 5 average rating, 108 reviews

Bright, spacious luxury basement apartment

Condo in Humber Bay Shores

A modern living area is featured, showcasing a white sofa adorned with colorful pillows. A round coffee table is centered in front of a wall-mounted TV. Large sliding doors open to a balcony, framed by greenery and offering city views.

4.93 out of 5 average rating, 188 reviews

Hidden gem in Humber bay shores Toronto w/ parking