Family-friendly holiday rentals in Ajax

4.92 out of 5 average rating, 453 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!

A spacious back deck features a hot tub and seating area, surrounded by greenery. Large glass doors provide a view into the living room, while a cooking area and dining table are positioned outdoors. A metal container holds beverages, inviting relaxation.

4.93 out of 5 average rating, 105 reviews

Luxury Kitchen/King Beds/Hot Tub Table+Beds for 24

Bring your family or team together in this luxurious home! Beautifully refurnished in 2022, including a new hot tub and new hotel-quality mattresses & linens, this 4000 sq. ft house is ideally suited for large families or athletic teams. Featuring a remodeled kitchen w/ gas stove, 7 new beds (3 king), gym, office, smart TVs, 4 parking spaces & fast Wi-Fi. Only 5 minutes from the 401 & Ajax Go Train station, accessing the city is a breeze. Tennis + playground 50 meters away. *3 extra beds avail

4.87 out of 5 average rating, 223 reviews

The exterior of a two-story home showcases a brick façade with a blue garage door. A welcoming front porch features seating, while a neatly landscaped pathway leads to the entrance. Ample windows allow natural light to brighten the space.

Home in Whitby

Cheerful 4-bedroom home with huge patio

This bright and airy 4 bedroom 3 bathroom home is perfect for a family or a friends getaway. High speed internet and full amenities. Minutes from Deercreek Golf Course, the NEW Thermëa spa, top rated restaurants, supermarkets, and shopping. Easily accessible by highway 401 or 407/412. 45-min drive to downtown Toronto. 10-min drive to Whitby GO Train station. Perfect for families, business trip or a weekend getaway, your stay here is sure to be convenient and effortless. Long-term stays welcome.

4.92 out of 5 average rating, 118 reviews

A cozy living area is visible, featuring a gray sofa beside a small table adorned with a candle. Soft lighting illuminates the space, highlighting a long hallway leading to a kitchen equipped with stainless steel appliances. A piece of wall art depicting a serene ocean scene is hung on the wall.

Bungalow in Ajax

Private Basement in Ajax w/ Separate Entrance

Cozy & Modern Basement Apartment in Ajax. Perfect for work or leisure, this 1-bedroom suite features a cozy living area and equipped kitchenette with microwave, fridge, coffee machine & essentials. No stove available. Just 5 mins from Hwy 401, Ajax GO Station, Ajax-Pickering Hospital & Pickering Casino Resort. No pets, due to allergies. Early check-in/late check-out available for an extra fee. Due to Airbnb fee disclosure changes, 15.5% of the daily rate goes to Airbnb. MAX 2 guests

4.95 out of 5 average rating, 229 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.

4.94 out of 5 average rating, 194 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.

Flat 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.

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.

4.85 out of 5 average rating, 266 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.

4.98 out of 5 average rating, 197 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 • 65 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.

4.93 out of 5 average rating, 259 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.

Flat 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.

5.0 out of 5 average rating, 141 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.

4.8 out of 5 average rating, 137 reviews

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.

Guest suite in Ajax

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.

The exterior of a spacious three-story house is presented, featuring a stone and brick facade. Large windows provide ample natural light, and a well-kept front yard is visible. A driveway accommodates multiple vehicles, with a blend of greenery enhancing the welcoming appearance.

4.94 out of 5 average rating, 259 reviews

Spacious 3 Bedroom walkout Basement Apartment

Spacious cozy 3-bedroom entire walkout basement apartment ( not the entire house) with a separate entrance, located close to grocery stores ( Metro, Longos ,Shoppers )and other malls. Not far away from highway 401 and 407 . 5 mins to Deer Creek Golf & Banquet Facility, 15 mins drive to Lakeridge Ski resort.

Popular amenities for Ajax family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.89 out of 5 average rating, 118 reviews

The modern townhome exterior features a clean brick facade and large windows providing ample natural light. A set of steps leads to the main entrance, framed by black railings on either side. A small potted plant sits at the base of the steps.

Townhouse in Pickering

The Cyberspace (No cleaning fees, Private Hot Tub)

4.9 out of 5 average rating, 349 reviews

Guest suite in Pickering

Hot Tub Oasis | 35 Min to DT | Main Floor Suite

4.86 out of 5 average rating, 146 reviews

The geodesic dome features a modern white exterior, set against a backdrop of trees. A wooden deck extends from the dome, leading to a covered gazebo, with a pathway of wood chips guiding the approach. Soft sunlight filters through the branches, creating a serene atmosphere.

Dome in Uxbridge

The Bubble Glamping Dome

4.88 out of 5 average rating, 820 reviews

A cozy living area features a brick fireplace with a warm flame, complemented by soft lighting from decorative lanterns. A coffee table is adorned with candles and a chilled bottle of champagne, while comfortable seating invites relaxation.

Guest suite in Pickering

* HOT TUB* Guest Suite - Minutes to the Beach!

4.94 out of 5 average rating, 287 reviews

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.

Flat in Whitby

Serenity Suite w/Sauna-Your Entire Apt Awaits You

4.92 out of 5 average rating, 120 reviews

A bright sunroom is showcased with a glass ceiling and walls, providing expansive views of the surrounding nature. A glass dining table is surrounded by black chairs, resting on a soft area rug. The space offers a connection to the outdoors while remaining sheltered.

Home in Scarborough

Ravine Paradise ! heated pool and hot tub!

4.96 out of 5 average rating, 179 reviews

Flat in Oshawa

Family Friendly | HOT TUB | Near Toronto & UOIT

4.82 out of 5 average rating, 135 reviews

An outdoor dining area features a long table set with plates and glasses, complemented by decorative elements like flowers. Soft string lights illuminate the space above, creating a warm ambiance. Nearby, a spa-like hot tub is situated under a wooden gazebo.

Home in Oshawa

Summer Getaway with HotTub, PoolTable • Sleeps 10+

Family- and pet-friendly home rentals

4.86 out of 5 average rating, 140 reviews

A warm living area features a large leather sofa paired with a circular chair. A rustic wooden coffee table is positioned in front. Natural light filters through sheer curtains, illuminating the space with a cozy ambiance. A wood-burning fireplace is framed by vertical wood paneling.

Home in Pickering

Cosy 3-Bedroom Home in Quiet Cul-de-Sac.

4.87 out of 5 average rating, 110 reviews

A bright and open living area features a green velvet couch with decorative cushions, positioned next to a low white coffee table. Framed artwork adorns the walls, complemented by greenery in the corner. A light-colored rug adds warmth to the polished floor.

Townhouse in Whitby

NEWLY RENOVATED, 3 Bdrm Modern Oasis W/ Parking!!!

4.88 out of 5 average rating, 153 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)

4.98 out of 5 average rating, 357 reviews

A spacious living area features a variety of seating options, including a cozy couch and rocking chairs. Large windows allow natural light to enter, illuminating the lush indoor plants. Decorative rugs and artwork add character to the eclectic decor, creating a relaxed atmosphere.

Farm stay in Uxbridge

Private Loft w Sauna, Fireplace, Wi-Fi & Projector

4.89 out of 5 average rating, 144 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

4.79 out of 5 average rating, 243 reviews

A serene landscape of golden grasses and vibrant trees reflects in calm water. The scene captures a natural environment, inviting contemplation and enjoyment of the surrounding flora and fauna.

Guest suite in Pickering

Muskoka on the City

4.95 out of 5 average rating, 201 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.

Flat 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.

4.96 out of 5 average rating, 27 reviews

Cozy 4BR Near 401, 407 & Toronto

Family-friendly home rentals with a pool

Guest suite in Scarborough

A spacious backyard features a large swimming pool surrounded by lush greenery. An umbrella provides shade to a seating area, while trees encircle the space, enhancing privacy. A fenced perimeter ensures safety, and the pool is inviting under dappled sunlight.

4.88 out of 5 average rating, 112 reviews

1BR Bluffs | Pool + Yard | Pets Ok | EV Charger

4.92 out of 5 average rating, 217 reviews

The indoor swimming pool area features a tiled pool surrounded by natural light from large skylights. Two colorful floats are positioned on the water surface, and glass doors provide a view of the outdoors, enhancing the open and airy feel of the space.

Villa in Toronto

Toronto Vacation | ➊ The One Toronto Villa

Guest suite in Scarborough

A modern outdoor space features a large in-ground pool with vibrant blue water. An elegant fire pit sits in the foreground, its flames flickering above reflective glass stones. Surrounding the pool, tall wooden fences provide privacy, complemented by outdoor chairs positioned nearby.

4.9 out of 5 average rating, 145 reviews

Custom Luxury 2BR | Marble Pool | Games | Fire Pit

4.85 out of 5 average rating, 109 reviews

A private outdoor space features a hot tub positioned beside a blue swimming pool. Surrounding amenities include a charcoal grill, dining table, and lounge chairs set on a wooden deck, with trees providing natural shade and decorative lighting enhancing the evening atmosphere.

Home in Toronto

Toronto Pool Retreat

5.0 out of 5 average rating, 204 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.

Flat in Newmarket

The Hilton BnB Adult Luxury Suite

5.0 out of 5 average rating, 160 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.

Apartment in Yorkdale

The Penty: Luxurious Penthouse with Pool, Hot Tub

Apartment in Downtown Toronto

A rooftop pool reflects the blue sky while providing views of the CN Tower and surrounding modern buildings. Lounge chairs are positioned beside the pool, creating a relaxed atmosphere. The clear water invites enjoyment against the urban backdrop.

4.94 out of 5 average rating, 176 reviews

Rooftop Pool Condo with CN Tower View