Family-friendly holiday rentals in Oshawa

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Oshawa

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

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Guest favourite
French doors with multiple panes provide a view into the living space, where a neutral-toned sofa and wall art can be seen. A potted plant stands in the corner, while a rich wooden floor enhances the inviting atmosphere.
Guest suite in Oshawa
4.72 out of 5 average rating, 126 reviews

Basement suite with Home Theatre

Make some memories at this unique and family-friendly place. Come and enjoy this newly renovated basement suite with separate private entrance with free parking at premises. Entertain yourself with your favorite movies in your own personal home theatre on a 120" screen and 360 degree surround sound system. Walking distance from shopping centers, restaurants, park and cinema hall. Very close proximity to Highway 401 and 407. This property is located in family friendly North Oshawa neighborhood.

Guest favourite
A spacious living area is furnished with a light-colored tufted couch, positioned in front of large windows that provide ample natural light and views of greenery. Sleek side tables with decorative accents are placed on either side of the couch, enhancing the room's functionality.
Guest suite in Whitby
4.92 out of 5 average rating, 101 reviews

2 King beds| Park free| Kitchen| Thermea Spa| WiFi

Our modern suite is perfect for a peaceful getaway within the GTA. Hassle free self check-in. Great for work or relaxation. Equipped with a chef's kitchen, open living space & laundry. A ravine lot with large windows opening up to views of the city in winter and nature in the summer. 2 king bedrooms with one washroom. Work space setup with wifi . Access to patio and free parking on premises. This is a WALKOUT BSMT APT & some noise may be heard from the upstairs unit, we have 3 young kids.

Top Guest favourite
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
4.93 out of 5 average rating, 160 reviews

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.

Guest favourite
A well-maintained exterior of a single-story brick residence is highlighted, featuring a manicured lawn and vibrant flowerpots along the entrance. A vehicle is parked in the driveway, and decorative accents add a welcoming touch to the home.
Apartment in Donevan
4.93 out of 5 average rating, 911 reviews

Just like home

This is an fully furnished basement apartment Quiet neighborhood close to bus stop, shopping and restaurants. Ten minute drive to Oshawa Center and downtown Oshawa. Reserve parking in driveway on left side. Breakfast ingredients are included; Eggs, Waffles, Cereal ,Toast, Coffee , Tea and etc. Our guests can rest assured that the bedding is washed and changed with each and every new guest, and for those who stay for a week or more , bedding is changed every five days or upon request.

Top Guest favourite
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
4.98 out of 5 average rating, 322 reviews

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

Welcome to the LOFT - A private, eclectically designed spa-inspired unique stay in the historic Webb Schoolhouse, less than an hour from Toronto. Featured in TORONTO LIFE, this private loft includes your own sauna, unique hanging bed, wood stove, kitchenette and is filled with art, and huge tropical plants as well as a projector & giant screen for epic movie nights. Relax and recharge, roam the grounds and enjoy the beautiful outdoor spaces, the permaculture farm, animals, and fire pit.

Guest favourite
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
4.87 out of 5 average rating, 108 reviews

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

Welcome to your home away from home!!! A Clean, Cozy and Visually Interesting Luxury Home located just outside of Downtown Whitby and minutes to Hwy 401 & 407. This Trendy Townhome boasts tons of eye catching decor and is filled with every amenity your heart could desire. Equipped with 2 King beds, a bunk bed and 2 full couches this Modern Townhome is perfect for a medium to large sized family or a handful of friends or associates looking for the perfect short or long term stay.

Top Guest favourite
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.
Home in Ajax
4.99 out of 5 average rating, 175 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.

Top Guest favourite
A decorative wooden sign features the word 'LOVE' in large letters, set against a soft background with a subtle text pattern. The sign is positioned within a cozy setting, enhancing the ambiance of the space.
Apartment in Whitby
4.96 out of 5 average rating, 419 reviews

LOVE and Relax at Dream Catcher Retreat

Are you looking for the perfect getaway? 😊 Retreat yourself to a Luxurious, Charming and Modern Suite with a splash of glam.✨ Perfect for couples, families or business trips. Enjoy the Fireplace with a glass of Cabernet Sauvignon🍷Perhaps you would also like to partake in a game of pool on our custom pool table 🎱, or take a hot rainfall shower in a delightful Stone Spa Shower💦. But, most importantly, our place is yours to relax and unwind😊

Guest favourite
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
4.9 out of 5 average rating, 146 reviews

Spacious Guest Suite near 401 with parking

Welcome to our spacious and stylish 1 bedroom in the basement, perfectly suited for couples or individuals seeking a memorable stay. Nestled in a centrally located location, this hidden gem offers quick and easy access to all the amenities you could wish for. Centrally located, just 2 mins from the 401, gas stations, and McDonald's, and 5 mins from Costco. Durham College is a quick 15-min drive. License Number RHSTR2025001

Top Guest favourite
A small dining area is created with a round table covered by a patterned tablecloth. Two black chairs flank the table, which features a subtle floral centerpiece. A scenic landscape photograph hangs on the wall, adding visual interest to the space.
Home in Oshawa
4.94 out of 5 average rating, 170 reviews

Cozy Basement Suite in Oshawa

Welcome to Your Home Away From Home! Nestled in a peaceful neighborhood, our charming basement suite offers the perfect blend of comfort and convenience for travelers, whether you're here for business or leisure. Walking distance from shopping centers, restaurants, park and cinema hall. Very close proximity to Highway 401 and 407. This property is located in family friendly North Oshawa neighborhood.

Guest favourite
The master bedroom features a modern bed with dark blue bedding, complemented by abstract wall art. A bedside table holds a lamp, providing soft lighting. Wooden flooring enhances the room's warmth, while natural light enters through a window covered with blinds.
Home in Donevan
4.87 out of 5 average rating, 248 reviews

Whole place! Close to hwy 401

★ Why book a room when you can have a luxurious 1 bedroom main floor in a detached house. ★ Everything is newer and decorated with love. ★ Its approx. 03 minutes drive to highway 401 and around 05 minutes to restaurants and stores. ★ 47 amenities have been added so far for your stay ★ Last but not least, price is very affordable and it's not a basement

Superhost
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.
Apartment in Windfields
4.8 out of 5 average rating, 123 reviews

4BR Escape with HotTub, Bbq & PoolTable

Escape to a stylish home near Toronto, perfect for up to 10 guests. This family-friendly retreat features a private hot tub, indoor pool table, backyard bbq grill: gass, dedicated workspace, and a beautiful backyard oasis. Enjoy modern amenities, a fully equipped kitchen, and easy access to the city. Ideal for family getaways or celebrations with friends.

Popular amenities for Oshawa family-friendly rentals

When is the best time to visit Oshawa?

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Avg. price$170 NZD$167 NZD$163 NZD$163 NZD$168 NZD$184 NZD$190 NZD$197 NZD$179 NZD$167 NZD$179 NZD$187 NZD
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Quick stats about holiday rentals that are family-friendly in Oshawa

  • Total holiday rentals

    Explore 260 holiday rentals in Oshawa

  • Nightly prices starting at

    Oshawa holiday rentals start at $34 NZD per night before taxes and fees

  • Verified guest reviews

    Over 7,470 verified reviews to help you choose

  • Pet-friendly accommodation

    Find 90 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    180 properties have a dedicated workspace

  • Wi-Fi availability

    260 of Oshawa holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Oshawa rentals

  • 4.7 Average rating

    Oshawa stays receive an average rating of 4.7 out of 5 from guests

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