Family-friendly holiday rentals in Whitby

A view from the hallway leads into a well-lit open living space. The kitchen features modern appliances, while a cozy seating area with two chairs and a sofa is visible. The floor is adorned with warm wood tones, enhancing the inviting atmosphere.

4.92 out of 5 average rating, 103 reviews

Modern 2 Bedroom Guest Suite in Whitby

This stylish place to stay is perfect for an individual, couple, or a small family visiting Whitby. Gorgeous newly built 2 bedroom 1 bath legal basement approx 950 sqf (registered with Town of Whitby, meets building code requirements) at one of the best neighborhoods in Whitby. Walking distance to Walmart, Superstore, Dollarama, LCBO,and many more. One parking spot available on the driveway Steps away from the bus stop. 1.3 kms from Thermëa spa. Wifi, netflix & Amazon Prime are included.

FamilyIndoor spacesAccuracy

4.96 out of 5 average rating, 281 reviews

Guesthouse in Whitby

One bedroom apartment/guesthouse.

Welcome to your peaceful private getaway located north of the 401 in Whitby. Guest will have the entire apartment with separate entrance to themselves. This newly constructed apartment is equipped with a fully functional kitchen, bathroom, living room and bedroom. Apartment comes with Wifi, 43” television with Amazon Prime TV services. Guest will have a designated parking space on the driveway. Please refrain from smoking inside the unit, smoke alarm are interconnected, and are highly sensitive.

KitchenFamilyAir conditioning

4.92 out of 5 average rating, 447 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!

FamilyKitchenSleep quality

4.87 out of 5 average rating, 221 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.

FamilyKitchenQuiet

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.

4.94 out of 5 average rating, 185 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.

Indoor spacesFamilyLocation

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.

4.94 out of 5 average rating, 285 reviews

Serenity Suite w/Sauna-Your Entire Apt Awaits You

LONG-TERM stays welcome. A short drive to Thermea Spa Village. This is a beautiful, newly renovated, spacious basement apartment, perfect for two. Located in Whitby Shores (w/ hot tub) just a few minutes’ walk to Lake Ontario, a park, & trails, the house is situated in a quiet and friendly neighbourhood. It is close to all amenities - shopping, movie theatre, and other entertainment options, restaurants, GO Train station, Hwy 401, and easy access to Hwy 407. We look forward to meeting you!

KitchenIndoor spacesOutdoor spaces

4.9 out of 5 average rating, 343 reviews

Guest suite in Pickering

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

Completely private studio suite kitchenette (no full kitchen)(no stove)(no oven) Airbnb is a separate unit with a separate entrance Exclusive hot tub access Modern space with Fireplace and 55 inch smart TV for streaming Fast Wi-Fi Approximately 30 minutes from downtown Toronto 15min to Thermea Spa, Frenchman’s Bay, Durham Live Casino, Toronto Zoo/Porsche Experience Center Parking spot for SUV size car. Trucks will not fit. Safe and secure with a disclosed exterior entrance camera

Indoor spacesKitchenHeating

4.98 out of 5 average rating, 353 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

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.

Indoor spacesFamilyCheckout

4.86 out of 5 average rating, 144 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

Escape to a luxury geodesic dome on our scenic farm, nestled at the edge of the forest. Fully equipped with heating, cooling, a private washroom, deck, and hot tub, it’s the perfect blend of comfort and nature. Explore the farm, meet our sheep, chickens, and livestock guardian dog, or hike over 100 acres of connected regional forest. Whether you’re relaxing under the stars or adventuring outdoors, this unique glamping retreat promises an unforgettable experience.

KitchenFamilyOutdoor spaces

4.78 out of 5 average rating, 151 reviews

A modern living area features a gray sectional sofa and two light-colored chairs positioned around a glass coffee table. A wall-mounted television is situated above a contemporary electric fireplace, with a decorative plant adding a touch of greenery to the space.

Guest suite in Whitby

Luxury 2 Bedroom Apartment - 5 mins to Thermea Spa

★ Very nice apartment! Clean, spacious, and modern ★ ☞ Fully Private unit!!! ☞ Fully equipped kitchen!!!! With all the required machines and pots ☞ Extended Kitchen Island ☞ All rooms w/ queen + Sheets and Duvet !!!!!! ☞ 55” smart Samsung TV w/ Netflix + Samsung sound bar with Sub ☞ Central AC + Heating ☞ On-site washer + dryer ☞ Parking → 1 on the driveway!!!! ☞ 700mbps wifi ☞ Open Concept 5 mins → Thermëa spa village 12 mins → Whitby and Ajax GO Station

KitchenIndoor spacesLocation

4.82 out of 5 average rating, 255 reviews

A cozy living area is furnished with a light-colored sofa and two blue armchairs, creating a comfortable seating arrangement. A glass coffee table sits at the center, and a television is mounted on the wall displaying content. A piece of abstract wall art adorns the space.

Guest suite in Whitby

Two Bedroom Basement Apartment

Have fun with the whole family at this stylish place. This space has all the amenities including Free WIFI, Netflix, Laundry, and a full Kitchen. Only 6 minutes drive from highway 401, 10 mins drive from Oshawa Mall, 5 mins drive from down town Whitby, and 5 mins drive from Whitby Entertainment Centrum (Landmark Cinemas and Restaurants, Good Life Gym). Also close by are other kids entertainment places such as, Flying Squirrel, Sky Zone, and Reptilia.

Indoor spacesKitchenHospitality

4.96 out of 5 average rating, 423 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😊

FamilyIndoor spacesCheck-in

Popular amenities for Whitby family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.9 out of 5 average rating, 114 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)

KitchenIndoor spacesAccess

4.82 out of 5 average rating, 133 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+

FamilyIndoor spacesValue

4.88 out of 5 average rating, 817 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!

Indoor spacesKitchenComfort

4.88 out of 5 average rating, 196 reviews

A hot tub is positioned on a patio, providing views of the serene lake and distant horizon. Red outdoor chairs surround a firepit, while an umbrella offers shade nearby. The scene is framed by lush greenery and a stony beachfront, enhancing the tranquil setting.

Cottage in Bowmanville

“Lakeside Dreams”: All season HotTub w/lake views

KitchenFamilyAmenities

4.94 out of 5 average rating, 245 reviews

A private hot tub is positioned on a wooden deck beneath a lattice covering, allowing for relaxed soaking. Lounge chairs are arranged nearby, and vibrant greenery and decorative flowers provide a natural backdrop. A swimming pool can be seen in the distance, enhancing the outdoor ambiance.

Home in Port Perry

Home away from home with a hot tub and pool

KitchenFamilyBathroom

4.93 out of 5 average rating, 104 reviews

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.

Home in Ajax

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

Indoor spacesKitchenBathroom

4.9 out of 5 average rating, 589 reviews

Dome in Port Perry

North Geodome - Birchwood Luxury Camping

KitchenFamilyHeating

4.92 out of 5 average rating, 118 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!

KitchenFamilyParking

Family- and pet-friendly home rentals

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!!!

KitchenIndoor spacesAccess

4.9 out of 5 average rating, 266 reviews

A glamping dome is set amidst a lush green landscape, reflected in a serene pond featuring lily pads and blooming flowers. Towering trees provide a natural backdrop, while a wooden deck extends from the dome, enhancing the outdoor experience.

Dome in East Gwillimbury

Deerleap Glamping Dome

Indoor spacesFamilyBarbecue

4.86 out of 5 average rating, 136 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.

Indoor spacesFamilyAccess

A modern lounge area features a curved, light-colored sofa with a textured throw pillow. A round, soft coffee table sits in the center. Natural light enters through a small window, complemented by two sleek wall sconces enhancing the simple yet stylish decor.

4.8 out of 5 average rating, 107 reviews

Modern & Luxurious Basement Stay

Indoor spacesFamilyHot tub

Shipping container in Clarington

An outdoor stone wall shower is positioned next to a wooden deck, leading to a private pond. The deck features a covered area with dining furniture. Lush greenery surrounds the space, and sunlight illuminates the scene under a clear blue sky.

4.98 out of 5 average rating, 117 reviews

Rustic Ridge

FamilyIndoor spacesGetting around

4.98 out of 5 average rating, 562 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)

KitchenFamilySleep quality

4.93 out of 5 average rating, 257 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

FamilyKitchenSleep quality

4.88 out of 5 average rating, 149 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)

KitchenFamilyDecor

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

Indoor spacesFamilyQuiet

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, 142 reviews

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

KitchenIndoor spacesQuiet

Condo in Davisville Village

A modern living space features a spacious seating area with a gray sofa and a bright orange accent chair. A dining table with plants stands nearby. Natural light floods the room through a glass sliding door leading to a balcony, offering views of the city skyline.

4.85 out of 5 average rating, 155 reviews

1Brm 2beds 5*Cozy, Hot tub, Midtown, Subway 5mins

FamilyIndoor spacesParks

Condo in Davisville Village

A modern living space is highlighted by large windows offering panoramic city views. A deep red area rug anchors the room, complementing the sleek furniture. Two barstools and a compact table are positioned near the kitchen, providing a functional dining space.

4.94 out of 5 average rating, 291 reviews

SpectacularPenthouse VIEWS/ POOL /free Parking

Indoor spacesKitchenOutdoor spaces

4.82 out of 5 average rating, 380 reviews

A modern living area is showcased with a deep blue velvet sofa adorned with two decorative pillows. A glass coffee table rests atop a patterned rug, accompanied by two stylish gold side tables. Large abstract artwork is displayed on the wall, complementing the light-filled space.

Condo in Toronto

Spacious Downtown (midtown) 2bed 2 bath free parki

FamilyIndoor spacesView

Condo in Davisville Village

A comfortable living area features a sofa adorned with decorative cushions and two accent chairs. A cozy area rug with geometric patterns lies beneath, while a dining bar with seating for four is visible in the open-concept kitchen, complemented by stainless steel appliances.

4.93 out of 5 average rating, 190 reviews

Large & Bright 2BR+Den in Midtown w/ Free Parking

KitchenFamilyTV

4.9 out of 5 average rating, 93 reviews

A view overlooking a well-maintained garden featuring vibrant flower planters along a railing. A refreshing, circular swimming pool is visible, surrounded by lush green grass and foliage, creating a serene outdoor space.

Home in Whitby

Clean, spacious, poolside entire lower level apt

FamilyIndoor spacesCleanliness