Family-friendly holiday rentals in Mississauga

Guesthouse in Mississauga

A serene backyard is highlighted by a clear swimming pool surrounded by natural stone coping. Comfortable seating arrangements with dark wicker chairs and a sleek table are positioned nearby, offering a relaxing spot. Lush greenery frames the area, providing a peaceful atmosphere.

4.91 out of 5 average rating, 106 reviews

“CasaDeLeon”- Modern and cozy Lakeview guesthouse

YES Hot tub and heated pool are open! Forget your worries in this spacious & serene space. King+queen air/4 twin , lrg patio doors overlooking lush greenery in private backyard oasis. Enjoy in/outdoor living & access to private basketball court, trampoline. Landscaped backyard w deck, bbq, tons of board games, 4K projector (stream from G00gle chromecast) for large screen media / movies, and wine fridge, espresso bar, fridge w ice maker, full bathroom, heated flooring. **25+ ID & waiver req**

KitchenIndoor spacesOutdoor spaces

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.

4.95 out of 5 average rating, 182 reviews

Luxury Stay w/phenomenal view!

Enjoy a stylish experience at this centrally located property. Sunset lovers are going to love this one! Starbucks, restaurants, grocery shops, dentists, pharmacies, and much more ON THE MAIN FLOOR. Walking distance to Mississauga’s largest mall Square one. 15 mins drive from airport. 20 mins drive to Downtown Toronto. Lakeshore south view from balcony. Gym, swimming pool, jacuzzi, sauna, piano room, cards room, stretching room, outdoor bbq, and much more in this unique one of a kind property.

FamilyKitchenLong stay

5 out of 5 average rating, 19 reviews

Brand New 1BR or 2BR Basement Suite near Airport

✨ For groups of more than two, a separate room with an ensuite bathroom is provided. The Space: Newly renovated basement suite. ✈️ Location: 15 min to Airport | 30 min to Downtown Toronto | Near Square One & Transit. 🛁 Ensuite: All bedrooms feature private attached bathrooms. 🔐 Access: Separate entrance with secure keypad entry. 🛡️ Privacy: smart locks on all bedroom doors. 🍳 Kitchen: Fully equipped kitchen & relaxing dining/common areas. 🚗 Parking: 1 FREE parking in the driveway.

Indoor spacesKitchenGetting around

4.98 out of 5 average rating, 328 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 spacesFamilyBathroom

4.99 out of 5 average rating, 135 reviews

A private hot tub is situated on a rooftop terrace, surrounded by privacy screens. Soft lighting is positioned around the area, creating an inviting ambiance. Steam rises gently from the hot tub's surface, hinting at a warm and relaxing experience.

Home in Oakville

Modern Executive Townhome w/ Rooftop Hot Tub Oasis

Stylish contemporary townhome in Oakville! The perfect retreat for couples, families, and friends alike. Experience the rooftop terrace, complete with a Private Jacuzzi Hot Tub that provides the ultimate relaxation experience! It's the perfect spot to unwind after a long day of sightseeing or to enjoy an evening under the stars. You'll love the stunning and spacious living areas, fully equipped kitchen, and two comfortable bedrooms. Close to Three Major Highways in a Central Location!

Indoor spacesKitchenCleanliness

A spacious living area features a large sectional sofa adorned with numerous soft white throw pillows. A modern glass coffee table is centered on a textured area rug, while wall art depicting a seaside landscape adds a touch of character to the bright, well-lit space.

4.96 out of 5 average rating, 178 reviews

3 Bedroom Apartment - Heart of Mississauga

Welcome home! Whether you are traveling with family or friends, for business or simply in between moving, or renovations, this charming 3 bedroom first floor apartment is perfect for long and short term stays. Along with all amenities you may need during your stay, professional cleaning is provided in-between stays. The most central location in Mississauga, minutes away from shops, restaurants and parks. We invite you to enjoy your stay and find a home away from home!

FamilyIndoor spacesParking

5 out of 5 average rating, 108 reviews

A backyard seating area is viewed, featuring a dark outdoor sectional couch with a black coffee table placed on a striped rug. Surrounding the heated saltwater pool are lounge chairs and lush greenery, creating a serene outdoor space.

Guesthouse in Brampton

Bright and Airy Guest Suite with Pool

Large windows, high ceilings, fresh modern decor, cedar sauna, fitness room and backyard pool best describes our Garden Suite. Spoil yourself in everything this space has to offer. Featuring a comfy queen size bed sheeted with luxury cotton and down duvet. A large queen pull-out couch offers space for extra sleepers. Take some time to refine your culinary skills with the well appointed kitchen. Don't overpack, your in-unit washer and dryer will keep your clothes clean.

FamilyIndoor spacesCleanliness

Guest suite in Mississauga

An open and modern layout showcases a spacious living area seamlessly connected to a kitchen, with a generously sized sleeping area featuring a plush bed. Glass panels and wooden beams create an inviting atmosphere, while stylish decor complements the aesthetic of the space.

4.99 out of 5 average rating, 246 reviews

Newly renovated stylish apartment close to Airport

**No parties or gatherings allowed** Newly renovated, large, spacious and cozy apartment 10 min from Airport. Brand new kitchen, bathroom with shower, laminate flooring, built in closet, living area and laundry. Enjoy comfy KING size bed! Family friendly and quite neighborhood. Close to SquareOne, Sherway Gardens, MiWay, highways, and Downtown. Close to shopping, grocery, and recreation centers. Completely Separate entrance. Free parking spot on the driveway.

FamilyKitchenTV

5 out of 5 average rating, 62 reviews

Guest suite in Hamilton

Springtime! Steam shower+breakfast+rooftop hottub

Nestled in a picturesque escarpment community overlooking the historic town of Dundas, The Hayloft is a charming getaway for anyone looking for an escape and a breath of fresh air. Relax in the steam shower inside or the hot tub on the fully private rooftop deck overlooking gardens. Take a nap on the lounge chairs. Visit with the chickens, make friends with the fish or the frogs. Unwind at night with a movie in bed, with breakfast (surcharge) in the morning.

Indoor spacesFamilyLocation

Guest suite in Mississauga

4.92 out of 5 average rating, 89 reviews

Cozy Private Suite | Free Parking | Close to 403

🌟 THE EXPERIENCE Escape to your own private oasis in Churchill Meadows! This spotless 1-bedroom basement apartment offers everything you need: a fully-equipped kitchen, in-unit laundry, blazing-fast WiFi, and free parking, all just 30 minutes from downtown Toronto. Perfect for: - Business travelers needing a quiet workspace - Couples exploring the GTA - Anyone wanting hotel amenities at home prices - Extended stays with laundry access.

KitchenIndoor spacesCheck-in

4.92 out of 5 average rating, 71 reviews

Luxury 2.5Br-2Bath 1 Prk Condo SQ1 Striking Views

****Brand new, less than a month old**** Experience luxury in the heart of Mississauga! Enjoy our stylish, 2BR+den condo with breathtaking city views. Steps from shopping, dining, transit. Features ENDY mattresses, Smart TVs, high-speed internet, fully-equipped kitchen, private balcony, and secure parking. Sleeps 7 comfortably. Perfect for groups, families, or business travelers. Your comfort, convenience, and style await!

Indoor spacesFamilyLocation

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.

4.89 out of 5 average rating, 123 reviews

Condo in Heart of Mississauga

Just an 8-minute walk to Square One Mall, this cozy condo is perfectly located — 15 minutes from Pearson Airport, with easy access to highways and public transit. Downtown Toronto is just a 30-minute drive away (traffic permitting). Inside, you’ll find a comfortable bed, a private terrace to relax on, and the convenience of one free designated parking spot included with your stay.

Indoor spacesKitchenComfort

Popular amenities for Mississauga family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.94 out of 5 average rating, 162 reviews

Luxury 2BR Condo w/ Skyline Views & Balcony

KitchenFamilyCheck-in

4.89 out of 5 average rating, 120 reviews

Home in Clarkson

4BR Cottage - Hot Tub & Monthly Stays (50% OFF)

KitchenIndoor spacesAmenities

4.92 out of 5 average rating, 102 reviews

Home in Toronto

Backyard Oasis | Hot Tub & Playground | Near DT

KitchenIndoor spacesLaundry

4.93 out of 5 average rating, 179 reviews

The hillside villa features multiple levels with large windows offering expansive views. Smooth wooden decks are visible, surrounded by greenery, while a staircase leads to the entry. Reflective glass accents enhance the modern design, blending harmoniously with the natural surroundings.

Villa in Burlington

Waterfront Hillside Villa

FamilyIndoor spacesHeating

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.

4.86 out of 5 average rating, 210 reviews

Beautiful Penthouse with Breathtaking View

Indoor spacesKitchenNearby

5 out of 5 average rating, 144 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

KitchenIndoor spacesLocation

4.99 out of 5 average rating, 182 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

FIFA: 4BR: 365 Days Open- Heated Pool & Hot Tub

FamilyKitchenPool

4.98 out of 5 average rating, 627 reviews

A vibrant sunset is captured with layers of orange, red, and yellow hues across the sky. Silhouetted trees and foliage frame the image, creating a contrasting foreground against the colorful backdrop.

Guest suite in Hamilton

Country Getaway in Puslinch

KitchenIndoor spacesComfort

Family- and pet-friendly home rentals

4.9 out of 5 average rating, 141 reviews

Gorgeous & Modern 2Bed 2Bath Sq1 Condo Corner unit

KitchenFamilyAccess

4.92 out of 5 average rating, 221 reviews

Two brown horses are depicted in a snow-covered outdoor setting, closely positioned with their noses touching. Flakes of snow gently fall around them, creating a serene winter scene, while a house and snow-covered trees are subtly blurred in the background.

Bungalow in Hamilton

Horse Ranch with Hot tub

FamilyKitchenAir conditioning

4.96 out of 5 average rating, 113 reviews

A sunset over the water is portrayed, with a golden sun reflecting on the calm surface. The horizon features a silhouette of trees, creating a serene atmosphere. Soft waves ripple gently in the foreground, enhancing the tranquil setting.

Apartment in Toronto

Toronto Island Wonderland View

KitchenFamilyOutdoor spaces

Guest suite in Mississauga

A cozy bedroom with a spacious bed dressed in white bedding and accented by neutral-colored pillows. Two bedside lamps illuminate the space, complemented by artwork featuring botanical prints on the wall. Natural light filters through a small window, enhancing the calm atmosphere.

4.94 out of 5 average rating, 186 reviews

Bright apartment/basement in Mississauga

KitchenIndoor spacesAir conditioning

A spacious outdoor area is surrounded by lush green grass, with well-maintained trees and shrubs. Several wooden structures, including a gazebo and small sheds, are set against a clear blue sky, offering a peaceful atmosphere for relaxation.

4.89 out of 5 average rating, 61 reviews

Cute 1-Bedroom apartment in heart of Mississauga

KitchenIndoor spacesBackyard

5 out of 5 average rating, 25 reviews

The Calm House | 5 mins Walk to Square One Mall

Indoor spacesKitchenComfort

4.89 out of 5 average rating, 185 reviews

A charming two-story detached home is framed by well-maintained greenery and colorful flowerbeds. A paved driveway leads up to the garage, with light brick finishes on the exterior contrasting against the blue sky. The inviting entrance is accentuated by potted plants.

Home in Oakville

3Bd 2.5Bth House w/ Pool Table, Swing, Outdoor BBQ

KitchenFamilyBathroom

4.98 out of 5 average rating, 328 reviews

The exterior of the cabin features a rustic wooden facade with two windows and a central door. A dog stands on the steps, flanked by two cozy chairs. Decorative elements include a pumpkin and potted flowers adding charm to the welcoming outdoor space.

Tiny home in Acton

Farmview Sunset Cabin

KitchenFamilyCleanliness

Family-friendly home rentals with a pool

4.72 out of 5 average rating, 36 reviews

Bright 2BR Walk-Out Suite | 2 Parking | Walk to GO

FamilyIndoor spacesParking

A modern living area features a plush dark sofa adorned with decorative pillows. A glass coffee table sits in the center, complemented by a patterned area rug. Natural light filters through sheer vertical blinds, and framed artwork is displayed on the wall.

4.91 out of 5 average rating, 11 reviews

Cozy Modern Loft Near Square One

Indoor spacesKitchenLocation

A modern house exterior is displayed, featuring a well-maintained lawn and landscaped garden. The driveway is paved with gravel and concrete, leading to a covered porch area. Large windows provide an inviting entrance, while shaded trees contribute to a pleasant outdoor setting.

4.78 out of 5 average rating, 37 reviews

Comfortable &Stylish 4BD Stay Near Toronto Airport

KitchenFamilyPool

4.83 out of 5 average rating, 66 reviews

Modern 2BR/2BA Condo w/ Pool & Parking near YYZ

FamilyKitchenTV

5 out of 5 average rating, 5 reviews

Sleek 2BR Stay Near Square One & Downtown

HospitalityLocationView

A well-equipped kitchen features white cabinetry and modern stainless-steel appliances, including a stove and dishwasher. Natural light pours in through a window adorned with potted plants. A tile floor leads to a dining area with wooden chairs, creating an inviting space for meal preparation and gatherings.

4.89 out of 5 average rating, 9 reviews

Swimming pool, king size bed. Our oasis.

Indoor spacesKitchenGetting around

4.8 out of 5 average rating, 220 reviews

A backyard oasis features a sun-drenched inground pool surrounded by lush perennial gardens. A stone patio is equipped with shaded lounge areas and outdoor seating, creating an inviting space for relaxation. The two-story house overlooks the pool, complementing the tranquil environment.

Apartment in Milton

Backyard Oasis Guesthouse.

Indoor spacesKitchenLocation