Family-friendly holiday rentals in Scarborough

4.88 out of 5 average rating, 826 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!

Welcome to the Hidden Gem - Romanic Zen Den! Your separate entrance will lead you to your lower level of the bungalow and is the perfect place to find your inner zen after enjoying the beautiful outdoors of Pickering. Elevate your experience with add-on packages! *there is another guest unit on the main floor. You will hear signs of life from above *9 pm pls no loud noise outside 4 min walk to Beach 12 min Casino 11 min Zoo 7 min Mall/Movies 18 min Thermea Spa 30 min Dwntwn Toronto

KitchenIndoor spacesNearby

4.93 out of 5 average rating, 122 reviews

A bright living space is showcased with comfortable seating and a large wall-mounted TV. A window allows natural light to fill the room, highlighting modern decor elements like framed art. The area is clean and inviting, creating a welcoming atmosphere for guests.

Home in Scarborough

Our Home -3 bedrms, for 1 to 5 to stay

This is the place for your next stay in Toronto. Step into this modern, cozy ground-floor private suite, tastefully adorned and nestled in an upscale neighborhood of Scarborough, Ontario. Whether you're a traveler, student, professional, or just seeking a spot, this is it. Relax alone or with loved ones here. There is a Kitchenette with with a single burner, Air Fryer, Toaster, Kettle, Microwave and BBQ. Please note that host occupies upper level of home and there is no full kitchen avail.

FamilyKitchenCleanliness

4.94 out of 5 average rating, 109 reviews

The kitchen features modern cabinetry and a spacious island with seating for two. Pendant lights hang above the island, illuminating the granite countertops. The area is accented with a detailed backsplash, and large windows allow natural light to brighten the space.

Home in East York

Cozy 5BR | 4 Bath | 10 Min to DT | Free Parking

Luxurious 5BR/4BA home just 10 mins to downtown Toronto-perfect for family reunions, wedding groups, and large gatherings! Sleeps 12 in comfort with open-concept living, a fully equipped kitchen, 4 Smart TV's, fast Wi-Fi, and a cozy bar area. Enjoy a spacious backyard w/large deck, BBQ, books, board and card games for relaxing nights. Includes free driveway parking, 2 in-unit laundries, keyless self check-in, refined finishes, hotel-quality bedding, and plush towels. Luxury. Comfort. Together.

Indoor spacesFamilyLocation

4.81 out of 5 average rating, 137 reviews

A cozy living area is presented with a light-colored couch adorned with throw pillows, facing a circular coffee table. Two armchairs are placed on a soft area rug. An accent mirror reflects the space, while a plant adds a touch of greenery to the corner.

Home in Pickering

Family Friendly Basement with Separate Entrance!

Open concept basement apartment (No walls separating rooms) 1 Queen bed and a Futon folds out into a Double bed . Accommodates Family of 4, NOT 4 Adults (2Adults/2children) . Separate entrance/ONE prkg spot. Located in a quiet neighbourhood in Pickering. Family friendly, NO parties/gatherings. Close to public Transit. 5 minutes drive from U Of T (Scarborough) Close to Toronto Zoo, PanAm Center, Go Stn and Hwy- 30 mins to Downtown Toronto. PLEASE read ALL house rules prior to booking.

KitchenFamilyValue

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.

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

Enjoy this beautiful, sun-filled, private suite with a large pool and secluded, fenced yard in a safe, upscale and serene forested neighbourhood where deer and other wildlife are often spotted. A short walk to public transit (TTC, GO Trains), shopping, restaurants, parks and scenic trails to the top of the Bluffs, with breathtaking views of Lake Ontario. Hike down to the waterfront trail to Bluffers Park Beach and Marina. Fast Fibre Internet. Parking for multiple vehicles. EV Charger.

KitchenFamilyCondition

4.89 out of 5 average rating, 114 reviews

4.87 out of 5 average rating, 142 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.

Contemporary 3 bed, 2 bath home w/ a European-feel. Centrally located on a low traffic court. Spacious, clean & bright! Featuring a large walk-out family room, high ceilings and wood-burning fireplace. Renovated w/ wood floors throughout. Large sunny west-facing backyard + 6 car-park on the driveway. Enjoy many unique amenities like our chromo-therapy steam room & outdoor Brazilian hammock. Walking distance to strip plaza, restaurants & parks. A comfortable home away from home!

Indoor spacesKitchenBarbecue

4.87 out of 5 average rating, 177 reviews

A comfortable lounge area features a dark sectional sofa adorned with decorative pillows. A soft ottoman complements the seating arrangement. A lamp provides subtle lighting, while a vase with decorative branches adds a touch of elegance to the space.

Home in Markham

Cozy basement in Markham

Cozy 1 bedroom basement apartment for 2 with separate entrance at the heart of Markham. This accommodation boasts a very central location in Markham. Walking distance to Pacific Mall, 7 minutes drive to Markville Mall, 4 minutes drive to Denison Centre, quick access to Highway 407 and many more. It is also a few steps away from Denison park. Spacious bedroom with queen bed, fully equipped kitchen, lounge with TV, a spacious modern bathroom and dining area.

FamilyKitchenAir conditioning

4.78 out of 5 average rating, 250 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

Located in Rouge National Urban Park, steps from a beautiful lake and beach(Note:beach was temporarily closed by government now).Enjoy hiking, kayaking, biking, and fishing nearby. Close to Toronto Zoo, Seaton Trail, highways, restaurants, shopping malls, and Rouge Hill GO Station. Bright ground-level suite with a private entrance, kitchen, dining area, TV, bathroom, and queen bedroom. Includes Wi-Fi and laundry. Perfect for a peaceful and convenient stay!

Indoor spacesFamilyParks

4.99 out of 5 average rating, 187 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: 365 Days Open- Heated Pool & Hot Tub

A Private Luxury Getaway in Toronto’s Most Coveted Neighbourhood Escape to an extraordinary 4-bedroom luxury home in Toronto’s iconic Beaches, where sophisticated design meets relaxed lakeside living. This top 1% rated Airbnb property offers an unforgettable weekend experience—perfect for families, couples, or a curated group of friends seeking both comfort and wow-factor. A year round private heated pool and hot tub are yours to enjoy !

FamilyKitchenCleanliness

Guesthouse in Scarborough

Private Coach House near the Bluffs

This separate, minimalist, self-contained space is a perfect escape for one, and can intimately accommodate two. Wake up in natural light with the essential of home: premium queen mattress, hypoallergenic, 100% cotton linens, private bathroom, toiletries and meal preparation basics. No kitchen. Prepared meals, groceries + delivery close by. No TV. No housekeeping fees. 20-minute getaway from the downtown core, east end near the lake.

KitchenIndoor spacesAmenities

4.96 out of 5 average rating, 137 reviews

4.86 out of 5 average rating, 111 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

Spacious and private family home with 5 bedrooms, sleeping up to 10 guests. Enjoy a seasonal pool open May to September (not heated), an all-season hot tub, large backyard, and games area with ping pong, air hockey, and foosball. Includes a fully equipped kitchen, multiple living spaces, and 3.5 bathrooms. Conveniently near Hwy 401, DVP/404, shopping, and supermarkets. Respectful family and group stays only — no parties.

Indoor spacesKitchenBathroom

4.93 out of 5 average rating, 75 reviews

A charming exterior of a spacious home is showcased, featuring a blend of stone and wood accents. Neatly trimmed hedges line a stone pathway that leads to the entrance. The well-maintained landscaping is complemented by a driveway and a garage.

Home in Scarborough

Private Pool Lakeview House

Enjoy a memorable visit when you stay in this unique place. Absolutely stunning waterfront cozy home near the Toronto bluffs beach. This is a gorgeous place in a classy neighbourhood with everything you need. Private pool and spacious yard with extraordinary views. Walking distance to the beach, Go transit, restaurants, grocery, pharmacy and more. You'll love it!

KitchenFamilyAmenities

Popular amenities for Scarborough family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A comfortable living area is presented with a light-colored sectional sofa and a brown leather armchair. A modern entertainment unit displays a flat-screen television, complemented by framed artwork on the walls. A soft area rug partially covers the wooden floor, enhancing the inviting atmosphere.

4.94 out of 5 average rating, 129 reviews

Luxury Downtown Condo For 4 (CN Tower Views)

KitchenFamilyGetting around

Superhost

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

Indoor spacesKitchenOutdoor spaces

4.86 out of 5 average rating, 158 reviews

4.89 out of 5 average rating, 123 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)

FamilyIndoor spacesHeating

A bright living space showcases a comfortable sofa beside a round glass table. A large TV is mounted on a textured wall. Natural light floods in from floor-to-ceiling windows, revealing city views, while a cozy bedroom is visible through an open doorway.

4.93 out of 5 average rating, 126 reviews

Stylish 1BR on Toronto’s Harbourfront

Indoor spacesKitchenSleep quality

4.94 out of 5 average rating, 109 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

FamilyKitchenComfort

Apartment in Downtown Toronto

A bright bedroom features a spacious bed with striped pillows and a soft, draped throw. Two framed artworks adorn the white wall above the bed. A small plant is positioned next to a bedside table, enhancing the tranquil ambiance of the space.

Modern Condo in Downtown Core

KitchenIndoor spacesAmenities

4.95 out of 5 average rating, 113 reviews

4.92 out of 5 average rating, 117 reviews

Home in Toronto

Backyard Oasis | Hot Tub & Playground | Near DT

FamilyKitchenCleanliness

4.91 out of 5 average rating, 330 reviews

Apartment in The Beaches

Honey House in the Beach City reg# str-2209gvsrvh

KitchenIndoor spacesSolo travel

Family- and pet-friendly home rentals

4.89 out of 5 average rating, 146 reviews

A comfortable seating area is presented with two light-colored armchairs, each adorned with decorative pillows. A low, round coffee table features a small vase of flowers. A floor lamp stands beside the seating area, and natural light streams in through a large window.

Townhouse in Markham

*BRAND NEW*Perfect 4 BR Townhouse Markham *Sleep 8

KitchenFamilyAmenities

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.

New Custom-Built | Marble Pool + BBQ | Toronto

FamilyIndoor spacesCheck-in

4.91 out of 5 average rating, 148 reviews

4.94 out of 5 average rating, 208 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

Indoor spacesKitchenCheck-in

4.91 out of 5 average rating, 107 reviews

A swimming pool is featured in a serene outdoor space, surrounded by lush greenery and tall trees. The circular pool is complemented by a stone wall background. A shaded seating area with a table and chairs is nearby, promoting relaxation and enjoyment.

Home in Don Mills

Casa Meya - Toronto Poolhouse Villa

KitchenIndoor spacesLayout

4.86 out of 5 average rating, 545 reviews

A cozy living and dining area features a wooden dining table set with plates and glassware. Two plush sofas surround a glass coffee table in front of a television, while bright yellow flowers add a pop of color to the space. Light-colored walls enhance the inviting atmosphere.

Apartment in Markham

spaciuos 2BD 3-6 ppl homestyle BSMT豪宅精装带窗地下一层130平

FamilyKitchenAccess

4.86 out of 5 average rating, 117 reviews

A sandy beach is depicted under a clear blue sky, featuring a small lifeguard station with a red roof positioned to the right. Colorful beach chairs are arranged in a row, with calm waters stretching into the distance.

Apartment in The Beaches

Cute retro beach flat

KitchenIndoor spacesAccess

4.98 out of 5 average rating, 367 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

Indoor spacesFamilyBathroom

4.99 out of 5 average rating, 155 reviews

The living area features a gray sofa adorned with decorative cushions, accompanied by a glass coffee table displaying natural accents. A dining table sits nearby, complemented by a piece of vibrant wall art. Soft lighting and polished concrete floors enhance the airy atmosphere.

Home in Toronto

Private Bright "Beach Hill" Lower Guest Suite

KitchenIndoor spacesOutdoor spaces

Family-friendly home rentals with a pool

Apartment in Downtown Toronto

Good Looking Condo Across from CN TOWER & MTCC

KitchenIndoor spacesAccess

4.85 out of 5 average rating, 142 reviews

Superhost

A bright living area features a modern orange sectional sofa and a wooden coffee table. Large windows offer views of the cityscape. A dining area with high chairs is positioned beside a compact kitchen, with red cabinetry adding a pop of color.

4.84 out of 5 average rating, 167 reviews

Beautiful Condo Across CN Tower and MTCC

KitchenIndoor spacesAir conditioning

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.

4.95 out of 5 average rating, 163 reviews

Lakeside Condo /Pool/ Walking Trail/Parking/CNE

Indoor spacesFamilyCheckout

4.99 out of 5 average rating, 168 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

KitchenFamilyAccess

4.9 out of 5 average rating, 170 reviews

A modern condominium building is showcased from a street view, highlighting two tall, sleek towers with an expansive glass façade. The ground level features a multi-story section with large windows and contemporary architectural elements, set against a clear blue sky.

Condo in Mississauga

Beautiful & Cozy 2Bed 2Bath Condo Steps to Square1

Indoor spacesFamilyAccuracy

4.88 out of 5 average rating, 120 reviews

A spacious open concept living area features light wooden flooring and modern furnishings. The kitchen is equipped with stainless steel appliances and a large island. Natural light floods in through floor-to-ceiling windows, highlighting a stylish area rug with circular patterns and a cozy seating arrangement.

Loft in Downtown Toronto

Modern Downtown Loft with Private Garden

Indoor spacesFamilyParking

A light-filled bedroom features a spacious bed dressed in crisp white linens. Two bedside tables with lamps stand on either side. A large window provides a glimpse of the city outside, complemented by a decorative indoor plant and modern wall art.

4.97 out of 5 average rating, 192 reviews

Luxury Downtown Condo For 6 (Near CN Tower)

FamilyIndoor spacesCheck-in