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

KitchenFamilyView

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.

4.93 out of 5 average rating, 122 reviews

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.

Indoor spacesFamilyComfort

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.

FamilyKitchenParks

5.0 out of 5 average rating, 125 reviews

A cozy living room is illuminated by natural light, featuring a modular grey sofa with vibrant orange and white accents. A modern gas fireplace provides warmth against a textured wall, while shelves display books and decor. A flat-screen television is mounted above the fireplace.

Home in Toronto

Bright & Spacious 3BR Family Home | Walk to Subway

Stay in a bright & spacious 3 BR home just steps from Coxwell Subway, with direct access to downtown Toronto in 10 minutes. Perfect for families, small groups, or business stays, this home combines space, comfort, and unbeatable transit access in one of Toronto’s best walkable neighbourhoods. This family friendly home is full of natural light and features a spacious kitchen, cozy gas fireplace and a sunroom that opens onto a patio. Unwind in the spa bathroom with a soothing soaker tub.

Indoor spacesFamilyCheck-in

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.

Indoor spacesFamilyLocation

4.89 out of 5 average rating, 114 reviews

4.86 out of 5 average rating, 156 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.

Indoor spacesFamilyHot tub

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.

Indoor spacesFamilyLaundry

4.79 out of 5 average rating, 249 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!

KitchenFamilyCondition

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 !

FamilyKitchenHospitality

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 spacesAccuracy

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.

FamilyIndoor spacesCleanliness

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

Casa Meya : This exclusive modern and fully renovated Villa at 2024. Upper Floor : Beautiful Kitchen with brand new Bosch and LG appliances. An Island to host 4 guests plus a 6 seats Dining Table. 85" Samsung QLED TV to watch included Premium TV channels. Master Bedroom ( KING ) - 65" TV / 1st Bathroom 2nd Bedroom ( QUEEN ) - 42" TV / 2nd Bathroom Lower Floor : 3rd Bedroom ( QUEEN ) - 42" TV / 3rd Bathroom

Indoor spacesFamilyNearby

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)

KitchenIndoor spacesLocation

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

KitchenIndoor spacesCheck-in

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 spacesKitchenParking

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.

4.95 out of 5 average rating, 113 reviews

Modern Condo in Downtown Core

FamilyIndoor spacesNearby

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)

Indoor spacesFamilyHot tub

A round marble dining table is featured in the center, surrounded by wooden chairs. Above hangs a stylish light fixture. A decorative hockey-themed wall art is displayed, reflecting local culture. The open kitchen area includes modern appliances and a neutral color scheme, enhancing the inviting space.

4.92 out of 5 average rating, 184 reviews

Canadiana Downtown Condo w/King Bed + Free Parking

Indoor spacesFamilyWi-Fi

4.91 out of 5 average rating, 330 reviews

Apartment in The Beaches

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

KitchenFamilyParking

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.

“CasaDeLeon”- Modern and cozy Lakeview guesthouse

KitchenIndoor spacesCheckout

4.89 out of 5 average rating, 116 reviews

Family- and pet-friendly home rentals

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.

FamilyIndoor spacesParking

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

KitchenIndoor spacesWi-Fi

A bright sleeping area features a spacious bed adorned with crisp white linens and a soft gray throw. A large wall clock adds a focal point, while light fixtures enhance the ambiance. A small window allows natural light in, complemented by a leafy plant.

4.86 out of 5 average rating, 138 reviews

* Private Unit: Bright, Spacious Lakeside Suite *

Indoor spacesKitchenLaundry

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

KitchenFamilyHospitality

4.91 out of 5 average rating, 148 reviews

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

Spacious 2BD 3-6 ppl homestyle BSMT mansion with window basement 130sqm

FamilyIndoor spacesAir conditioning

4.98 out of 5 average rating, 366 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

KitchenFamilyBreakfast

4.94 out of 5 average rating, 175 reviews

Private | Steam Sauna Shower | Free Parking

Indoor spacesKitchenLayout

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

Indoor spacesFamilyBeach

Family-friendly home rentals with a pool

4.85 out of 5 average rating, 142 reviews

Good Looking Condo Across from CN TOWER & MTCC

Indoor spacesKitchenWi-Fi

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

Indoor spacesKitchenWalkability

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)

KitchenFamilyLocation

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

KitchenFamilyComfort

A modern living room features a gray oversized sectional sofa adorned with various decorative pillows. A circular wooden coffee table and a potted plant enhance the space. The wall is decorated with a large, abstract artwork, and light filters through sheer curtains, creating a serene atmosphere.

4.99 out of 5 average rating, 159 reviews

The Fort York Flat

Indoor spacesFamilyNearby

4.92 out of 5 average rating, 165 reviews

Skyline Condo | Free Parking | Steps to CN Tower

KitchenFamilyAmenities

A spacious living area features a large sectional sofa adorned with decorative cushions. A modern coffee table is centered in front of a wall-mounted TV, providing a focal point. A minimalist console table is present, accompanied by wall art and a plant on display.

4.78 out of 5 average rating, 152 reviews

2BR Across from CN Tower & MTCC

Indoor spacesFamilyBarbecue

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.