Family-friendly holiday rentals in Scarborough

4.88 out of 5 average rating, 825 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

Indoor spacesKitchenValue

4.95 out of 5 average rating, 133 reviews

A modern living space is highlighted by a spacious bed and an entertainment area featuring a large wall-mounted TV. A cozy seating arrangement includes a soft couch and a stylish armchair. Ambient lighting is provided by a chandelier above, complemented by a decorative fire feature.

Guesthouse in Pickering

Luxury Ground-Level "Suite Escape"

"Suite Escape" offers a luxurious private guest suite in Pickering, Ontario. Fully equipped w/ a cozy Queen Bed, spa bathroom, workstation, 65” TV, A/C, fireplace, & kitchenette. Conveniently located to Hwy 401 & 407, GO Train, Durham Transit, malls, cinemas, casinos, waterfront & hiking trails, golf courses + wineries within a short walk or drive. Downtown Toronto & Pearson Airport is 30-40 mins away. Immerse yourself in luxury, tranquility, and easy access to the best of Pickering and beyond.

KitchenFamilyAir conditioning

4.94 out of 5 average rating, 108 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 spacesKitchenOutdoor spaces

4.92 out of 5 average rating, 104 reviews

A bright living room is highlighted by large windows covered with shutters, allowing natural light to fill the space. A modern chandelier suspends from the ceiling, and a flat-screen TV is mounted on a stone wall. Comfortable seating includes a blue sofa and two yellow chairs, surrounding a glass coffee table.

Home in Toronto

Urban Haven | Entire Main floor | Indoor Parking

"Elysian Urban Haven" is a luxurious residence designed to cater to various categories of travelers, promising an extraordinary experience in the heart of midtown Toronto. This exquisite residence features three bedrooms, two washrooms, and a full kitchen, equipped with top-of-the-line appliances, ceramic countertops. The location is truly a gem with easy access to major highways and downtown. Whether guests plan to explore the city or attend important meetings, this ensures convenience.

Indoor spacesKitchenHospitality

4.86 out of 5 average rating, 143 reviews

A cozy living area features a plush sectional sofa facing a flat-screen TV. Natural light filters through two large windows adorned with sheer curtains. A small armchair and a coffee table sit nearby, enhancing the comfortable space for relaxation or entertainment.

Home in Markham

New 3BR House, Free Parking, Family & Business

Welcome to your cozy home in Markham/Toronto East -bright, fully furnished 3 bedroom house designed for family comfort, and longer stays. Whether you’re visiting for family, work, or a peaceful break, you’ll find everything you need to settle in easily. - 2 comfortable workstations - Toddler-friendly: crib, high chairs, games - 2 parking spots (garage, driveway) - Close to stores, restaurants, parks, HWY 7/407/401, 15 min drive to Unionville and Toronto Zoo, downtown Toronto 30-40 min drive

FamilyKitchenLocation

Guest suite in Unionville

An open kitchen area showcases modern cabinets, a microwave, and a refrigerator, all complemented by a marble-topped circular dining table with four chairs. A sofa bed with a black and white animal print provides additional seating, while a large window allows natural light to enter the space.

Markham, Ontario. Top 1% on AirBnB Ranking.

Downtown Markham. Near grocery stores, Malls, Pan Am Centre, Markham's York University, Main St. Unionville, and restaurants. Transit access to Toronto via the GO train station or by car via the DVP. This modern sub basement has a big window, private full kitchen and bathroom, W/D, A/C, heating, one car parking, comfortable Queen size bed, sofa bed, and a 55" TV. We're very proud to be listed as a "Super Host", "Guest Favourite" & ranked in the top 1% of house listings based on reviews.

FamilyKitchenGetting around

4.94 out of 5 average rating, 125 reviews

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.

FamilyIndoor spacesDecor

4.89 out of 5 average rating, 114 reviews

4.91 out of 5 average rating, 101 reviews

Apartment in Markham

Modern Entire Apartment| Sleeps 5 |Free Parking

Welcome to your stylish and comfortable home away from home! This modern 1 bedroom + den apartment is perfect for couples, business travelers, or small families looking for a relaxing stay with all the essentials. 🏡 The Space Enjoy a beautifully designed unit featuring: • 🛏️ Spacious 1 bedroom + den (ideal for extra sleeping or workspace) • 🛋️ Bright living area with contemporary décor • 🍳 Fully equipped modern kitchen • 🚿 Clean, upgraded bathroom Free parking

Indoor spacesKitchenValue

4.79 out of 5 average rating, 248 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!

KitchenIndoor spacesLaundry

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 !

Indoor spacesFamilyQuiet

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.

FamilyKitchenComfort

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.

KitchenIndoor spacesComfort

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

Condo in Downtown Toronto

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.

Luxury Downtown Condo For 4 (CN Tower Views)

KitchenIndoor spacesLayout

4.94 out of 5 average rating, 129 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)

Indoor spacesKitchenAccuracy

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

KitchenFamilyBarbecue

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

KitchenFamilyTV

Condo in Downtown Toronto

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.

Stylish 1BR on Toronto’s Harbourfront

Indoor spacesFamilyCheck-in

4.93 out of 5 average rating, 126 reviews

4.91 out of 5 average rating, 330 reviews

Apartment in The Beaches

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

Indoor spacesFamilyQuiet

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

Indoor spacesKitchenNearby

4.89 out of 5 average rating, 116 reviews

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, 112 reviews

Modern Condo in Downtown Core

FamilyKitchenAir conditioning

Family- and pet-friendly home rentals

4.86 out of 5 average rating, 138 reviews

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.

Home in Scarborough

* Private Unit: Bright, Spacious Lakeside Suite *

FamilyKitchenParks

4.87 out of 5 average rating, 141 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.

KitchenFamilyPets

4.98 out of 5 average rating, 365 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

KitchenIndoor spacesBathroom

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

Indoor spacesKitchenPets

4.9 out of 5 average rating, 147 reviews

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

FamilyKitchenLaundry

4.84 out of 5 average rating, 193 reviews

A dining area features a large table surrounded by six black chairs, set under a round chandelier. Soft natural light enters through a set of windows, illuminating the light-colored walls and a framed wall art depicting a serene landscape. A potted plant adds a touch of greenery.

Home in Toronto

100m to Subway! Bright Spacious 3Br Danforth Home

FamilyKitchenGetting around

4.94 out of 5 average rating, 206 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 spacesFamilyHospitality

4.98 out of 5 average rating, 221 reviews

A comfortable living area features a gray sofa with decorative pillows. Natural light enters through large sliding glass doors leading to a private deck. A patterned rug covers the hardwood floor, and potted plants add greenery to the space. A lamp stands beside the sofa.

Guest suite in Toronto

Bright East-Toronto 2 Bedroom Near Subway

Indoor spacesFamilyCondition

Family-friendly home rentals with a pool

4.92 out of 5 average rating, 165 reviews

Skyline Condo | Free Parking | Steps to CN Tower

Indoor spacesFamilySleep quality

4.86 out of 5 average rating, 103 reviews

The exterior view of the two-story house is framed by lush trees, showcasing large windows that allow natural light to filter inside. A balcony extends from the second floor, providing outdoor space. The structure features a blend of wood and siding materials.

Home in Uxbridge

The Ridge Roost - Uxbridge Township

KitchenFamilyAmenities

4.82 out of 5 average rating, 122 reviews

A spacious living area is featured, with large windows offering natural light and views of the city. A comfortable gray sofa is situated alongside a vibrant red armchair. A wooden coffee table rests on a patterned rug, complemented by a flat-screen TV and decorative artwork.

Condo in Etobicoke

Humber Bay Family Friendly condo w Terrace&Parking

KitchenFamilySleep quality

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

FamilyKitchenCheckout

4.96 out of 5 average rating, 123 reviews

Home in Erin Mills

Luxurious 2 bdr suite near SQ1, UTM, parking/pool

FamilyIndoor spacesLong stay

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

FamilyKitchenCleanliness

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

KitchenFamilyEV charging