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Family-friendly holiday rentals in Winter Garden

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Winter Garden

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Top guest favourite
A white door with a glass panel leads into the studio, framed by a decorative welcome mat on stone pavers. Lush green plants are positioned beside the door, adding a natural touch to the entrance. Soft shadows from nearby foliage create a calming atmosphere.
Guest suite in College Park
4.97 out of 5 average rating, 233 reviews

New Mid Century-Modern Studio

Enjoy your stay in this beautifully decorated studio with all the conveniences of home. The bed is Queen. We are located in College Park of Orlando. On Edgewater Drive there are restaurants, bars, and boutique shops. Close to downtown , 30 min. from all the attractions, and 5 min. from one of the city’s largest hospitals, 23 miles from ORMC airport. Walking distance from the historic Dubsdread Golf Club and restaurant. Pet fee required. Please make sure to add the pet to the reservation.

Guest favourite
A small, white house is framed by vibrant greenery and colorful plants. The front door, painted blue, adds a pop of color, while large windows allow light to fill the space. A wooden deck leads up to the entrance, enhancing the welcoming appeal.
Home in Winter Garden
4.91 out of 5 average rating, 206 reviews

Cozy Winter Garden Home 20 MINUTES FROM DISNEY

Get the small home-town feeling and still be only 20 minutes from Disney. This little house is perfect for a couple or small family who wants to visit Orlando and all the attractions, but also get away from the traffic & stay in a desirable small town setting. Located a mile from downtown Winter Garden - home to the number 1 rated farmer's market by American Farmland Trust, & the 22-mile West Orange Trail that's home to runners, bicyclists and anyone else who wants to enjoy the sunshine.

Top guest favourite
The exterior of a renovated cottage is showcased, featuring a welcoming front porch with two wooden chairs. Potted plants are placed on the porch and along the walkway, while a wooden fence stands in the background, enhancing privacy.
Cottage in Winter Garden
4.99 out of 5 average rating, 168 reviews

The Heart of Winter Garden: Walk to shops & dining

Stay in a completely renovated 1937 cottage that's located in the heart of historic downtown Winter Garden. It's walking distance from all of the shops, restaurants, and events (including the #1 rated farmers market in the nation every Saturday) that make Winter Garden one of the most desirable cities in Florida. Sit on the front porch and watch as people bike and jog on the famous West Orange Trail, or rent a bike from the corner and join them. The home is close to all major highways.

Guest favourite
A vibrant sunset reflects off the surface of a lake, with hues of orange, pink, and purple blending into the sky. Silhouetted trees frame the scene, adding depth to the tranquil waterscape, which sparkles gently as daylight fades.
Guest suite in Ocoee
4.82 out of 5 average rating, 165 reviews

Charming Studio with Garden (West of Orlando)

We are proud to present a No Smoking on Premises Airbnb. My studio apartment is just the perfect place to hangout. There is a nice fire pit on the back patio and logs to relax with friends and enjoy the warm weather. The black gravel parking space in front is for the use of the Studio guests. The main house guests park in the driveway. We have an onsight massage therapist that can come to your place as an upgrade. Text me for more details. Please NO SMOKING on premises.

Top guest favourite
An open studio layout is showcased, featuring a comfortable queen bed with decorative pillows and a soft throw blanket. A multi-functional sofa and coffee table are positioned in front of a flat-screen TV. A dining table for four is also visible, enhancing the inviting atmosphere.
Home in Minneola
4.97 out of 5 average rating, 153 reviews

Cozy Studio Near Disney/Universal/Training center

This cozy stylish studio, detached guest house is perfect for short-term or extended stay in the beautiful city of Minneola. Sleeps 2, can accommodate up to 4. Features a large backyard and a fire pit.  Close to Downtown Clermont, National Training Center, and 35 minutes to Disney World and other major attractions. This tranquil space features a queen bed with 3" memory foam mattress topper and a spacious living space that has a Multi-Functional Sofa that converts into a Bed.

Superhost
A modern living space is presented, featuring an open layout that includes a kitchen with dark cabinetry and a dining area with a circular table. Stylish bar stools line the kitchen counter, and a television is positioned in the lounge area, which is complemented by a cozy blue sofa.
Home in Ocoee
4.82 out of 5 average rating, 125 reviews

★★House in Little Loma ★★ 4 beds ★ Jacuzzi

Enjoy this charming remodeled home with 3 bedrooms, 2 bathrooms, and a JACUZZI waiting for your and your family. Each room has a TV. The kitchen has all you need to make a home cook dinner after a really fun day!!! A minute walking distance to VANDERGRIFT CENTRAL PARK which features: Baseball Fields (Lighted), Basketball Court, Volleyball, Boardwalk, Concession Stand, Fishing Dock, Football Field, Non-Motorized Boat Launch, Parking, Picnic Tables, Playground, Restrooms

Superhost
A small bedroom features a spacious bed with a patterned white and navy coverlet. A window with light curtains allows natural light to enter. A wooden shelf with various items is visible next to a desk with a lamp. A closet door reflects the room's layout.
Guest suite in Orlando
4.73 out of 5 average rating, 845 reviews

Cozy & Private Studio close to the Attractions

Is a small space completely private attached to the side of the house with a separated entrance from the main area. Clean, quite and safe. The studio has a bedroom, a bathroom and there is also an area with microwave, mini fridge, toaster and coffee maker. Wi-fi is available. You’ll be located 17 minutes from Universal Studios and 25 minutes from Disney World driving. Feels free to contact us at any time, we would be happy to help you in any way possible. HABLAMOS ESPAÑOL

Top guest favourite
A comfortable living area features a spacious couch with reclining sections and soft cushions. A Smart TV is placed on a black media console next to a stylish clock, while light filters through striped curtains. A small table holds a notepad, providing additional convenience.
Flat in Minneola
4.96 out of 5 average rating, 131 reviews

Spacious Apartment In Minneola

This spacious 1 bedroom / 1 bathroom apartment is located West of Orlando in the beautiful town of Minneola right next to Clermont in the heart of Central Florida and is perfect for a short or long term stay. Features a large bedroom & bathroom, comfortable couch w/ dual recliners, plenty of closet space & storage, and a Smart TV. Kitchen is stocked with all the essentials and has a dishwasher, gas stove, refrigerator w/ ice maker, coffee maker, microwave and crockpot.

Guest favourite
A modern bedroom features a spacious bed layered with crisp white linens against a neutral wall. A tall dresser with a natural wood finish stands beside a chair. Natural light enters through two windows, and decorative elements like wall art and plants add a touch of style.
Guest suite in Winter Garden
4.83 out of 5 average rating, 374 reviews

Private In-Law Suite Near Disney/Universal/DT

This newly renovated, modern, and clean Mother-in-Law Suite is freshly designed with bright colors and all new furnishings. Everything is thoughtfully selected to create the perfect Airbnb stay. You'll have coffee, decaf, tea, 200mbps Wi-Fi, and high-end mattresses for the perfect night's sleep. You'll stay in the Orlando area, 20min from Disney/Universal/DT Orlando, and minutes from DT Winter Garden, shopping center, & famous 22mile West Orange Bike trail

Top guest favourite
A living area features a plush sofa and two armchairs arranged around a circular coffee table. Natural light filters through the window, illuminating the space. A vibrant area rug anchors the seating area, while a bouquet of flowers adds a touch of color on the table.
Home in Winter Garden
4.99 out of 5 average rating, 135 reviews

Downtown Winter Garden, Florida

Charming two bedroom, one bathroom home just three blocks from downtown Winter Garden Florida. Across the street from the West Orange Bike Trail and walking distance to restaurants, Splash pond, shopping and Farmers Market. The fenced in back yard is shaded by a 100 year old live oak tree. There is a “no pet policy” at the house. We do not accept guests under the age of 12. There are NO cameras on or around the property. I respect the privacy of my guests.

Guest favourite
A cozy bedroom features a black platform bed dressed in a navy and white patterned duvet. A wooden dresser stands adjacent to the bed, and a small desk is positioned nearby. Natural light illuminates the space, highlighting the serene beach artwork on the wall.
Guest suite in Eatonville
4.97 out of 5 average rating, 193 reviews

Private entrance/bathroom 10 min from DT Orlando

Welcome to your home away from home! Our cozy room with a attached bathroom is the perfect retreat for your visit to Orlando. Located just 10min from downtown Orlando, 30min from MCO and Disney, and 20 min from Universal, you'll have the best of both worlds - convenience and comfort. Whether you're here for business or pleasure, our room is the perfect place to call your temporary home. Book your stay with us today and experience the best of our city.

Top guest favourite
A welcoming outdoor space is presented with two patterned armchairs and a wicker chair arranged around a glass-topped table. A decorative wall feature adds texture, while potted plants and a decorative heron enhance the tranquil atmosphere. Warm light filters through the area.
Guest house in Winter Garden
4.93 out of 5 average rating, 100 reviews

Blue Heron Bungalow

The Blue Heron Bungalow is located within walking distance of downtown Winter Garden, where you can find great dining, shops, and entertainment. You can also connect with the West Orange Trail and enjoy 22 miles of walking, running, or biking. If you get adventurous Walt Disney World is less than 30 minutes away, as well as many other attractions. Located in the golf cart district.

Popular amenities for Winter Garden family-friendly rentals

When is the best time to visit Winter Garden?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price£113£104£116£106£96£100£99£102£82£104£112£112
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C17°C

Quick stats about holiday rentals that are family-friendly in Winter Garden

  • Total holiday rentals

    Explore 70 holiday rentals in Winter Garden

  • Verified guest reviews

    Over 1,930 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    60 of Winter Garden holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Winter Garden rentals

  • 4.9 Average rating

    Winter Garden stays are highly rated by guests – averaging 4.9 out of 5!