Family-friendly vacation rentals in Winter Garden

Find and book unique family-friendly homes on Airbnb

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

  • Total vacation rentals

    Explore 50 vacation rentals in Winter Garden

  • Nightly prices starting at

    Winter Garden vacation rentals start at G$8,367 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,580 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Winter Garden vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Winter Garden rentals

  • 4.8 Average rating

    Winter Garden stays are highly rated by guests—averaging 4.8 out of 5!

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 favorite
A bright living area features two rattan chairs positioned on a decorative area rug. Framed artwork adorns the wall behind the chairs. A dining area is visible in the background, with a modern table and pendant lighting, creating a welcoming space.
Home in Winter Garden
4.97 out of 5 average rating, 132 reviews

Downtown Bungalow with fire pit and putting green

This 1920's home has been fully updated to include new kitchen, bath, fixtures, appliances, and more. The home has 2 bedrooms with one having a king bed and the other a queen bed. Beds feature super comfy Tuft & Needle mattresses ! Kitchen covers all of your basic cooking needs, has stainless appliances, refrigerator with ice maker, and Keurig coffee maker. The dining table comfortably seats 4 and is perfect for a meal or to use as a work space. New full size washer and dryer in carport laundry room. Grab a bottle of wine from Tony's less than 1 block away and relax in the screened-in front porch. Depending on the season grab a Valencia orange off the citrus tree in the back yard. You can use the entire home! There are 2 spacious bedrooms, 1 bath, dining room, kitchen, and a full washer and dryer in the laundry room (located in the carport). Owners live less than a mile away and are available as needed. We can meet you if you need anything! Just a few short steps from the famous Farmer's Market, Crooked Can Brewing, the Plant Street Market, the West Orange Bike Trail, Garden Theater, countless restaurants, and all that Downtown Winter Garden has to offer. This historic home is the perfect escape from the bustle of the tourist district, less than 30 minutes to Disney World, 25 minutes to Universal Studios, 30 minutes to Sea World. You can easily walk the 1 block to Plant St where most of the amenities of Downtown Winter Garden are located. You'll be just 25 minutes from Universal Studios and I-Drive via the Turnpike and 25 minutes from Disney via hwy 429. Also if you are into biking you can rent them at Wheel Works or the West Orange trail head and hit the famous West Orange Trail. There is a 2 car covered carport on site. Across the street from an elementary school so during the school year, there is some traffic in the morning and afternoon. Please be mindful and a good neighbor!

Top guest favorite
Guesthouse in Winter Garden
4.9 out of 5 average rating, 105 reviews

A place with a view

Welcome to Your Secluded Getaway Enjoy a quiet retreat minutes from supermarkets and Florida’s top attractions. Urgent care , Emergency room & Hospital are all nearby Top Attractions Island H2O: 23m | Epcot: 27m | SeaWorld: 32m Disney Springs: 34m | Universal: 36m Legoland: 1h | Busch Gardens: 1h 27m Shopping & Dining Winter Garden/Clermont14m Outlets 28m | Florida Mall 35m | I-Drive 40m Travel MCO Airport 40m Oversized Parking: Dedicated space for boats, RVs, and moving trucks. storage only

Guest favorite
Home in Oak Ridge
5 out of 5 average rating, 101 reviews

Harmony | Heated Pool | 10 min Universal & Epic.

Welcome to Harmony House: We want to Be your Host in Orlando! Let us show you why you should book with us: 🏡 1800 ft2 ground floor house 🌇 Top Location 🎢10 Min Universal Studios 🎢13 Min Epic Universe 🏰 20 Min Magic Kingdom 🛍️20 MIn Disney Springs 📺 4 Smart TVs 🛜 Fast WIFI 🧑‍🍳 Fully equipped kitchen 💻 Dedicated work space 🅿️ Free Onsite parking 🍗BBQ - Outside dining 🏊‍♀️Heated Private Pool 🗑️Washer & Dryer 👫Kids friendly 🎱⛳️🏓Family games: Pool Table, Golf, Ping PongTable

Top guest favorite
A spacious outdoor area features a large pool with crystal-clear water, accompanied by a hot tub and a soothing water fountain. Surrounding the pool, a stone patio hosts multiple seating areas beneath a pergola, providing a serene setting for relaxation.
Home in Orlando
4.97 out of 5 average rating, 107 reviews

Unique Spacious Home w/ Pool near Downtown Orlando

Nestled on a quiet street, 15 mins from Downtown Orlando. This home has a massive pool, hot tub, water fountain, real outdoor and indoor fire place, outdoor patio area w/seating. The Kitchen is equipped with everything you need to make delicious meals, and there are two living areas to provide ample space for relaxation. There is also a designated office area to take work calls. ☀ College Park – 10 mins ☀ Downtown Orlando – 15 mins ☀ Universal Studios – 28 mins ☀ Walt Disney World – 34 mins

Top guest favorite
Bungalow in Davenport
4.98 out of 5 average rating, 102 reviews

Spectacular sunset villa, stunning saltwater pool

Stunning sunset villa. Spectacular saltwater pool & spa. On the safe secure Highlands Reserve golf course . Beautiful conservation & golf course views. Luxury bespoke villa with 3 large bedrooms 2 bathrooms & occasional sofa bed in den. Fabulous deck ,private outlook . Walking distance Public,shops,restaurants or 5 min drive.15 mins Disney ,35 universal. Pool/Spa heat advised Oct/ April at an additional cost. There is a ring door bell at the property. NO EV charging allowed at the property

Guest favorite
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
4.92 out of 5 average rating, 225 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 favorite
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, 197 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.

Top guest favorite
The exterior of the property features a fenced yard with shaded trees and a front lawn leading to a single-story house. A pool area with protective mesh surrounds the heated pool, illuminated with vibrant LED lights in evening settings. Indoor spaces exhibit an open layout with natural light and comfortable seating.
Home in Minneola
4.98 out of 5 average rating, 196 reviews

Spacious Getaway ~ Heated LED Pool & Ping Pong

Welcome to your Spacious Getaway! Exterior Features: ★ LED Lights in Pool and on Pool Cage ★ Fenced-in yard & Fire-pit ★ Doorbell & Driveway Camera for safety Interior Features: ★ Ping Pong Table ★Large Shower in Master Bathroom ★ROKU on each TV Extras: ★ Heated Pool up to 95 Degrees - $50 per day (Pool Water is normally at 75 degrees without the Pool Heater) ⚠️ Pet-Friendly, but the pet must be added to the reservation ($75 Pet fee)⚠️ {Willing to Negotiate Monthly Prices}

Top guest favorite
Home in Clermont
4.87 out of 5 average rating, 134 reviews

Mario-Themed Home! | Disney 30 Min | Pool + Lake

🍄 Mario's Mini Mansion is a boutique Mario-themed getaway for small families (1-3 kids) and local staycations. > Custom Yoshi’s Fort (queen + twin XL bunk + LIFE-SIZE Yoshi!) > King loft bedroom upstairs > 75" Smart TV + Nintendo Switch (Mario Wonder + games) > 4 streaming TVs > Heated neighborhood pool + large screened patio > Efficient kitchen with Breville Oven/Air Fryer > Sleeps 5 Glow-in-the-dark details, Mario games & more! Something magical for the whole family 🎮

Guest favorite
A treehouse is illuminated by warm string lights, nestled among large branches under a deep blue sky. The structure features large windows allowing views of the surrounding greenery, with a cozy seating area visible inside. A wooden walkway leads to the entrance.
Treehouse in St. Cloud
4.97 out of 5 average rating, 1,149 reviews

TreeHouse in the Cloud, (Close toTheme Parks

The treehouse is a private getaway for a couple that want to experience the magic. Check out video tours on U-Tube. Type in Treehouse in the Cloud. There have been several movie and other photo shoots done on property. Please text request and details, and we can negotiate fees. Our other AirBnB is just next door; Country gem horses close to Theme parks [link] Which is 1,000 sq ft and sleeps six.

Top guest favorite
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, 159 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 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 favorite
A scenic view overlooking Starke Lake is presented, featuring a spacious deck with railing. A tranquil pool is visible in the foreground, while vibrant clouds reflect the colors of a sunset in the background, enhancing the natural beauty of the surroundings.
Home in Ocoee
4.9 out of 5 average rating, 180 reviews

Lakeview Sunsets with Loft Escape West of Orlando

We are proud to announce No Smoking on premises property. This Duplex A Lake house overlooks Starke Lake in Central Florida. Great fishing, magnificent sunsets and Disney fireworks every night . Close to Disney 19 miles & 12 miles to Universal & 14 miles to Downtown Orlando. Other activities include air boating, Cape Cape Canaveral and centrally located just 1 hour from ocean or gulf. Please NO SMOKING on premises.

Popular amenities for Winter Garden family-friendly rentals

When is the best time to visit Winter Garden?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$32,840 GYDG$33,050 GYDG$33,259 GYDG$29,284 GYDG$26,356 GYDG$27,611 GYDG$27,402 GYDG$28,239 GYDG$22,591 GYDG$24,892 GYDG$26,983 GYDG$34,095 GYD
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