
Holiday houses in Winter Garden
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Top-rated holiday rentals in Winter Garden
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Experience Downtown Winter Garden, One Block from It All
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!

Waterfront EPIC views, Dock, wildlife Near Disney
Experience the stunning sunrise views over Lake Apopka from our newly refurbished, elegantly appointed 4-bedroom, 2.5-bath vacation home in Winter Garden, FL. This haven is close to Orlando's Universal Studios 20 min, Disney World 25 min) & shopping (Mall of Millenia, premium outlets 17 min) Modern amenities, spacious layout that promises relaxation and convenience making the perfect home for exploring all local attractions and enjoying Florida's natural beauty. Minutes from City Swimming Pool

NEW 1BRM Guesthouse | King Bed | Central Florida
Nestled in a private and central location, this newly constructed space offers everything needed for a relaxing stay. The space is perfect for up to four guests, featuring a king size bed, full kitchen, and smart TVs in every room. Enjoy the convenience of high-speed Wi-Fi, a spacious shower, washer / dryer, and a private driveway. Located close to Downtown, Theme Parks, the Stadiums, I-Drive, Wekiva Springs, Shopping, Dining, and More! Everything needed for your short term or long term stay.

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.

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.

Modern Villa in Minneola near Disney, Orlando
Newly renovated modern villa 3 bed/2 bath cozy home nestled amongst beautiful oak trees and close to Downtown Clermont, National training center, and 35 minutes to Disney World and other major attractions. Home features soft comfy beds including one king, one queen, and two twin beds all with 3" memory foam mattress toppers. The kitchen is fully stocked with spices, coffee/tea station, blender and slow cooker. Game room located in the garage is equipped with foosball and air hockey.

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.

Coastal Cottage in Clermont
Welcome to our newly renovated coastal cottage! Located in the heart of Clermont, only 1 mile from downtown, the south lake trail, & only minutes from all of the best restaurants, shopping, & coffee shops in Clermont! This is the perfect location for triathletes in training or families visiting Disney World (or any of the theme parks) – Orlando’s best attractions are less than 30 miles away! This sweet & sunny lakeside studio has everything you’ll need for a comfortable visit!

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.

Sleek Modern Gateway 10 Min to Parks Pets Allowed
Welcome to Your Magical Gateway – Just 10 Minutes from Orlando's Magical Parks! Location: Perfectly located for Disney and Universal, our apartment offers a peaceful retreat with all the comforts of home. Whether you’re here to explore the magic unwind, or even stay for longer terms, you’ll love every moment of our cozy space. The property sleeps 4 people! PLEASE CONTACT US TO INQUIRY ABOUT ADDITIONAL POTENTIAL DISCOUNTS FOR MULTIPLE DAYS STAY

Green Mountain Getaway (No indoor Smoking or Pets)
(Non Smoker & No Pets) A secluded lot surrounded by FL’s beautiful tropical landscape. Golfer? We are 3 min. from the beautiful Bella Collina's luxury 18 hole golf course, a Nick Faldo design. Also 8 min. from Sanctuary Ridge Golf Club, a more affordable option. Biker? “Killarney Station", is an affordable place to rent bikes or bring your own to ride the beautiful 26 mile trail. 28 minutes to all the attractions!

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 holiday rentals
Other great holiday rentals in Winter Garden

Studio Guest House (Private Not Shared)

20-30 min. Disney, Universal & Downtown Orlando

Oakland Trails

comfortable stay

Cozy Bed and Bath in downtown Winter Garden, FL

The Cottage in Winter Garden Sleeps 5

Next to Universal Studio& I Drive:Cozy Room w/Pool

Moonlight Room
When is the best time to visit Winter Garden?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $176 NZD | $172 NZD | $174 NZD | $174 NZD | $176 NZD | $183 NZD | $179 NZD | $183 NZD | $167 NZD | $174 NZD | $195 NZD | $176 NZD |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°C |
Frequently Asked Questions
What are the best places to stay in Winter Garden?
Staying near historic Plant Street provides walkable access to shops, restaurants, and local entertainment. Residential neighborhoods around downtown have a range of rental options for visitors seeking a quieter atmosphere.
What are the best things to do in Winter Garden with kids?
Children can explore playgrounds and parks, spot wildlife along the West Orange Trail, or visit interactive exhibits at local museums. Seasonal events and performances at the Garden Theatre are also family favorites.
What are some of the best things to do in Winter Garden?
Explore the West Orange Trail, browse market stands and local shops on Plant Street, and catch live performances at the Garden Theatre. Creative eateries and public art add to the downtown experience.
How is the weather in Winter Garden?
Winter Garden experiences warm, humid summers around 88-92°F (31-33°C), with heavy rainfall, and milder winters near 49-72°F (10-22°C). Spring and fall provide comfortable weather for outdoor activities and exploring the area.
When is the best time to visit Winter Garden?
Late fall through early spring is often recommended for comfortable temperatures, fewer rain showers, and outdoor events. Warmer and wetter summer months are favored by those seeking local festivals and a lush landscape.
What are the best places to visit in Winter Garden?
Explore the West Orange Trail for cycling and walking, discover the lively Winter Garden Farmers Market, and enjoy storefronts and eateries along historic Plant Street. The Garden Theatre is often recommended for performances.
What are some hiking trails in Winter Garden?
The West Orange Trail is frequently suggested for cycling, walking, and jogging, with scenic spots under shady oaks. Some local parks also have nature paths for shorter walks surrounded by native plants.
What are some family activities we can do in Winter Garden?
Families often enjoy biking or strolling the West Orange Trail, catching a show at the Garden Theatre, and sampling local goods at the Farmers Market. Parks and splash pads add extra options for children.
What are some of the best day trip ideas from Winter Garden?
Consider exploring nearby nature preserves, visiting regional art museums, or touring local gardens and lakes. Theme parks and other Central Florida attractions are also frequently suggested for day excursions.
Are there any pet friendly accommodations available in Winter Garden?
Many vacation rentals around downtown Winter Garden and nearby neighborhoods welcome pets. Public parks and the West Orange Trail make it easy to explore the area with your dog.
What are some local tips for visiting Winter Garden?
Explore the area early in the day to make the most of the cooler hours, especially in summer. Weekends bring lively markets and street events, while weekdays offer a quieter downtown atmosphere.
What is Winter Garden known for?
Winter Garden is known for its tree-lined historic downtown, vibrant arts scene, and roots in citrus farming. The city often draws visitors who enjoy outdoor activities, public art, and locally owned eateries.
What are the best hidden gems to explore in Winter Garden?
Explore boutique shops tucked along side streets, small art galleries, and scenic spots along the West Orange Trail. The Central Florida Railroad Museum provides an engaging look at regional history.
What are the best foods to try in Winter Garden?
Try Southern-inspired dishes, fresh seafood, and locally made desserts in Winter Garden. Seasonal produce often features in market finds, and flavors inspired by citrus farming roots are frequently suggested.
What should I bring for a trip to Winter Garden?
Pack lightweight clothing for warm weather, a hat, sunscreen, and comfortable shoes for walking. During wetter seasons or summer, a rain jacket or umbrella is also practical.
What is the nightlife in Winter Garden like?
Winter Garden has a relaxed nightlife scene with neighborhood breweries, cozy wine bars, and occasional live music at local venues. Many people also gather around the historic downtown area for evening entertainment and casual dining.
What are the most popular events or festivals in Winter Garden?
Winter Garden has a bustling weekly farmers market, seasonal music and arts festivals, and holiday parades that draw visitors year-round. Food-centered street events and family gatherings are often scheduled on weekends and during local holidays.
Are there family friendly vacation rentals in Winter Garden?
Winter Garden has a range of vacation rentals that are well-suited for families, especially near parks and downtown. Many options provide extra space, kitchens, and easy access to neighborhood attractions.
Quick stats about holiday rentals in Winter Garden

Total holiday rentals
Explore 140 holiday rentals in Winter Garden

Verified guest reviews
Over 4,510 verified reviews to help you choose

Family-friendly holiday rentals
70 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 30 rentals that welcome pets

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
130 of Winter Garden holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Winter Garden rentals

4.9 Average rating
Winter Garden stays are highly rated by guests—averaging 4.9 out of 5!
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