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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!

Designer Guest Suite Near Disney/Universal/DT

This newly renovated, modern, and clean apartment has been freshly designed with wonderful & 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 with thick memory foam toppers 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

Stay A While

Welcome to Your Secluded Getaway, which has been recently updated in July 2026. Enjoy a quiet retreat minutes from supermarkets and Florida’s top attractions. Top Attractions Island H2O: 23m | Epcot: 27m | SeaWorld: 32m Disney Springs: 34m Universal: 36m Legoland: 1h | Busch Gardens: 1h 27m Shopping & Dining Winter Garden/Clermont 14m Outlets: 28m | Florida Mall: 35m | I-Drive: 40m Travel MCO Airport: 40m Oversized Parking: Dedicated space for boats, RVs, and moving trucks storage only

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.

The Swift House

Steps from Plant St. This private cute cottage with Modern amenities is a Swiftie Oasis. Even if you aren’t a fan- you will love the designated off street covered parking, Fenced in .25 acre back yard, delicious restaurants, coffee shops, French bistro, brewery, wine bar, rooftop lounges, shops, the W Orange trail, top farmers market, festivals and more. Walk to the lake! Very Safe. 20 mins to Disney. Enjoy the charm of Historic Downtown WG or stay in and indulge in all things Taylor $wift.

Emerald Grove - Close to Disney

2 Bedroom | 2 Bath | Prime Winter Garden Location | Near Disney & Universal Nestled in the heart of charming Winter Garden, this beautifully designed 2-bedroom, 2-bath apartment offers the perfect blend of modern luxury and small-town charm — just 20 minutes from Walt Disney World and Orlando’s top attractions. Located on the iconic Plant Street, you’ll be steps away from historic downtown Winter Garden, home to popular restaurants, boutiques, coffee shops, and the famous West Orange Trail.

Winter Garden Butterfly Retreat

Enjoy this quiet retreat in Winter Garden. One block from the 22-mile West Orange Trail. Walk into town under a canopy of oak trees and Spanish moss. Enjoy our historic downtown coffee shops, restaurants, ice cream parlor and farmer's market. This is a private 2-room suite with bathroom, kitchenette, independent driveway, patio and entrance. Unit is part of a larger home where owner lives, but private with no shared spaces. A great stop for cyclists! Bike parking available in the garage.

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.

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.

Cozy cottage in Winter Garden

This newly renovated, cute and cozy home is just what you're looking for your vacation in Orlando/Winter Garden area! It is in close proximity to Winter Garden Downtown with great restaurants, cafes and farmers market. Also the famous West Orange bike trail is just 4 minutes away by bike. If you plan to visit Disney or Universal they're less than 30 minutes away. You'll have a great time at this comfortable place to stay.

WATERFRONTWntrGdnPoolHSE VIEWS Dock Wildl Nr Disn

Enjoy the breathtaking sunrise views of Lake Apopka from this newly refurbished and well appointed 4 bed, 2.5 bath vacation home in Winter Garden, Fl. While the house offers total tranquility and relaxation, it is only a short drive from Orlando’s numerous theme parks (Universal Studios 20 min, Disney World 30 min) and all other local attractions (Mall of Millenia and premium outlet malls 20 min drive)