Spacious garage apartment in Winter Garden that sleeps four.

Winter Garden, Florida
$212 avg/night
Bed 2

Bed

Bath 1

Bath

Home Guest House

Property Type

Sleep 4

Max Sleeps

This 2BR, 1BA light-filled gem can accommodate four people and is located a short walk or bike ride to beautiful downtown Winter Garden, lovingly called “a charming little city with a juicy past,” with a wide array of award-winning restaurants, shops, and authentic old-Florida charm. In addition to our famous Farmers’ Market, we have the 29-mile West Orange Bike Trail, the Garden Theatre, Lake Apopka, and easy access to all of Orlando’s major attractions, as well as Central Florida’s off-the-beaten-path destinations.

This property is located in a quiet neighborhood in the heart of one of Florida’s most dynamic small towns. We are within close walking distance (less than 5 minutes) of three parks: Newton Park, the town’s historic Lake Apopka waterfront, with a boat ramp, wooden dock, and two community centers and the Farnsworth City pool; Bradford Memorial Park, a quiet park excellent for fishing and walking; and the Jessie Brock Community Center, with a 1/3 mile fitness walk and recreation center.

A further five-minute walk (or 3-minute bike ride) and you’re in beautiful downtown Winter Garden, a true gem. We’re often told it's like a scene from a movie set (which it has been, over the years) with a wealth of shops, wine bars, award-winning restaurants and pubs, and often some seasonal event happening, such as the Bloom and Grow Flower Show, Friday’s on the Plaza live music, Heritage and Music Festival, and of course, our famous award-winning Farmer’s Market open every Saturday from 8 am to 1 pm.

We are also home to two small museums (The Heritage Museum and the Central Florida Railroad Museum) as well as the SoBo Art Gallery. The Garden Theatre presents a full season of live theatre performances, concerts, and movies.

There are too many dining and drinking options to mention but they range from fine dining at The Chef’s Table to tasty Thai food at Thai Blossom Restaurant to the Crooked Can Brewing Company located in the Plant Street Market.

And all of it is connected by our famous Rails to Trails West Orange Bike Trail that runs straight through the center of town, connecting all the way from Clermont to Apopka. Along the way, you’ll find the Oakland Nature Preserve and multiple rest stations and parks. We have two bikes you can borrow as well as a nearby bike shop if you need or want to rent a different style.

And of course, we are located 30-40 minutes from Central Florida's famous theme parks such as Walt Disney World, Universal Studios, SeaWorld, and more. (You didn't think we forgot about that, did ya ) Winter Garden is also just over an hour from Kennedy Space Center and about 60 minutes from either of Florida's beautiful coasts and wonderful beaches.

IMPORTANT:

1) The guest house is located above our detached, 4-car garage and IS ONLY ACCESSIBLE BY USING THE STAIRS.
2) If you have a significant allergy to cats, this may not be the best guest house for you. A cat has lived in this building in the past and we have several cats on the property. Just something to think about before requesting to book with us. 3) In hot weather we don’t run the AC system lower than 76 degrees. We have a heat-pump HVAC system and it can only effectively cool the inside of the space to -20 degrees below the outside temperature. Trying to cool the space further by drastically lowering the thermostat to drastically cool can freeze the coils and in doing so stop the AC system from cooling altogether. IMPORTANT: We ask you don’t request to stay with us if running the AC no lower than 76 is an issue for you.

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • MORE

    Books Smoke-free Property Computer Monitor Desk Desk Chair Dryer Iron/ironing Board
  • OUTDOOR

    Garden
  • INTERNET

    Available In All Rooms: Free WiFi Available In Some Public Areas: Internet Access
  • GUEST SERVICES

    Laundry Facilities Snow Sports Gear
  • FAMILY FRIENDLY

    Dining Table Kitchen Laundry Facilities Microwave Refrigerator Separate Living Room
  • ACTIVITIES NEARBY

    Basketball Birdwatching Cycling Ecotours Fishing Fitness Center Access Golfing Health/beauty Spa Wildlife And Game Walks
  • BEDROOM

    Air Conditioning Bed Sheets Heating
  • BATHROOM

    Hair Dryer Shampoo Shower Soap Toilet Paper Towels
  • ENTERTAINMENT

    TV
  • FOOD AND DRINK

    Coffee/tea Maker Cookware/dishes/utensils Dining Table Dishwasher Ice Maker Kitchen Microwave Oven Paper Towels Refrigerator Stovetop Toaster

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 4

Map Map

School District Rates & Availability

Review Review

  • Kelly and Tim S.

    Submitted Feb 15, 2026

    Stayed Feb 13, 2026

    Very roomy, comfortable and clean apartment. Beautiful and quiet area with lots to do nearby. Great communication from hosts.

  • Cristy W.

    Submitted Feb 12, 2026

    Stayed Feb 7, 2026

    What a great find close to the center of town and our family. The property is lovely and feels private. It is clean, well stocked and maintained with care and love. Will definitely return.

  • Terri P.

    Submitted Feb 8, 2026

    Stayed Feb 3, 2026

    We truly enjoyed our stay in the garage apartment. It was a lovely combination of old charm meets modern amenities. The apartment was furnished with everything needed for both short or long term stays. The grounds were well kept with beautiful mature trees. The host, Mike, was quick to respond and greeted us personally when we arrived. We would definitely stay here again and will recommend it to friends and family.

  • Eileen E.

    Submitted Feb 3, 2026

    Stayed Jan 24, 2026

    We had the opportunity to meet our hosts who were very welcoming and helpful with restaurant recommendations. The apartment is a short 10 minute walk from Plant St, a delightful street of restaurants and shops.

  • Kristy M.

    Submitted Jan 7, 2026

    Stayed Dec 23, 2025

    Host were very nice and engaging. They place is in a perfect location of winter garden everything you could possibly need is there would definitely stay again

  • Cindi S.

    Submitted Dec 13, 2025

    Stayed Dec 11, 2025

    This is an older but well kept and clean above garage apartment. It was nicely decorated. Our issue was there were 2 beds and a futon but the futon could not be opened and used and we had 3 adults. One person had to sleep on the futon unopened which was not very comfortable. I would like to have known this issue prior.

  • Michele K.

    Submitted Dec 8, 2025

    Stayed Dec 6, 2025

    Great time.. close to little town center.. walkable.

  • Jeremiah G.

    Submitted Jul 5, 2025

    Stayed Jun 26, 2025

    Met my brothers in Winter Garden for a week of bike rides and Spacecroutons.com podcast production. Mike and Stasha were great. Loved the location and the French Pastries in town.

  • Laura Wilbanks R.

    Submitted Jun 22, 2025

    Stayed Jun 2, 2025

    Clean and spacious apartment in a quiet and beautiful place.

  • Robert G.

    Submitted Jun 10, 2025

    Stayed May 22, 2025

    Our hosts were outstanding. Location is great for the downtown markets and restaurants.

  • Joe K.

    Submitted Apr 23, 2025

    Stayed Apr 20, 2025

    Very clean and comfortable. Highly recommended.

  • Donald T.

    Submitted Apr 22, 2025

    Stayed Mar 1, 2025

    Friends came to Winter Garden to train for upcoming bicycle tour because of direct access to the West Orange and South Lake trails and the town of Winter Garden with numerous restaurants and breweries

  • Donald T.

    Submitted Apr 5, 2025

    Stayed Mar 22, 2025

    Super nice property a few blocks from downtown Winter Garden and direct access to the West Orange Trail and the South Lake Trail

  • Scott K.

    Submitted Feb 9, 2025

    Stayed Feb 5, 2025

    The whole area is cool. The apartment was cool. I feel cooler now that I did before I stayed here.

  • Ed A.

    Submitted Jan 16, 2025

    Stayed Jan 4, 2025

    My wife and I spent 9 nights at the Winter Garden Guesthouse. The accommodations were wonderful. We wanted a place that would allow us to walk to downtown Plant St. The Guesthouse is .6 of a mile away. A brisk walk took about 12 minutes and a leisurely stroll only took 20 minutes. Lakeview Ave has sidewalks on at least one side of the street and the walk is through a very nice, safe neighborhood. I felt completely safe walking home one evening around midnight. I have never stayed at a place that had everything so very well documented. Each cabinet and drawer was labeled as well as every light switch. It made it very easy to find things. The bathroom was extremely clean. Although it only has a single sink, the counter top on each side of the sink was very wide and allowed my wife and me to share this bathroom very comfortably. They provided two bicycles for our use during our stay. Although my wife and I do not cook when we are on vacation, the kitchen seemed very well stocked. There were several bookcases in the living area with a couple of hundred books and magazines to read. We had one minor issue with the bathroom sink draining slowly. We reported it to Mike and within 10 minutes he was up and had it repaired. All in all a wonderful stay. We would highly recommend this place and if we return to Winter Garden, we would most definitely consider staying here again.

  • Will P.

    Submitted Nov 4, 2024

    Stayed Nov 1, 2024

    We stayed at this property in a quiet neighborhood with tons of charm when we came to.meet my new granddaughter in nearby Minneola. This above-garage apartment had some many nice personal touches, and the hosts were so nice and helpful every step of this fun experience! Unbearable location for a great price!

  • Keifer O.

    Submitted Oct 7, 2024

    Stayed Oct 5, 2024

    Quiet and great proximity to downtown Winter Garden.

  • Anita A.

    Submitted May 24, 2024

    Stayed May 18, 2024

    My husband and I fell in love with Winter Garden and this spacious apartment offers you the real feel to be part of this beautiful town/community. The apartment is so close to the down center yet in a quiet nestled neighborhood and in walking distance to the board walk of Lake Apopka. The place is beautifully renovated and offers you about anything you would need to make your stay special, incl. 2 bikes the host offers up as part of your stay. Having the bikes available to us, made the stay extra special. We look forward to our next visit!!!

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Total

Includes taxes and fees
$212+
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