Mid Century Hipster

Photo gallery for Mid Century Hipster

A bedroom with a bed, two windows, a wall-mounted air conditioner, and a painting.
A kitchen with white cabinets, a bar area with metal chairs, a ceiling fan, and pendant lights.
A kitchen with white cabinets, a wooden beam ceiling, pendant lights, a window with blinds, a painting of flowers, and a door.
A modern two-story house with a stone facade, a covered porch, and a well-maintained garden.
A living room with a sectional sofa, a patterned rug, a ceiling fan, and wall decor.

Reviews

9.6 out of 10
Exceptional

Highlights

  • The great outdoors
    Guests love the outdoor space here.
  • Firepit available
    One of the few properties with a dedicated outdoor firepit.
  • At the centre of it all
    Stay in a top rated central location, steps from the best attractions, dining, and entertainment.
  • Discover nearby landmarks
    Near West Orange Trail

Popular amenities

  • Balcony or patio
  • Barbecue
  • Air-conditioning
  • Pet-friendly
  • Refrigerator
  • Internet

Explore the area

View map
Winter Garden, FL
  • Place, Garden Theatre
    ‪8 min walk‬
  • Place, West Orange Trail
    ‪9 min walk‬
  • Place, Winter Garden Heritage Museum
    ‪9 min walk‬
  • Airport, Orlando, FL (MCO-Orlando Intl.)
    ‪30 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

1 Queen Bed

2 bathrooms

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Outdoor play area
Garden
Dining area

Add dates for prices

Similar properties

Interior
House with large deck, walking distance to Historic Downtown Winter Garden
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  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
9.8 out of 10, Exceptional, (30 reviews)
House with large deck, walking distance to Historic Downtown Winter Garden

About the area

Winter Garden

Located in Winter Garden, this holiday home is in the city centre. Orlando International Premium Outlets and Mall at Millenia are worth checking out if shopping is on the agenda, while those wishing to experience the area's popular attractions can visit Magic Kingdom® Park and Walt Disney World® Resort. Looking to enjoy an event or a game? See what's going on at Camping World Stadium or Kia Center. Spend some time exploring the area's activities, including birdwatching.
View more Holiday homes in Winter GardenOpens in a new window
Map
Winter Garden, FL

What's nearby

  • Winter Garden Art Association - 6 min walk - 0.6 km
  • Central Florida Railroad Museum - 8 min walk - 0.7 km
  • Garden Theatre - 8 min walk - 0.7 km
  • West Orange Trail - 9 min walk - 0.8 km
  • Winter Garden Heritage Museum - 9 min walk - 0.8 km

Getting around

  • Orlando Station - 19 min drive
  • Kissimmee, FL (ISM-Kissimmee Gateway) - 45 min drive

Restaurants

  • ‪Crooked Can Brewing Company - ‬15 min walk
  • ‪Culver's - ‬14 min walk
  • ‪The Whole Enchilada - ‬12 min walk
  • ‪Rosallie - ‬12 min walk
  • ‪4 Rivers Smokehouse - ‬12 min walk

Frequently asked questions

Is Mid Century Hipster pet-friendly?

Yes, this property allows cats and dogs (limit 2 total) with a maximum weight of up to 23 kg per pet.

How much does it cost to stay at Mid Century Hipster ?

As of 13 Nov 2026, prices found for a 1-night stay for 2 adults at Mid Century Hipster on 22 Nov 2026 start from NZ$744, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Mid Century Hipster ?

On-site parking is available at the property.

What time is check-in at Mid Century Hipster ?

Check-in begins at 3:00 PM.

What time is check-out at Mid Century Hipster ?

Checkout is at 11:00 AM.

Where is Mid Century Hipster located?

Located in the heart of Winter Garden, this holiday home is within a 15-minute walk of West Orange Trail and Garden Theatre. Lake Butler and AdventHealth Winter Garden are also within 3 miles (5 km).

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 12 out of 15 reviews
Rating 8 - Good. 2 out of 15 reviews
Rating 6 - Okay. 1 out of 15 reviews
Rating 4 - Poor. 0 out of 15 reviews
Rating 2 - Terrible. 0 out of 15 reviews

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

9.2/10

Location

9.6/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Loved our stay!! Very comfortable, cozy, close to downtown Winter Garden. Nicely decorated, very clean and cheery, would stay again
Stayed 3 nights in Feb 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice comfortable house! Liked the easy walk to Downtown Winter Garden…our primary reason for staying here.
Stayed 3 nights in Dec 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Loved it!

Fantastic place to stay!
Stayed 7 nights in Mar 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Cozy home for a family vacation

Our stay was great, the house had everything in working order and was the perfect size and location for our group
Stayed 3 nights in Apr 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Stay

This house is features super comfy beds and a giant couch for relaxing! Love staying at this location!
Stayed 6 nights in Oct 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Winter Garden Getaway

Our trip was all we hoped for. Clean accommodations, plenty of TP, soap, shampoo, dishwasher detergent, laundry detergent, trash bags etc. to get us started. Located within walking distance to Plant Street, we’re we spent time each day. Our host was friendly and very responsive to us.
Stayed 28 nights in Feb 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Clean and close to everything

Everything was very easy. Property was well maintained and easy to navigate to all of the local attractions. Communication was very prompt from the host when we needed it. Thanks and hope to see you again in the future!
Stayed 7 nights in Dec 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy

Winter Garden Hipster

We had a lovely time visiting Winter Garden. The home was perfect and within walking distance to the historical downtown district with lots of great restaurants and boutiques. Our host, Mary Anne could not have been more helpful. She gave us lots of information about where to eat and visit. It was a wonderful vacation get away.
Stayed 16 nights in Mar 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Celebrate with family

It is a sweet home and the location is fantastic! Downtown is fabulous and it was great not having to drive anywhere. The house is clean and has extra amenities you do not normally get like coffee pods, spices etc. only comment would be for additional bath towels. Awesome trip!
Stayed 3 nights in Jul 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Hipster

House was 3 bedrooms with 2 bath. Neighborhood was quiet. House was very clean
Stayed 4 nights in Apr 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Winter Garden Jewel

This is a lovely home that was spotless and nicely appointed. It’s a large house with three bedrooms, two full baths and three bedrooms, kitchen and living room. Easily it could accommodate 8. Communication with the owner was almost immediate! Peaceful walk to downtown Winter Garden. Make sure you go to the Saturday Market if you’re in town. We would definitely stay here again.
Stayed 5 nights in Sep 2023
Response from VrboOwner on 5 Oct 2023
Thank you for the kind review! Happy to have you back anytime!
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, listing accuracy

Winter Garden Hipster

Host is incredibly responsive and very understanding about early check in, late check out, etc. Listing was accurate. House was clean, bedrooms nicely appointed, but the door to the backyard is in the bathroom off the kitchen, next to the master. You step out onto a small area of gravel, no concrete. It made keeping the bathroom floor clean, very challenging. We stayed with our dog, used this door frequently.
Stayed 3 nights in Mar 2024
Verified review

6/10 Okay

Liked: Cleanliness, check-in, communication, location
Disliked: Listing accuracy
Although the property inside had the promised hipster vibe, we didn’t realize that meant we had no working AC in the Master Bedroom. The next day they placed a portable AC that smelled like a sewer. The third day they placed a working window Unit. We reported that the TV wasn’t working on the first day and didn’t receive a proper remote onto the forth or fifth day. The area is pretty good. ACE hardware is across the street. The home was well stocked with paper towels, toilet paper, garbage bags etc. The back yard is a disaster area and is mainly weeds.. Broken glass, especially near what remains of a fire pit area. Dangerous for dogs or children. The grill hadn’t been cleaned from the previous tenants. The house has large roomy areas. The biggest problem is neglect. The doors have some dried out corroded weather stripping which allows heat and a constant supply of beetles. The bathrooms have no AC and non working exhaust vents. I wouldn’t stay here again. Although I do love the area. I was refunded a small amount for our inconvenience. I have detailed pictures to back up all of my complaints.
Stayed 7 nights in May 2026
Response from VrboOwner on 12 Jul 2026
Suzanne’s stay was the perfect storm of if something could go wrong it did with AC and remote. I think past reviews and ratings identify that this is not a typical stay at this is any of our rentals. We unfortunately can’t control an AC timing issue and all was working prior to check in and no issues reported by prior guests. When advised of the AC issue we brought over a portable AC unit. Again it was working fine and cooling and then there was an issue with a smell coming from unit which we’ve never had before. We brought over a window unit as soon as possible to address the smell There is no excuse for the fire pit area which has been addressed. We have a weekly lawn service and it’s not unusual for grass to be patchy, brown and sparse during dry periods and get greener once the rain starts. We allow pets and some larger animals may be rougher on the back yard than others but we know a lot of guests travel with their pets or have extended stays and need a fenced in yard. We strive to anticipate and address any issues as needed and fell short We did provide a discount to the guest and would have much preferred the AC unit to have worked as expected for unanticipated breakdowns which we can’t control.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great home base in WG

We really enjoyed all the room to spread out in Mary Anne's house. It is walkable into the downtown area, which was perfect for our needs. Winter Garden is perfectly placed in the Orlando area, and we enjoyed our time here very much. Would definitely rent again!
Stayed 6 nights in Jul 2021
Response from VrboOwner on 6 Aug 2021
Shannon was a great guest and we would welcome her back anytime!!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Would definetly go back

The home was as described. We enjoyed just watching life pass by on the front porch in the cushioned chairs. It's about 1/2 mile walk to the trail system, from there you can travel for miles. It was nice to be able to walk into town for restaurants and around the corner for groceries. Home had everything you needed, plus plenty of extras. We were there for 9 nights, and only purchased 2 extra kitchen items that we left for the next family. Just an FYI, this is not a completely flat ranch, while it is mainly level, there is a step into the family room, a step into the master bedroom, and a tiny step into the master bath. It didn't bother us, but really just an FYI. We walked or rode bikes every morning on the trails, and also took an evening walk in town. There are many great places to enjoy in the downtown area. If you are headed to Disney it was 20-40 minutes depending on if you paid to take 429... Take 429. And which park you were heading towards.
Stayed 9 nights in Feb 2021
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