The Guesthouse in Mills50

By Kismet Kohn

After a long day walking through Downtown Orlando, what better way to end the night than enjoying a fine glass of wine or perfectly crafted cocktail? The Guesthouse is truly a neighborhood bar, where downtown natives will spend their night laughing and socializing until closing time.

People sitting at bar at The Guesthouse

The Atmosphere

The Guesthouse has an earthy and calm atmosphere, which makes it a great bar to stop in after a long week. Bright white walls and the natural sunlight that the large windows bring in make you feel like you're right at home. You can stop by most days from 4:00 PM to 2:00 AM, with Saturday and Sunday opening at 1:00 PM.

Friends sitting around table at The Guesthouse

The bar is filled with plants and greenery throughout the building, making it feel natural and welcoming. There are some black and white prints on the walls as well, but the plants are what truly bring the color. Overall, The Guesthouse is flawless in its simplicity, and is the perfect pairing to its brighter sister bar next door - The Sunroom.

Plants sitting on table at front entrance

The Drinks

Like most bars, The Guesthouse can serve up any drink you’d like, including cocktails, wine, and beer, with my personal favorite being their Moscow Mule. If you’re a Game of Thrones fan, the Negroni is one of their specialties! The Hummingbird is also one of their best drinks, made from Prosecco, Elderflower liquor, soda water, and lemon. 

Bartender making drinks

The wine list really sets this location apart being that it is so extensive, and even offers options that are not usually found in Central Florida bars. If you want to taste some good wine that you can’t find anywhere else, definitely check out The Guesthouse!

Happy Hour

The Guesthouse is usually the busiest at their happy hour because the deals are incredible. Their cocktail menu prices decrease drastically to just $7 from 4:00 PM to 8:00 PM. Their house spirits are also only $5, and their wines are $8 but taste like they should cost at least $15 for a glass!

If you’re in the mood for beer, you don’t have to spend more than $4 on a draft. They even offer the Ravenous Pig’s IPA, a Central Florida staple.


All Images by The Guesthouse


If you want a bar with a bohemian feel and a chill atmosphere, definitely check out The Guesthouse. Their happy hour menu is perfect for the frugal college student or the socialite who doesn’t want to spend too much money on a night out. The location just adds to the appeal because there are so many restaurants and shops up and down Mills Ave, and it’s just minutes from Downtown Orlando!


The Guesthouse is located on Mills Ave, right next to its sister bar The Sunroom. This area is known for its independent restaurants, shops, and bars. If you want to grab food before your cocktail, the Black Rooster Taqueria next door offers some contemporary Mexican cuisine. There are also so many other food options up and down Mills50 including American, Latin, and Asian-inspired restaurants.

If you’ve spent the day shopping and perusing the independent stores and vintage shops in the area, take a break at The Guesthouse. Mills 50 is right around the corner from Downtown Winter Park and just a short drive from Downtown Orlando. Single family homes, condos, and townhomes sell in the mid-$400’s on average, and offer a unique location perfect for accessing the highway and surrounding areas.


The Orlando Real is sponsored by The Pozek Group. If you’re thinking of buying or selling a home in Orlando, reach out and we would love to help!

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