Superhost since 2015 · 4.87 rating
Experience hospitality, personally.
Every stay is curated by Juan — more than a booking, it's a connection to the local soul, hidden gems, and hand-picked homes. Book direct and stay with a Superhost.
Homes for you
See all
Meet your host
Juan Gutierrez
Juan personally hosts ten homes across downtown Orlando and Hollywood Beach, and co-hosts fourteen more family-sized homes across Central Florida. Book direct and skip the platform fees.
700+
Reviews
4.87★
Average
4 years
Superhosting
10
Homes total
Guest reviews
Our amazing reviews!
Across nearly every property, guests consistently call out our location, hospitality, and cleanliness as standouts.
Terruphispharr
4 days ago
A wonderful host and a beautiful place to stay as well
Erin
4 days ago
Juan's place was in an amazing location for a young group! The balcony was perfect for morning and night time meals. There are many bars and restaurants in the area that are walkable and fantastic. The space was very open and decorated beautifully. We enjoyed our stay!
Amanda
6 days ago
Our stay at Juan's spot in Thornton Park was great. Wonderful location in a very cool neighborhood - lots to do and explore on foot or by e-scooter/e-bike! Place was convenient and clean.
Roxanne
September 9
It was a beautiful place great location and had everything we needed. I would highly recommend. Looking forward to coming back and we would stay here again definitely.
Frequently asked questions
Is it cheaper to book directly with BookwithJuan?
Yes. Booking direct means no third-party platform fees added to your total, and you're in direct contact with our team for anything you need before or during your stay.
What's the difference between the Downtown Collection and Family & Group Homes?
The Downtown Collection is ten individually designed apartments and lofts around Lake Eola and Thornton Park, built for couples and solo travelers. Family & Group Homes are fourteen larger, co-hosted properties across Central Florida, built for bigger groups and longer stays.
Do your properties allow pets?
Pet policies vary by property — some of our homes are pet-friendly and others aren't. Check the individual listing before booking, or ask us directly.
What are your check-in and check-out times?
Times vary slightly by property and will be confirmed in your booking details, but most stays follow a standard afternoon check-in and late-morning check-out, with keyless self check-in throughout.
Can I request early check-in or late check-out?
Sometimes, depending on the property's schedule. Just ask — we'll always try to accommodate where we can.
What is your cancellation policy?
Cancellation policies can vary slightly by property, since each home may be set to a different policy tier. The exact terms for your stay will be shown at checkout and confirmed in your booking confirmation, so you'll always know the cancellation window before you pay. If your plans change, reach out directly and we'll do what we can to help.
Why guests book with Juan
Every home, personally vetted
Juan stays in each place before it joins the collection.
Book direct, book safe
Secure payments, transparent pricing, no hidden platform fees.
A real local, on call
Hidden gems, dinner reservations, and help whenever you need it.
Ready when you are.
10 hand-picked homes across 1 countries.







