Vacation rentals in Winter Park
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Winter Park
Guests agree: these stays are highly rated for location, cleanliness, and more.
Nestled behind my 1920's bungalow in one of Orlando’s best neighborhoods, The Shed is a local experience and retreat. Located in the city center, just a 5 min Uber to Amway, Soccer Stadium, and walking distance to the Sun Rail and hospital, you’ll love The Shed, because of its chill vibe and privacy. Perfect for couples, traveling medical professionals, and those new to AirBnB. Permit No STR-1011474 in gallery.
What guests are saying:“I loved "the shed" I wish I could've stayed longer ... even though it behind another house I felt that I was in my own space I could come and go as I pleased... I would definitely go back the location is amazing, and I was able to check in early to set up since it was a surprise for my wife (thank you Rosy). The only negative I could think of was the bed ... it has a huge dip in the middle but other than that it was perfect.”
Beautiful 2 bedroom apartment located just 10 miles north of Orlando and conveniently accessible to all the fun and entertainment of Central Florida. Located right off of East Semoran Blvd/Route 436, the apartment is in the prime location near a number of shopping centers and restaurants.
What guests are saying:“Great place! Easy to find, good location. Checkin was a breeze. The place is always clean. All of the amenities. The only thing that I could even think to say, is that I wish there were tvs in the bedrooms. But, for the value, you really can't beat it. Definitely recommend! Host is great, too!”
Newly Renovated & Sparkling Clean!! This private studio is nestled behind our 1950’s bungalow in Downtown Orlando’s most charming district. Enjoy urban living w/ a small town feel- bike along brick tree-lined streets to award-winning restaurants, shop small businesses, grab a drink at a local brewery, or stroll the farmers market! After the day’s adventures, unwind under market lights in your private backyard. Perfect for couples & traveling medical professionals (walking distance to hospital).
What guests are saying:“I had the pleasure of staying at Jon and Nicole's place for a week while in town for a class. Everything about my stay was wonderful. I loved all of the extra little personal touches: an umbrella, reusable shopping bag, beverages, toiletries, phone charger and even snacks! They checked in with me several times to make sure I didn't need anything or have any questions and were quick to respond each time I contacted them. I loved relaxing at the end of the day in the little outdoor seating area. The cottage is immaculate and perfectly decorated. I highly recommend a stay and hope to be back someday!”
