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Vacation rentals in Winter Park

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.

  • The Shed in Downtown Orlando
    SUPERHOSTEntire guest house · 2 guests · 1 bed · 1 bathroom
    The Shed in Downtown Orlando

    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.”

  • Cozy Apartment With Resort Style Amenities!
    Entire flat · 4 guests · 2 beds · 2 bathrooms
    Cozy Apartment With Resort Style Amenities!

    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!”

  • "Park Bungalow" in Downtown Orlando
    SUPERHOSTEntire guest house · 2 guests · 1 bed · 1 bathroom
    "Park Bungalow" in Downtown Orlando

    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!”

Holiday rentals for every style

Get the amount of space that is right for you.

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Popular amenities for Winter Park holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Winter Park

Cozy Apartment With Resort Style Amenities!
Entire flat
Cozy Apartment With Resort Style Amenities!
Price:₹5,110 / night
"Park Bungalow" in Downtown Orlando
SUPERHOSTEntire guest house
"Park Bungalow" in Downtown Orlando
Price:₹2,254 / night
The Shed in Downtown Orlando
SUPERHOSTEntire guest house
The Shed in Downtown Orlando
Price:₹4,133 / night
Atmospheric Studio in the Garden
SUPERHOSTEntire guest suite
Atmospheric Studio in the Garden
Price:₹5,711 / night
QUAINT UPDATED STUDIO IN WINTER PARK, FL
SUPERHOSTEntire guest suite
QUAINT UPDATED STUDIO IN WINTER PARK, FL
Price:₹2,630 / night
Winter Park Private Quaint Guest House
Entire guest house
Winter Park Private Quaint Guest House
Price:₹4,659 / night
East End Escape
SUPERHOSTEntire guest suite
East End Escape
Price:₹6,162 / night
Apt C -Modern Elegance in the Heart of Winter Park
SUPERHOSTEntire flat
Apt C -Modern Elegance in the Heart of Winter Park
Price:₹4,659 / night
Entire Cozy Beautiful 3 Bedroom Orlando Townhouse
SUPERHOSTEntire townhouse
Entire Cozy Beautiful 3 Bedroom Orlando Townhouse
Price:₹6,763 / night
#8 WELCOME HOME IN WINTER PARK
SUPERHOSTEntire guest house
#8 WELCOME HOME IN WINTER PARK
Price:₹4,359 / night
Historic home 30-min. from theme parks and beaches
Private room
Historic home 30-min. from theme parks and beaches
Price:₹4,509 / night
Chez Bienvenu
SUPERHOSTEntire guest house
Chez Bienvenu
Price:₹5,035 / night
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