Skip to content
Sign up
Log in
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. No smoking allowed. Permit No STR-1011474 in gallery.

    What guests are saying:

    “Great little space, great communication, and perfectly located in College Park. I arrived after dark but was pleasantly surprised by the scenery on the deck upon leaving. I am in College park often and Rosy’s place is at the top of the list for places to stay.”

  • 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!”

  • East End Escape
    SUPERHOSTEntire guest suite · 2 guests · 2 beds · 1 bathroom
    East End Escape

    Welcome to our neighborhood! A friendly community, walkable bars/shops/restaurants, and proximity to downtown are some of the reasons why we love to call south Winter Park ‘home’. We’re pleased to share it with you via East End Escape; a cozy and eclectic 260 sq. ft. space designed for an individual or couple. East End Escape is 30 minutes from Disney and the other parks, 5 minutes from Rollins College, Park Avenue, and Mills50, and an hour away from a few of the best beaches on the east coast.

    What guests are saying:

    “Awesome little guesthouse suite for you and your significant other to spend the night(s) at while visiting orlando! Very private despite being a house guest. We didn’t see or hear the owners at all. Would definitely recommend staying there over any other place in orlando. p.s. their dog is very cute if you get the chance to see him!”

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Winter Park holiday rentals

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

Other great holiday rentals in Winter Park

"Park Bungalow" in Downtown Orlando
SUPERHOSTEntire guest house
"Park Bungalow" in Downtown Orlando
Price:₹3,367 / night
Apt H -Walkabout in the Heart of Winter Park
SUPERHOSTEntire flat
Apt H -Walkabout in the Heart of Winter Park
Price:₹5,313 / night
Balfour Palms
SUPERHOSTEntire guest suite
Balfour Palms
Price:₹4,166 / night
Peaceful, full-featured condo near airport & parks
Entire apartment
Peaceful, full-featured condo near airport & parks
Price:₹2,781 / night
Entire Cozy Beautiful 3 Bedroom Orlando Townhouse
SUPERHOSTEntire townhouse
Entire Cozy Beautiful 3 Bedroom Orlando Townhouse
Price:₹6,734 / night
QUAINT UPDATED STUDIO IN WINTER PARK, FL
SUPERHOSTEntire guest suite
QUAINT UPDATED STUDIO IN WINTER PARK, FL
Price:₹2,694 / night
Chez Bienvenu
SUPERHOSTEntire guest house
Chez Bienvenu
Price:₹5,038 / night
Private Master Suite in College Park, Orlando FL
SUPERHOSTPrivate room
Private Master Suite in College Park, Orlando FL
Price:₹2,445 / night
Winter Park Charm (Close proximity to Park Ave)
SUPERHOSTEntire guest suite
Winter Park Charm (Close proximity to Park Ave)
Price:₹7,109 / night
Conveniently located Tiny House
SUPERHOSTTiny house
Conveniently located Tiny House
Price:₹3,754 / night
Winter Park Suite with Private Entrance & Kitchen
SUPERHOSTEntire guest suite
Winter Park Suite with Private Entrance & Kitchen
Price:₹5,612 / night
Atmospheric Studio in the Garden
SUPERHOSTEntire guest suite
Atmospheric Studio in the Garden
Price:₹5,836 / night
Show all