Skip to content

Holiday rentals in Lake Osceola

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Lake Osceola

Guests agree: these stays are highly rated for location, cleanliness, and more.

  1. Entire guest house
  2. Winter Park
Winter Park Oasis B

Enjoy your stay at the Winter Park Oasis! This cozy, newly remodeled 2 bedroom private unit, is in a charming and historic neighborhood! This Oasis is a short drive from park ave restaurants, Rollins college, downtown Orlando and our beautiful beaches. Wifi and 3 car parking is included. Wake up in this bright bungalow, located right in the heart of Winter Park. I love the atmosphere in my neighborhood, you will find unique architecture, good restaurants, and beautiful local parks.

PLUS
  1. Entire rental unit
  2. Winter Park
Mid-Century Modern Luxury Directly off Park Avenue

Start the day under a large rain-head shower in this bright and fresh 1950s home. Full of color and refinements throughout, the original hardwood floors have been refinished, and the new tiled kitchen features stainless-steel appliances.

SUPERHOST
  1. Entire rental unit
  2. Winter Park
Historic Architecturally Distinctive Apartment 520

Fabulous architecturally designed Winter Park apartment with volume pecky cypress ceiling, custom cabinetry, gourmet galley style kitchen and French doors leading to brick patio. Decorated in casual modern chic this luxurious apartment is the perfect place to relax and unwind close to the best of the best Winter Park has to offer. The historic Barbour House is located one block from world renowned Park Avenue with it's luxury shops and gourmet restaurants. Short drive to Disney and beaches

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Other great holiday rentals in Lake Osceola

SUPERHOST
  1. Entire guest house
  2. Winter Park
Cottage *SALE: 1 mile to Rollins College, Park Ave
SUPERHOST
  1. Entire townhouse
  2. Winter Park
Beautiful Downtown Winter Park
SUPERHOST
  1. Entire guest house
  2. Winter Park
Winter Park Oasis
  1. Entire rental unit
  2. Winter Park
College quater charming Winter Park Historic Dist
SUPERHOST
  1. Entire home
  2. Winter Park
Cute bungalow minutes walk from Park Ave.
SUPERHOST
  1. Private room
  2. Winter Park
Blissful Winter Park Stay
  1. Entire bungalow
  2. Winter Park
Absolutely Perfect Winter Park Location!
SUPERHOST
  1. Entire home
  2. Winter Park
Best House in Town !
  1. Entire apartment
  2. Winter Park
Greatest Location in Winter Park! (2)
SUPERHOST
  1. Entire home
  2. Winter Park
Beautiful Home close to Downtown !!
SUPERHOST
  1. Entire bungalow
  2. Winter Park
Pink bungalow !
  1. Entire home
  2. Winter Park
Winter Park Oasis A
  1. Airbnb
  2. United States
  3. Florida
  4. Orange County
  5. Winter Park
  6. Lake Osceola