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Vacation rentals in Lake Osceola

Vacation 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.

Spacious and Private in lovely Winter Park Orlando
SUPERHOST
Entire flat · 4 guests · 1 bed · 1 bathroom

Spacious and Private in lovely Winter Park OrlandoConveniently located just outside the prestigious Interlachen Country Club, this spacious apartment is 5 mins away from the Lake Howell Plaza where there is also a Walgreens across the street. Enjoy the friendly neighborhood where walkers, joggers, & cyclist can be seen going about their day. The exceptional shops, boutiques, and restaurants of Park Ave are also around a 5 min drive. Location Is Everything!!! 25-35 min from Universal, 35-45 min from Disney, & 15 min to downtown Orlando.

Leave Your Mark, In The Heart Of Winter Park.
SUPERHOST
Entire house · 2 guests · 1 bed · 1 bathroom

Leave Your Mark, In The Heart Of Winter Park.You are right in the heart of Winter Park! Welcome to the Historical district of College quarter. You are steps from some of the most amazing views, cuisine, wine, and parks. Just follow the red brick roads and your heart will fill with joy and happiness. Your walks will lead you to shops, boutiques, restaurants and more. You’ve landed in the most amazing town in Central Florida with no better location. Feel free to extend your stay to enjoy your best life in Winter Park!!!

Signature Barbour House Apt With King Size Bed 203
SUPERHOST
Entire flat · 4 guests · 2 beds · 2 bathrooms

Signature Barbour House Apt With King Size Bed 203Historic architecture, luxury décor and a location in the heart of downtown Winter Park makes the Barbour House a one-of-a-kind place to stay. • Oversized living space overlooking a courtyard garden. • Property designed by famed architect James Gamble Rogers II. • Two bedrooms, two baths, fully equipped kitchen, washer/dryer, veranda • Other luxurious appointments include fine linens, custom-chosen art, hardwood floors

Holiday rentals for every style

Get the amount of space that is right for you.

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Popular amenities for Lake Osceola holiday rentals

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

Other great holiday rentals in Lake Osceola

Winter Park Oasis
SUPERHOSTEntire guest house
Winter Park Oasis
Price:€110 / night
Winter Park Suite with Private Entrance & Kitchen
SUPERHOSTEntire guest suite
Winter Park Suite with Private Entrance & Kitchen
Price:€64 / night
DOWNTOWN WINTER PARK, 3 blocks to Park Ave/Rollins
SUPERHOSTPrivate room
DOWNTOWN WINTER PARK, 3 blocks to Park Ave/Rollins
Price:€72 / night
Mid-Century Luxury Directly off Park Ave (2nd flr)
SUPERHOSTEntire flat
Mid-Century Luxury Directly off Park Ave (2nd flr)
Price:€175 / night
Olde Winter Park/ Rollins College
SUPERHOSTPrivate room
Olde Winter Park/ Rollins College
Price:€85 / night
Mid-Century Modern Luxury Directly off Park Avenue
PLUSEntire flat
Mid-Century Modern Luxury Directly off Park Avenue
Price:€175 / night
Winter Park Bungalow
SUPERHOSTEntire guest house
Winter Park Bungalow
Price:€59 / night
Cute bungalow minutes walk from Park Ave.
SUPERHOSTEntire house
Cute bungalow minutes walk from Park Ave.
Price:€176 / night
A Rare Jewel in the heart of Winter park. Can walk
SUPERHOSTEntire house
A Rare Jewel in the heart of Winter park. Can walk
Price:€250 / night
Charming, Spanish Cottage in heart of Winter Park
SUPERHOSTEntire house
Charming, Spanish Cottage in heart of Winter Park
Price:€187 / night
Mid Century Modern Bungalow in Olde Winter Park
SUPERHOSTEntire bungalow
Mid Century Modern Bungalow in Olde Winter Park
Price:€99 / night
Barbour House 301
SUPERHOSTEntire flat
Barbour House 301
Price:€80 / night
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