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Vacation rentals in Winter Park

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Top-rated holiday rentals in Winter Park

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

Cornell Cottage - Quaint & Cozy w/Outdoor Kitchen
SUPERHOST
Entire cottage · 2 guests · 1 bed · 1 bath

Cornell Cottage - Quaint & Cozy w/Outdoor KitchenNewly renovated guest suite using original reclaimed materials to create a modern vintage farmhouse vibe. Centrally located in highly desirable Winter Park - less than 10-mins to downtown Orlando. 5-mins to grocery & convenience stores, 8-mins to restaurants & shopping, 20-mins to Disney & Universal Studios. Cottage includes comfortable queen-size bed, work station / dining area, fridge, microwave, access to free parking & Wi-Fi, friendly neighborhood, self check-in, & sanitized for your safety.

Private Master Suite in College Park, Orlando FL
SUPERHOST
Private room · 2 guests · 1 bed · 1 private bath

Private Master Suite in College Park, Orlando FLSafe, friendly & quiet community just minutes from the highway, theme parks, shopping and dining! Be among the first to experience this newer home! Enjoy a queen bed with premium mattress, WiFi, Roku Smart TV, desk, fridge, coffee machine, and microwave. The bathroom is private and connected to the suite.

St. Augustine suite
SUPERHOST
Entire guest suite · 2 guests · 1 bed · 1 bath

St. Augustine suiteLuxurious space with PRIVATE ENTRANCE, PRIVATE BATHROOM and breakfast kitchenette. Located on a large lake front property with amenities that include private dock, pool, large manicured lawns and much more. Ideal for canoeing, watching the sun rise or doing nothing at all. Close to theme parks and beaches. Spring Valley is a peaceful community with age old oak tree , Ample shopping and award winning restaurants very nearby. Come play or rejuvenate your soul in this picturesque setting

Holiday rentals for every style

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Popular amenities for Winter Park holiday rentals

  • Kitchen
  • Wi-Fi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Winter Park

SUPERHOST
  1. Entire guesthouse
  2. Orlando
Bright + Modern Downtown Guesthouse near Lake Eola
$100 AUD per night
$100.00 AUD total
SUPERHOST
  1. Entire guesthouse
  2. Orlando
Oasis Garden Cottage -cozy, chic, near everything!
$89 AUD per night
$89.00 AUD total
SUPERHOST
  1. Entire bungalow
  2. Winter Park
The Garden Room - (Contactless Check-In & Out)
$167 AUD per night
$167.00 AUD total
SUPERHOST
  1. Entire guesthouse
  2. Orlando
The Loft in College Park
$94 AUD per night
$94.00 AUD total
SUPERHOST
  1. Private room
  2. Winter Park
Pura Vida Home 2
$43 AUD per night
$43.00 AUD total
SUPERHOST
  1. Entire guest suite
  2. Orlando
Tropical Oasis in the Heart of Downtown Orlando ☀️🌿
$81 AUD per night
$81.00 AUD total
SUPERHOST
  1. Entire house
  2. Winter Park
Entire Cute House near Golf, Parks, and Town.
$112 AUD per night
$112.00 AUD total
SUPERHOST
  1. Entire guest suite
  2. Orlando
Cozy Suite Near Orlando Airport
$68 AUD per night
$68.00 AUD total
SUPERHOST
  1. Tiny house
  2. Orlando
The Little Tree House at Country Club of Orlando
$134 AUD per night
$134.00 AUD total
  1. Private room
  2. Orlando
Private room heart of Downtown Orlando with pool
$85 AUD per night
$85.00 AUD total
SUPERHOST
  1. Entire guest suite
  2. Winter Park
East End Escape - (Contactless Check-In & Out)
$137 AUD per night
$137.00 AUD total
SUPERHOST
  1. Entire loft
  2. Orlando
Bright City Flat| Heart of Orlando's Best| Baldwin
$140 AUD per night
$140.00 AUD total

Nearby destinations