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Vacation rentals in Winter Park

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Top-rated vacation rentals in Winter Park

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

Adorable and espacious, 2 Beds, and great location
Entire guest suite · 6 guests · 2 beds · 1 bath
Adorable and espacious, 2 Beds, and great locationEnjoy this beatiful and spacious place in the midle of everyting, fully fence backyard, 10 minutes from romantic Park Ave and scenic boat tour of Winter Park. 20 min. Downtown Orlando, 30 min all major atracction, Walk to Pharmacy, Bouling Center, supermarkets and restaurants. Keep it simple at this peaceful and centrally-located place.
Get a Little Glam in a Retro Palm Beach-Style Boudoir
PLUS
Entire rental unit · 2 guests · 1 bed · 1 bath
Get a Little Glam in a Retro Palm Beach-Style BoudoirUnpack those vintage dresses and fit right in at a charm-filled pied-à-terre. An ode to Palm Beach and Old Florida, the home showcases corals, golds, and teals, tropical fruit and flamingo motifs, and a little '50s kitsch thrown in for good measure.
Winter Park Oasis
SUPERHOST
Entire guesthouse · 4 guests · 4 beds · 1 bath
Winter Park OasisEnjoy your stay at the Winter Park Oasis! This cozy 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 2 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.

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Other great vacation rentals in Winter Park

  1. Entire residential home
  2. Altamonte Springs
Cozy Blue Bungalow
$70 per night
SUPERHOST
  1. Entire villa
  2. Winter Park
Balfour Villa
$171 per night
  1. Entire guest suite
  2. Winter Park
Modern and Gorgeous Apt Studio 1b1b at Winter Park
$88 per night
SUPERHOST
  1. Entire guest suite
  2. Winter Park
Winter Park Getaway
$80 per night
  1. Entire residential home
  2. Winter Park
Modern Mediterranean Residence | Bohemian Hideaway
$301 per night
  1. Entire residential home
  2. Orlando
Walk to everything adorable Mills 50 home!
$115 per night
  1. Entire residential home
  2. Orlando
Hot Tub ☀️ Fire Pit 🔥 Pets 🐾 King Bed ⭐️ Location
$104 per night
SUPERHOST
  1. Entire residential home
  2. Orlando
Quiet and Comfy Orlando Home - Close To It All
$82 per night
SUPERHOST
  1. Entire residential home
  2. Orlando
Spacious, Bright, Clean Home In Central Orlando
$113 per night
SUPERHOST
  1. Private room
  2. Orlando
Private Master Suite in College Park, Orlando FL
$43 per night
SUPERHOST
  1. Entire cottage
  2. Winter Park
Cornell Cottage - Quaint & Cozy w/Outdoor Kitchen
$87 per night
  1. Entire residential home
  2. Winter Park
Winter Park Hideaway
$88 per night