Winter Park Vacation Rentals, Houses & More


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Areas near Winter Park

Great rentals within 20 miles that match your search

1 / 12

Beautiful Luxury Lakeside Penthouse Vista Cay

  • 3
  • 6
  • 3 nights min

$168

Details

1 / 35

3 Bedroom at Westgate Resort and Spa Wonderful Vac

  • 3
  • 12
  • 7 nights min

$284

Details

1 / 58

Take in a serene lake view from this comfortable and relaxing 3-bedroom condo

  • 3
  • 8
  • 2 nights min

$141

Details

1 / 6

Executive 2 bedroom villa with kitchen at SPM Blue Tree Resort

  • 2
  • 5
  • 3 nights min

$297

Details

1 / 8

Executive Apartment

  • 2
  • 4
  • 7 nights min

$86

Details

1 / 28

Villa 176 Watersong Resort, Orlando

  • 5
  • 10
  • 7 nights min

$298

Details

1 / 40

Aviana 7Br/4.5Bt Villa with Pool, Games

  • 7
  • 22
  • Min stay varies

$249

Details

1 / 24

ORLANDO {1BR Condo} Grande Villas Resort

  • 1
  • 4
  • 1 night min

$99

Details

1 / 22

COMFORT INN INTERNATIONAL DR ~ SLEEPS 4 ~ FREE WIFI/FREE SHUTTLES/FREE BREAKFAST

  • Studio
  • 4
  • 1 night min

$80

Details

1 / 27

Marriott's Grande Vista - Studio

  • Studio
  • 4
  • 4 nights min

$192

Details

1 / 15

Serene Home Away from Home

  • 2
  • 4
  • 3 nights min

$60

Details

1 / 27

ORLANDO/OLD TOWN **1BR LUXURY CONDO** Star Island Resort on Lake Cecile

  • 1
  • 4
  • Min stay varies

$129

Details

1 / 66

Beautiful three-story townhome with 3 bedrooms and 3.5 baths

  • 3
  • 8
  • 2 nights min

$167

Details

1 / 25

Marriott's Cypress Harbour - 2 Bedroom

  • 2
  • 8
  • 4 nights min

$199

Details

1 / 50

Coral Cay #4 - 4 Bedroom Townhouse w/ Hot Tub

  • 4
  • 10
  • 3 nights min

$102

Details

1 / 48

Disney new 6 Bed/6br Luxury Jacuzzi Pool Home at ChampionsGate

  • 6
  • 14
  • Min stay varies

$100

Details

1 / 71

Stunning 3-bedroom first floor condo with modern furnishings & relaxing patio

  • 3
  • 8
  • 2 nights min

$167

Details

1 / 24

Vista Cay 3BR, 2BTH condo right next to The Convention Center VC146

  • 3
  • 8
  • Min stay varies

$148

Details

1 / 22

Wyndham's Bonnet Creek 2 BD/2BA Deluxe Villa

  • 2
  • 6
  • 2 nights min

$75

Details

1 / 7

Westgate Palace - Fri-Fri, Sat-Sat, Sun-Sun only!

  • 2
  • 6
  • 7 nights min

$312

Details

1 / 22

Disney for the Holidays! 1-Bedroom Villa Orlando

  • 1
  • 4
  • 5 nights min

$169

Details

1 / 18

Championsgate - Close to parks and attractions

  • 8
  • 17
  • Min stay varies

$351

Details

1 / 37

Travel Themed Getaway Orlando / Winter Park

  • 1
  • 2
  • Min stay varies

$76

Details

1 / 22

Botanical Gardens - Orlando / Winter Park

  • 1
  • 2
  • Min stay varies

$81

Details

1 / 27

Surfs Up Theme - Winter Park/Orlando

  • 1
  • 2
  • Min stay varies

$76

Details

1 / 20

Winter Park-College Park-Orlando -2

  • 1
  • 2
  • Min stay varies

$81

Details

1 / 10

Brand New, Large 4 Bedroom, 3 Bath, close to downtown!

  • 4
  • 7
  • 1 night min

$147

Details

1 / 27

Winter Park-College Park-Orlando-1

  • 1
  • 2
  • Min stay varies

$81

Details

1 / 35

"Lakeside" in old Winter Park (exclusive 32789zip)

  • 4
  • 8
  • Min stay varies

$595

Details

1 / 13

2br - 1000ft2 - Winter Park House

  • 2
  • 5
  • 7 nights min

$144

Details

1 / 24

Turquoise Paradise

  • 1
  • 3
  • 1 night min

$46

Details

1 / 11

The Ritz

  • 3
  • 5
  • 1 night min

$85

Details

1 / 18

Championsgate - Close to parks and attractions

  • 8
  • 18
  • Min stay varies

$351

Details

1 / 35

The Cottage on Lake Fairview, Orlando.

  • 3
  • 6
  • 3 nights min

$351

Details

1 / 18

Championsgate - Perfect for friends sharing

  • 8
  • 18
  • Min stay varies

$351

Details

1 / 28
1 / 40

Renovated Lakefront Cottage -Great Location!

  • 1
  • 4
  • 1 night min

$99

Details

1 / 9

Welcome home to Winter Park!

  • 1
  • 2
  • 3 nights min

$85

Details

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