Winter Park Vacation Rentals, Houses & More


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Areas near Winter Park

Great rentals within 20 miles that match your search

1 / 7

Luxury 1 Bedroom Deluxe Unit near Disney

  • 1
  • 4
  • 7 nights min

$172

Details

1 / 6

Smoky Mountain 5 Star resort

  • 1
  • 4
  • 7 nights min

$201

Details

1 / 58

Richly decorated and full of all the modern luxuries of a high-class hotel!

  • 3
  • 6
  • 2 nights min

$141

Details

1 / 4

Marriott's Grande Vista

  • 2
  • 8
  • 7 nights min

$228

Details

1 / 58

3-bedroom, 3.5 bath townhome perfect for a family getaway!

  • 3
  • 8
  • 2 nights min

$167

Details

1 / 28

Brand New Home, Amazing Resort Community, Private Pool, Game Room, SHD4742

  • 6
  • 13
  • Min stay varies

$274

Details

1 / 26

Villa 2605, Windsor Hills Resort, Orlando, Flroida

  • 6
  • 14
  • 5 nights min

$348

Details

1 / 6

The Fountains Resort - September 7-11, 2017

  • 2
  • 6
  • 4 nights min

$199

Details

1 / 16

CHRISTMAS in DISNEY WORLD

  • 1
  • 4
  • 7 nights min

$250

Details

1 / 50

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

  • 4
  • 10
  • 3 nights min

$102

Details

1 / 44

Brand new 3-story townhome at Vista Cay Resort, close to supermarket

  • 3
  • 8
  • 2 nights min

$169

Details

1 / 4

Grand Hotel Orlando

  • 1
  • 4
  • 2 nights min

$150

Details

1 / 33

Westgate Lakes Resort & Spa Villa in ORLANDO , FLA

  • 2
  • 8
  • 7 nights min

$143

Details

1 / 23

Lucaya Village 4br close to Disney Parks & Outlets

  • 4
  • 10
  • Min stay varies

$120

Details

1 / 8

December 16th to 21st, Deluxe One BR, Bonnet Creek Resort, in Orlando, FL

  • 1
  • 4
  • 5 nights min

$196

Details

1 / 25

ORLANDO [Cozy Studio] Cypress Pointe Resort

  • 1
  • 2
  • 1 night min

$89

Details

1 / 23

Florida Vacation Villas Club: 2 Bedrooms / 2 Baths

  • 2
  • 6
  • 7 nights min

$125

Details

1 / 56

Penthouse with spectacular lakeview!!!

  • 3
  • 10
  • 2 nights min

$188

Details

1 / 35

3 Bedroom at Westgate Resort and Spa Wonderful Vac

  • 3
  • 12
  • 7 nights min

$284

Details

1 / 37

Travel Themed Getaway Orlando / Winter Park

  • 1
  • 2
  • Min stay varies

$76

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 / 18

Championsgate - Close to shops and restaurants

  • 8
  • 18
  • Min stay varies

$351

Details

1 / 35

The Cottage on Lake Fairview, Orlando.

  • 3
  • 6
  • 3 nights min

$351

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 / 27

Surfs Up Theme - Winter Park/Orlando

  • 1
  • 2
  • Min stay varies

$76

Details

1 / 18

Championsgate - 8 miles to Disney World

  • 8
  • 17
  • Min stay varies

$351

Details

1 / 22

Botanical Gardens - Orlando / Winter Park

  • 1
  • 2
  • Min stay varies

$81

Details

1 / 11

The Ritz

  • 3
  • 5
  • 1 night min

$85

Details

1 / 18

Championsgate - Just 15 minutes to Disney World

  • 8
  • 18
  • Min stay varies

$351

Details

1 / 40

Renovated Lakefront Cottage -Great Location!

  • 1
  • 4
  • 1 night min

$99

Details

1 / 24

Turquoise Paradise

  • 1
  • 3
  • 1 night min

$46

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 / 28
1 / 9

Welcome home to Winter Park!

  • 1
  • 2
  • 3 nights min

$85

Details

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