Windermere Rentals

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4,226 Houses

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Private Home in the Heart of Orlando!

Windermere guest house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$115

The Best Location!!! 2-bedroom condo in Intl Area

Windermere apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$103

Mickey & Pluto's Orlando Hideaway Close to Parks

Windermere apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 9

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Price per night from

$184

Cozy and Comfy Lakeview 1BD in Central Orlando

Windermere apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$146

Splendid 3 Bd Close to Disney * Magic Village 7527

Windermere house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$124

Cozy, spacious, and well located 2bdr apartment!

Windermere apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$103

4bd Cozy Green Oasis/Pool/ClosetoDisney (Sleeps 6)

Windermere apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$197

staySky Suites

Windermere condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$1,290

Great rentals within 20 miles that match your search

1Treasure Point Villa

Loughman house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$145

Amazing & Cozy Townhome 7562SA - Summerville Resort *15min-Disney Parks*

Four Corners house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$178

LUXOR DISNEY HOME - 8Beds 6Baths Private Pool w/Spa

Four Corners house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 17

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Price per night from

$439

Brand New 5-Bedroom 5-Bathroom Villa Storey Lake Resort Community

Kissimmee house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

Responds fast! avg. 1 hour 30 minutes

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Price per night from

$289

FS59000 - Terra Verde Resort - 7 Bed 4.5 Baths Villa

Kissimmee villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 14

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Price per night from

$365

FS259220 - Solara Resort - 4 Bed 3.5 Baths Villa

Kissimmee villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$266

FS251014 - Solara Resort - 4 Bed 4.5 Baths Townhouse

Kissimmee townhouse

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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Price per night from

$215

FS263883 - Reunion Resort - 5 Bed 5.5 Baths Villa

Kissimmee villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

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Price per night from

$337

FS283830 - Storey Lake Resort - 4 Bed 3 Baths Townhouse

Kissimmee townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$215

FS309887 - Solara Resort - 9 Bed 7 Baths Villa

Kissimmee villa

  • 9 bedrooms
  • 7 bathrooms
  • sleeps 21

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Price per night from

$557

FS106609 - Windsor At Westside Resort - 4 Bed 3.5 Baths Townhome

Kissimmee townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$200

FS106857 - Windsor At Westside Resort - 8 Bed 6 Baths Villa

Kissimmee villa

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 16

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Price per night from

$472

FS295690 - Windsor At Westside Resort - 8 Bed 5 Baths Villa

Kissimmee villa

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 16

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Price per night from

$537

FS313056 - Storey Lake Resort - 5 Bed 5 Baths Villa

Kissimmee villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$337

FS314856 - Emerald Island Resort - 3 Bed 3 Baths Townhouse

Kissimmee townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$200

FS316440 - Storey Lake Resort - 9 Bed 5 Baths Villa

Kissimmee villa

  • 9 bedrooms
  • 5 bathrooms
  • sleeps 18

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Price per night from

$557

FS322009 - Storey Lake Resort - 4 Bed 3 Baths Townhouse

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$215

FS324500 - Glenbrook Resort - 4 Bed 3.5 Baths Villa

Clermont villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$200

FS362035 - Windsor At Westside Resort - 8 Bed 6 Baths Villa

Kissimmee villa

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 16

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Price per night from

$486

FS327620 - Storey Lake Resort - 9 Bed 5 Baths Villa

Kissimmee villa

  • 9 bedrooms
  • 5 bathrooms
  • sleeps 18

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Price per night from

$557

FS329887 - Sonoma Resort - 5 Bed 5 Baths Villa

Kissimmee villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

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Price per night from

$337

FS271937 - Reunion Resort - 3 Bed 2 Baths Condo

Kissimmee condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$179

FS288846 - Serenity - 3 Bed 3 Baths Townhouse

Clermont townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$150

Family Friendly 4 Bedrooms Close to Disney at Champions Gate Resort 958

Four Corners house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 14

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Price per night from

$123

FS333722 - Champions Gate Resort - 8 Bed 5 Baths Villa

Kissimmee villa

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 16

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Price per night from

$422

FS322852 - Champions Gate Resort - 8 Bed 5 Baths Villa

Kissimmee villa

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 16

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Price per night from

$537

FS346710 - The Encore Club Resort - 10 Bed 8 Baths Villa

Kissimmee villa

  • 10 bedrooms
  • 8 bathrooms
  • sleeps 20

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Price per night from

$680

BT64618 - Veranda Palms Resort - 5 Bed 4.5 Baths Villa

Kissimmee villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

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Price per night from

$299

FS238935 - Storey Lake Resort - 4 Bed 3 Baths Townhouse

Kissimmee townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$215

FS239004 - Windsor At Westside Resort - 7 Bed 5.5 Baths Villa

Kissimmee villa

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

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Price per night from

$494

Viewing 38 of 4,226
rentals in Windermere

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