Vacation Rentals & Villas in Winter Garden

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2,660 villas

Beautiful one bedroom apartment seconds from Disney

Winter Garden villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$149

Great rentals within 20 miles that match your search

Exclusive 5 bedroom townhouse at Paradise Palms

Kissimmee townhouse

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 1 hour 51 minutes

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$183

Bonnet Creek Resort ツ 1BR SLEEPS 4 Wyndham Orlando Condo Rental!

Orlando condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$91

Gorgeous 3/2 Private Pool Home

Davenport villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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$200

Marriott's Cypress Harbor Resort

Orlando house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$343

Military owned and operated Free Heated pool and spa 8 miles to Disney

Clermont house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

“Great House for the price.” This is a bargain house. Everything you need is already here. From strollers and bikes to all the pool toys. People have contributed along the way too which is nice to be able to leave things behind knowing they will be used. My only complaint would be that it takes about 30 minutes to get to the parks unless you know the alternative routes. Most people don't. Otherwise this place is fantastic.

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$166

Newly remodeled Condo at Legacy Dunes with easy access - resort amenities

Kissimmee condo

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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$129

Gibson Grove Villa

Orlando house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 38 minutes

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$148

Fireworks on the 4th if July at Disney. Mickey is waiting for you.

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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$351

Disney Memories. Beautiful 4 Bedroom, 3 Bath,

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 57 minutes

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Price per night from

$172

Responds fast! avg. 2 hours 40 minutes

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$599

Your VIP Home in Orlando!!!

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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$211

The Fountains (Bluegreen)

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 24 minutes

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$257

Great Furnished Resort aval in Orlando

Kissimmee condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$229

2 BD Bonnet Creek in Gates of DisneyWorld

Orlando hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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$303

Disney's Saratoga Springs Resort & Spa

Orlando villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$400

Deluxe Townhome, plus pool area TV!

Clermont townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Deluxe townhouse” Had a great time, The condo was very nice pleasant surroundings, would book there again. Close to many restaurants, and places to visit. Main thing it was close to Disney.

Responds fast! avg. 1 hour 34 minutes

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$137

Orlando' Sunshine Resort - 2 Bedrooms, 2 Baths

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 24 minutes

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$97

BAHAMA BAY 2 BR/2BA PLATINUM CONDO NEAR DISNEY

Davenport condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$114

South-facing Pool Home near Disney World

Davenport house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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$193

Last week of April. The best place near Disney.

Kissimmee apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$227

Dazzling 3 BR/2 BA Ground Floor Condo Near Disney

Kissimmee condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$154

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$170

1 Deluxe Studio Villa

Kissimmee villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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$132

Updated Villa with Pool & Spa Near Disney!

Clermont house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Awesome” My wife and I stayed here and loved it. The house was clean and comfortable and had all the amenities needed for a vacation home that truly was a home away from home. The pool and spa were the perfect way to start and end the day after the parks and were very private with fencing and shrubs surrounding them. I've rented other homes in the area this was the best and I will definitely be coming back with the whole family. Excellent 5 stars

Responds fast! avg. 33 minutes

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$154

Spectacular light show- Polynesian Villa Lakefront

Orlando villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 5

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$628

Newly decorated at Reunion Resort with golf views

Reunion townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$160

VACATION VILLAGE AT PARKWAY OVERVIEW

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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$457

Cozy One Bedroom Villa in Gorgeous Resort & Spa

Kissimmee villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$180

Two-Bedroom Villa

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$490

Responds fast! avg. 2 hours 44 minutes

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Price per night from

$343

Premium Kissimmee Timeshare rental

Kissimmee villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$327

Vacation Villages at Parkway

Kissimmee apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$114

Prestige 3: New Lux Home, South Fc Lake View, Pool

Kissimmee villa

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 20

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Price per night from

$685

Smoky Mountain 5 Star resort

Orlando condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$229

Orlando Florida - Westgate Lakes Resort!

Orlando condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$151

Four Bedroom home near Disney/Orlando

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$120

4 Bedroom Villa 2 Miles from Disney Entrance

Kissimmee villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$137

Viewing 38 of 2,660
rentals in Winter Garden

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