Vacation Rentals & Villas in Winter Garden

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2,862 villas

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Spend the Holidays in the Heart of the Orlando District

Winter Garden studio

  • Studio
  • 1 bathroom
  • sleeps 4

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Price per night from

$114

Beautiful one bedroom apartment seconds from Disney

Winter Garden villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$150

Great rentals within 20 miles that match your search

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

Orlando condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$91

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Price per night from

$171

Wyndham Bonnet Creek Resort

Orlando hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 53 minutes

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Price per night from

$339

1 Deluxe Studio Villa

Kissimmee villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$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. 1 hour 17 minutes

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Price per night from

$155

Spectacular light show- Polynesian Villa Lakefront

Orlando villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 5

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Price per night from

$631

VACATION VILLAGE AT PARKWAY OVERVIEW

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$459

Cozy One Bedroom Villa in Gorgeous Resort & Spa

Kissimmee villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$181

Two-Bedroom Villa

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$493

Responds fast! avg. 2 hours 21 minutes

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Price per night from

$345

Premium Kissimmee Timeshare rental

Kissimmee villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$328

Vacation Villages at Parkway

Kissimmee apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$115

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

$689

3 bedroom Townhouse close to Disney

Kissimmee townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$339

Smoky Mountain 5 Star resort

Orlando condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$230

Disney 2 Miles, Pool/Spa Home, Game Room,Themed Be

Orlando house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

“Perfect!” We had a wonderful experience, the house was even nicer than I expected. Bonus game room was a nice surprise. Clean, simple to find, and close to everything!

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Price per night from

$263

Orlando Florida - Westgate Lakes Resort!

Orlando condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$152

Four Bedroom home near Disney/Orlando

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$121

4 Bedroom Villa 2 Miles from Disney Entrance

Kissimmee villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$138

8br/6ba pool villa from $260/nt ,Close to Disney

Kissimmee house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 18

“Mrs” Me and my family really enjoyed staying at the property rental it was ever thing we need in a vaction rental.

Responds fast! avg. 1 hour 27 minutes

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Price per night from

$345

A week of dream in a resort

Orlando house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$200

1 Week Rental in Orlando, FL 2 Bdm Deluxe Villa Close to Theme Parks

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$197

Beautiful 2 BR, 2BA Orlando Florida!

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$493

Wyndham Bonnet Creek Florida at Disney

Buena Ventura Lakes condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 1 minutes

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Price per night from

$101

Responds fast! avg. 30 minutes

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Price per night from

$114

1-bedroom / 1-bath Sleeps 4 in Orlando - 1 week

Williamsburg apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$99

Lovely villa on Emerald Island-4 miles from Disney

Kissimmee villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$173

Marriott's Sabal Palms

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$459

Windsor Palms 4/3 Pr. Pl., Hot Tub, Jacuzzi/Games

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Amazing house!” We have amazing family time! This house is excellent with great location! We'll be back soon! I recommend

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Price per night from

$177

Stunning Disney Vacation Rental Villa

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$172

2br - 2200ft2 - Beautiful one story 2 bed/3bath

Orlando house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

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Price per night from

$361

$1250+fees sleep 6, available Dec 24-Dec 31, 2022 Resort Fantasy World II

Kissimmee villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$194

Spacious villa near Disney

Four Corners house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 11

Responds fast! avg. 29 minutes

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Price per night from

$114

2br - 1000ft2 - Winter Park House

Winter Park house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$115

Weston Magic in Orlando

Clermont house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$127

2 Bedroom Condo WestGate Palace

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$322

Viewing 38 of 2,862
rentals in Winter Garden

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