Vacation Rentals & Villas in Winter Garden

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4,264 villas

' Special' 5 Star Vacation Home Near Attractions

Winter Garden house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$224

Spend the Holidays in the Heart of the Orlando District

Winter Garden studio

  • Studio
  • 1 bathroom
  • sleeps 4

Price per night from

$114

Beautiful one bedroom apartment seconds from Disney

Winter Garden villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$149

Great rentals within 20 miles that match your search

Santosh Cove Lakeview Home

Kissimmee house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$344

2nd Floor One Bedroom Runaway Beach Club Resort

Kissimmee villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$172

The Florida Pad

Kissimmee villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$190

Lilo's Paradise in Windsor Hills

Kissimmee villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 11

Price per night from

$802

Price per night from

$487

Doorstep of Disney! 2-Bedroom Condo in Kissimmee

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$275

N7 - BEST PRICE MATCH * Mins to Disney/WaterPark/Arcade/Bar/Gym/Golf/AC/WiFi

Kissimmee house

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 24

Price per night from

$458

“Quick Disney Ger Away” The house was just as it was described & it was very clean. The pool was great for our 5 yr old grandaughter to play in with a shallower area at one end & lots of pool toys. Our 12 yr old son loved the basketball hoop for pool & hot tub was great for us, the adults. The location of house was about 20 min to the Magic Kingdom & 1-1/2 hr to Cocoa Beach. There were many restaurants, shops & things to do nearby. Beds were very comfortable & neighborhood was nice & quiet. We had a great stay with no problems. Janet was very accomodating & friendly when we booked our reservation. We will definately be back!

Price per night from

$189

Rent my time share for a week for up to 295000.

Central Florida condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$409

The best place to Orlando

Orlando apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$184

Vacation Villa EE12

Kissimmee villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$250

Luxurious spacious villa for rent 21 minutes to Disney

Orlando villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$321

Bonnet Creek Resort

Old Town condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$287

4 Bedrooms / 3 Bathrooms / Compass Bay (3167 TC)

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 12 minutes

Price per night from

$142

Grand 9 Bed Near Disney

Four Corners house

  • 9 bedrooms
  • 6 bathrooms
  • sleeps 22

Price per night from

$527

Cozy Family Vacation WL8988

Kissimmee house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Price per night from

$165

Relaxing Stay at Vista Cay

Orlando apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 53 minutes

Price per night from

$170

Prestige 5: Lux Windsor West, S Fc Pool, Lake View

Kissimmee house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 20

“Awesome vacation.” We were very impressed with this home. We had all the comforts of home. Spacious area, quite neighborhood. We enjoyed the hot tub and pool. It was a short drive without much traffic to Disney. We would recommend this home to others.

Price per night from

$687

Orange Lake Resort Villa, 2br/2ba (Kissimmee)

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$228

Cozy One Bedroom Villa in Gorgeous Resort & Spa

Kissimmee villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$180

Two-Bedroom Villa

Orlando villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$491

Responds fast! avg. 3 hours 50 minutes

Price per night from

$344

3 Bedrooms / 2 Bathrooms / Seven Dwarfs (10-105 LC)

Kissimmee house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Responds fast! avg. 2 hours 12 minutes

Price per night from

$118

Premium Kissimmee Timeshare rental

Kissimmee villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$328

Vacation Villages at Parkway

Kissimmee apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$115

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

Kissimmee villa

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 20

Price per night from

$687

3 bedroom Townhouse close to Disney

Kissimmee townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$338

Smoky Mountain 5 Star resort

Orlando condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$229

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!

Price per night from

$263

Orlando Florida - Westgate Lakes Resort!

Orlando condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$151

Four Bedroom home near Disney/Orlando

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$121

4 Bedroom Villa 2 Miles from Disney Entrance

Kissimmee villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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

Price per night from

$344

A week of dream in a resort

Orlando house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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

Price per night from

$196

Viewing 38 of 4,264
rentals in Winter Garden

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