Windermere Rentals

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6,050 Houses

Private Home in the Heart of Orlando!

Windermere guest house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$115

West Lucaya Village 17

Windermere house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$135

The Farm House - Great Location + Pet Friendly!

Windermere villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 11

Responds fast! avg. 3 hours 7 minutes

Price per night from

$177

Theme Park Retreat | 4BR near Universal Studios

Windermere house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 11

Price per night from

$360

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

Windermere apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$102

Mickey & Pluto's Orlando Hideaway Close to Parks

Windermere apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 9

Price per night from

$184

Cozy and Comfy Lakeview 1BD in Central Orlando

Windermere apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$145

Cozy, spacious, and well located 2bdr apartment!

Windermere apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$102

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

Windermere apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$196

Rustic Hideaway - Great Location + Pet Friendly!

Windermere villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 11

Responds fast! avg. 3 hours 7 minutes

Price per night from

$189

Splendid 3 Bd Close to Disney * Magic Village 7527

Windermere house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$145

staySky Suites

Windermere condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$1,285

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

Luxury Dream Townhome with Pool SL4814

Kissimmee house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$1,233

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

Price per night from

$182

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

2 Bed / 2 Bath Resort Condo near Disney

Davenport condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Wonderful, amazing” The condo was huge and beautiful, it had everything we needed and then some. The owner was very helpful and went beyond expectation to meet our needs and make our vacation awesome. Shops and fun excitement was just a 15-20 min drive. The pool was wonderful.

Price per night from

$172

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

Beautiful Villa in the community of Solterra

Loughman villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$297

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

' Special' 5 Star Vacation Home Near Attractions

Winter Garden house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$224

Cozy Family Vacation WL8988

Kissimmee house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Price per night from

$165

5 Suites Luxury Single Home with private pool RE1492

Kissimmee house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

Price per night from

$1,233

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

5 Bed/3 Bath Orlando Dream Holiday Home

Loughman house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

Price per night from

$206

ChampionsGate Best Florida Vacation Home

Orlando house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$217

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

Viewing 38 of 6,050
rentals in Windermere

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