Windermere Rentals

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6,059 Houses

Private Home in the Heart of Orlando!

Windermere guest house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 9 minutes

Price per night from

$115

West Lucaya Village 17

Windermere house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$136

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

$1,234

2nd Floor One Bedroom Runaway Beach Club Resort

Kissimmee villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$172

Price per night from

$218

The Florida Pad

Kissimmee villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$189

Modern Tropical Pool Home East Orlando

Orlando house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$252

Price per night from

$182

Lilo's Paradise in Windsor Hills

Kissimmee villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 11

Price per night from

$802

DISNEY DREAM LUXURY HOME PRIVATE WATERPARK POOL SPA

Kissimmee house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

“Perfect- it was better than what we had imagined.” The communication with the owner was what really surprised me. He was very responsive to all of my questions prior to our arrival. The house was very clean and in a great location. We were 15 minutes from Magic Kingdom and had many stores around the location of the house. I would not doubt to referred this home to anyone looking to spend a weekend in Orlando. We will definitely visit again!

Price per night from

$457

Price per night from

$487

Amazing Lake View Home near Disney

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 24 minutes

Price per night from

$160

Doorstep of Disney! 2-Bedroom Condo in Kissimmee

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$275

Best location! beautiful Penthhouse near Disney

Orlando apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$228

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

Springbank Townhouse

Kissimmee townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 2 hours 46 minutes

Price per night from

$160

The best place to Orlando

Orlando apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$184

Exceptional Vista Cay Property

Orlando house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 46 minutes

Price per night from

$155

Vacation Villa EE12

Kissimmee villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$249

Minions Retreat, Disney are our neighbors. Free 5g WIFI

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$103

Luxurious spacious villa for rent 21 minutes to Disney

Orlando villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$321

Spectacular Lake View 5 Br Villa, Close To Disney!

Four Corners villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$572

Luxury All 10 Suite Villa in Encore, mins to Disney

Kissimmee house

  • 10 bedrooms
  • 10 bathrooms
  • sleeps 24

“Great home for large families!” Great house for our exceptionally large family. Private pool was nice and the water park in the community kept the kids going all day! We did find a broken foosball table and dining chair. Also took the time to tighten up all the remaining dining chairs to prevent them from being damaged. Overall, the family loved it!

Price per night from

$687

Near to Disney with Private Pool/Spa and Game Room

Davenport villa

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$198

Viewing 38 of 6,059
rentals in Windermere

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