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Windermere Rentals

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17,620 Houses

PARADISE

Windermere house

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$1,000

Studio Suite Near Disney & Sea World w/ Resort Pool, Hot Tub, Dining & WiFi

Windermere studio

Studio / 1 bathroom / sleeps 4

Price per night from

$130

Family-Family Condo w/ WiFi, Free Shuttle to Theme Parks, Resort Dining & Pool

Windermere house

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$308

Private Home in the Heart of Orlando!

Windermere guest house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$119

Price per night from

$154

Family-Friendly Villa w/ WiFi Available, Free Theme Park Shuttle & Resort Pool

Windermere house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$236

Deluxe Family-Friendly Villa w/ WiFi, Resort Pool & Free Theme Park Shuttle

Windermere house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$249

Cinderella's other Castle

Windermere house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$414

Cayman Cottage

Windermere house

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$237

NEW! Orlando Condo w/ Pool ~2 Miles to Universal!

Windermere condo

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 5 minutes

Price per night from

$78

Family-Friendly Condo w/ WiFi, Free Shuttle to Theme Parks, Resort Pool & Dining

Windermere house

3 bedrooms / 2 bathrooms / sleeps 12

Price per night from

$463

West Lucaya Village 17 - Modern townhouse near Disney

Windermere house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 21 minutes

Price per night from

$129

2701 · (2701) LUXURY Lakefront unit with pool views

Windermere house

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$91

Price per night from

$178

Lucaya Village Resort 4 Bedroom TownHome

Windermere townhouse

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 26 minutes

Price per night from

$139

Lucaya Village Resort 4 Bedroom Home 2901EW14

Windermere house

4 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$129

8032 Sand Bar Drive

Windermere house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$161

Great rentals within 20 miles that match your search

Amazing views from the pool! Windsor Hills Resort!

Four Corners house

6 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$208

Luxury Six Bedroom Home - Close to Disneyworld

Four Corners villa

6 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$202

VISTA CAY. New!POOLSIDE ESCAPE NEAR ALL PARKS, ATTRACTIONS & INTERNATIONAL DRIVE

Orlando apartment

3 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 1 hour 31 minutes

Price per night from

$290

477-ORLANDO-15 Min FROM DISNEY & OMNI RESORT

Four Corners house

8 bedrooms / 6 bathrooms / sleeps 26

Price per night from

$320

ORLANDO-CHAMPIONS GATE-15 Min FROM DISNEY & OMNI RESORT

ChampionsGate house

4 bedrooms / 1 bathroom / sleeps 11

Price per night from

$118

1580-ORLANDO-15 Min FROM DISNEY & OMNI RESORT

ChampionsGate house

8 bedrooms / 6 bathrooms / sleeps 17

Price per night from

$284

730-ORLANDO-CHAMPIONS GATE-15 Min FROM DISNEY & OMNI RESORT

Four Corners house

4 bedrooms / 1 bathroom / sleeps 11

Price per night from

$118

Beautiful Private Villa Close To Disney Parks

Davenport villa

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$187

3 Bedroom Condo, Windsor Palms Resort *10 MINUTES from DISNEY* (105)

Four Corners villa

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$119

Luxurious

Orlando apartment

3 bedrooms / 4 bathrooms / sleeps 8

“Absolutly Wonderful!” Best value, best decor, most room for the $ Would have had to pay 3x more for a resort suite of the same size!

Price per night from

$164

Brand New 5BD/4BA & private pool home next to Disney & Universal

Kissimmee house

5 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 2 hours 41 minutes

Price per night from

$187

1570-ORLANDO-CHAMPIONS GATE-15 Min. da DISNEY & OMNI RESORT-

ChampionsGate house

5 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$152

3 MILES FROM DISNEY / SUN LAKE / 2 BED / 2 BATH/

Kissimmee condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 59 minutes

Price per night from

$118

At Last You can Rent the Perfect Luxury Villa on Solterra Resort, minutes from

Loughman villa

6 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$255

The WHITE HOUSE 25 min from Disney

Zellwood house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$230

139 - Luxury 2 Masterbed/bath Unit with Garden View - International Drive

Orlando apartment

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 43 minutes

Price per night from

$223

How to Rent Your Own Private Luxury Holiday Villa on Champions Gate Resort

Loughman villa

8 bedrooms / 5 bathrooms / sleeps 16

Price per night from

$394

Stunning 4 bed villa with south facing pool and spa

Davenport house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$141

Sheraton Vistana Fountains II - Timeshare

Kissimmee hotel apartment

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$159

Stunning 7 bedroom Villa Lake Berkley, Private pool and Jacuzzi

Kissimmee house

7 bedrooms / 4 bathrooms / sleeps 14

Price per night from

$212

Gorgeous 6BR 6Bth Champions Gate Home with Private Pool, Spa and Gameroom

ChampionsGate house

6 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 1 hour 4 minutes

Price per night from

$274

Viewing 38 of 17,620
rentals in Windermere

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