Updating...

More filters

Wireless Internet
Air conditioning
Swimming pool
Private pool

Heated pool
Private indoor pool
Balcony or terrace
Washing machine
Jacuzzi or hot tub
Garden
Internet access
Grill
Cot available
High chair
Sea view
Safe
Dishwasher
Children's pool
Games room
Table tennis
Clothes dryer
Pool or snooker table
Shared outdoor pool (heated)
Private outdoor pool (unheated)
Private outdoor pool (heated)
Shared indoor pool
Shared outdoor pool (unheated)
Cribs
Ceiling Fans
Fax machine
Climbing frame
Video player
Freezer
Kettle
Toaster
Iron
Hair dryer
Stove
Fridge
Microwave
Boat available
Linen provided
Towels provided
Bicycles available
Swing set or jungle gym
Trampoline
Private fishing lake or river
Staffed property
Housekeeping Included

See all

Less

Pets
Parking
Car not required
Children under 5

Smoking allowed
Non-Smoking property
Smoking - Ask
Elevator access
Wheelchair adapted
Wheelchair accessible

See all

Less

City breaks
Skiing – property near ski resort
Walking trips
Tennis in town

Nightlife
Water sports
Horse riding
Fishing
Cycling trips
Golf course on site or within 15 min walk
Golf within 30mins drive
Waterfront
Lakefront

See all

Less

6,034 Houses

Sort by:

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

$206

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

$153

Theme Park Retreat | 4BR near Universal Studios

Windermere house

4 bedrooms
3 bathrooms

sleeps 11

Price per night from

$359

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

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

$183

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

staySky Suites

Windermere condo

1 bedroom
1 bathroom

sleeps 4

Price per night from

$1,282

Great rentals within 20 miles that match your search

Luxury Dream Townhome with Pool SL4814

Kissimmee house

5 bedrooms
4 bathrooms

sleeps 10

Price per night from

$1,232

2nd Floor One Bedroom Runaway Beach Club Resort

Kissimmee villa

1 bedroom
1 bathroom

sleeps 4

Price per night from

$172

Spacious Vacation Townhouse at Vista Cay(266653)

Pine Castle townhouse

3 bedrooms
4 bathrooms

sleeps 7

Price per night from

$123

Wonderful Themed Vacation Home CG1648

ChampionsGate house

5 bedrooms
5 bathrooms

sleeps 12

Price per night from

$1,232

Family Vacation Home 15 Min to Disney BV4562

Kissimmee townhouse

4 bedrooms
3 bathrooms

sleeps 10

Price per night from

$123

Amazing Apt at Storey Lake 10Min to Disney(272985)

Kissimmee condo

2 bedrooms
2 bathrooms

sleeps 4

Price per night from

$1,232

Charming Mickey Mouse Vacation Home with private pool CG1516

ChampionsGate house

6 bedrooms
6 bathrooms

sleeps 13

Price per night from

$313

Adorable Vacation Apartment at Vista Cay (266645)

Pine Castle apartment

3 bedrooms
2 bathrooms

sleeps 6

Price per night from

$137

Excellent Apartment at Storey Lake (273064)

Kissimmee condo

2 bedrooms
2 bathrooms

sleeps 4

Price per night from

$1,232

Comfortable Vacation Apartment (266630)

Orlando apartment

3 bedrooms
2 bathrooms

sleeps 7

Price per night from

$123

Luxury Apartment at Storey Lake (273066)

Kissimmee condo

2 bedrooms
2 bathrooms

sleeps 4

Price per night from

$1,232

Modern Vacation Home with Themed Bedrooms CG1593

ChampionsGate house

5 bedrooms
5 bathrooms

sleeps 12

Price per night from

$1,232

Lovely Vacation Single Home with private pool CG1646

ChampionsGate house

5 bedrooms
5 bathrooms

sleeps 12

Price per night from

$1,232

Fantastic Apartment at Storey Lake (273059)

Kissimmee condo

2 bedrooms
2 bathrooms

sleeps 4

Price per night from

$1,232

Awesome Apartment at Storey Lake (273067)

Kissimmee condo

3 bedrooms
2 bathrooms

sleeps 6

Price per night from

$1,232

Lovely Vacation Apartment (266618)

Orlando apartment

3 bedrooms
2 bathrooms

sleeps 6

Price per night from

$123

Modern Vacation Apartment (266617)

Orlando apartment

3 bedrooms
2 bathrooms

sleeps 6

Price per night from

$135

Beautiful Themed Single Vacation Home with private pool CG9159

ChampionsGate house

6 bedrooms
6 bathrooms

sleeps 13

Price per night from

$269

Adorable Vacation Apartment at Vista Cay(266616)

Orlando apartment

3 bedrooms
2 bathrooms

sleeps 6

Price per night from

$134

The Best Vacation Home with barbecue grill and private pool CG1524

ChampionsGate house

6 bedrooms
5 bathrooms

sleeps 10

Price per night from

$307

Amazing Apartment at Storey Lake only 10 minutes from Disney (SL47312)

Kissimmee condo

2 bedrooms
2 bathrooms

sleeps 4

Price per night from

$154

Beautiful Vacation Apartment (266646)

Pine Castle apartment

3 bedrooms
2 bathrooms

sleeps 6

Price per night from

$135

Beautiful Apartment at Storey Lake only 10 minutes from Disney (SL47311)

Kissimmee condo

3 bedrooms
2 bathrooms

sleeps 6

Price per night from

$185

Fabulous Apartment at Storey Lake only 10 minutes from Disney (SL47313)

Kissimmee condo

2 bedrooms
2 bathrooms

sleeps 4

Price per night from

$124

Charming Vacation Townhome with Private Pool (CG1576)

ChampionsGate townhouse

4 bedrooms
3 bathrooms

sleeps 8

Price per night from

$185

Adorable Vacation Single Home with Private Pool and Game Room (CG1592)

ChampionsGate house

5 bedrooms
5 bathrooms

sleeps 12

Price per night from

$236

Great Single Vacation Home with Private Pool (CG9153)

ChampionsGate house

6 bedrooms
6 bathrooms

sleeps 13

Price per night from

$301

Viewing 38 of 6,034
rentals in Windermere

Also consider

Four Corners 1,951 properties
Kissimmee 1,771 properties
Orlando 881 properties
Davenport 779 properties
ChampionsGate 344 properties
Loughman 204 properties
Lake Buena Vista 74 properties
Haines City 45 properties
Intercession City 29 properties
Bay Lake 28 properties
The Villages 27 properties
Pine Castle 24 properties
Poinciana 14 properties
Lakeland 13 properties
Lake Placid 12 properties
Oviedo 10 properties
Buena Ventura Lakes 10 properties
Ocala 10 properties
Dunnellon 7 properties
St. Cloud 6 properties
Winter Haven 5 properties
Sanford 5 properties
Altamonte Springs 5 properties
Palm Coast 173 properties
Indian Shores 169 properties
Naples Park 47 properties
Zephyrhills 18 properties
Seminole 14 properties
Bal Harbour 14 properties
Doral 10 properties
Bay Pines 8 properties

Windermere Rentals

Per night

6,034 Houses

Viewing 38 of 6,034rentals in Windermere

Also consider

Viewing 38 of 6,034
rentals in Windermere