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Luxury Houses for Rent in Windermere, FL

25 rentals

5426 Gemgold Ct - Photo 1 of 1

10h ago

Luxury house for rent in Windermere

Single Family Residence - WINDERMERE, FL

5426 Gemgold Ct, Windermere, FL 34786

Luxury | Walk-in closets | Swimming pool

4 beds

2 baths

$4,350

$4,200

Price drop

House for rent

Top amenities
Carpet
Fitness Center
Swimming Pool
2533 Ridgewind Way - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

2533 Ridgewind Way, Windermere, FL 34786

Luxury | Swimming pool | Garage parking

4 beds

3 baths

$3,999

House for rent

Available Jan 15

Top amenities
Hardwood Floor
On-Site Management
Package Service
Swimming Pool
5723 Oxford Moor Boulevard #1 - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

5723 Oxford Moor Boulevard - 1

5723 Oxford Moor Boulevard #1, Windermere, FL 34786

Luxury | Swimming pool | Controlled access

4 beds

5 baths

$8,500

House for rent

Available Dec 19

Top amenities
Garage Parking
On-Site Laundry
4748 Blue Major Drive - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

4748 Blue Major Drive, Windermere, FL 34786

Luxury | Swimming pool | Fitness center

3 beds

2 baths

$3,100

House for rent

Top amenities
Fitness Center
In-Unit Laundry
Microwave
7347 Millstone Street #1 - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Windermere

7347 Millstone Street - 1

7347 Millstone Street #1, Windermere, FL 34786

Luxury | Swimming pool | In-unit laundry

2 beds

2 baths

$2,150

House for rent

Available Sep 23

Top amenities
Dishwasher
Garage Parking
In-Unit Laundry
Microwave
Residents Lounge
Swimming Pool
4012 Isabella Circle #1 - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

4012 Isabella Circle - 1

4012 Isabella Circle #1, Windermere, FL 34786

Luxury

6 beds

5 baths

$14,800

House for rent

Available Oct 20

Nearby rental good for eco-living

$3,700

Bay Hill

Nearby rental good for pet owners

$2,960

Ocoee

6533 Cartmel Lane - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

Single Family Residence - WINDERMERE, FL

6533 Cartmel Lane, Windermere, FL 34786

Luxury | Walk-in closets | Swimming pool

4 beds

3 baths

$8,995

House for rent

Top amenities
Ceiling Fan
Fireplace
Hardwood Floor
High Ceilings
On-Site Laundry
Swimming Pool
9508 Pine Terrace Court - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

Single Family Residence - WINDERMERE, FL

9508 Pine Terrace Court, Windermere, FL 34786

Luxury | Swimming pool | In-unit laundry

3 beds

2 baths

$3,700

$3,300

Price drop

House for rent

Top amenities
Ceiling Fan
Garage Parking
In-Unit Laundry
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6060 Roseate Spoonbill Drive - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

Single Family Residence - WINDERMERE, FL

6060 Roseate Spoonbill Drive, Windermere, FL 34786

Luxury | Swimming pool | In-unit laundry

3 beds

2 baths

$3,500

House for rent

Top amenities
Air Conditioning
Carpet
In-Unit Laundry
Swimming Pool
101 Lee Street - Photo 1 of 1

5d+ ago

Luxury Windermere house for rent in Windermere

Single Family Residence - WINDERMERE, FL

101 Lee Street, Windermere, FL 34786

Luxury | Balcony | Swimming pool

5 beds

4 baths

$8,000

$7,500

Price drop

House for rent

Top amenities
Air Conditioning
Fireplace
High Ceilings
In-Unit Laundry
On-Site Laundry
Swimming Pool
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Find sweet deals near Windermere

These rentals are 10%-30% cheaper than the local average price for similar rentals.

$1,990

Ocoee

$2,575

Winter Garden

$2,760

Winter Garden

$2,499

Orlando

7508 Lake Albert Drive - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

7508 Lake Albert Dr

7508 Lake Albert Drive, Windermere, FL 34786

Luxury | Walk-in closets | Swimming pool

4 beds

3 baths

$4,200

House for rent

Top amenities
Air Conditioning
Fireplace
Garage Parking
5243 West Lake Butler Road - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

5243 West Lake Butler Road, Windermere, FL 34786

Luxury | Balcony | Swimming pool

3 beds

3 baths

$12,000

House for rent

Available Nov 20

Top amenities
Ceiling Fan
Fitness Center
Garage Parking
In-Unit Laundry
On-Site Management
Storage
7165 Horizon Cir - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

Stunning 5-Bedroom Pool Home on Nearly 2 Acres!

7165 Horizon Cir, Windermere, FL 34786

Luxury | Walk-in closets | Swimming pool

5 beds

4 baths

$7,640

House for rent

Top amenities
Fireplace
Garage Parking
Hardwood Floor
In-Unit Laundry
Package Service
307 W 4th Ave - Photo 1 of 1

5d+ ago

Luxury Windermere house for rent in Windermere

Single Family Residence - WINDERMERE, FL

307 W 4th Ave, Windermere, FL 34786

Luxury | Walk-in closets | Swimming pool

4 beds

3 baths

$5,900

House for rent

Top amenities
Ceiling Fan
High Ceilings
In-Unit Laundry
On-Site Laundry
Storage
4012 Isabella Cir - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

4012 Isabella Circle - 1

4012 Isabella Cir, Windermere, FL 34786

Luxury | Swimming pool | Controlled access

6 beds

5 baths

$14,800

House for rent

Available Oct 20

Top amenities
Swimming Pool
6910 Corley Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

6910 Corley Ave, Windermere, FL 34786

Luxury

3 beds

2 baths

$3,000

House for rent

14415 Crest Palm Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

14415 Crest Palm Ave, Windermere, FL 34786

Luxury | Outdoor space | Dishwasher

6 beds

3 baths

$4,500

House for rent

11919 Sheltering Pine Drive - Photo 1 of 1

5d+ ago

Luxury house for rent in Orlando

House for rent

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2543 Balforn Tower Way #NA - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

$3,250 - 4 Bedroom 2 Bathroom Waterfront Home In Stoneybrook West, Winter Garden With Great Amenities

2543 Balforn Tower Way #NA, Winter Garden, FL 34787

Luxury | Swimming pool | Fitness center

4 beds

2 baths

$3,500

$3,250

Price drop

House for rent

Available Dec 1

Top amenities
Assigned Parking
Fitness Center
Garage Parking
In-Unit Laundry
Swimming Pool
1091 Wickerwood Street - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

1091 Wickerwood Street, Ocoee, FL 34761

Luxury | Walk-in closets | Swimming pool

3 beds

2 baths

$2,150

$1,990

Price drop

House for rent

Available Oct 22

Top amenities
Ceiling Fan
Garage Parking
On-Site Laundry
1239 Juniper Hammock Street - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

1239 Juniper Hammock Street, Winter Garden, FL 34787

Luxury | Walk-in closets | On-site laundry

5 beds

4 baths

$3,065

$2,770

Price drop

House for rent

Available Oct 22

Top amenities
Garage Parking
On-Site Laundry
744 Westcliffe Dr - Photo 1 of 1

2d ago

Our team has verified this company

Verified

744 Westcliffe Dr, Winter Garden, FL 34787

Luxury | Outdoor space | Garage parking

4 beds

2 baths

$2,970

House for rent

Available Dec 12

Top amenities
Ceiling Fan
Garage Parking
2297 Blake Way - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

2297 Blake Way, Ocoee, FL 34761

Luxury | Walk-in closets | On-site laundry

3 beds

2 baths

$2,240

House for rent

Available Jan 20

Top amenities
Ceiling Fan
Fireplace
On-Site Laundry
272 Regal Downs Circle - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

272 Regal Downs Circle, Winter Garden, FL 34787

Luxury | Walk-in closets | On-site laundry

4 beds

2 baths

$2,575

House for rent

Available Jan 20

Top amenities
On-Site Laundry
254 Regal Downs Circle - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

254 Regal Downs Circle, Winter Garden, FL 34787

Luxury | Walk-in closets | On-site laundry

4 beds

2 baths

$3,870

$2,760

Price drop

House for rent

Available Jan 1

Top amenities
Garage Parking
High Ceilings
On-Site Laundry
Showing 1 - 25 of 25 results
Home > House Rentals in Windermere > Windermere Luxury Houses For Rent
Updated: December 18, 2025

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Discover luxury Windermere, FL houses for rent

🌇Available luxury house rentals25 houses
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