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Luxury Houses for Rent in Windermere, FL

25 rentals available

6436 Golden Dewdrop Trl - Photo 1 of 1

3d ago

Luxury house for rent in Windermere

Residential Lease, WINDERMERE, FL

6436 Golden Dewdrop Trl, Windermere, FL 34786

Luxury | Balcony | Swimming pool

3 beds

2.5 baths

$4,000

12740 Langstaff Dr - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Windermere

Residential Lease, WINDERMERE, FL

12740 Langstaff Dr, Windermere, FL 34786

Luxury | Swimming pool | Fitness center

2 beds

2.5 baths

$2,250

Reams Rd & Legado Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

Reams Rd & Legado Dr, Windermere, FL 34786

Luxury | Swimming pool | In-unit laundry

4 beds

2.5 baths

$5,500

Vivaro Isle Way & Procida Isle Ln - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

Vivaro Isle Way & Procida Isle Ln, Windermere, FL 34786

Luxury | Swimming pool | In-unit laundry

3 beds

3 baths

$3,950

6020 Marleon Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

Residential Lease, WINDERMERE, FL

6020 Marleon Dr, Windermere, FL 34786

Luxury | Walk-in closets | Swimming pool

5 beds

4.5 baths

$8,900

8794 Crescendo Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

Residential Lease, WINDERMERE, FL

8794 Crescendo Ave, Windermere, FL 34786

Luxury | Walk-in closets | Swimming pool

4 beds

3 baths

$4,800

Nearby rental good for eco-living

$1,650

Metro West

Nearby rental good for pet owners

Crescendo Ave & Gold Creek Trail - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

Crescendo Ave & Gold Creek Trail, Windermere, FL 34786

Luxury | Walk-in closets | Swimming pool

4 beds

3 baths

$4,800

10914 Ledgement Ln - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

Residential Lease, WINDERMERE, FL

10914 Ledgement Ln, Windermere, FL 34786

Luxury | Swimming pool | Dishwasher

4 beds

3.5 baths

$5,490

$4,990

Price drop

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Langstaff Dr & Danforth Dr - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Windermere

Langstaff Dr & Danforth Dr, Windermere, FL 34786

Luxury | In-unit laundry | Air conditioning

2 beds

2.5 baths

$2,350

6119 Payne Stewart Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

Residential Lease, WINDERMERE, FL

6119 Payne Stewart Dr, Windermere, FL 34786

Luxury | Walk-in closets | In-unit laundry

3 beds

3.5 baths

$14,500

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Find sweet deals near Windermere

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

$3,870

Windermere

$5,900

Orlando

$3,495

Winter Garden

$3,895

Windermere

14422 Crest Palm Ave - Photo 1 of 1
New construction

5d+ ago

Luxury house for rent in Windermere

Residential Lease, WINDERMERE, FL

14422 Crest Palm Ave, Windermere, FL 34786

Luxury | Walk-in closets | In-unit laundry

4 beds

4 baths

$4,500

9701 Lake Isleworth Ct - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

Residential Lease, WINDERMERE, FL

9701 Lake Isleworth Ct, Windermere, FL 34786

Luxury | Walk-in closets | In-unit laundry

4 beds

3 baths

$11,500

8524 Danforth Dr - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Windermere

Residential Lease, WINDERMERE, FL

8524 Danforth Dr, Windermere, FL 34786

Luxury | Walk-in closets | Swimming pool

2 beds

2.5 baths

$2,350

11820 Waterstone Loop Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

Residential Lease, WINDERMERE, FL

11820 Waterstone Loop Dr, Windermere, FL 34786

Luxury | Walk-in closets | Swimming pool

4 beds

3 baths

$6,990

11406 Waterstone Loop Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

Residential Lease, WINDERMERE, FL

11406 Waterstone Loop Dr, Windermere, FL 34786

Luxury | Walk-in closets | Carpet

5 beds

6 baths

$9,500

497 Goldenmoss Loop - Photo 1 of 1

5d+ ago

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Verified

497 Goldenmoss Loop, Ocoee, FL 34761

Luxury

3 beds

2 baths

$2,545

11719 Bella Milano Ct - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

11719 Bella Milano Ct Windermere, FL 34786

11719 Bella Milano Ct, Windermere, FL 34786

Luxury | Swimming pool | Garage parking

5 beds

4.5 baths

$3,870

626 Westhampton Ct - Photo 1 of 1

14h ago

Our team has verified this company

Verified

626 Westhampton Ct Winter Garden, FL 34787

626 Westhampton Ct, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

4 beds

4 baths

$3,749

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7330 Westpointe Blvd #431 - Photo 1 of 1

5d+ ago

Luxury Metro West house for rent in Orlando

1800 Bardmoor Hill Cir - Photo 1 of 1

2d ago

Luxury Metro West house for rent in Orlando

1800 Bardmoor Hill Cir, Orlando, FL 32835

Luxury | Swimming pool | In-unit laundry

4 beds

3 baths

$3,900

Oakland Pl & Vistamere Ct - Photo 1 of 1

5d+ ago

Luxury house for rent in Orlando

Oakland Pl & Vistamere Ct, Orlando, FL 32819

Luxury | Swimming pool | In-unit laundry

5 beds

4.5 baths

$4,700

1831 Abbots Hill Dr - Photo 1 of 1

5d+ ago

Luxury Metro West house for rent in Orlando

Residential Lease, ORLANDO, FL

1831 Abbots Hill Dr, Orlando, FL 32835

Luxury | Swimming pool | In-unit laundry

3 beds

2.5 baths

$3,300

Talaria Dr & Zori Ln - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

Talaria Dr & Zori Ln, Windermere, FL 34786

Luxury | Walk-in closets | Swimming pool

4 beds

3 baths

$3,600

839 Rosemere Cir - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Orlando

Residential Lease, ORLANDO, FL

839 Rosemere Cir, Orlando, FL 32835

Luxury | In-unit laundry | Garage parking

4 beds

2 baths

$3,100

$3,000

Price drop

8021 Sandberry Blvd #NA - Photo 1 of 1

5d+ ago

Luxury Sand Lake Hills house for rent in Doctor Phillips

$3300-Spacious 3BR + Huge Bonus Room | 2.5BA | Dr. Phillips | Fenced Yard | Pet Friendly

8021 Sandberry Blvd #NA, Doctor Phillips, FL 32819

Luxury | Walk-in closets | Fitness center

3 beds

2.5 baths

$3,300

$3,200

Price drop

Showing 1 - 25 of 25 results
Home > House Rentals in Windermere > Windermere Luxury Houses For Rent
Updated: September 19, 2026

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Pet friendly houses in Windermere, FL17 rentals

17 rentals

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Discover luxury Windermere, FL houses for rent

🌇Available luxury house rentals25 houses
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❄️With air conditioning
🚗With garage parking
🍃With outdoor space
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