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Luxury Houses for Rent in Windermere, FL

25 rentals available

5243 Isleworth Country Club Dr - Photo 1 of 1

1d ago

Luxury house for rent in Windermere

5243 Isleworth Country Club Dr, Windermere, FL 34786

Luxury | Roof deck | Walk-in closets

4 beds

5.5 baths

$25,000

House for rent

Top amenities
Fireplace
Fitness Center
Hardwood Floor
In-Unit Laundry
Roof Deck
Swimming Pool
6431 Chatham View Ct - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

Single Family Residence - WINDERMERE, FL

6431 Chatham View Ct, Windermere, FL 34786

Luxury | Walk-in closets | Swimming pool

5 beds

4.5 baths

$5,800

House for rent

Top amenities
Dishwasher
Garage Parking
In-Unit Laundry
11406 Waterstone Loop Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

Single Family Residence - WINDERMERE, FL

11406 Waterstone Loop Dr, Windermere, FL 34786

Luxury | Walk-in closets | Swimming pool

5 beds

6 baths

$9,500

House for rent

Top amenities
Carpet
Dishwasher
Fireplace
In-Unit Laundry
Swimming Pool
6873 Northwich Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

6873 Northwich Dr, Windermere, FL 34786

Luxury | Swimming pool | In-unit laundry

3 beds

2.5 baths

$3,395

House for rent

Available Jun 8

Top amenities
Garage Parking
In-Unit Laundry
On-Site Laundry
On-Site Management
Package Service
Swimming Pool
7231 Sangalla Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

Single Family Residence - WINDERMERE, FL

7231 Sangalla Dr, Windermere, FL 34786

Luxury | Walk-in closets | Swimming pool

5 beds

4.5 baths

$7,800

$6,800

Price drop

House for rent

Top amenities
Hardwood Floor
In-Unit Laundry
Swimming Pool
12645 Salomon Cove Dr - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Windermere

12645 Salomon Cove Drive - main - 12645...

12645 Salomon Cove Dr, Windermere, FL 34786

Luxury | Outdoor space | Garage parking

1 bed

1 bath

$1,349

House for rent

Available Jun 1

Nearby rental good for eco-living

$3,345

Bay Hill

Nearby rental good for pet owners

$3,030

Winter Garden

9094 Outlook Rock Trl - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

9094 Outlook Rock Trl, Windermere, FL 34786

Luxury | On-site management

3 beds

2.5 baths

$3,500

House for rent

Available May 20

Top amenities
On-Site Management
5243 W Lake Butler Rd - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

5243 W Lake Butler Rd, Windermere, FL 34786

Luxury | Balcony | Swimming pool

3 beds

3 baths

$8,999

House for rent

Available Jun 1

Top amenities
Ceiling Fan
Controlled Access
Fitness Center
In-Unit Laundry
On-Site Management
Storage
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8588 Powder Ridge Trl - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

House for rent

3636 Lake Buynak Rd - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

Single Family Residence - WINDERMERE, FL

3636 Lake Buynak Rd, Windermere, FL 34786

Luxury | In-unit laundry | Garage parking

2 beds

2 baths

$3,500

House for rent

Top amenities
Fireplace
In-Unit Laundry
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Find sweet deals near Windermere

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

$5,800

Windermere

$1,349

Windermere

$1,500

Windermere

$2,350

Sand Lake Hills

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

$5,475

House for rent

Top amenities
Dishwasher
Garage Parking
High Ceilings
In-Unit Laundry
9701 Lake Isleworth Ct - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

Single Family Residence - WINDERMERE, FL

9701 Lake Isleworth Ct, Windermere, FL 34786

Luxury | Walk-in closets | In-unit laundry

3 beds

3 baths

$12,500

House for rent

Top amenities
Dishwasher
Fireplace
High Ceilings
In-Unit Laundry
2324 Lielasus Dr - Photo 1 of 1

4d ago

Our team has verified this company

Verified

2324 Lielasus Dr Orlando, FL 32835

2324 Lielasus Dr, Orlando, FL 32835

Luxury | Walk-in closets | Garage parking

4 beds

3 baths

$3,495

House for rent

Available Jun 18

6320 Morning Mist Ln - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

6320 Morning Mist Ln Orlando, FL 32819

6320 Morning Mist Ln, Doctor Phillips, FL 32819

Luxury | Walk-in closets | Outdoor space

4 beds

2 baths

$3,195

House for rent

Available Jun 25

7280 Westpointe Blvd - Photo 1 of 1

5d+ ago

Luxury Metro West house for rent in Orlando

Luxury | Swimming pool | Fitness center

2 beds

2 baths

$1,800

House for rent

Top amenities
Microwave
8108 Bluestar Cir - Photo 1 of 1

1d ago

Luxury Sand Lake Hills house for rent in Doctor Phillips

SINGLE_FAMILY - Ranch - Orlando, FL

8108 Bluestar Cir, Doctor Phillips, FL 32819

Luxury | Swimming pool | In-unit laundry

4 beds

2 baths

$2,350

House for rent

Top amenities
Fireplace
High Ceilings
In-Unit Laundry
Storage
Swimming Pool
1363 Glenwick Dr - Photo 1 of 1

2d ago

Luxury Reserve At Belmere house for rent in Lake Butler

1363 Glenwick Dr, Lake Butler, FL 34786

Luxury | Swimming pool | Fitness center

3 beds

2 baths

$4,000

House for rent

Top amenities
Controlled Access
In-Unit Laundry
Swimming Pool
3013 Barrymore Ct - Photo 1 of 1

3d ago

Luxury Metro West house for rent in Orlando

Single Family Residence - ORLANDO, FL

3013 Barrymore Ct, Orlando, FL 32835

Luxury | Swimming pool | In-unit laundry

3 beds

2 baths

$2,995

House for rent

Top amenities
Dishwasher
Garage Parking
In-Unit Laundry
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1207 Almond Tree Ct - Photo 1 of 1

4d ago

Luxury house for rent in Orlando

Single Family Residence - ORLANDO, FL

1207 Almond Tree Ct, Orlando, FL 32835

Luxury | Swimming pool | Fitness center

4 beds

2.5 baths

$3,500

House for rent

Top amenities
Ceiling Fan
Dishwasher
Fitness Center
Garage Parking
In-Unit Laundry
5722 Bay Side Dr - Photo 1 of 1

4d ago

Luxury Bay Hill house for rent in Bay Hill

Single Family Residence - ORLANDO, FL

5722 Bay Side Dr, Bay Hill, FL 32819

Luxury | Swimming pool | In-unit laundry

4 beds

2 baths

$3,500

House for rent

Top amenities
Fireplace
High Ceilings
In-Unit Laundry
Swimming Pool
9142 Sabal Palm Cir - Photo 1 of 1

4d ago

Luxury house for rent in Windermere

House for rent

6434 Rockingtree Ln - Photo 1 of 1

5d+ ago

Luxury Sand Lake Hills house for rent in Doctor Phillips

House (Detached) - Orlando, FL

6434 Rockingtree Ln, Doctor Phillips, FL 32819

Luxury | Walk-in closets | In-unit laundry

3 beds

2 baths

$2,600

House for rent

Top amenities
Ceiling Fan
In-Unit Laundry
13121 Zori Ln - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

Single Family Residence - WINDERMERE, FL

13121 Zori Ln, Windermere, FL 34786

Luxury | Walk-in closets | Swimming pool

5 beds

4 baths

$4,550

House for rent

Top amenities
Carpet
Dishwasher
Garage Parking
High Ceilings
On-Site Laundry
Storage
2031 Wintermere Pointe Dr - Photo 1 of 1

2h ago

Luxury house for rent in Winter Garden

2031 Wintermere Pointe Dr, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

4 beds

2 baths

$3,695

$3,450

Price drop

House for rent

Top amenities
Carpet
Ceiling Fan
Dishwasher
In-Unit Laundry
3356 Bellington Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Orlando

3356 Bellington Dr, Orlando, FL 32835

Luxury | Swimming pool | In-unit laundry

4 beds

3.5 baths

$5,399

House for rent

Available Jun 3

Top amenities
In-Unit Laundry
On-Site Management
Package Service
Storage
Showing 1 - 25 of 25 results
Home > House Rentals in Windermere > Windermere Luxury Houses For Rent
Updated: June 21, 2026

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Pet friendly houses in Windermere, FL18 rentals

18 rentals

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Discover luxury Windermere, FL houses for rent

🌇Available luxury house rentals25 houses
⭐Popular amenities, ,
🍽With dishwasher
❄️With air conditioning
🚗With garage parking
🍃With outdoor space
🏠With photos