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Luxury Houses for Rent in Windermere, FL

25 rentals

Lascala & Roberson - Photo 1 of 1

20h ago

Luxury house for rent in Windermere

3/2 single family home -Luxury living in Windermere

Lascala & Roberson, Windermere, FL 34786

Luxury | Walk-in closets | Air conditioning

3 beds

2 baths

$3,300

House for rent

Available May 10

3636 Lake Buynak Rd - Photo 1 of 1

3d 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
11745 Via Lucerna Cir - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

Single Family Residence - WINDERMERE, FL

11745 Via Lucerna Cir, Windermere, FL 34786

Luxury | Walk-in closets | Swimming pool

4 beds

2.5 baths

$4,689

$4,400

Price drop

House for rent

Top amenities
High Ceilings
In-Unit Laundry
Swimming Pool
801 W 2nd Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

801 W 2nd Ave, Windermere, FL 34786

Luxury | Balcony | Swimming pool

5 beds

6.5 baths

$15,999

House for rent

Available Apr 26

Top amenities
Elevator
Fireplace
On-Site Laundry
On-Site Management
Package Service
Storage
9094 Outlook Rock Trl - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

9094 Outlook Rock Trl, Windermere, FL 34786

Luxury

3 beds

2.5 baths

$3,500

House for rent

Available May 2

13014 Langstaff Dr - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Windermere

COMING SOON! Beautiful 2 Bed 2.5 Bath Townhouse! Make an offer! Apply Today!

13014 Langstaff Dr, Windermere, FL 34786

Luxury | In-unit laundry | Garage parking

2 beds

2.5 baths

$2,100

House for rent

Top amenities
Assigned Parking
Ceiling Fan
Dishwasher
Garage Parking
In-Unit Laundry

Nearby rental good for eco-living

$2,300

Bel-Aire Woods

Nearby rental good for pet owners

12654 Langstaff Dr - Photo 1 of 1
3D tour

5d+ ago

Luxury townhouse for rent in Windermere

12654 Langstaff Dr, Windermere, FL 34786

Luxury | Swimming pool | In-unit laundry

2 beds

2.5 baths

$2,150

House for rent

Top amenities
In-Unit Laundry
Microwave
Swimming Pool
8520 Greenbank Blvd - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

Single Family Residence - WINDERMERE, FL

8520 Greenbank Blvd, Windermere, FL 34786

Luxury | Swimming pool | In-unit laundry

3 beds

2 baths

$3,150

House for rent

Top amenities
Dishwasher
Fireplace
In-Unit Laundry
Swimming Pool
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8414 Vivaro Isle Way - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

Single Family Residence - WINDERMERE, FL

8414 Vivaro Isle Way, Windermere, FL 34786

Luxury | Walk-in closets | Swimming pool

5 beds

4 baths

$5,250

House for rent

Top amenities
Ceiling Fan
Dishwasher
Garage Parking
In-Unit Laundry
Swimming Pool
13845 Ancilla Blvd - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Windermere

Townhouse - WINDERMERE, FL

13845 Ancilla Blvd, Windermere, FL 34786

Luxury | Walk-in closets | Swimming pool

2 beds

2 baths

$2,435

House for rent

Top amenities
Dishwasher
Fitness Center
Garage Parking
In-Unit Laundry
On-Site Laundry
Storage
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Find sweet deals near Windermere

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

$5,250

Windermere

$3,700

Orlando

$2,800

Winter Garden

$2,310

Winter Garden

13466 Zori Ln - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

Single Family Residence - WINDERMERE, FL

13466 Zori Ln, Windermere, FL 34786

Luxury | Swimming pool | In-unit laundry

4 beds

3 baths

$4,500

House for rent

Top amenities
Ceiling Fan
Dishwasher
Fireplace
Garage Parking
High Ceilings
In-Unit Laundry
11051 Coniston Way - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

Single Family Residence - WINDERMERE, FL

11051 Coniston Way, Windermere, FL 34786

Luxury | Walk-in closets | Swimming pool

5 beds

5.5 baths

$13,500

House for rent

Top amenities
Carpet
Garage Parking
High Ceilings
In-Unit Laundry
Storage
Swimming Pool
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

$9,999

House for rent

Available Apr 27

Top amenities
Ceiling Fan
Controlled Access
Fitness Center
In-Unit Laundry
On-Site Management
Storage
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
High Ceilings
In-Unit Laundry
Swimming Pool
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
2273 Kettle Dr - Photo 1 of 1

5d+ ago

Luxury Metro West house for rent in Orlando

2273 Kettle Dr, Orlando, FL 32835

Luxury

5 beds

4 baths

$4,495

$4,195

Price drop

House for rent

7832 Barberry Dr - Photo 1 of 1

3d ago

Luxury house for rent in Orlando

Single Family Residence - ORLANDO, FL

7832 Barberry Dr, Orlando, FL 32835

Luxury | In-unit laundry | Outdoor space

3 beds

2 baths

$2,700

House for rent

Top amenities
Fireplace
In-Unit Laundry
7846 Snowberry Cir - Photo 1 of 1

5d+ ago

Luxury house for rent in Orlando

Single Family Residence - ORLANDO, FL

7846 Snowberry Cir, Orlando, FL 32819

Luxury | Swimming pool | In-unit laundry

5 beds

2.5 baths

$3,700

House for rent

Top amenities
Air Conditioning
Ceiling Fan
Dishwasher
In-Unit Laundry
On-Site Laundry
Swimming Pool
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750 Home Grove Dr #1 - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

750 HOMEGROVE DR - 1

750 Home Grove Dr #1, Winter Garden, FL 34787

Luxury

4 beds

2 baths

$2,800

House for rent

Available May 1

7841 Belvoir Dr - Photo 1 of 1

5d+ ago

Luxury Metro West house for rent in Orlando

Single Family Residence - ORLANDO, FL

7841 Belvoir Dr, Orlando, FL 32835

Luxury | Walk-in closets | In-unit laundry

4 beds

3 baths

$3,500

$3,300

Price drop

House for rent

Top amenities
Dishwasher
In-Unit Laundry
7705 Apple Tree Cir - Photo 1 of 1

5d+ ago

Luxury house for rent in Orlando

Single Family Residence - ORLANDO, FL

7705 Apple Tree Cir, Orlando, FL 32819

Luxury | Walk-in closets | Swimming pool

4 beds

5 baths

$8,500

House for rent

Top amenities
Ceiling Fan
Fireplace
Garage Parking
High Ceilings
In-Unit Laundry
Swimming Pool
455 Winter Grove Blvd - Photo 1 of 1
New construction

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

455 Winter Grove Blvd, Winter Garden, FL 34787

Luxury | In-unit laundry | Garage parking

5 beds

3.5 baths

$5,800

$5,090

Price drop

House for rent

Top amenities
Dishwasher
In-Unit Laundry
8101 Canyon Lake Cir - Photo 1 of 1

5d+ ago

Luxury house for rent in Orlando

Single Family Residence - ORLANDO, FL

8101 Canyon Lake Cir, Orlando, FL 32835

Luxury | Walk-in closets | Swimming pool

4 beds

3 baths

$3,700

House for rent

Top amenities
Ceiling Fan
Dishwasher
Fireplace
High Ceilings
In-Unit Laundry
7843 Saint Andrews Cir - Photo 1 of 1

5d+ ago

Luxury Metro West house for rent in Orlando

Single Family Residence - ORLANDO, FL

7843 Saint Andrews Cir, Orlando, FL 32835

Luxury | Outdoor space | Garage parking

4 beds

2.5 baths

$3,500

House for rent

1351 Glenwick Dr - Photo 1 of 1

5d+ ago

Luxury Reserve At Belmere house for rent in Lake Butler

Single Family Residence - WINDERMERE, FL

1351 Glenwick Dr, Lake Butler, FL 34786

Luxury | Swimming pool | In-unit laundry

5 beds

4 baths

$4,500

House for rent

Top amenities
In-Unit Laundry
Swimming Pool
Showing 1 - 25 of 25 results
Home > House Rentals in Windermere > Windermere Luxury Houses For Rent
Updated: May 4, 2026

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Discover luxury Windermere, FL houses for rent

🌇Available luxury house rentals25 houses
⭐Popular amenities, ,
🍽With dishwasher
❄️With air conditioning
🍃With outdoor space
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