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Luxury Houses for Rent in Windermere, FL

25 rentals

11316 Rapallo Ln - Photo 1 of 1

15m ago

Luxury house for rent in Windermere

11316 Rapallo Ln, Windermere, FL 34786

Luxury | Swimming pool | Fitness center

3 beds

2 baths

$3,095

House for rent

Top amenities
Dishwasher
Garage Parking
In-Unit Laundry
Residents Lounge
Swimming Pool
1927 Watermere Ln - Photo 1 of 1

3d ago

Luxury house for rent in Windermere

Single Family Residence - WINDERMERE, FL

1927 Watermere Ln, Windermere, FL 34786

Luxury | Walk-in closets | Swimming pool

4 beds

3 baths

$5,500

House for rent

Top amenities
Ceiling Fan
Dishwasher
In-Unit Laundry
Swimming Pool
11377 Evesham Dr - Photo 1 of 1

4d ago

Luxury townhouse for rent in Windermere

Townhouse - WINDERMERE, FL

11377 Evesham Dr, Windermere, FL 34786

Luxury | Balcony | Walk-in closets

2 beds

2 baths

$2,400

$2,200

Price drop

House for rent

Top amenities
Garage Parking
In-Unit Laundry
On-Site Laundry
11994 Mckinnon Rd - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

Luxury | Swimming pool | Outdoor space

4 beds

3 baths

$4,500

House for rent

307 W 4th Ave - Photo 1 of 1

5d+ ago

Luxury Windermere house for rent in Windermere

307 W 4th Ave, Windermere, FL 34786

Luxury | Walk-in closets | Swimming pool

4 beds

3 baths

$6,000

House for rent

Top amenities
Ceiling Fan
High Ceilings
In-Unit Laundry
On-Site Laundry
Storage
4303 Isabella Cir - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

4303 Isabella Cir, Windermere, FL 34786

Luxury | Walk-in closets | Swimming pool

7 beds

4 baths

$18,000

House for rent

Top amenities
Ceiling Fan
Dishwasher
Furnished
In-Unit Laundry
Swimming Pool

Nearby rental good for eco-living

$2,700

Bay Hill

Nearby rental good for pet owners

$2,250

Winter Garden

6926 Cucamelon Ct - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

Luxury | Walk-in closets | Swimming pool

5 beds

4 baths

$5,200

House for rent

Top amenities
Furnished
14451 Bluebird Park Rd - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

Luxury Above-Garage Studio with Private Entrance - Available Soon in Windermere’s Summerport!

14451 Bluebird Park Rd, Windermere, FL 34786

Luxury | Walk-in closets | Swimming pool

Studio

1 bath

$1,250

House for rent

Available Oct 1

Top amenities
Air Conditioning
In-Unit Laundry
Microwave
On-Site Laundry
Swimming Pool
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7508 Lake Albert Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

7508 Lake Albert Dr

7508 Lake Albert Dr, Windermere, FL 34786

Luxury | Walk-in closets | Swimming pool

4 beds

3 baths

$4,800

House for rent

Top amenities
Air Conditioning
Fireplace
2113 Grove Point Ln - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

Single Family Residence - WINDERMERE, FL

2113 Grove Point Ln, Windermere, FL 34786

Luxury | Walk-in closets | Swimming pool

4 beds

3 baths

$5,500

House for rent

Top amenities
Dishwasher
Fireplace
Furnished
Garage Parking
In-Unit 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.

$1,250

Windermere

$2,250

Winter Garden

$2,125

Winter Garden

$3,285

Winter Garden

13542 Gorgona Isle Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

Single Family Residence - WINDERMERE, FL

13542 Gorgona Isle Dr, Windermere, FL 34786

Luxury | Walk-in closets | Swimming pool

4 beds

3 baths

$4,200

House for rent

Top amenities
Dishwasher
Garage Parking
In-Unit Laundry
3278 Downs Cove Rd - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

Single Family Residence - WINDERMERE, FL

3278 Downs Cove Rd, Windermere, FL 34786

Luxury | In-unit laundry | Outdoor space

3 beds

2 baths

$3,999

House for rent

Top amenities
Ceiling Fan
In-Unit Laundry
721 Magnolia St #727 - Photo 1 of 1

5d+ ago

Luxury Windermere house for rent in Windermere

Single Family Residence - WINDERMERE, FL

721 Magnolia St #727, Windermere, FL 34786

Luxury | In-unit laundry | Outdoor space

2 beds

1 bath

$2,200

House for rent

Top amenities
In-Unit Laundry
6107 Talaria Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

Single Family Residence - WINDERMERE, FL

6107 Talaria Dr, Windermere, FL 34786

Luxury | Walk-in closets | Swimming pool

4 beds

3 baths

$4,950

House for rent

Top amenities
Ceiling Fan
Fitness Center
Garage Parking
High Ceilings
In-Unit Laundry
Swimming Pool
9742 Green Island Cv - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

Single Family Residence - WINDERMERE, FL

9742 Green Island Cv, Windermere, FL 34786

Luxury | Walk-in closets | Swimming pool

3 beds

3 baths

$13,500

House for rent

Top amenities
Ceiling Fan
Fireplace
Garage Parking
In-Unit Laundry
8905 S Bay Dr - Photo 1 of 1

5d+ ago

Luxury Bay Hill house for rent in Bay Hill

Luxury | Outdoor space

4 beds

3 baths

$4,595

House for rent

14415 Crest Palm Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Windermere

Luxury | Outdoor space | Dishwasher

6 beds

3 baths

$4,500

House for rent

Daniels Landing Cir #13939 - Photo 1 of 1

2d ago

Our team has verified this company

Verified

$2,250 3 Bedroom 2.5 bathroom Townhouse In Winter Garden With Great Amenities

Daniels Landing Cir #13939, Winter Garden, FL 34787

Luxury | Swimming pool | Fitness center

3 beds

2 baths

$2,250

House for rent

Available Nov 17

Top amenities
Air Conditioning
Assigned Parking
Fitness Center
Hardwood Floor
In-Unit Laundry
Swimming Pool
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1317 S Park Ave - Photo 1 of 1

1d ago

Our team has verified this company

Verified

1317 S Park Ave, Winter Garden, FL 34787

Luxury

3 beds

2 baths

$2,980

$2,125

Price drop

House for rent

Available Nov 12

1091 Wickerwood St - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

Luxury | Walk-in closets | Swimming pool

3 beds

2 baths

$2,140

House for rent

Available Oct 27

Top amenities
On-Site Laundry
Swimming Pool
12951 Overstreet Rd - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

12951 Overstreet Rd, Windermere, FL 34786

Luxury | Walk-in closets | Swimming pool

4 beds

3 baths

$2,955

House for rent

Available Nov 17

Top amenities
Ceiling Fan
Hardwood Floor
High Ceilings
On-Site Laundry
Swimming Pool
8500 Sugar Palm Ct - Photo 1 of 1

3d ago

Our team has verified this company

Verified

8500 Sugar Palm Ct, Orlando, FL 32835

Luxury | Balcony | Swimming pool

4 beds

2 baths

$3,300

$3,160

Price drop

House for rent

Top amenities
In-Unit Laundry
On-Site Management
Listings within 10 miles
1239 Juniper Hammock St - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

1239 Juniper Hammock St, Winter Garden, FL 34787

Luxury | Walk-in closets | On-site laundry

5 beds

4 baths

$3,285

House for rent

Available Oct 30

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

5d+ ago

Our team has verified this company

Verified

744 Westcliffe Dr, Winter Garden, FL 34787

Luxury | Outdoor space | Garage parking

4 beds

2 baths

$2,945

House for rent

Available Nov 26

Top amenities
Garage Parking
Hardwood Floor
2297 Blake Way - Photo 1 of 1

1d 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

$2,265

House for rent

Available Dec 22

Top amenities
Ceiling Fan
Fireplace
On-Site Laundry
Showing 1 - 25 of 25 results
Home > House Rentals in Windermere > Windermere Luxury Houses For Rent
Updated: October 19, 2025

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Discover luxury Windermere, FL houses for rent

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