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Luxury Houses for Rent in Winter Garden, FL

44 rentals

15601 Dahoon Holly Ln - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

15601 Dahoon Holly Ln, Winter Garden, FL 34787

Luxury | Fitness center | In-unit laundry

4 beds

2 baths

$4,200

House for rent

Top amenities
Dishwasher
Fitness Center
In-Unit Laundry
7267 Summerlake Groves St - Photo 1 of 1

4d ago

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7267 Summerlake Groves St Winter Garden, FL 34787

7267 Summerlake Groves St, Winter Garden, FL 34787

Luxury | Walk-in closets | Outdoor space

3 beds

2 baths

$3,165

House for rent

Available Sep 18

16124 Azure Key St - Photo 1 of 1

3m ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

16124 Azure Key St, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

5 beds

4 baths

$4,800

House for rent

Top amenities
Ceiling Fan
Fitness Center
Garage Parking
In-Unit Laundry
On-Site Laundry
Storage
15702 Shorebird Ln - Photo 1 of 1

23h ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

15702 Shorebird Ln, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

5 beds

4 baths

$5,300

$5,100

Price drop

House for rent

Top amenities
Carpet
Fitness Center
Garage Parking
Hardwood Floor
In-Unit Laundry
Swimming Pool
4624 Prairie Creek St - Photo 1 of 1

2d ago

Luxury house for rent in Winter Garden

4624 Prairie Creek St, Winter Garden, FL 34787

Luxury | Swimming pool | Fitness center

3 beds

2 baths

$3,100

$2,900

Price drop

House for rent

Top amenities
Dishwasher
In-Unit Laundry
1301 1301 Eastern Pecan Place-207 #207 - Photo 1 of 1

3d ago

Luxury townhouse for rent in Winter Garden

1301 1301 Eastern Pecan Place-207 #207, Winter Garden, FL 34787

Luxury | Swimming pool | In-unit laundry

1 bed

1 bath

$1,400

House for rent

Top amenities
Controlled Access
In-Unit Laundry
Microwave
Residents Lounge

Nearby rental good for eco-living

Nearby rental good for pet owners

Nearby rental good for social life

228 Deepcove Rd - Photo 1 of 1

4d ago

Luxury townhouse for rent in Winter Garden

228 Deepcove Rd, Winter Garden, FL 34787

Luxury

2 beds

2 baths

$2,250

$1,995

Price drop

House for rent

14336 Orchard Hills Blvd - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

14336 Orchard Hills Blvd, Winter Garden, FL 34787

Luxury | Fitness center | In-unit laundry

3 beds

2 baths

$2,990

House for rent

Top amenities
Carpet
Dishwasher
Garage Parking
In-Unit Laundry
On-Site Laundry
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15465 Hamlin Park Dr - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Garden

15465 Hamlin Park Dr, Winter Garden, FL 34787

Luxury | Fitness center | In-unit laundry

3 beds

3 baths

$3,100

House for rent

Top amenities
Dishwasher
Fitness Center
In-Unit Laundry
Microwave
8926 Bismarck Palm Dr - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Garden

Townhouse - WINTER GARDEN, FL

8926 Bismarck Palm Dr, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

3 beds

2 baths

$2,900

House for rent

Top amenities
Ceiling Fan
Dishwasher
Garage Parking
In-Unit Laundry
Swimming Pool
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Find sweet deals in Winter Garden

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

$1,400

1301 1301 Eastern Pecan Place-207 #207

$1,795

17528 Placidity Ave

$1,549

633 W Ella J Gilmore St

$2,875

6472 Tabebuia Pkwy

11045 Bostwick Aly - Photo 1 of 1
New construction

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

11045 Bostwick Aly, Winter Garden, FL 34787

Luxury | Walk-in closets | Fitness center

4 beds

3 baths

$4,000

House for rent

Top amenities
Dishwasher
Fitness Center
Garage Parking
In-Unit Laundry
On-Site Laundry
Storage
9849 Lost Creek Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

9849 Lost Creek Dr, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

5 beds

3 baths

$5,500

House for rent

Top amenities
Dishwasher
In-Unit Laundry
Swimming Pool
5204 Citrus Leaf Blvd - Photo 1 of 1
New construction

5d+ ago

Luxury house for rent in Winter Garden

5204 Citrus Leaf Blvd, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

5 beds

4 baths

$5,000

$4,800

Price drop

House for rent

Top amenities
Dishwasher
In-Unit Laundry
8186 Topsail Pl - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

8186 Topsail Pl, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

5 beds

4 baths

$5,100

House for rent

Top amenities
Carpet
Dishwasher
Fitness Center
Garage Parking
In-Unit Laundry
On-Site Laundry
14037 Pecan Orchard Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

14037 Pecan Orchard Dr, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

5 beds

4 baths

$4,800

House for rent

Top amenities
Carpet
Dishwasher
Garage Parking
In-Unit Laundry
On-Site Laundry
14423 Hampshire Bay Cir - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

14423 Hampshire Bay Cir, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

4 beds

3 baths

$5,500

House for rent

Top amenities
Ceiling Fan
Dishwasher
Furnished
Garage Parking
High Ceilings
In-Unit Laundry
760 Walkers Grove Ln - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Garden

Townhouse - WINTER GARDEN, FL

760 Walkers Grove Ln, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

3 beds

2 baths

$3,000

House for rent

Top amenities
Garage Parking
In-Unit Laundry
5957 Glory Bower Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

5957 Glory Bower Dr, Winter Garden, FL 34787

Luxury | Swimming pool | In-unit laundry

3 beds

2 baths

$3,200

House for rent

Top amenities
Garage Parking
In-Unit Laundry
On-Site Laundry
Swimming Pool
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1369 Broken Oak Dr #46A - Photo 1 of 1

5d+ ago

Luxury Tucker Oaks townhouse for rent in Winter Garden

1369 Broken Oak Dr #46A, Winter Garden, FL 34787

Luxury

2 beds

2 baths

$1,950

House for rent

9378 Bradleigh Dr - Photo 1 of 1
New construction

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

9378 Bradleigh Dr, Winter Garden, FL 34787

Luxury | Balcony | Walk-in closets

4 beds

3 baths

$4,950

House for rent

Top amenities
Carpet
Dishwasher
Hardwood Floor
High Ceilings
In-Unit Laundry
Swimming Pool
16555 Wingspread Loop - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

16555 Wingspread Loop, Winter Garden, FL 34787

Luxury | Swimming pool | Fitness center

4 beds

3 baths

$4,400

House for rent

Top amenities
Carpet
Dishwasher
Garage Parking
High Ceilings
In-Unit Laundry
694 Brooks Field Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

694 Brooks Field Dr, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

6 beds

4 baths

$6,500

House for rent

Top amenities
Carpet
Dishwasher
High Ceilings
In-Unit Laundry
11015 Hollow Bay Dr - Photo 1 of 1
New construction

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

11015 Hollow Bay Dr, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

4 beds

3 baths

$4,800

House for rent

Top amenities
Dishwasher
Garage Parking
In-Unit Laundry
6364 Tabebuia Pkwy - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Garden

Townhouse - Winter Garden, FL

6364 Tabebuia Pkwy, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

3 beds

2 baths

$2,900

House for rent

Top amenities
Garage Parking
In-Unit Laundry
Swimming Pool
5885 Chestnut Chase Rd - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Garden

5885 Chestnut Chase Rd, Winter Garden, FL 34787

Luxury | Swimming pool | Fitness center

2 beds

2 baths

$2,500

House for rent

9225 Holliston Creek Pl - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

9225 Holliston Creek Pl, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

5 beds

4 baths

$5,000

House for rent

Top amenities
Air Conditioning
Carpet
Dishwasher
Garage Parking
Storage
Swimming Pool
Advertisement
14005 Peach Orchard Way - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

14005 Peach Orchard Way, Winter Garden, FL 34787

Luxury | Swimming pool | In-unit laundry

5 beds

3 baths

$4,800

House for rent

Top amenities
In-Unit Laundry
16689 Broadwater Ave - Photo 1 of 1
3D tour

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

16689 Broadwater Ave, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

7 beds

6 baths

$9,980

House for rent

Top amenities
Dishwasher
Garage Parking
High Ceilings
In-Unit Laundry
16944 Hamlin Oasis Loop - Photo 1 of 1
New construction

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

16944 Hamlin Oasis Loop, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

3 beds

2 baths

$3,100

House for rent

Top amenities
Garage Parking
In-Unit Laundry
17061 Seville Orange Rd - Photo 1 of 1
New construction

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

17061 Seville Orange Rd, Winter Garden, FL 34787

Luxury | Swimming pool | In-unit laundry

3 beds

2 baths

$3,100

House for rent

Top amenities
Dishwasher
In-Unit Laundry
5954 Cypress Hill Rd - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

5954 Cypress Hill Rd, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

4 beds

3 baths

$4,300

House for rent

Top amenities
Carpet
Ceiling Fan
Dishwasher
In-Unit Laundry
Storage
Swimming Pool
17582 Lake Star Rd - Photo 1 of 1
New construction

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

17582 Lake Star Rd, Winter Garden, FL 34787

Luxury | In-unit laundry | Outdoor space

4 beds

3 baths

$4,850

House for rent

Top amenities
In-Unit Laundry
12500 Encore At Ovation Way - Photo 1 of 1
New construction

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

12500 Encore At Ovation Way, Winter Garden, FL 34787

Luxury | In-unit laundry | Garage parking

3 beds

2 baths

$3,200

House for rent

Top amenities
High Ceilings
In-Unit Laundry
12832 Lavender Bloom Aly - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

12832 Lavender Bloom Aly, Winter Garden, FL 34787

Luxury | Dishwasher

3 beds

2 baths

$3,250

House for rent

Advertisement
11051 Bostwick Aly - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

11051 Bostwick Aly, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

3 beds

2 baths

$3,000

House for rent

Top amenities
Dishwasher
Furnished
In-Unit Laundry
Swimming Pool
7984 Wood Sage Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

7984 Wood Sage Dr, Winter Garden, FL 34787

Luxury | Swimming pool | Fitness center

3 beds

2 baths

$3,100

House for rent

Top amenities
Fitness Center
Hardwood Floor
In-Unit Laundry
16090 Malay Ginger Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

16090 Malay Ginger Dr, Winter Garden, FL 34787

Luxury | Walk-in closets | Fitness center

4 beds

3 baths

$4,250

House for rent

Top amenities
Ceiling Fan
Dishwasher
Fitness Center
Garage Parking
In-Unit Laundry
17882 Adrift Rd - Photo 1 of 1
New construction

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

17882 Adrift Rd, Winter Garden, FL 34787

Luxury | Swimming pool | Fitness center

4 beds

3 baths

$3,999

House for rent

Top amenities
Dishwasher
Fitness Center
In-Unit Laundry
Swimming Pool
7514 John Hancock Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

7514 John Hancock Dr, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

5 beds

5 baths

$11,000

House for rent

Top amenities
Dishwasher
Fitness Center
Garage Parking
In-Unit Laundry
1350 Winter Green Way - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Garden

Townhouse - WINTER GARDEN, FL

1350 Winter Green Way, Winter Garden, FL 34787

Luxury | In-unit laundry | Ceiling fan

2 beds

1 bath

$2,000

House for rent

Top amenities
In-Unit Laundry
17552 Lake Star Rd - Photo 1 of 1
New construction

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

17552 Lake Star Rd, Winter Garden, FL 34787

Luxury | In-unit laundry | Outdoor space

4 beds

3 baths

$5,000

House for rent

Top amenities
Carpet
Garage Parking
In-Unit Laundry
7519 Mandarin Grove Way - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

7519 Mandarin Grove Way, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

5 beds

4 baths

$5,130

House for rent

Top amenities
Ceiling Fan
Garage Parking
In-Unit Laundry
Microwave
On-Site Laundry
Advertisement
14676 Seton Creek Blvd - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

14676 Seton Creek Blvd, Winter Garden, FL 34787

Luxury | Swimming pool | In-unit laundry

3 beds

2 baths

$3,000

House for rent

Top amenities
In-Unit Laundry
On-Site Laundry
14791 Crimson Bluff Aly - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

14791 Crimson Bluff Aly, Winter Garden, FL 34787

Luxury | Swimming pool | Outdoor space

3 beds

2 baths

$2,900

House for rent

Showing 1 - 44 of 44 results
Home > House Rentals in Winter Garden > Winter Garden Luxury Houses For Rent
Updated: September 27, 2025

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Pet friendly houses in Winter Garden, FL36 rentals

36 rentals

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Discover luxury Winter Garden, FL houses for rent

🌇Available luxury house rentals44 houses
⭐Popular amenities, ,
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