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Luxury Houses for Rent in Winter Garden, FL

34 rentals available

7759 Green Mountain Way - Photo 1 of 1

5h ago

Luxury house for rent in Winter Garden

Residential Lease, WINTER GARDEN, FL

7759 Green Mountain Way, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

6 beds

6.5 baths

$6,950

353 Lake Amberleigh Dr - Photo 1 of 1

15h ago

Luxury house for rent in Winter Garden

353 Lake Amberleigh Dr, Winter Garden, FL 34787

Luxury | Swimming pool | In-unit laundry

4 beds

2.5 baths

$5,700

$4,985

Price drop

12597 Clear Sapphire Dr - Photo 1 of 1
New construction

1d ago

Luxury house for rent in Winter Garden

Beautiful fully furnished efficiency for rent in Winter Garden!

12597 Clear Sapphire Dr, Winter Garden, FL 34787

Luxury | Swimming pool | In-unit laundry

1 bed

1 bath

$1,300

15465 Hamlin Park Dr - Photo 1 of 1

2d ago

Luxury townhouse for rent in Winter Garden

15465 Hamlin Park Dr, Winter Garden, FL 34787

Luxury | Fitness center | In-unit laundry

3 beds

3.5 baths

$2,975

12462 Westfield Lakes Cir - Photo 1 of 1

2d ago

Luxury house for rent in Winter Garden

Residential Lease, WINTER GARDEN, FL

12462 Westfield Lakes Cir, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

4 beds

3 baths

$4,300

10 Broad St - Photo 1 of 1

2d ago

Luxury house for rent in Winter Garden

10 Broad St, Winter Garden, FL 34787

Luxury | In-unit laundry | Fireplace

3 beds

2 baths

$3,100

Nearby rental good for eco-living

$2,925

Oakland

Nearby rental good for pet owners

15066 Chapter Way - Photo 1 of 1

4d ago

Luxury townhouse for rent in Winter Garden

Residential Lease, WINTER GARDEN, FL

15066 Chapter Way, Winter Garden, FL 34787

Luxury | Swimming pool | Fitness center

3 beds

3 baths

$3,000

16477 Silver Brook Way - Photo 1 of 1
New construction

4d ago

Luxury house for rent in Winter Garden

Residential Lease, WINTER GARDEN, FL

16477 Silver Brook Way, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

5 beds

4.5 baths

$6,200

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15387 Hamlin Park Dr - Photo 1 of 1
New construction

5d+ ago

Luxury townhouse for rent in Winter Garden

Residential Lease, WINTER GARDEN, FL

15387 Hamlin Park Dr, Winter Garden, FL 34787

Luxury | Storage | Garage parking

3 beds

3.5 baths

$4,000

13504 Autumn Harvest Ave - Photo 1 of 1
New construction

5d+ ago

Luxury townhouse for rent in Winter Garden

Residential Lease, WINTER GARDEN, FL

13504 Autumn Harvest Ave, Winter Garden, FL 34787

Luxury | Swimming pool | In-unit laundry

3 beds

3 baths

$3,200

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Find sweet deals in Winter Garden

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

$1,300

12597 Clear Sapphire Dr

$2,550

747 Citrus Cove Dr

$2,560

1337 Brandy Lake View Cir

$2,399

1521 Loch Avich Rd

15027 Groveside Rd - Photo 1 of 1
New construction

5d+ ago

Luxury townhouse for rent in Winter Garden

Residential Lease, WINTER GARDEN, FL

15027 Groveside Rd, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

3 beds

2.5 baths

$3,150

15051 Groveside Rd - Photo 1 of 1
New construction

5d+ ago

Luxury townhouse for rent in Winter Garden

Residential Lease, WINTER GARDEN, FL

15051 Groveside Rd, Winter Garden, FL 34787

Luxury | Walk-in closets | Fitness center

3 beds

2.5 baths

$3,000

15039 Groveside Rd - Photo 1 of 1
New construction

5d+ ago

Luxury townhouse for rent in Winter Garden

Residential Lease, WINTER GARDEN, FL

15039 Groveside Rd, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

3 beds

2.5 baths

$3,000

6722 Havenleaf Ave - Photo 1 of 1
New construction

5d+ ago

Luxury house for rent in Winter Garden

Residential Lease, WINTER GARDEN, FL

6722 Havenleaf Ave, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

5 beds

3.5 baths

$5,200

$4,950

Price drop

10264 Love Story St - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Residential Lease, WINTER GARDEN, FL

10264 Love Story St, Winter Garden, FL 34787

Luxury | Swimming pool | Fitness center

5 beds

3 baths

$5,300

$4,900

Price drop

8204 Topsail Pl - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Residential Lease, WINTER GARDEN, FL

8204 Topsail Pl, Winter Garden, FL 34787

Luxury | Balcony | Walk-in closets

6 beds

5 baths

$6,000

15813 Sweet Lemon Way - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

15813 Sweet Lemon Way, Winter Garden, FL 34787

Luxury | Garage parking | On-site management

3 beds

2.5 baths

$2,945

720 Parkmont Pl - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

720 Parkmont Pl, Winter Garden, FL 34787

Luxury

3 beds

2 baths

$3,700

$3,000

Price drop

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17013 Haggerty Hollow Dr - Photo 1 of 1
New construction

5d+ ago

Luxury townhouse for rent in Winter Garden

Residential Lease, WINTER GARDEN, FL

17013 Haggerty Hollow Dr, Winter Garden, FL 34787

Luxury | In-unit laundry | Garage parking

3 beds

2.5 baths

$2,950

6366 Flat Lemon Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Residential Lease, WINTER GARDEN, FL

6366 Flat Lemon Dr, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

4 beds

3.5 baths

$4,250

17736 Porter Rd - Photo 1 of 1
New construction

5d+ ago

Luxury townhouse for rent in Winter Garden

Residential Lease, WINTER GARDEN, FL

17736 Porter Rd, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

3 beds

2.5 baths

$3,100

38 Live Oak Rd - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Residential Lease, WINTER GARDEN, FL

38 Live Oak Rd, Winter Garden, FL 34787

Luxury | In-unit laundry | Furnished

3 beds

3 baths

$5,250

671 E Plant St - Photo 1 of 1

5d+ ago

Luxury Courtlea Oaks townhouse for rent in Winter Garden

Residential Lease, WINTER GARDEN, FL

671 E Plant St, Winter Garden, FL 34787

Luxury | Swimming pool | In-unit laundry

3 beds

2.5 baths

$3,950

17740 Porter Rd - Photo 1 of 1
New construction

5d+ ago

Luxury townhouse for rent in Winter Garden

Residential Lease, WINTER GARDEN, FL

17740 Porter Rd, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

3 beds

2.5 baths

$3,000

467 Winter Grove Blvd - Photo 1 of 1
New construction

5d+ ago

Luxury house for rent in Winter Garden

WG 467 Winter Grove Boulevard

467 Winter Grove Blvd, Winter Garden, FL 34787

Luxury | Swimming pool | Fitness center

5 beds

3.5 baths

$4,995

15075 Tea Tree Dr - Photo 1 of 1
New construction

5d+ ago

Luxury house for rent in Winter Garden

Residential Lease, WINTER GARDEN, FL

15075 Tea Tree Dr, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

4 beds

3 baths

$5,800

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4753 Terrace Bluff St #1 - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

4753 Terrace Bluff Street - 1

4753 Terrace Bluff St #1, Winter Garden, FL 34787

Luxury | In-unit laundry | Air conditioning

4 beds

4.5 baths

$3,950

7573 Green Mountain Way - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

7573 Green Mountain Way, Winter Garden, FL 34787

Luxury | Swimming pool | Fitness center

4 beds

4 baths

$8,000

9247 LEGADO Drive - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Residential Lease, WINTER GARDEN, FL

9247 LEGADO Drive, Winter Garden, FL 34787

Luxury | In-unit laundry | Outdoor space

4 beds

2.5 baths

$5,500

15543 Waterleigh Cove Dr - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Garden

15543 Waterleigh Cove Dr, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

3 beds

2 baths

$2,950

17552 Lake Star Rd - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Residential Lease, WINTER GARDEN, FL

17552 Lake Star Rd, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

4 beds

3.5 baths

$4,500

16902 Hamlin Oasis Loop - Photo 1 of 1
New construction

5d+ ago

Luxury house for rent in Winter Garden

Residential Lease, WINTER GARDEN, FL

16902 Hamlin Oasis Loop, Winter Garden, FL 34787

Luxury | In-unit laundry | On-site laundry

3 beds

2.5 baths

$3,250

14411 Hampshire Bay Cir - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Residential Lease, WINTER GARDEN, FL

14411 Hampshire Bay Cir, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

4 beds

4 baths

$6,000

10207 Atwater Bay Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

10207 Atwater Bay Dr

10207 Atwater Bay Dr, Winter Garden, FL 34787

Luxury | Balcony | Swimming pool

5 beds

4.5 baths

$8,500

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Home > House Rentals in Winter Garden > Winter Garden Luxury Houses For Rent
Updated: September 26, 2026

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Pet friendly houses in Winter Garden, FL43 rentals

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