Houses for Rent in Winter Garden, FL

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ABOUT THIS HOME
House for Rent in Winter Garden:
Experience effortless living in this beautifully furnished 1-bedroom, 1-bathroom garage apartment in the highly desirable Oakland Trails community. Ideally located near the West Orange Trail,...

$1,595/mo

1 bed1 bath576 sq ft

2089 White Feather Loop, Oakland, FL 34787

Pets welcome • A/C • Car-dependent

(407) 408-7616

ABOUT THIS HOME
House for Rent in Winter Garden:
Four Bedroom 2 bath Chapin Station Winter Garden home with NEW LAMINATE FLOORING throughout, VAULTED ceilings, HUGE family room and Lanai! Spacious master suite features a garden tub, and separate...

$2,995/mo

Total price

4 beds2 baths2,047 sq ft

1239 Dunbrooke St, Winter Garden, FL 34787

Available 09/15 • Car-dependent

(407) 306-7700

ABOUT THIS HOME
House for Rent in Winter Garden:
This 3 bedroom 2 bath home is located in the Regency Oaks community near local shops, dining, and schools with quick access to West Colonial, 429, the Turnpike, the 408, and the Winter Garden...

$2,795/mo

3 beds2 baths1,668 sq ft

442 Home Grove Dr, Winter Garden, FL 34787

Pets welcome • Parking • A/C

ABOUT THIS HOME
House for Rent in Winter Garden:
Please note, our homes are available on a first-come, first-serve basis and are not reserved until the lease is signed by all applicants and security deposits are collected. Rent this home by August...

$2,405/mo

3 beds2.5 baths1,857 sq ft

1725 Portcastle Cir, Winter Garden, FL 34787

Parking • A/C • Car-dependent

(833) 252-7403

ABOUT THIS HOME
House for Rent in Winter Garden:
Apply now or schedule your self-tour today and take the first step toward getting more than just a place to live. Rent with FirstKey Homes for a home that's right for you, plus professional service...

$2,721/mo

Total price

4 beds2.5 baths1,606 sq ft

1961 Portcastle Cir, Winter Garden, FL 34787

Available 09/02 • Pets welcome • A/C

(844) 395-3959

ABOUT THIS HOME
House for Rent in Winter Garden:
Charming two-story home for rent offering 3 bedrooms, 2.5 bathrooms, and a spacious loft, perfect for a home office, playroom, or additional living space. The main living area and upstairs loft...

$2,600/mo

3 beds2.5 baths1,857 sq ft

1944 Portcastle Cir, Winter Garden, FL 34787

Pets welcome • Laundry in unit • Parking

Property at 1708 Portcastle Cir, Winter Garden, FL, 34787, 4 beds, 2.5 baths, [object Object]

$2,429/mo

4 beds2.5 baths1,606 sq ft

1708 Portcastle Cir, Winter Garden, FL 34787

Property at 12946 Grovehurst Ave, Winter Garden, FL, 34787, 4 beds, 2.5 baths, [object Object]

$3,100/mo

4 beds2.5 baths2,529 sq ft

12946 Grovehurst Ave, Winter Garden, FL 34787

Property at 739 Reflections Ln, Winter Garden, FL, 34787, 4 beds, 2.5 baths, [object Object]

$3,400/mo

4 beds2.5 baths4,046 sq ft

739 Reflections Ln, Winter Garden, FL 34787

Property at 806 Lost Grove Cir, Winter Garden, FL, 34787, 5 beds, 3 baths, [object Object]

$3,495/mo

5 beds3 baths3,462 sq ft

806 Lost Grove Cir, Winter Garden, FL 34787

Property at 720 Parkmont Pl, Winter Garden, FL, 34787, 3 beds, 2 baths, [object Object]

$3,965/mo

3 beds2 baths2,210 sq ft

720 Parkmont Pl, Winter Garden, FL 34787

Property at 703 Bainbridge Loop, Winter Garden, FL, 34787, 3 beds, 2 baths, [object Object]

$2,999/mo

3 beds2 baths2,022 sq ft

703 Bainbridge Loop, Winter Garden, FL 34787

Property at 6206 Point Hancock Dr, Winter Garden, FL, 34787, 4 beds, 3.5 baths, [object Object]

$3,100/mo

4 beds3.5 baths3,177 sq ft

6206 Point Hancock Dr, Winter Garden, FL 34787

Property at 8119 Laughing Gull St, Winter Garden, FL, 34787, 4 beds, 2 baths, [object Object]

$3,500/mo

4 beds2 baths2,043 sq ft

8119 Laughing Gull St, Winter Garden, FL 34787

Property at 2158 Wintermere Pointe Dr, Winter Garden, FL, 34787, 4 beds, 3 baths, [object Object]

$3,600/mo

4 beds3 baths2,966 sq ft

2158 Wintermere Pointe Dr, Winter Garden, FL 34787

Property at 314 S Boyd St, Winter Garden, FL, 34787, 2 beds, 2 baths, [object Object]

$2,050/mo

2 beds2 baths1,054 sq ft

314 S Boyd St, Winter Garden, FL 34787

Property at 1105 Lincoln Ter, Winter Garden, FL, 34787, 3 beds, 1 bath, [object Object]

$2,000/mo

3 beds1 bath814 sq ft

1105 Lincoln Ter, Winter Garden, FL 34787

Property at 1030 Maxey Dr, Winter Garden, FL, 34787, 4 beds, 1.5 baths, [object Object]

$1,846/mo

4 beds1.5 baths1,289 sq ft

1030 Maxey Dr, Winter Garden, FL 34787

Property at 1198 Maxey Dr, Winter Garden, FL, 34787, 3 beds, 1.5 baths, [object Object]

$1,890/mo

3 beds1.5 baths1,145 sq ft

1198 Maxey Dr, Winter Garden, FL 34787

Property at 747 Citrus Cove Dr, Winter Garden, FL, 34787, 4 beds, 2 baths, [object Object]

$2,680/mo

4 beds2 baths1,990 sq ft

747 Citrus Cove Dr, Winter Garden, FL 34787

Property at 1331 Daniels Cove Dr, Winter Garden, FL, 34787, 4 beds, 2 baths, [object Object]

$2,500/mo

4 beds2 baths1,371 sq ft

1331 Daniels Cove Dr, Winter Garden, FL 34787

Property at 273 Avalon Rd, Winter Garden, FL, 34787, 4 beds, 2 baths, [object Object]

$2,995/mo

4 beds2 baths2,459 sq ft

273 Avalon Rd, Winter Garden, FL 34787

Property at 1631 Sherbourne St, Winter Garden, FL, 34787, 3 beds, 2.5 baths, [object Object]

$2,680/mo

3 beds2.5 baths1,709 sq ft

1631 Sherbourne St, Winter Garden, FL 34787

Property at 1914 Sherbourne St, Winter Garden, FL, 34787, 3 beds, 2.5 baths, [object Object]

$2,625/mo

3 beds2.5 baths1,356 sq ft

1914 Sherbourne St, Winter Garden, FL 34787

Property at 1938 Sherbourne St, Winter Garden, FL, 34787, 3 beds, 2 baths, [object Object]

$2,475/mo

3 beds2 baths1,260 sq ft

1938 Sherbourne St, Winter Garden, FL 34787

Property at 1078 Woodson Hammock Cir, Winter Garden, FL, 34787, 4 beds, 2 baths, [object Object]

$2,949/mo

4 beds2 baths2,505 sq ft

1078 Woodson Hammock Cir, Winter Garden, FL 34787

Property at 1337 Brandy Lake View Cir, Winter Garden, FL, 34787, 4 beds, 2 baths, [object Object]

$2,595/mo

4 beds2 baths1,813 sq ft

1337 Brandy Lake View Cir, Winter Garden, FL 34787

Property at 559 Grand Royal Cir, Winter Garden, FL, 34787, 3 beds, 2 baths, [object Object]

$2,215/mo

3 beds2 baths1,268 sq ft

559 Grand Royal Cir, Winter Garden, FL 34787

Property at 2227 Oakington St, Winter Garden, FL, 34787, 4 beds, 2 baths, [object Object]

$2,995/mo

4 beds2 baths1,867 sq ft

2227 Oakington St, Winter Garden, FL 34787

Property at 988 Glenview Cir, Winter Garden, FL, 34787, 4 beds, 3 baths, [object Object]

$2,596/mo

4 beds3 baths2,022 sq ft

988 Glenview Cir, Winter Garden, FL 34787

Property at 2413 Prairie View Dr, Winter Garden, FL, 34787, 4 beds, 3 baths, [object Object]

$4,000/mo

4 beds3 baths3,000 sq ft

2413 Prairie View Dr, Winter Garden, FL 34787

Property at 15219 Starleigh Rd, Winter Garden, FL, 34787, 3 beds, 2.5 baths, [object Object]

$2,500/mo

3 beds2.5 baths1,492 sq ft

15219 Starleigh Rd, Winter Garden, FL 34787

Property at 3425 Turningwind Ln, Winter Garden, FL, 34787, 6 beds, 4 baths, [object Object]

$5,600/mo

6 beds4 baths3,210 sq ft

3425 Turningwind Ln, Winter Garden, FL 34787

Property at 181 Zachary Wade St, Winter Garden, FL, 34787, 5 beds, 3 baths, [object Object]

$3,200/mo

5 beds3 baths2,950 sq ft

181 Zachary Wade St, Winter Garden, FL 34787

Property at 1544 Loch Avich Rd, Winter Garden, FL, 34787, 4 beds, 2.5 baths, [object Object]

$2,981/mo

4 beds2.5 baths2,199 sq ft

1544 Loch Avich Rd, Winter Garden, FL 34787

Property at 14413 Magnolia Ridge Loop, Winter Garden, FL, 34787, 3 beds, 3 baths, [object Object]

$3,400/mo

3 beds3 baths2,203 sq ft

14413 Magnolia Ridge Loop, Winter Garden, FL 34787

Property at 17987 Gourd Neck Loop, Winter Garden, FL, 34787, 6 beds, 4 baths, [object Object]

$5,400/mo

6 beds4 baths4,704 sq ft

17987 Gourd Neck Loop, Winter Garden, FL 34787

Property at 9240 Woodcrane Dr, Winter Garden, FL, 34787, 5 beds, 4 baths, [object Object]

$4,799/mo

5 beds4 baths3,760 sq ft

9240 Woodcrane Dr, Winter Garden, FL 34787

Property at 17459 Chateau Pine Way, Clermont, FL, 34711, 3 beds, 2.5 baths, [object Object]

$2,700/mo

3 beds2.5 baths1,944 sq ft

17459 Chateau Pine Way, Clermont, FL 34711

Property at 9306 Mira Valle Ln, Winter Garden, FL, 34787, 3 beds, 2.5 baths, [object Object]

$2,850/mo

3 beds2.5 baths1,956 sq ft

9306 Mira Valle Ln, Winter Garden, FL 34787

Property at 9350 Woodcrane Dr, Winter Garden, FL, 34787, 3 beds, 2.5 baths, [object Object]

$2,850/mo

3 beds2.5 baths1,829 sq ft

9350 Woodcrane Dr, Winter Garden, FL 34787

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Based on information submitted to the MLS GRID as of Fri Aug 14 2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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