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Winter Park

Luxury listings for rent in Winter Park

18 of 18 Homes

COMPARE

$226,700

2228 Winter Woods Blvd Blvd, Winter Park, FL

Listing Courtesy of RS EQUITY SERVICE LLC., RADHA RAMBILAS - 347-557-4113

$158,700

1740 STATE ROAD 436, Winter Park, FL

Listing Courtesy of THE OUTLIER GROUP., JOYCE TEIXEIRA - 813-312-4231

$93,080

330 W MORSE BLVD 104, Winter Park, FL

Listing Courtesy of CORCORAN PREMIER REALTY., VINCENT SCARLATOS - 407-718-2378

$84,000

687 HAROLD, Winter Park, FL

Listing Courtesy of RCI REAL ESTATE INC.., DEVIN GREENE - 407-236-2380

$72,000

1501 W FAIRBANKS Ave, Winter Park, FL

Listing Courtesy of AMERICAN HORIZONS REALTY., ALEX FREIRE - 407-325-7215

$42,000

663 HAROLD, Winter Park, FL

Listing Courtesy of RCI REAL ESTATE INC.., DEVIN GREENE - 407-236-2380

$41,886

931 S SEMORAN 208, Winter Park, FL

Listing Courtesy of LPT REALTY, LLC., DANIEL YASELLS PEREZ - 321-947-5611

$29,150

2306 LEE Rd, Winter Park, FL

Listing Courtesy of CENTURY 21 CARIOTI., AHMED EL KOMY - 407-994-6154

$12,000

541 W CANTON, Winter Park, FL

4 br3 BA, 1 HALF BA3,553 sf

Listing Courtesy of PREMIER SOTHEBY'S INTL. REALTY., BIANCA KHOURY - 407-797-1121

$10,000

1620 PALM, Winter Park, FL

6 br4 BA, 1 HALF BA3,806 sf

Listing Courtesy of MAINFRAME REAL ESTATE., ROB GAUDREAU - 407-579-2737

$9,900

1442 PALM, Winter Park, FL

5 br6 BA2,735 sf

Listing Courtesy of KELLER WILLIAMS REALTY AT THE PARKS., MAGDALENA CUPRYS - 863-599-4101

$8,900

660 OSCEOLA 101, Winter Park, FL

3 br3 BA, 1 HALF BA2,714 sf

Listing Courtesy of CORCORAN PREMIER REALTY., JENNIFER KING - 407-595-3272

$8,500

440 CLARENDON, Winter Park, FL

4 br3 BA, 1 HALF BA3,184 sf

Listing Courtesy of FANNIE HILLMAN & ASSOCIATES., MEG DOLAN - 321-948-0701

$7,995

2234 HOWARD, Winter Park, FL

4 br5 BA, 1 HALF BA3,295 sf

Listing Courtesy of COLDWELL BANKER REALTY., RAQUEL ELLIOTT - 407-921-3772

$7,500

1750 CAROLLEE Ln, Winter Park, FL

4 br3 BA, 1 HALF BA3,249 sf

Listing Courtesy of PREMIER SOTHEBY'S INTL. REALTY., MICHELLE HOCHFELDER - 407-221-5073

$7,250

1368 HIBISCUS, Winter Park, FL

4 br2 BA, 1 HALF BA2,394 sf

Listing Courtesy of CHARLES RUTENBERG REALTY ORLANDO., PATRICIA ZIMATH, LLC - 321-318-1050

$6,000

1049 N KENTUCKY Ave, Winter Park, FL

3 br2 BA, 1 HALF BA2,112 sf

Listing Courtesy of THE AGENCY FL., TAB BISH LLC - 855-450-0442

$6,000

301 W COMSTOCK Ave, Winter Park, FL

2 br2 BA, 1 HALF BA1,500 sf

Listing Courtesy of THE SYDGAN CORP., SYDNEY BROWNLEE - 407-644-3151

Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. 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. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed.

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LAST UPDATE DATE On SEP 25 2026 AT 11:58 PM COORDINATED UNIVERSAL TIME (UTC).