Winter Park | Luxury Homes for Rent & Real Estate

$226,700

/ Month

2228 Winter Woods Blvd Blvd, Winter Park, FL

88,268 sf

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

$158,700

/ Month

1740 STATE ROAD 436, Winter Park, FL

15,042 sf

virtual tour

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

Empty room, Interior, Marble, Recessed Lighting

Interior, Marble, Recessed Lighting, Wood Texture Flooring

Interior, Kitchen, Wood Texture Flooring

Empty room, Interior, Wood Texture Flooring

Dining room, Interior, Marble, Recessed Lighting

Bathroom, Glass Shower, Interior, Wood Texture Flooring, Wooden Walls

Bathroom, Glass Shower, Interior, Marble Walls, Wood Texture Flooring

$80,050

/ Month

2250 LEE Rd 100-120, Winter Park, FL

21,740 sf

virtual tour

Listing Courtesy of INNOVATIVE REALTY, LLC, JUSTIN RECCA - 407-772-5555

Empty room, Interior, Wooden Beams, Wood Texture Flooring

Interior, Stone Walls, Wood Texture Flooring

Bathroom, Interior, Wood Texture Flooring

Empty room, Interior, Stone Walls, Wood Texture Flooring

$56,400

/ Month

1790 STATE ROAD 436, Winter Park, FL

2,100 sf

Listing Courtesy of MILLENIUM REALTY GROUP, IGLI DOSTI - 407-760-7058

price reduced

$48,867

/ Month

931 S SEMORAN Blvd 208, Winter Park, FL

2,327 sf

Listing Courtesy of EXP REALTY LLC, NAUSHEEN AHMAD - 248-635-4219

Empty room, Interior, Recessed Lighting, Wood Texture Flooring

$42,140

/ Month

1976 W FAIRBANKS Ave, Winter Park, FL

1,925 sf

virtual tour

Listing Courtesy of DIDOMENICO REALTY GROUP, MICHAEL DIDOMENICO, JR - 407-922-3277

Interior, Recessed Lighting, Wood Texture Flooring

Interior, Kitchen, Recessed Lighting, Wood Texture Flooring

$35,775

/ Month

2828 Casa Aloma Way 600, Winter Park, FL

1,431 sf

virtual tour

Listing Courtesy of AFFINITY REALTY LLC, MATTHEW FONG - 321-274-3287

Attached, Exterior, Facade, French Provincial

Backyard, Exterior, Facade, French Provincial

Attached, Backyard, Exterior, Facade, Queen Anne Victorian

Glass Ceilings, Interior, Pool, Sun Room

Fireplace, Interior, Living room, Recessed Lighting, Wood Texture Flooring

Fireplace, Interior, Kitchen, Living room, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Dining room, Fireplace, Interior, Kitchen, Living room, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Home Office, Interior, Recessed Lighting, Wood Texture Flooring

Dining room, Interior, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Dining room, Interior, Kitchen, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Chandelier, Dining room, Interior, Kitchen, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Interior, Kitchen, Pendant Lights, Recessed Lighting, Stainless Steel Appliances, Wood Texture Flooring

Fireplace, Interior, Kitchen, Living room, Pendant Lights, Recessed Lighting, Stainless Steel Appliances, Wood Texture Flooring

Dining room, Interior, Kitchen, Living room, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Interior, Kitchen, Stainless Steel Appliances

Dining room, Interior, Kitchen, Pendant Lights, Recessed Lighting, Stainless Steel Appliances, Wood Texture Flooring

Chandelier, Dining room, Interior, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Interior, Walk-in Closets, Wood Texture Flooring

Bathroom, Glass Shower, Interior, Marble Walls, Recessed Lighting

Bedroom, Interior, Recessed Lighting, Wood Texture Flooring

Interior, Recessed Lighting, Walk-in Closets, Wood Texture Flooring

Bathroom, Dual Sink Vanities, Free Standing Baths, Glass Shower, Interior, Marble, Marble Walls, Recessed Lighting

Bathroom, Free Standing Baths, Interior, Marble, Marble Walls, Pendant Lights

Bathroom, Glass Shower, Interior, Marble Walls

Bathroom, Glass Shower, Interior, Marble, Marble Walls, Recessed Lighting

Bathroom, Free Standing Baths, Interior, Marble, Marble Walls

Bathroom, Bedroom, Glass Shower, Interior, Marble Walls, Recessed Lighting, Wood Texture Flooring

Bathroom, Bedroom, Dual Sink Vanities, Glass Shower, Interior, Marble, Marble Walls, Wood Texture Flooring

Bedroom, Home Office, Interior, Recessed Lighting, Wood Texture Flooring

Bathroom, Interior, Marble, Marble Walls, Wood Texture Flooring

Bathroom, Dual Sink Vanities, Interior, Marble, Marble Walls

Interior, Living room, Marble, Pendant Lights, Recessed Lighting

Dining room, Interior, Living room, Marble, Pendant Lights, Recessed Lighting

Dining room, Interior, Kitchen, Living room, Marble, Pendant Lights, Recessed Lighting

Interior, Living room, Marble, Recessed Lighting

Dining room, Interior, Kitchen, Marble, Pendant Lights, Recessed Lighting

Interior, Kitchen, Marble, Pendant Lights, Recessed Lighting

Bathroom, Glass Shower, Interior, Recessed Lighting

Bedroom, Interior, Marble, Recessed Lighting

Billiard Table, Game Room, Interior, Marble, Pendant Lights, Recessed Lighting

$19,500

/ Month

1860 VIA CONTESSA, Winter Park, FL

8 br6 BA7,000 sf

virtual tour

Listing Courtesy of SIERRA REALTY GROUP LLC, SYLVESTER HARDING - 407-557-3119

price reduced

Interior, Kitchen, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Interior, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Interior, Kitchen, Marble Walls, Recessed Lighting, Stainless Steel Appliances, Wood Texture Flooring

Chandelier, Interior, Kitchen, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Chandelier, Fireplace, Interior, Recessed Lighting, Wood Texture Flooring

Empty room, Fireplace, Interior, Recessed Lighting, Wood Texture Flooring

Chandelier, Empty room, Interior, Recessed Lighting, Wood Texture Flooring

Elevator, Interior, Recessed Lighting, Wood Texture Flooring

Interior, Marble, Recessed Lighting, Washer

Bathroom, Empty room, Interior, Recessed Lighting, Wood Texture Flooring

Fireplace, Interior, Wood Texture Flooring

Empty room, Interior, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Chandelier, Empty room, Interior, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Bathroom, Chandelier, Empty room, Interior, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Bathroom, Chandelier, Free Standing Baths, Interior, Marble

Bathroom, Chandelier, Dual Sink Vanities, Interior, Marble, Recessed Lighting

Bathroom, Free Standing Baths, Interior, Marble

Chandelier, Interior, Recessed Lighting, Walk-in Closets, Wood Texture Flooring

$14,900

/ Month

649 N PARK Ave, Winter Park, FL

3 br3 BA, 2 HALF BA3,180 sf

Listing Courtesy of PREMIER SOTHEBY'S INTL. REALTY, DREW HENNER - 407-406-0662

Dining room, Interior, Kitchen, Wood Texture Flooring

Interior, Living room, Recessed Lighting, Wood Texture Flooring

Interior, Kitchen, Stainless Steel Appliances, Wood Texture Flooring

Interior, Kitchen, Recessed Lighting, Stainless Steel Appliances, Wood Texture Flooring

Dining room, Interior, Kitchen, Living room, Pendant Lights, Recessed Lighting, Stainless Steel Appliances, Wood Texture Flooring

Chandelier, Dining room, Interior, Wood Texture Flooring

Chandelier, Dining room, Interior, Kitchen, Recessed Lighting, Wood Texture Flooring

Bathroom, Dual Sink Vanities, Interior, Recessed Lighting

Bathroom, Dual Sink Vanities, Glass Shower, Interior, Recessed Lighting, Wood Texture Flooring

Bathroom, Bedroom, Dual Sink Vanities, Interior, Recessed Lighting, Wood Texture Flooring

Home Office, Interior, Recessed Lighting

Attached, Backyard, Exterior, Facade, Farmhouse

$9,500

/ Month

1420 MAGNOLIA Ave, Winter Park, FL

4 br3 BA, 1 HALF BA3,174 sf

virtual tour

Listing Courtesy of HOST MANAGEMENT GROUP LLC, LUKASZ SOKOLOWSKI - 407-680-1234

price reduced

Fireplace, Interior, Stone Walls, Wooden Ceilings

Fireplace, Interior, Living room, Recessed Lighting, Stone Walls

Fireplace, Interior, Living room, Recessed Lighting, Stone Walls, Wooden Walls

Interior, Kitchen, Recessed Lighting, Stainless Steel Appliances

Fireplace, Interior, Pendant Lights, Recessed Lighting, Stone Walls

Empty room, Interior, Pendant Lights, Recessed Lighting

Empty room, Interior, Water, Wooden Ceilings, Wooden Walls

Empty room, Interior, Sun Room, Wooden Ceilings, Wood Texture Flooring

Bathroom, Glass Shower, Interior, Wood Texture Flooring

$8,990

/ Month

2020 VENETIAN Way, Winter Park, FL

4 br3 BA, 1 HALF BA4,188 sf

virtual tour

Listing Courtesy of PALMANO GROUP RE BROKERAGE LLC, NADIA MOAYERI - 310-877-2839

price reduced

Chandelier, Interior, Kitchen, Stainless Steel Appliances

Interior, Kitchen, Pendant Lights, Stainless Steel Appliances

Interior, Kitchen, Pendant Lights, Recessed Lighting, Stainless Steel Appliances

$7,150

/ Month

1841 HARLAND PARK Dr, Winter Park, FL

4 br3 BA, 1 HALF BA3,470 sf

virtual tour

Listing Courtesy of SELECTIVE REALTY GROUP LLC, CRAIG LUIZ - 407-493-0774

Bathroom, Dual Sink Vanities, Interior, Recessed Lighting, Tile Countertops

Empty room, Fireplace, Interior, Wood Texture Flooring

Bathroom, Dual Sink Vanities, Interior, Recessed Lighting, Wood Texture Flooring

Fireplace, Interior, Recessed Lighting, Wood Texture Flooring

$6,200

/ Month

960 GEORGIA Ave, Winter Park, FL

4 br4 BA3,654 sf

Listing Courtesy of CORCORAN PREMIER REALTY, ALISON ASHBY - 407-310-8209

Exterior, Facade, Brick Facade, Farmhouse

Empty room, Fireplace, Interior, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Empty room, Fireplace, Interior, Pendant Lights, Recessed Lighting, Stone Walls, Wood Texture Flooring

Billiard Table, Game Room, Interior, Recessed Lighting, Wooden Beams, Wood Texture Flooring, Wooden Walls

Billiard Table, Game Room, Interior, Pendant Lights, Recessed Lighting, Wooden Beams, Wood Texture Flooring, Wooden Walls

Billiard Table, Game Room, Interior, Living room, Recessed Lighting, Wooden Beams, Wood Texture Flooring, Wooden Walls

Interior, Sun Room, Wood Texture Flooring

Bathroom, Interior, Recessed Lighting, Wooden Beams

Bathroom, Bedroom, Glass Shower, Interior, Recessed Lighting, Wooden Beams, Wood Texture Flooring

Bedroom, Interior, Recessed Lighting, Wooden Beams, Wood Texture Flooring

Fitness Equipment, Interior, Wooden Beams

Interior, Wooden Beams, Wooden Ceilings, Wooden Walls

$6,000

/ Month

2330 WESTMINSTER Ct, Winter Park, FL

5 br3 BA3,296 sf

virtual tour

Listing Courtesy of COMPASS FLORIDA LLC, BRANDON GEERS - 941-928-5152

contract signed

Empty room, Fireplace, Interior, Kitchen, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Chandelier, Empty room, Fireplace, Interior, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Bathroom, Dual Sink Vanities, Interior, Recessed Lighting, Walk-in Closets

Bathroom, Interior, Recessed Lighting, Wood Texture Flooring

Bathroom, Glass Shower, Interior, Recessed Lighting, Wood Texture Flooring

Interior, Utility Closets, Washer, Wood Texture Flooring

$6,000

/ Month

1140 S PENNSYLVANIA Ave, Winter Park, FL

3 br3 BA2,390 sf

virtual tour

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

price reduced

Backyard, Exterior, Facade, Queen Anne Victorian

Chandelier, Empty room, Interior, Pendant Lights, Wood Texture Flooring

Chandelier, Empty room, Interior, Wood Texture Flooring

$5,400

/ Month

1580 OAKHURST Ave, Winter Park, FL

4 br2 BA, 1 HALF BA2,406 sf

Listing Courtesy of KELLER WILLIAMS WINTER PARK, LISA GOULD - 407-721-7612

Backyard, Exterior, Facade, Spanish Mediterranean

Empty room, Interior, Pendant Lights, Wood Texture Flooring

Empty room, Interior, Kitchen, Recessed Lighting, Wood Texture Flooring

Chandelier, Interior, Kitchen, Pendant Lights, Recessed Lighting

Interior, Kitchen, Pendant Lights, Recessed Lighting

$5,300

/ Month

1710 OAKHURST Ave, Winter Park, FL

4 br4 BA3,714 sf

virtual tour

Listing Courtesy of FANNIE HILLMAN & ASSOCIATES, JACKIE O'LEARY - 407-718-0887

price reduced

Attached, Exterior, Facade, Brick Facade, Ranch

Empty room, Fireplace, Interior, Stone Walls, Wood Texture Flooring

Fireplace, Interior, Stone Walls, Wood Texture Flooring

Bathroom, Dual Sink Vanities, Interior, Wood Texture Flooring

Bathroom, Empty room, Interior, Wood Texture Flooring

$5,050

/ Month

2627 VERONA Trl, Winter Park, FL

4 br3 BA2,422 sf

virtual tour

Listing Courtesy of REALSOURCE PROPERTY MANGNT LLC, RICK SEIN - 407-716-0459

FIND YOUR FAVORITE PLACE TO BE

FOR RENT

VIEW: MAP AND LIST

Luxury listings for rent in Winter Park

FEATURED IMAGE: DEFAULT

SORT BY: DE EXCLUSIVES

2228 Winter Woods Blvd Blvd, Winter Park, FL

1740 STATE ROAD 436, Winter Park, FL

2250 LEE Rd 100-120, Winter Park, FL

1790 STATE ROAD 436, Winter Park, FL

931 S SEMORAN Blvd 208, Winter Park, FL

1976 W FAIRBANKS Ave, Winter Park, FL

2828 Casa Aloma Way 600, Winter Park, FL

1860 VIA CONTESSA, Winter Park, FL

649 N PARK Ave, Winter Park, FL

1420 MAGNOLIA Ave, Winter Park, FL

2020 VENETIAN Way, Winter Park, FL

1841 HARLAND PARK Dr, Winter Park, FL

960 GEORGIA Ave, Winter Park, FL

2330 WESTMINSTER Ct, Winter Park, FL

1140 S PENNSYLVANIA Ave, Winter Park, FL

1580 OAKHURST Ave, Winter Park, FL

1710 OAKHURST Ave, Winter Park, FL

2627 VERONA Trl, Winter Park, FL