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, Wood Texture Flooring

Empty room, Interior, Recessed Lighting, Wood Texture Flooring

Bathroom, Interior, 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

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

Empty room, Interior, Marble, 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

Empty room, 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

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

Chandelier, Interior, Recessed Lighting, Wood Texture Flooring

Interior, Recessed Lighting, Wood Texture Flooring

Elevator, Interior, Recessed Lighting, Wood Texture Flooring

Interior, Marble, Recessed Lighting, Washer

Exterior, Fireplace, Outdoor Kitchen, 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, Interior, Marble Walls, Recessed Lighting

Bathroom, Free Standing Baths, Interior, Marble

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

$12,480

/ 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

Bedroom, Interior, Wood Texture Flooring

Chandelier, Interior, Wood Texture Flooring

Chandelier, Interior, Wooden Ceilings, Wood Texture Flooring

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

Interior, Living room, Recessed Lighting, Wood Texture Flooring

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

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

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

Fireplace, Interior, Recessed Lighting, Wooden Beams

Fireplace, Interior, Living room, Recessed Lighting, Wooden Beams, Wooden Ceilings, Wood Texture Flooring

Fitness Equipment, Interior, Wood Texture Flooring

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

Interior, Kitchen, Stainless Steel Appliances, Wood Texture Flooring

Bathroom, Dual Sink Vanities, Free Standing Baths, Interior, Recessed Lighting, Wooden Walls

$11,000

/ Month

1661 HILLCREST Ave, Winter Park, FL

4 br3 BA, 1 HALF BA3,104 sf

virtual tour

Listing Courtesy of ROYALTY R E BOUTIQUE INC, DOMENIQUE LOMBARDO - 407-474-7000

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

$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

price reduced

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

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

Interior, Kitchen, Recessed Lighting, Wood Texture Flooring

Empty room, Interior, Pendant Lights, Wood Texture Flooring

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

$6,995

/ Month

1205 MAYFIELD Ave, Winter Park, FL

4 br5 BA3,948 sf

virtual tour

Listing Courtesy of RE/MAX 200 REALTY, MO JABR - 407-571-1441

price reduced

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

Empty room, Fireplace, Interior, Wood Texture Flooring

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

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

Fireplace, Interior, Recessed Lighting, Wood Texture Flooring

Interior, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Fireplace, Interior, Wood Texture Flooring

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

$5,600

/ Month

960 GEORGIA Ave, Winter Park, FL

4 br4 BA3,654 sf

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

price reduced

Backyard, Exterior, Facade, Queen Anne Victorian

Chandelier, Empty room, Interior, Wood Texture Flooring

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

$5,200

/ 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

price reduced

Attached, Exterior, Facade, Brick Facade, Ranch

Interior, Kitchen, Wood Texture Flooring

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

Interior, Living room, Recessed Lighting

Dining room, Interior, Kitchen, Living room, Recessed Lighting, Stainless Steel Appliances

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

Bathroom, Dual Sink Vanities, Glass Shower, Interior, Recessed Lighting

$4,900

/ Month

2952 DE BROCY Way, Winter Park, FL

4 br2 BA, 1 HALF BA1,856 sf

virtual tour

Listing Courtesy of BELMONT REALTY, SUMMER HORNBURG - 407-495-8134

contract signed

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

Bathroom, Dual Sink Vanities, Interior, Recessed Lighting

$4,900

/ Month

159 BURKS Cir, Winter Park, FL

5 br3 BA2,508 sf

virtual tour

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

price reduced

Backyard, Exterior, Facade, Spanish Mediterranean

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

Chandelier, Interior, Kitchen, Pendant Lights, Recessed Lighting

Interior, Kitchen, Pendant Lights, Recessed Lighting

$4,850

/ 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

Interior, Kitchen, Pendant Lights, Wood Texture Flooring

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

Interior, Pendant Lights, Wood Texture Flooring

Interior, Living room, Pendant Lights, Wood Texture Flooring

Interior, Living room, Wood Texture Flooring

Interior, Sun Room, Wood Texture Flooring

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

$4,850

/ Month

104 S INTERLACHEN Ave 114, Winter Park, FL

2 br2 BA1,143 sf

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

price reduced

Dining room, Fireplace, Interior, Pendant Lights, Wood Texture Flooring

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

Home Office, Interior, Wood Texture Flooring

$4,800

/ Month

2227 HOWARD Dr, Winter Park, FL

3 br2 BA, 1 HALF BA2,196 sf

virtual tour

Listing Courtesy of REALTY ONE GROUP MAGIC CITY, JULIAN CORREA - 407-990-2360

Attached, Backyard, Exterior, Facade, Mediterranean

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

Dining room, Interior, Living room, Pendant Lights

Dining room, Interior, Living room, Pendant Lights, Wood Texture Flooring

Bedroom, Interior, Pendant Lights, Wood Texture Flooring

Fitness Equipment, Gym, Interior, Recessed Lighting

$4,750

/ Month

1368 BLUE STEM Ln, Winter Park, FL

4 br3 BA, 1 HALF BA2,589 sf

virtual tour

Listing Courtesy of ECO LUXE REALTY, STEPHEN DOWNES - 941-724-1086

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Luxury listings for rent in Winter Park

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2228 Winter Woods Blvd Blvd, Winter Park, FL

1740 STATE ROAD 436, Winter Park, FL

1976 W FAIRBANKS Ave, Winter Park, FL

1860 VIA CONTESSA, Winter Park, FL

649 N PARK Ave, Winter Park, FL

1661 HILLCREST Ave, Winter Park, FL

2020 VENETIAN Way, Winter Park, FL

1841 HARLAND PARK Dr, Winter Park, FL

1205 MAYFIELD Ave, Winter Park, FL

960 GEORGIA Ave, Winter Park, FL

1580 OAKHURST Ave, Winter Park, FL

2627 VERONA Trl, Winter Park, FL

2952 DE BROCY Way, Winter Park, FL

159 BURKS Cir, Winter Park, FL

1710 OAKHURST Ave, Winter Park, FL

104 S INTERLACHEN Ave 114, Winter Park, FL

2227 HOWARD Dr, Winter Park, FL

1368 BLUE STEM Ln, Winter Park, FL