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

Interior, Recessed Lighting, Wood Texture Flooring

Empty room, 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

price reduced

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

Interior, Pendant Lights, Recessed Lighting, Wood Texture Flooring

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

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

Interior, Walk-in Closets, 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

Interior, Recessed Lighting, Walk-in Closets, 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

Attached, Exterior, Facade, Mediterranean

Attached, Exterior, Facade, Spanish Mediterranean

Chandelier, Interior, Wooden Beams, Wood Texture Flooring

Chandelier, Fireplace, Interior, Pendant Lights, Wooden Beams, Wood Texture Flooring

Interior, Wooden Beams, Wood Texture Flooring

Chandelier, Empty room, Fireplace, Interior, Wooden Beams, Wood Texture Flooring

Fireplace, Interior, Pendant Lights, Wooden Beams, Wood Texture Flooring

Interior, Kitchen, Stainless Steel Appliances, Wood Texture Flooring

Interior, Recessed Lighting, Wooden Beams, Wood Texture Flooring

Chandelier, Empty room, Interior, Wood Texture Flooring

Bathroom, Dual Sink Vanities, Glass Shower, Interior

$14,000

/ Month

909 SEMINOLE Dr, Winter Park, FL

3 br2 ba2,009 sf

virtual tour

Listing Courtesy of KELLY PRICE & COMPANY LLC, KELLY PRICE - 407-645-4321

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

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

Interior, Kitchen, Recessed Lighting, Stone Walls, Wood Texture Flooring

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

Dining room, Interior, Pendant Lights, Wood Texture Flooring

Home Office, Interior, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Bedroom, Interior, Recessed Lighting, Wood Texture Flooring

Bathroom, Interior, Recessed Lighting, Wood Texture Flooring

Bedroom, Interior, Water, Wood Texture Flooring

$6,800

/ Month

2237 HOWARD Dr, Winter Park, FL

3 br2 ba, 1 half ba2,008 sf

virtual tour

Listing Courtesy of COLEDEV REAL ESTATE LLC, RYAN FEELY - 321-663-1433

price reduced

Interior, Living room, Recessed Lighting

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

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

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

Dining room, Interior, Recessed Lighting

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

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

Interior, Sun Room, Wood Texture Flooring

Home Office, Interior, Wood Texture Flooring

Bedroom, Interior, Recessed Lighting, Walk-in Closets

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

Bathroom, Dual Sink Vanities, Interior, Marble

$6,800

/ Month

311 E MORSE Blvd 2-3, Winter Park, FL

2 br2 ba1,964 sf

virtual tour

Listing Courtesy of CHARLES RUTENBERG REALTY ORLANDO, ASHLEY JACOBS - 407-448-6310

price reduced

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

Interior, Living room, Recessed Lighting, Wood Texture Flooring

Bathroom, Glass Shower, Interior, Marble

Bedroom, Interior, Wood Texture Flooring

Bathroom, Dual Sink Vanities, Interior, Recessed Lighting

Bathroom, Glass Shower, Interior, Recessed Lighting

$5,995

/ Month

433 CAROLINA Ave, Winter Park, FL

5 br3 ba, 1 half ba2,700 sf

virtual tour

Listing Courtesy of LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV, VALENTINA RODRIGUEZ - 407-486-5312

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

Interior, Kitchen, Stainless Steel Appliances

Interior, Kitchen, Recessed Lighting, Stainless Steel Appliances

Fitness Equipment, Interior, Wood Texture Flooring

$5,900

/ 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

price reduced

Chandelier, Dining room, Interior, Living room, Recessed Lighting, Wooden Beams, Wood Texture Flooring

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

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

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

Chandelier, Dining room, Interior, Living room, Wood Texture Flooring

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

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

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

Home Office, Interior, Pendant Lights, Wood Texture Flooring

$5,750

/ Month

1791 SPRUCE Ave, Winter Park, FL

3 br2 ba1,776 sf

virtual tour

Listing Courtesy of KELLER WILLIAMS WINTER PARK, BETSY BRETON-GARCIA, PA - 407-580-5350

Backyard, Exterior, Facade, Queen Anne Victorian

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

Empty room, Fireplace, Interior, Wood Texture Flooring

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

$5,600

/ 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

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

Interior, Kitchen, Pendant Lights, 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

price reduced

Dining room, Interior, Wood Texture Flooring

Interior, Living room, Wood Texture Flooring

Home Office, Interior, Living room, Recessed Lighting, Wooden Beams, Wood Texture Flooring

Home Office, Interior, Recessed Lighting, Wooden Beams, Wood Texture Flooring

Dining room, Interior, Recessed Lighting, Wood Texture Flooring

Dining room, Interior, Living room, Wooden Beams, Wood Texture Flooring

Dining room, Interior, Wooden Beams, Wood Texture Flooring

Home Office, Interior, Living room, Recessed Lighting, Wood Texture Flooring

Dining room, Interior, Living room, Recessed Lighting, Wooden Beams

Interior, Recessed Lighting, Wooden Beams

$4,740

/ Month

1313 W FAIRBANKS Ave A, Winter Park, FL

3,000 sf

virtual tour

Listing Courtesy of INVESTOR'S REAL ESTATE LLC, FREDDIE CRESPO - 407-687-0634

Interior, Living room, Stone Walls, Wood Texture Flooring

$4,600

/ Month

336 BLUE HERON Dr, Winter Park, FL

3 br2 ba, 1 half ba1,754 sf

virtual tour

Listing Courtesy of LPT REALTY, LLC, CLAUDIA MONTES - 407-484-5261

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

Bathroom, Dual Sink Vanities, Glass Shower, Interior, Marble

$4,340

/ Month

332 N PHELPS Ave, Winter Park, FL

3 br2 ba1,570 sf

virtual tour

Listing Courtesy of KELLER WILLIAMS REALTY AT THE PARKS, DAVID DRAWDY, JR. - 407-629-4420

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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

2250 LEE Rd 100-120, Winter Park, FL

1790 STATE ROAD 436, Winter Park, FL

931 S SEMORAN Blvd 208, Winter Park, FL

2828 Casa Aloma Way 600, Winter Park, FL

649 N PARK Ave, Winter Park, FL

909 SEMINOLE Dr, Winter Park, FL

2237 HOWARD Dr, Winter Park, FL

311 E MORSE Blvd 2-3, Winter Park, FL

433 CAROLINA Ave, Winter Park, FL

2227 HOWARD Dr, Winter Park, FL

1791 SPRUCE Ave, Winter Park, FL

1580 OAKHURST Ave, Winter Park, FL

2952 DE BROCY Way, Winter Park, FL

1313 W FAIRBANKS Ave A, Winter Park, FL

336 BLUE HERON Dr, Winter Park, FL

332 N PHELPS Ave, Winter Park, FL