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

$52,358

/ 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

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

Interior, Wine Storage, Wood Texture Flooring

Chandelier, Dining room, Interior, Wood Texture Flooring

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

Fireplace, Interior, Recessed Lighting, Wood Texture Flooring

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

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

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

Bedroom, Chandelier, Interior, Pendant Lights, Wood Texture Flooring

Bathroom, Dual Sink Vanities, Interior, Recessed Lighting

Bathroom, Bedroom, Glass Shower, Interior, Pendant Lights, Recessed Lighting, Wood Texture Flooring

Bedroom, Interior, Pendant Lights, Wood Texture Flooring

Bedroom, Interior, Wood Texture Flooring

Home Office, Interior, Wood Texture Flooring

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

Home Office, Interior, Recessed Lighting, Wood Texture Flooring

$15,000

/ Month

1421 PLACE PICARDY, Winter Park, FL

5 br4 ba, 2 half ba4,461 sf

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

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

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

Glass Ceilings, Interior, Pool, Sun Room

Attached, Backyard, Exterior, Facade, Solar Panels, French Provincial

Bedroom, Chandelier, Interior, Wood Texture Flooring

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

Bedroom, Chandelier, Home Office, Interior

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

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

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

Interior, Kitchen, Marble Walls, Wood Texture Flooring

Chandelier, Interior, Wood Texture Flooring

Interior, Living room, Recessed Lighting, Wood Texture Flooring

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

Interior, Living room, Wood Texture Flooring

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

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

$10,500

/ Month

2234 VIA LUNA, Winter Park, FL

6 br3 ba, 1 half ba3,554 sf

virtual tour

Listing Courtesy of LOKATION, IRAM HASHMI - 703-626-5989

Detached Garage, Exterior, Facade, Georgian

Interior, Pendant Lights, Wood Texture Flooring

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

Empty room, Interior, Pendant Lights, Wood Texture Flooring

Bathroom, Dual Sink Vanities, Interior, Marble

Bathroom, Dual Sink Vanities, Interior, Marble, Wood Texture Flooring

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

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

Bathroom, Dual Sink Vanities, Interior, Wood Texture Flooring

Bathroom, Glass Shower, Interior, Wood Texture Flooring

Glass Ceilings, Interior, Pool, Sun Room, Wood Texture Flooring

$7,250

/ Month

1368 HIBISCUS Ave, Winter Park, FL

4 br2 ba, 1 half ba2,394 sf

virtual tour

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

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

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

Bedroom, Interior, Recessed Lighting, Walk-in Closets

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

$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

Bathroom, Glass Shower, Interior, Marble

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

price reduced

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

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

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

Interior, Kitchen, Stainless Steel Appliances

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

Bedroom, Interior, Living room, Pendant Lights, Recessed Lighting, Wood Texture Flooring

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

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

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

Dining room, Interior, Wood Texture Flooring

Interior, Utility Closets, Washer, Wood Texture Flooring

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

$5,500

/ Month

860 N DENNING Dr, Winter Park, FL

3 br2 ba, 1 half ba1,405 sf

virtual tour

Listing Courtesy of PROPERTIES IN TOWN, JAVIER PAREDES - 352-361-6478

contract signed | price reduced

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

Bathroom, Free Standing Baths, Interior, Wood Texture Flooring

$5,490

/ Month

782 S PENNSYLVANIA Ave 1, Winter Park, FL

3 br2 ba, 1 half ba2,354 sf

virtual tour

Listing Courtesy of BEYCOME OF FLORIDA LLC, STEVEN KOLENO - 804-656-5007

price reduced

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

FIND YOUR FAVORITE PLACE TO BE

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

1421 PLACE PICARDY, Winter Park, FL

649 N PARK Ave, Winter Park, FL

909 SEMINOLE Dr, Winter Park, FL

2234 VIA LUNA, Winter Park, FL

1368 HIBISCUS Ave, Winter Park, FL

2237 HOWARD Dr, Winter Park, FL

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

433 CAROLINA Ave, Winter Park, FL

860 N DENNING Dr, Winter Park, FL

782 S PENNSYLVANIA Ave 1, Winter Park, FL

1313 W FAIRBANKS Ave A, Winter Park, FL

336 BLUE HERON Dr, Winter Park, FL