2 Bedroom Rentals in Winter Park, FL

2 Bedroom Rentals for Rent in Winter Park, FL

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24 of 35 Listings

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2 Bedroom Rentals for Rent in Winter Park, FL

24 of 35 Listings

New15

35 listings

2 Bedroom Rentals for Rent in Winter Park, FL

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24 of 35 Listings

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2 Bedroom Rentals for Rent in Winter Park, FL

24 of 35 Listings

New15

Active

$1,895/mo

2 bd · 3 ba · 960 sqft

307 Sandlewood Trl, Winter Park, FL

Matthew Kirsch · REAL PROPERTY MANAGEMENT AND REALTY

New12Active

$1,525/mo

2 bd · 2 ba · 1,018 sqft

2941 Antique Oaks Cir #80, Winter Park, FL

Summer Hornburg · BELMONT REALTY

24Active

$1,900/mo

2 bd · 2 ba · 1,173 sqft

2503 Tahoe Cir #2503, Winter Park, FL

Carissa Lawhun · FLORIDA REALTY INVESTMENTS

45Active

$2,149/mo

2 bd · 3 ba · 1,250 sqft

2300 Barbados Dr, Winter Park, FL

Cristian Cen Chen · SIMPSON REALTY LLC

30Active

$2,500/mo

2 bd · 1 ba · 924 sqft

800 W Canton Ave, Winter Park, FL

Kelly Price · KELLY PRICE & COMPANY LLC

18Active

$1,600/mo

2 bd · 2 ba · 1,063 sqft

7453 Daniel Webster Dr #a5, Winter Park, FL

Laila Dkhissi · LA ROSA REALTY PREMIER LLC

13Active

$1,600/mo

2 bd · 2 ba · 1,020 sqft

163 Scottsdale Sq #163, Winter Park, FL

Simone Pinto de Almeida Santos · NOVA REAL ESTATE SERVICES INC

21Active

$1,550/mo

2 bd · 2 ba · 1,018 sqft

2918 Antique Oaks Cir #30, Winter Park, FL

Kyle Petteway · EXIT REAL ESTATE RESULTS

17Active

$2,000/mo

2 bd · 2 ba · 1,040 sqft

155 Stefanik Rd, Winter Park, FL

Paul Jimenez · URBANISTA BROKERS

12Active

$1,395/mo

2 bd · 2 ba · 840 sqft

3651 N Goldenrod Rd #C201, Winter Park, FL

Matthew Kirsch · REAL PROPERTY MANAGEMENT AND REALTY

18Active

$1,800/mo

2 bd · 1 ba · 737 sqft

1107 S Pennsylvania Ave, Winter Park, FL

Simone Pinto de Almeida Santos · NOVA REAL ESTATE SERVICES INC

14Active

$2,095/mo

2 bd · 3 ba · 1,550 sqft

2577 Galliano Cir, Winter Park, FL

Shawn Beard · RE/MAX 200 REALTY

13Active

$1,600/mo

2 bd · 1 ba · 881 sqft

1695 Lee Rd #a113, Winter Park, FL

Yigit Orer · EMPIRE NETWORK REALTY

Price Reduced18Active

$1,575/mo

2 bd · 2 ba · 840 sqft

3651 N Goldenrod Rd #a103, Winter Park, FL

Youree Lundy · KELLER WILLIAMS ADVANTAGE III

10Active

$1,700/mo

2 bd · 2 ba · 990 sqft

7336 Forest Hill Ct #240, Winter Park, FL

Mara Brasil · REALIZE INTERNATIONAL REALTY L

Price Reduced19Active

$1,695/mo

2 bd · 2 ba · 1,037 sqft

652 Saint Johns Ct #652, Winter Park, FL

Marina Gamundi · KELLER WILLIAMS ADVANTAGE III

19Active

$1,850/mo

2 bd · 3 ba · 1,495 sqft

2481 Tahoe Cir #2481, Winter Park, FL

Sebastian Lozano · COLDWELL BANKER REALTY

23Active

$1,995/mo

2 bd · 2 ba · 988 sqft

937 Aragon Ave, Winter Park, FL

Vivian Lippi · LIPPI REALTY LLC

Price Reduced20Active

$1,695/mo

2 bd · 1 ba · 800 sqft

1720 Miller Ave, Winter Park, FL

Bobby Keen · KEEN REALTY GROUP, INC.

Price Reduced14Active

$1,800/mo

2 bd · 1 ba · 1,604 sqft

1618 Indiana Ave, Winter Park, FL

Brock Stocksett · HOMEVEST REALTY

Price Reduced14Active

$1,800/mo

2 bd · 1 ba · 802 sqft

1618 Indiana Ave #1616, Winter Park, FL

Brock Stocksett · HOMEVEST REALTY

Price Reduced22Active

$1,595/mo

2 bd · 3 ba · 1,031 sqft

7446 Wynnewood Sq #190, Winter Park, FL

Scott Butts · KIMBRIDGE REALTY, LLC

Price Reduced10Active

$1,525/mo

2 bd · 2 ba · 1,024 sqft

2530 Kamnic Ct, Winter Park, FL

Matthew Kirsch · REAL PROPERTY MANAGEMENT AND REALTY

Price Reduced11Active

$1,450/mo

2 bd · 1 ba · 1,000 sqft

1434 Minnesota Ave, Winter Park, FL

Ruth Harris · COLDWELL BANKER REALTY

Listing data & MLS disclosures

Stellar MLS: 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. Copyright © 2026 MLS GRID. All Rights Reserved.

Winter Park, FL community profile

Population: 31,855
Median income: $98,252
Housing units: 15,404
People per sq. mi.: 1,409.5
Area: 22.6 sq. mi.

Source: HJN community data

Explore Winter Park rentals

Listing data & MLS disclosures

Stellar MLS: 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. Copyright © 2026 MLS GRID. All Rights Reserved.

Winter Park, FL community profile

Population: 31,855
Median income: $98,252
Housing units: 15,404
People per sq. mi.: 1,409.5
Area: 22.6 sq. mi.

Source: HJN community data

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Listing data & MLS disclosures

Winter Park, FL community profile

Explore Winter Park rentals

Listing data & MLS disclosures

Winter Park, FL community profile