Rentals Under $2,000/mo in Winter Park, FL

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3 beds Houses With a pool

Rentals Under $2,000/mo for Rent in Winter Park, FL

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24 of 40 Listings

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Rentals Under $2,000/mo for Rent in Winter Park, FL

24 of 40 Listings

24Active
$1,900/mo
2 bd · 2 ba · 1,173 sqft
2503 Tahoe Cir #2503, Winter Park, FL
Carissa Lawhun · FLORIDA REALTY INVESTMENTS
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
33Active
$2,000/mo
3 bd · 3 ba · 1,565 sqft
7101 Swallow Run, Winter Park, FL
Jackie O'Leary · FANNIE HILLMAN & ASSOCIATES
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
12Active
$1,800/mo
3 bd · 3 ba · 1,151 sqft
3367 River View Way #450, Winter Park, FL
Hao Jun Chang · CINO INTERNATIONAL INC
17Active
$1,800/mo
1 bd · 1 ba · 705 sqft
759 Antonette Ave, Winter Park, FL
Meg Dolan · FANNIE HILLMAN & ASSOCIATES
13Active
$1,600/mo
2 bd · 1 ba · 881 sqft
1695 Lee Rd #a113, Winter Park, FL
Yigit Orer · EMPIRE NETWORK REALTY
Price Reduced12Active
$1,099/mo
1 bd · 1 ba · 590 sqft
7309 Daniel Webster Dr #O4, Winter Park, FL
Nancy Guadagnino · SPECIALIZED PROPERTY MANAGEMENT
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
17Active
$1,640/mo
2 bd · 2 ba · 1,038 sqft
3068 Autumn Ct #Na, Winter Park, FL
Angela Fettig · KELLER WILLIAMS REALTY AT THE PARKS
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 Reduced19Active
$1,095/mo
1 bd · 1 ba · 735 sqft
1000 S Semoran Blvd #305, Winter Park, FL
Melissa Vance · MAINFRAME REAL ESTATE
Price Reduced13Active
$1,600/mo
2 bd · 3 ba · 1,031 sqft
3370 Cedar Springs Pl #156, Winter Park, FL
Wendy Lin · SPRINGHILL PROPERTIES LLC
Price Reduced20Active
$1,695/mo
2 bd · 1 ba · 800 sqft
1720 Miller Ave, Winter Park, FL
Bobby Keen · KEEN REALTY GROUP, INC.
82Active
$1,850/mo
3 bd · 2 ba · 1,149 sqft
1695 Lee Rd #E215, Winter Park, FL
Jenaia Fowlkes · FOWLKES REALTY CO
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

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