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3 beds Houses With a pool

88 listings

Rentals Under $5,000/mo for Rent in Winter Park, FL

Rentals Under $5,000/mo for Rent in Winter Park, FL

24 of 88 Listings

Rentals Under $5,000/mo for Rent in Winter Park, FL

24 of 88 Listings

23Active

$2,300/mo

2 bd · 1 ba · 709 sqft

500 N Pennsylvania Ave #G, Winter Park, FL

Sylvia Young · FLORIDA RENTAL TEAM

$2,200/mo

3 bd · 2 ba · 1,266 sqft

Address withheld · Winter Park, FL

Kirsten Cantello · TRUSTHOME PROPERTIES INC

$1,900/mo

2 bd · 2 ba · 1,173 sqft

2503 Tahoe Cir #2503, Winter Park, FL

Carissa Lawhun · FLORIDA REALTY INVESTMENTS

$2,149/mo

2 bd · 3 ba · 1,250 sqft

2300 Barbados Dr, Winter Park, FL

Cristian Cen Chen · SIMPSON REALTY LLC

$2,800/mo

3 bd · 3 ba · 2,378 sqft

2305 Shadowland Loop, Winter Park, FL

Laura Lerma · 2 GOOD REALTY

$2,500/mo

2 bd · 1 ba · 924 sqft

800 W Canton Ave, Winter Park, FL

Kelly Price · KELLY PRICE & COMPANY LLC

$2,300/mo

4 bd · 3 ba · 1,611 sqft

7487 Canford Ct #5, Winter Park, FL

Jiny Lee · THE FLORIDA LOUNGE REALTY LLC

$3,995/mo

3 bd · 4 ba · 1,760 sqft

737 Minnesota Ave, Winter Park, FL

Marilyn Kuczynski · FLORIDA HOMES SALES & MANAGEMENT LLC

$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

$2,800/mo

5 bd · 4 ba · 1,442 sqft

2181 Linden Rd, Winter Park, FL

Paula Chavez · KELLER WILLIAMS ADVANTAGE III

$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

$2,000/mo

3 bd · 3 ba · 1,565 sqft

7101 Swallow Run, Winter Park, FL

Jackie O'Leary · FANNIE HILLMAN & ASSOCIATES

$1,550/mo

2 bd · 2 ba · 1,018 sqft

2918 Antique Oaks Cir #30, Winter Park, FL

Kyle Petteway · EXIT REAL ESTATE RESULTS

$4,140/mo

4 bd · 4 ba · 3,094 sqft

2352 Kestrel Perch Pl, Winter Park, FL

Angela Fettig · KELLER WILLIAMS REALTY AT THE PARKS

$2,000/mo

2 bd · 2 ba · 1,040 sqft

155 Stefanik Rd, Winter Park, FL

Paul Jimenez · URBANISTA BROKERS

$3,500/mo

3 bd · 3 ba · 1,715 sqft

1667 Mizell Ave, Winter Park, FL

Justin LaManna · HOMEVEST REALTY

$2,400/mo

3 bd · 2 ba · 1,570 sqft

2809 W Fairbanks Ave, Winter Park, FL

Anne Coburn · H. & H. REALTY, INC.

$2,100/mo

3 bd · 2 ba · 1,174 sqft

3217 Royal St, Winter Park, FL

Stephen Murphy · DALTON WADE INC

$2,200/mo

3 bd · 2 ba · 1,467 sqft

Address withheld · Winter Park, FL

Kirsten Cantello · TRUSTHOME PROPERTIES INC

$2,500/mo

3 bd · 2 ba · 1,277 sqft

4870 Seminole Ave, Winter Park, FL

Tamara Mazo Ferro · COLDWELL BANKER REALTY

$1,395/mo

2 bd · 2 ba · 840 sqft

3651 N Goldenrod Rd #C201, Winter Park, FL

Matthew Kirsch · REAL PROPERTY MANAGEMENT AND REALTY

Price Reduced38Active

$2,798/mo

5 bd · 3 ba · 2,300 sqft

5354 Lanyard Ct, Winter Park, FL

Johanna Chandler · LPT REALTY, LLC

$2,800/mo

3 bd · 3 ba · 2,308 sqft

2452 Firstlight Way, Winter Park, FL

Yan Zuo · EAST PEARL REALTY

$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

1 2…4

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The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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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

Rentals Under $5,000/mo in Winter Park, FL