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3 beds Houses With a pool

17 listings

Rentals with a Pool for Rent in Winter Park, FL

Rentals with a Pool for Rent in Winter Park, FL

17 Listings

Rentals with a Pool for Rent in Winter Park, FL

17 Listings

47Active

$8,500/mo

4 bd · 4 ba · 3,184 sqft

440 Clarendon Ave, Winter Park, FL

Meg Dolan · FANNIE HILLMAN & ASSOCIATES

$3,995/mo

3 bd · 4 ba · 1,760 sqft

737 Minnesota Ave, Winter Park, FL

Marilyn Kuczynski · FLORIDA HOMES SALES & MANAGEMENT LLC

$12,000/mo

4 bd · 4 ba · 3,553 sqft

541 W Canton Ave, Winter Park, FL

Bianca Khoury · PREMIER SOTHEBY'S INTL. REALTY

$7,500/mo

4 bd · 4 ba · 3,249 sqft

1750 Carollee Lane, Winter Park, FL

Michelle Hochfelder · PREMIER SOTHEBY'S INTL. REALTY

$2,500/mo

3 bd · 2 ba · 1,277 sqft

4870 Seminole Ave, Winter Park, FL

Tamara Mazo Ferro · COLDWELL BANKER REALTY

Price Reduced38Active

$2,798/mo

5 bd · 3 ba · 2,300 sqft

5354 Lanyard Ct, Winter Park, FL

Johanna Chandler · LPT REALTY, LLC

Price Reduced30Active

$3,800/mo

3 bd · 2 ba · 1,420 sqft

274 N Ranger Blvd, Winter Park, FL

Shannon Lee · EXPLORE FLORIDA REALTY SERVICES LLC

$10,000/mo

6 bd · 5 ba · 3,806 sqft

1620 Palm Ave, Winter Park, FL

Rob Gaudreau · MAINFRAME REAL ESTATE

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

Price Reduced42Active

$2,950/mo

4 bd · 3 ba · 2,151 sqft

7033 Easter St, Winter Park, FL

Tab Bish LLC · REAL BROKER, LLC

Price Reduced23Active

$4,000/mo

4 bd · 2 ba · 1,405 sqft

616 Ellendale Dr, Winter Park, FL

Elena Sanchez · BALDWIN PARK REALTY LLC

Price Reduced46Active

$7,250/mo

4 bd · 3 ba · 2,394 sqft

1368 Hibiscus Ave, Winter Park, FL

Patricia Zimath, LLC · CHARLES RUTENBERG REALTY ORLANDO

$9,900/mo

5 bd · 6 ba · 2,735 sqft

1442 Palm Ave, Winter Park, FL

Magdalena Cuprys · KELLER WILLIAMS REALTY AT THE PARKS

Price Reduced26Active

$7,995/mo

4 bd · 6 ba · 3,295 sqft

2234 Howard Dr, Winter Park, FL

Raquel Elliott · COLDWELL BANKER REALTY

Price Reduced20Active

$1,900/mo

2 bd · 1 ba · 1,500 sqft

151 N Orlando Ave #118, Winter Park, FL

Adriana Montes · FLORIDA DREAMS REALTY GRP INC

Price Reduced37Active

$1,700/mo

2 bd · 2 ba · 927 sqft

205 Lewfield Cir #205, Winter Park, FL

Eimi Moreno Carrera · LPT REALTY, LLC

Price Reduced15Active

$2,595/mo

3 bd · 2 ba · 1,650 sqft

3486 Bougainvillea Dr #B, Winter Park, FL

Smith Salomon · LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV

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With a pool

L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

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 with a Pool in Winter Park, FL