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

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

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24 of 162 Listings

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

24 of 162 Listings

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162 listings

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

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24 of 162 Listings

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

24 of 162 Listings

New19

Active

$1,300/mo

1 bd · 1 ba · 912 sqft

2025 San Marcos Dr SE #29, Winter Haven, FL

Avihai Sela · SAFETYNET REALTY

New35Active

$1,900/mo

3 bd · 2 ba · 1,716 sqft

1144 High Seas St, Winter Haven, FL

Amy Reynolds · LOCKHART & ASSOCIATES INC

17Active

$2,000/mo

3 bd · 3 ba · 1,386 sqft

3017 Captain Jax Way, Winter Haven, FL

Alisson Lopez Fuentes · LA ROSA REALTY ORLANDO LLC

18Active

$1,699/mo

3 bd · 2 ba · 1,357 sqft

247 Lake Eloise Pointe Blvd, Winter Haven, FL

Nancy Guadagnino · SPECIALIZED PROPERTY MANAGEMENT

6Active

$1,349/mo

2 bd · 1 ba · 914 sqft

3008 Saint Paul Dr #3008, Winter Haven, FL

Adan Ordonez · ADAN INVESTMENTS REAL ESTATE GROUP, PLLC

33Active

$1,950/mo

3 bd · 3 ba · 1,625 sqft

2533 Pine Pl, Winter Haven, FL

Jacob Hara · TRANSCEND REALTY

15Active

$1,799/mo

4 bd · 2 ba · 1,828 sqft

178 Fall Glo Rd, Winter Haven, FL

Nancy Guadagnino · SPECIALIZED PROPERTY MANAGEMENT

15Active

$1,195/mo

1 bd · 1 ba · 595 sqft

669 Avenue B NW #10, Winter Haven, FL

Colbey Amspaugh · COLBEY AMSPAUGH LICENSED REAL ESTATE BROKER

29Active

$1,800/mo

3 bd · 2 ba · 1,555 sqft

3942 Warbler Dr, Winter Haven, FL

Luanmarit Danos · SONARVI LLC

18Active

$1,150/mo

1 bd · 1 ba · 585 sqft

669 Avenue B NW #7, Winter Haven, FL

Colbey Amspaugh · COLBEY AMSPAUGH LICENSED REAL ESTATE BROKER

15Active

$1,195/mo

1 bd · 1 ba · 595 sqft

669 Avenue B NW #9, Winter Haven, FL

Colbey Amspaugh · COLBEY AMSPAUGH LICENSED REAL ESTATE BROKER

1Active

$500/mo

1 bd · 1 ba · 1,376 sqft

534 Avenue B NE #B, Winter Haven, FL

Rick Sein · REALSOURCE PROPERTY MANGNT LLC

12Active

$2,000/mo

3 bd · 2 ba · 1,560 sqft

216 Desoto Rd, Winter Haven, FL

Othner St. Fleurose · OSF REAL ESTATE SERVICE

7Active

$945/mo

2 bd · 1 ba · 644 sqft

2602 Trinity Cir NW #C, Winter Haven, FL

Jordan Clark · PALM LEAF PROPERTY MANAGEMENT

7Active

$1,050/mo

2 bd · 1 ba · 644 sqft

2600 Trinity Cir NW #C, Winter Haven, FL

Jordan Clark · PALM LEAF PROPERTY MANAGEMENT

12Active

$1,395/mo

2 bd · 2 ba · 1,073 sqft

259 Winter Ridge Blvd #259, Winter Haven, FL

Carmen Montes · CHARLES RUTENBERG REALTY ORLANDO

16Active

$1,450/mo

2 bd · 2 ba · 1,148 sqft

1550 11th St NE #F4, Winter Haven, FL

Julia Lombardo · LOMBARDO TEAM REAL ESTATE LLC

1Active

$1,400/mo

2 bd · 2 ba · 1,123 sqft

235 6th St NW #303, Winter Haven, FL

Linda Andre · COLDWELL BANKER REALTY

12Active

$950/mo

1 bd · 1 ba · 600 sqft

301 SE Avenue B #4, Winter Haven, FL

Liljana Masis · MASIS ROYALTY REAL ESTATE

14Active

$1,500/mo

3 bd · 2 ba · 1,077 sqft

601 Clayton Cir, Winter Haven, FL

Maritza Cruz · MIRANDA LANDA REALTY GROUP LLC

21Active

$1,795/mo

3 bd · 2 ba · 1,432 sqft

1688 Teagan Ln, Winter Haven, FL

Lucas Oliveira · HAINES AND HAVEN RESIDENTIAL

32Active

$1,895/mo

3 bd · 3 ba · 1,625 sqft

2417 Willow Way, Winter Haven, FL

Jacob Hara · TRANSCEND REALTY

Price Reduced16Active

$1,640/mo

3 bd · 1 ba · 1,000 sqft

206 4th Jpv St, Winter Haven, FL

Jessica Ennis · DARWIN HOMES, LLC.

Price Reduced11Active

$1,675/mo

3 bd · 2 ba · 1,426 sqft

1719 Terry Cir NE, Winter Haven, FL

Valentina Naumenko · MILA 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 Haven, FL community profile

Population: 58,351
Median income: $56,564
Housing units: 26,800
People per sq. mi.: 605.3
Area: 96.4 sq. mi.

Source: HJN community data

Explore Winter Haven 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 Haven, FL community profile

Population: 58,351
Median income: $56,564
Housing units: 26,800
People per sq. mi.: 605.3
Area: 96.4 sq. mi.

Source: HJN community data

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Listing data & MLS disclosures

Winter Haven, FL community profile

Explore Winter Haven rentals

Listing data & MLS disclosures

Winter Haven, FL community profile