Houses Under $2000 for Rent in Winter Haven, FL

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ABOUT THIS HOME
House Under $2000 for Rent in Winter Haven:
Private Room with Independent Entrance Experience privacy, comfort, and convenience in this recently remodeled private room with its own entrance, perfect for long-term stays. Located in a quiet nei

$800/mo

1 bed1 bath120 sq ft

604 Glad Rd Unit 5, Winter Haven, FL 33880

A/C • Dishwasher • Patio/Balcony

ABOUT THIS HOME
House Under $2000 for Rent in Winter Haven:
Cozy and clean private bedroom available for rent in a modern-build corner lot home located in Winter Haven. This listing is for the master bedroom with a private bathroom. Comes with everything shown

$750/mo

1 bed1 bath— sq ft

1806 Wallace Manor Ln, Winter Haven, FL 33880

Dogs welcome • Laundry in unit • A/C

ABOUT THIS HOME
House Under $2000 for Rent in Winter Haven:
home for rent in winterhaven located in the city of chain of lakes, disney, legoland and bok tower gardens. 90 mins from Tampa, bush gardens and spring parks. 50 mins to orlando near attractions disne

$1,500/mo

2 beds1 bath910 sq ft

611 34th St NW, Winter Haven, FL 33880

Cats welcome • Laundry in unit • A/C

ABOUT THIS HOME
House Under $2000 for Rent in Winter Haven:
high ceiling , great bedroom size , full kitchen and bathrrooms

$1,900/mo

4 beds2 baths1,948 sq ft

821 Cambridge Dr, Winter Haven, FL 33881

Laundry in unit • A/C • Dishwasher

ABOUT THIS HOME
House Under $2000 for Rent in Winter Haven:
AVAILABLE to rent August 1,2025 Two story Lakefront Townhouse, on chain of lakes, beautiful lake views from screened balcony and patio. Great in town location ( SE Winter Haven) walk to stores and re

$1,650/mo

2 beds1.5 baths1,320 sq ft

2374 Isle Royale Ct SE, Winter Haven, FL 33880

A/C • Dishwasher • Car-dependent

ABOUT THIS HOME
House Under $2000 for Rent in Winter Haven:
Available October 01, 2025. Newly interior painted and new carpet will be installed soon on the entire 2nd floor where the two bedroom suites are. New gas water heater. This property is located in the

$1,725/mo

2 beds2.5 baths1,281 sq ft

2376 Isle Royale Ct SE, Winter Haven, FL 33880

A/C • Dishwasher • Car-dependent

Property at 604 Glad Rd Unit 1, Winter Haven, FL, 33880, 1 bed, 1 bath, [object Object]

$750/mo

1 bed1 bath120 sq ft

604 Glad Rd Unit 1, Winter Haven, FL 33880

Property at 604 Glad Rd Unit 4, Winter Haven, FL, 33880, 1 bed, 1 bath, [object Object]

$750/mo

1 bed1 bath120 sq ft

604 Glad Rd Unit 4, Winter Haven, FL 33880

Property at 604 Glad Rd Unit 2, Winter Haven, FL, 33880, 1 bed, 1 bath, [object Object]

$750/mo

1 bed1 bath120 sq ft

604 Glad Rd Unit 2, Winter Haven, FL 33880

Property at 604 Glad Rd Unit 3, Winter Haven, FL, 33880, 1 bed, 1 bath, [object Object]

$750/mo

1 bed1 bath120 sq ft

604 Glad Rd Unit 3, Winter Haven, FL 33880

Property at 2648 Whispering Trails Dr, Winter Haven, FL, 33884, 3 beds, 2 baths, [object Object]

$1,550/mo

3 beds2 baths1,432 sq ft

2648 Whispering Trails Dr, Winter Haven, FL 33884

Property at 1286 Salisbury Dr, Winter Haven, FL, 33881, 4 beds, 2.5 baths, [object Object]

$1,995/mo

4 beds2.5 baths1,816 sq ft

1286 Salisbury Dr, Winter Haven, FL 33881

Property at 2665 Whispering Trails Dr, Winter Haven, FL, 33884, 4 beds, 2.5 baths, [object Object]

$1,939/mo

4 beds2.5 baths2,203 sq ft

2665 Whispering Trails Dr, Winter Haven, FL 33884

Property at 2672 Rutledge Ct, Winter Haven, FL, 33884, 2 beds, 2 baths, [object Object]

$1,900/mo

2 beds2 baths1,419 sq ft

2672 Rutledge Ct, Winter Haven, FL 33884

Property at 4520 Magnolia Preserve Ln, Winter Haven, FL, 33880, 3 beds, 2 baths, [object Object]

$1,849/mo

3 beds2 baths1,378 sq ft

4520 Magnolia Preserve Ln, Winter Haven, FL 33880

Property at 2401 Avenue A Ter NW, Winter Haven, FL, 33880, 3 beds, 2 baths, [object Object]

$1,895/mo

3 beds2 baths1,401 sq ft

2401 Avenue A Ter NW, Winter Haven, FL 33880

Property at 2614 Rutledge Ct, Winter Haven, FL, 33884, 2 beds, 2 baths, [object Object]

$1,699/mo

2 beds2 baths1,419 sq ft

2614 Rutledge Ct, Winter Haven, FL 33884

Property at 5887 Royal Hills Cir, Winter Haven, FL, 33881, 3 beds, 2 baths, [object Object]

$1,895/mo

3 beds2 baths1,836 sq ft

5887 Royal Hills Cir, Winter Haven, FL 33881

Property at 5761 Royal Hills Cir, Winter Haven, FL, 33881, 4 beds, 2 baths, [object Object]

$1,950/mo

4 beds2 baths2,148 sq ft

5761 Royal Hills Cir, Winter Haven, FL 33881

Property at 704 Overlook Grove Dr, Winter Haven, FL, 33884, 3 beds, 2 baths, [object Object]

$1,800/mo

3 beds2 baths1,275 sq ft

704 Overlook Grove Dr, Winter Haven, FL 33884

Property at 2633 Rutledge Ct, Winter Haven, FL, 33884, 2 beds, 2 baths, [object Object]

$1,650/mo

2 beds2 baths1,419 sq ft

2633 Rutledge Ct, Winter Haven, FL 33884

Property at 310 White Ibis Ln, Winter Haven, FL, 33884, 3 beds, 2 baths, [object Object]

$1,800/mo

3 beds2 baths1,674 sq ft

310 White Ibis Ln, Winter Haven, FL 33884

Property at 2181 Rose Blvd, Winter Haven, FL, 33881, 4 beds, 2.5 baths, [object Object]

$1,715/mo

4 beds2.5 baths2,121 sq ft

2181 Rose Blvd, Winter Haven, FL 33881

Property at 1632 Wallace Manor Blvd, Winter Haven, FL, 33880, 3 beds, 2 baths, [object Object]

$1,795/mo

3 beds2 baths1,556 sq ft

1632 Wallace Manor Blvd, Winter Haven, FL 33880

Property at 2689 Whispering Trails Dr, Winter Haven, FL, 33884, 3 beds, 2 baths, [object Object]

$1,850/mo

3 beds2 baths1,432 sq ft

2689 Whispering Trails Dr, Winter Haven, FL 33884

Property at 1811 Galloway Ter, Winter Haven, FL, 33881, 4 beds, 3 baths, [object Object]

$1,959/mo

4 beds3 baths2,248 sq ft

1811 Galloway Ter, Winter Haven, FL 33881

Property at 4140 Sophia Blvd, Winter Haven, FL, 33881, 3 beds, 2 baths, [object Object]

$1,750/mo

3 beds2 baths1,650 sq ft

4140 Sophia Blvd, Winter Haven, FL 33881

Property at 1811 5th St SE, Winter Haven, FL, 33880, 3 beds, 2 baths, [object Object]

$2,000/mo

3 beds2 baths1,852 sq ft

1811 5th St SE, Winter Haven, FL 33880

Property at 4214 Roberta Dr, Winter Haven, FL, 33881, 3 beds, 2 baths, [object Object]

$1,999/mo

3 beds2 baths1,690 sq ft

4214 Roberta Dr, Winter Haven, FL 33881

Property at 4237 Roberta Dr, Winter Haven, FL, 33881, 3 beds, 2 baths, [object Object]

$1,570/mo

3 beds2 baths1,711 sq ft

4237 Roberta Dr, Winter Haven, FL 33881

Property at 2164 Rose Blvd, Winter Haven, FL, 33881, 4 beds, 2 baths, [object Object]

$1,999/mo

4 beds2 baths1,851 sq ft

2164 Rose Blvd, Winter Haven, FL 33881

Property at 2410 Avenue C NW, Winter Haven, FL, 33880, 2 beds, 1 bath, [object Object]

$2,000/mo

2 beds1 bath— sq ft

2410 Avenue C NW, Winter Haven, FL 33880

Property at 4907 Summerfield Cir, Winter Haven, FL, 33881, 3 beds, 2 baths, [object Object]

$1,875/mo

3 beds2 baths1,688 sq ft

4907 Summerfield Cir, Winter Haven, FL 33881

Property at 4844 Summerfield Cir, Winter Haven, FL, 33881, 4 beds, 2 baths, [object Object]

$1,975/mo

4 beds2 baths1,756 sq ft

4844 Summerfield Cir, Winter Haven, FL 33881

Property at 1256 Salisbury Dr, Winter Haven, FL, 33881, 3 beds, 2 baths, [object Object]

$1,950/mo

3 beds2 baths1,836 sq ft

1256 Salisbury Dr, Winter Haven, FL 33881

Property at 2011 9th St NE, Winter Haven, FL, 33881, 3 beds, 2 baths, [object Object]

$1,650/mo

3 beds2 baths1,415 sq ft

2011 9th St NE, Winter Haven, FL 33881

Property at 1413 Wallace Manor Pass, Winter Haven, FL, 33880, 4 beds, 2 baths, [object Object]

$1,745/mo

4 beds2 baths1,842 sq ft

1413 Wallace Manor Pass, Winter Haven, FL 33880

Property at 6610 Crescent Loop, Winter Haven, FL, 33884, 3 beds, 2 baths, [object Object]

$1,900/mo

3 beds2 baths1,181 sq ft

6610 Crescent Loop, Winter Haven, FL 33884

Property at 4833 St James Ct, Winter Haven, FL, 33881, 3 beds, 2 baths, [object Object]

$1,895/mo

3 beds2 baths1,828 sq ft

4833 St James Ct, Winter Haven, FL 33881

Property at 2160 San Marcos Cir SE Unit 33880, Winter Haven, FL, 33880, 2 beds, 2 baths, [object Object]

$1,500/mo

2 beds2 baths1,250 sq ft

2160 San Marcos Cir SE Unit 33880, Winter Haven, FL 33880

Property at 6279 Red Herring Dr, Winter Haven, FL, 33881, 4 beds, 2 baths, [object Object]

$1,819/mo

4 beds2 baths1,852 sq ft

6279 Red Herring Dr, Winter Haven, FL 33881

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Based on information submitted to the MLS GRID as of Thu Sep 18 2025. 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.

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Houses Under $2000 for Rent in Winter Haven, FL

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