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Rentals Under $2,000/mo in Oldsmar, FL
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Buy

Start here

  • Homes for sale by state
  • Home buying tips
  • Before you start looking
  • The buying timeline

Afford it

  • Today's mortgage rates
  • Mortgage calculator
  • How much can I afford?
  • Get pre-approved

Make the deal

  • Writing a winning offer
  • Inspections & appraisals
  • Closing costs, itemized
  • Find a buyer's agent
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  • What's my home worth?
  • Compare selling options
  • Get an instant cash offer
  • Buy before you sell

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23 listings

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

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

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23 Listings
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Rentals Under $2,000/mo for Rent in Oldsmar, FL

23 Listings

  1. 121 Cypress Ln #121 — photo40Active

$1,850/mo

2 bd · 2 ba · 1,053 sqft

121 Cypress Ln #121, Oldsmar, FL

Vanessa Leonard · KELLER WILLIAMS REALTY- PALM HARBOR

  • 60 Woodlake Pl — photo38Active

    $1,800/mo

    2 bd · 2 ba · 924 sqft

    60 Woodlake Pl, Oldsmar, FL

    Karen Sewell · CHARLES RUTENBERG REALTY INC

  • 115 Windward Pl #115 — photo23Active

    $1,850/mo

    2 bd · 2 ba · 879 sqft

    115 Windward Pl #115, Oldsmar, FL

    Vanessa Leonard · KELLER WILLIAMS REALTY- PALM HARBOR

  • 123 Loblolly Ct #B — photo43Active

    $1,500/mo

    2 bd · 2 ba · 915 sqft

    123 Loblolly Ct #B, Oldsmar, FL

    Christina Paolillo · CHARLES RUTENBERG REALTY INC

  • 102 Palmetto Ct #2 — photo39Active

    $1,750/mo

    2 bd · 2 ba · 982 sqft

    102 Palmetto Ct #2, Oldsmar, FL

    Bedsy Renwanz · SANDPEAK REALTY

  • 216 Cypress Ln — photoPrice Reduced23Active

    $2,000/mo

    2 bd · 2 ba · 1,054 sqft

    216 Cypress Ln, Oldsmar, FL

    Fonda Dillard · BHHS FLORIDA PROPERTIES GROUP

  • 142 Woodlake Wynde #48 — photo17Active

    $1,600/mo

    2 bd · 2 ba · 924 sqft

    142 Woodlake Wynde #48, Oldsmar, FL

    Marsha Rantala, PA · FUTURE HOME REALTY INC

  • 435 Countryside Key Blvd — photo13Active

    $1,850/mo

    2 bd · 2 ba · 1,105 sqft

    435 Countryside Key Blvd, Oldsmar, FL

    Mindy Rovillo · IMAPP REALTY GROUP

  • 3136 St Clair Ave — photo1Active

    $1,700/mo

    2 bd · 2 ba · 1,075 sqft

    3136 St Clair Ave, Oldsmar, FL

    Nabil Basta · BASTA REALTY SOLUTIONS

  • 305 Meadow Ln #305 — photo27Active

    $1,700/mo

    2 bd · 2 ba · 879 sqft

    305 Meadow Ln #305, Oldsmar, FL

    Sandy Harris · PREFERRED REALTY GROUP, LLC

  • 208 Cypress Ct #208 — photoPrice Reduced25Active

    $1,675/mo

    2 bd · 2 ba · 1,054 sqft

    208 Cypress Ct #208, Oldsmar, FL

    Nick Acosta · LIPPLY REAL ESTATE

  • 270 Woodlake Wynde — photoPrice Reduced31Active

    $1,595/mo

    1 bd · 1 ba · 674 sqft

    270 Woodlake Wynde, Oldsmar, FL

    Karen Sewell · CHARLES RUTENBERG REALTY INC

  • 336 Countryside Key Blvd — photo27Active

    $1,895/mo

    2 bd · 3 ba · 1,110 sqft

    336 Countryside Key Blvd, Oldsmar, FL

    Qi Mai Mai · CENTURY 21 COASTAL ALLIANCE

  • 222 Caryl Way — photoPrice Reduced53Active

    $1,800/mo

    2 bd · 2 ba · 1,094 sqft

    222 Caryl Way, Oldsmar, FL

    Karen Sewell · CHARLES RUTENBERG REALTY INC

  • 134 Sycamore Ln #F — photoPrice Reduced24Active

    $1,500/mo

    2 bd · 2 ba · 915 sqft

    134 Sycamore Ln #F, Oldsmar, FL

    Jason Pithers · COLDWELL BANKER REALTY

  • 212 Caryl Way #212 — photoPrice Reduced22Active

    $2,000/mo

    3 bd · 2 ba · 1,292 sqft

    212 Caryl Way #212, Oldsmar, FL

    Mark Clark · RE/MAX REALTEC GROUP INC

  • 132 Douglas Rd W #a — photoPrice Reduced9Active

    $1,795/mo

    2 bd · 3 ba · 1,224 sqft

    132 Douglas Rd W #a, Oldsmar, FL

    Roy Kulp, PA · CHARLES RUTENBERG REALTY INC

  • 331 Countryside Key Blvd — photoPrice Reduced18Active

    $1,595/mo

    2 bd · 3 ba · 1,110 sqft

    331 Countryside Key Blvd, Oldsmar, FL

    Michael Spithoyanis · 1ST CLASS REAL ESTATE LLC

  • 115 Lakeview Pl #15 — photoPrice Reduced52Active

    $1,750/mo

    2 bd · 2 ba · 1,148 sqft

    115 Lakeview Pl #15, Oldsmar, FL

    Sibel Alpar · KELLER WILLIAMS SUBURBAN TAMPA

  • 108 Woodlands Ct #108 — photoPrice Reduced32Active

    $1,700/mo

    2 bd · 2 ba · 1,151 sqft

    108 Woodlands Ct #108, Oldsmar, FL

    Jo Walker · COASTAL PROPERTIES GROUP INTERNATIONAL

  • 135 Woodlake Wynde #135 — photoPrice Reduced31Active

    $1,950/mo

    2 bd · 2 ba · 924 sqft

    135 Woodlake Wynde #135, Oldsmar, FL

    Mark Fazzini · RE/MAX REALTEC GROUP INC

  • 250 Woodlake Wynde #250 — photoPrice Reduced17Active

    $1,600/mo

    2 bd · 2 ba · 924 sqft

    250 Woodlake Wynde #250, Oldsmar, FL

    Sandy Harris · PREFERRED REALTY GROUP, LLC

  • 336 Woodlake Wynde — photo45Active

    $2,000/mo

    2 bd · 2 ba · 924 sqft

    336 Woodlake Wynde, Oldsmar, FL

    Fonda Dillard · BHHS FLORIDA PROPERTIES GROUP

  • Explore Oldsmar rentals

    By price

    • Rentals Under $2,000/mo

    By bedrooms

    • 2 Bedroom Rentals
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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.

    Oldsmar, FL community profile

    Population
    15,092
    Median income
    $72,414
    Housing units
    6,425
    People per sq. mi.
    1,048.1
    Area
    14.4 sq. mi.

    Source: HJN community data