91

Winter Haven, FL Houses for Rent under $2,000

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  • /6

    $1,300 per month

    • 1 Bed
    • 1 Bath
    • 2,109 Sq Ft
    • House for Rent

    1453 Austin St Unit B, Winter Haven, FL 33884

    Charming PRIVATE ENTRANCE 1 - NEW bedroom apartment available for rent! Welcome to your new home! This beautiful apartment with living room, kitchen, 1 bathroom and 1 bedroom. Located in a quiet and friendly neighborhood in Eagle Lake, this space offers all the comfort and convenience you need. As for the location, it is close to shopping centers, restaurants, parks and public transportation.

    Agent Photo

    Isabel Melin Mora

    MELIN REALTY LLC

    (863) 208-5449

    1453 Austin St Unit B, Winter Haven, FL 33884
  • /11

    $1,600 per month

    • 2 Beds
    • 1 Bath
    • 626 Sq Ft
    • House for Rent

    1756 2nd St NE, Winter Haven, FL 33881

    VACANT, MOVE-IN READY & PET FRIENDLY! Lease for just $1,600/month! Located in the lovely and up-and-coming Winter Haven area, this completely remodeled historic 1930s home has been beautifully restored to its former glory. This charming home offers 2 bedrooms and 1 well-appointed full bathroom, perfect for comfortable living. Situated on an oversized, fully fenced corner lot—perfect for pets—the

    Agent Photo

    Daniel Hut

    HUT REALTY, LLC

    (863) 887-8920

    1756 2nd St NE, Winter Haven, FL 33881
  • /31

    $1,800 total monthly price

    • 4 Beds
    • 2 Baths
    • 1,368 Sq Ft
    • House for Rent

    3960 Avenue U NW, Winter Haven, FL 33881

    Don't miss out on this 4 bedroom home, at an amazing price. This home has been freshly painted and has ceramic tile throughout. The French doors lead to a paver patio that provides access to a huge backyard. The uncovered gazebo/patio area is perfect for those fire pit evenings. Your front covered patio gives you a Waterview of Lake Blue.

    3960 Avenue U NW, Winter Haven, FL 33881
  • /12

    $1,800 per month

    • 3 Beds
    • 1.5 Baths
    • 1,160 Sq Ft
    • House for Rent

    922 Martin Luther King Blvd NE, Winter Haven, FL 33881

    Move-in ready rental opportunity in a convenient Winter Haven location. This property offers comfortable living spaces, great natural light, and a functional layout ideal for families or professionals. Located near major roads, shopping, dining, and local amenities, providing both convenience and accessibility. Monthly rent is $1,800.Schedule your showing today—this opportunity won’t last.

    Leidy Marroquin Bello EXP REALTY LLC

    922 Martin Luther King Blvd NE, Winter Haven, FL 33881
  • /16

    $1,695 per month

    • 3 Beds
    • 2 Baths
    • 1,194 Sq Ft
    • House for Rent

    546 Lake Dexter Blvd, Winter Haven, FL 33884

    Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $1839.90. That covers your base rent, $1695.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    546 Lake Dexter Blvd, Winter Haven, FL 33884
  • /18

    $2,000 per month

    • 3 Beds
    • 2 Baths
    • 1,483 Sq Ft
    • House for Rent

    4973 Kaia Ave, Winter Haven, FL 33884

    Welcome to this brand-new 2025-built home located in the highly desirable Villa Mar community in Winter Haven! Offering 3 bedrooms, 2 full bathrooms, this modern residence combines style, functionality, and comfort in one beautifully designed floor plan. Step inside to an open-concept layout filled with natural light, creating the perfect space for both everyday living and entertaining. The

    Paola Martinez CENTURY 21 MCBRIDE REALTY GROUP

    4973 Kaia Ave, Winter Haven, FL 33884
  • /2

    $1,850 per month

    • 3 Beds
    • 2 Baths
    • 1,460 Sq Ft
    • House for Rent

    206 Kingshill Ct SE, Winter Haven, FL 33884

    Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.Coming soon! This home is currently being enjoyed by another resident but will be available soon. Please respect their privacy and do not disturb. You can complete the application process and reserve

    206 Kingshill Ct SE, Winter Haven, FL 33884
  • /14

    $2,000 per month

    • 3 Beds
    • 2 Baths
    • 1,483 Sq Ft
    • House for Rent

    3889 Giorgio Dr, Winter Haven, FL 33884

    Welcome to this brand-new 2025-built home located in the highly desirable Villa Mar community in Winter Haven! Offering 3 bedrooms, 2 full bathrooms, this modern residence combines style, functionality, and comfort in one beautifully designed floor plan. Step inside to an open-concept layout filled with natural light, creating the perfect space for both everyday living and entertaining. The

    Paola Martinez CENTURY 21 MCBRIDE REALTY GROUP

    3889 Giorgio Dr, Winter Haven, FL 33884
  • /18

    $1,865 per month

    • 3 Beds
    • 2 Baths
    • 1,407 Sq Ft
    • House for Rent

    148 Southern Breeze Lp, Winter Haven, FL 33880

    We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home

    148 Southern Breeze Lp, Winter Haven, FL 33880
  • /8

    $1,100 per month

    • 1 Bed
    • 1 Bath
    • 288 Sq Ft
    • House for Rent

    115 Avenue F SW Unit B, Winter Haven, FL 33880

    This brand-new studio apartment in Winter Haven offers efficient, low-maintenance living with an open layout and vinyl flooring throughout. The space features a bright main living area and a bathroom with a walk-in shower. With its fresh construction and easy-care design, the space maintains a straightforward, functional feel ideal for someone seeking a no-frills place to call home.

    Christin Davis PROPERTY MANAGEMENT OF POLK

    115 Avenue F SW Unit B, Winter Haven, FL 33880
  • /14

    $1,795 per month

    • 3 Beds
    • 2 Baths
    • 1,204 Sq Ft
    • House for Rent

    530 17th St NE, Winter Haven, FL 33881

    MOVE-IN READYThis home is move-in ready. Schedule your tour now or start your application today.Monthly Recurring Fees:$25.00 - Smart HomeWelcome to 530 17th Street in Winter Haven, FL, a 3-bedroom, 2-bathroom home offering approximately 1,204 square feet of versatile living space, designed with multiple areas to spread out and enjoy.Step inside to find tile

    530 17th St NE, Winter Haven, FL 33881
  • /29

    $1,485 per month

    • 2 Beds
    • 2 Baths
    • 1,105 Sq Ft
    • House for Rent

    1018 Sunshine Way SW, Winter Haven, FL 33880

    One or more photo(s) has been virtually staged. Check out this beautifully refreshed 2-bedroom, 2-bath rental home! This property features vaulted ceilings, a freshly painted interior, and tile flooring throughout the main living areas. The galley-style kitchen includes a cozy breakfast nook, perfect for casual dining.Enjoy the screened-in room overlooking a fully fenced backyard—ideal for

    John-Michael Elliott S & D REAL ESTATE SERVICE LLC

    1018 Sunshine Way SW, Winter Haven, FL 33880
  • /16

    $1,870 per month

    • 3 Beds
    • 2 Baths
    • 1,325 Sq Ft
    • House for Rent

    108 Brad Cir, Winter Haven, FL 33880

    Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening!Take advantage of the incredible location,

    108 Brad Cir, Winter Haven, FL 33880
  • /7

    $700 per month

    • 2 Beds
    • 1 Bath
    • 740 Sq Ft
    • House for Rent

    720 6th St NW Unit 3, Winter Haven, FL 33881

    Rent with confidence from a licensed Real Estate Brokerage. We have a quick and simple application process. Contact us through this website or call to set up a tour and apply today! WE PROUDLY WELCOME ALL PETS. Welcome to this cute 2-bed, 1-bath home! Our spacious layout is perfect for comfortable living. Enjoy the yard to unwind after a long day, enjoy the fresh air, and gather for fun-filled

    Erich Spivey ALABAMA LLC

    720 6th St NW Unit 3, Winter Haven, FL 33881
  • /16

    $1,850 per month

    • 3 Beds
    • 2 Baths
    • 2,469 Sq Ft
    • House for Rent

    517 Heather Glen Dr, Winter Haven, FL 33884

    Property Id: 2159794Welcome to 517 Heather Glen Drive, a well-maintained home that's ready for its next chapter. With updated photos showcasing its best angles, this property offers a clean, comfortable layout designed for everyday living without the hassle.Step inside to find a bright, open feel with functional living spaces that flow easily from room to room. The kitchen

    517 Heather Glen Dr, Winter Haven, FL 33884
  • /13

    $700 per month

    • 2 Beds
    • 1 Bath
    • 683 Sq Ft
    • House for Rent

    720 6th St NW Unit 2, Winter Haven, FL 33881

    Rent with confidence from a licensed Real Estate Brokerage. We have a quick and simple application process. Contact us through this website or call to set up a tour and apply today! WE PROUDLY WELCOME ALL PETS. Welcome to this cute 2-bed, 1-bath home! Our spacious layout is perfect for comfortable living. Enjoy the yard to unwind after a long day, enjoy the fresh air, and gather for fun-filled

    Erich Spivey ALABAMA LLC

    720 6th St NW Unit 2, Winter Haven, FL 33881
  • /18

    $1,909 per month

    • 3 Beds
    • 2 Baths
    • 1,541 Sq Ft
    • House for Rent

    497 Kensington View Dr, Winter Haven, FL 33880

    Move in by April 17, Get 2 Weeks Free! Discover spacious homes for rent at Kensington View in Winter Haven, FL. Pet-friendly living with access to Lakeland and Tampa Bay. Professionally managed by ARK Homes.

    497 Kensington View Dr, Winter Haven, FL 33880
  • /22

    $1,817 per month

    • 3 Beds
    • 2 Baths
    • 1,504 Sq Ft
    • House for Rent

    3304 White Indigo Rd, Winter Haven, FL 33884

    WINTER HAVEN NEW BUILD 3 BED/2 BATH HOME FOR RENT! MOVE-IN SPECIAL!Priced Low, Call Now! Very Clean Property, Move-in Ready, 2 Car Garage, Brand New Build—First Tenancy! Huge Master Suite, Eat-In Kitchen, Corian Countertops, Upgraded Kitchen, Brand New Kitchen, Carpeted Bedrooms, Laminate Wood-Look Flooring, COMMUNITY Pool, COMMUNITY Playground, COMMUNITY Multiple Lakes, COMMUNITY Walking &

    Jay Myers ORLANDO REALTY & PROPERTY MGNT

    3304 White Indigo Rd, Winter Haven, FL 33884
  • /16

    $1,715 per month

    • 3 Beds
    • 2 Baths
    • 1,269 Sq Ft
    • House for Rent

    606 Patrick Ave, Winter Haven, FL 33880

    Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening!Take advantage of the incredible location,

    606 Patrick Ave, Winter Haven, FL 33880
  • /14

    $1,900 per month

    • 2 Beds
    • 2 Baths
    • 1,250 Sq Ft
    • House for Rent

    227 Volusia Dr, Winter Haven, FL 33884

    Located in an established neighborhood this home offers 2 bedrooms and 2 bathrooms. Galley kitchen overlooking large fenced backyard. Inside laundry room and 2 car garage. Available and ready for immediate occupancy.

    Sue Ann Williamon THE HOME COMPANY

    227 Volusia Dr, Winter Haven, FL 33884
  • /18

    $1,955 per month

    • 4 Beds
    • 2 Baths
    • 1,715 Sq Ft
    • House for Rent

    851 Orleans Dr, Eagle Lake, FL 33839

    Some photos may feature virtual furniture staging, which is intended to help visualize the space and potential designs. The rental home does not come with any furniture shown in the images and these virtual images do not represent actual furnishings. Residents must furnish their own home.Please note that the advertised price may exclude additional fees. These include a $55 application fee per

    851 Orleans Dr, Eagle Lake, FL 33839
  • /18

    $1,700 per month

    • 3 Beds
    • 2 Baths
    • 1,194 Sq Ft
    • House for Rent

    606 Holt Cir, Winter Haven, FL 33880

    This 3 bedroom, 2 bathroom home brings a fun mix of comfort and flexibility, featuring a bonus room that’s ready to become whatever you need next — a home office, gaming room, craft space, or an extra spot to unwind. The interior offers an easy, functional flow with bedrooms that make the most of the home’s footprint, and the primary suite includes its own private bath for added

    Christin Davis PROPERTY MANAGEMENT OF POLK

    606 Holt Cir, Winter Haven, FL 33880
  • /16

    $1,740 per month

    • 3 Beds
    • 2 Baths
    • 1,252 Sq Ft
    • House for Rent

    3728 Imperial Dr, Winter Haven, FL 33880

    Beautiful, pet-friendly home coming soon! Apply now, Move-In is available on or after the listed date. Upon approval, $500 reservation deposit to reserve (applied to security deposit and/or refundable). Application fee: $50 per adult. Security Deposit: one month?s rent. Pet fees: $250 + $40/mo per pet. Some homes may include pool ($150/mo), septic ($15/mo), and/or HOA fees; other fees may apply.

    3728 Imperial Dr, Winter Haven, FL 33880
  • /10

    $1,775 per month

    • 3 Beds
    • 2 Baths
    • 1,336 Sq Ft
    • House for Rent

    2214 Avenue B SW, Winter Haven, FL 33880

    Available for immediate move-in! Experience the perfect blend of historic charm and modern updates in this beautifully remodeled 1957 home, ideally located in the heart of Winter Haven. Just off First Street and minutes from shopping, public transportation, and major roadways, this home offers both convenience and character. Inside, you'll find a contemporary interior with brand-new flooring and

    Sylvain Sara HOMETRUST REALTY GROUP

    2214 Avenue B SW, Winter Haven, FL 33880
  • /15

    $1,875 per month

    • 4 Beds
    • 2 Baths
    • 1,786 Sq Ft
    • House for Rent

    107 Fall Glo Rd, Winter Haven, FL 33880

    Please note that the advertised price may exclude additional fees. These include a $55 application fee per applicant; a one-time $75 admin fee; a $11 monthly utility management fee; other mandatory fees, if applicable, for pool maintenance, pet fees/rent, smart home, internet service, and propane refilling; and optional fees for services like self-guided tours with third-party provider Rently

    107 Fall Glo Rd, Winter Haven, FL 33880
  • /34

    $1,900 per month

    • 2 Beds
    • 2 Baths
    • 1,575 Sq Ft
    • House for Rent

    616 Crystals Blvd, Winter Haven, FL 33884

    Spacious and beautifully laid out home now available for rent! This open floor plan features 2 bedrooms, 2 bathrooms, plus a versatile flex space that can easily function as a third bedroom, office, or additional living area. Inside, you’ll find laminate flooring throughout with tile in the bathrooms, along with fresh interior paint and updated finishes that enhance the home’s overall appeal. The

    Jeff Inman FHG REALTY, LLC

    616 Crystals Blvd, Winter Haven, FL 33884
  • /15

    $1,760 per month

    • 4 Beds
    • 2 Baths
    • 1,989 Sq Ft
    • House for Rent

    948 Gotthard Pass Dr, Winter Haven, FL 33881

    We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home

    948 Gotthard Pass Dr, Winter Haven, FL 33881
  • /10

    $1,975 per month

    • 3 Beds
    • 2 Baths
    • 1,491 Sq Ft
    • House for Rent

    233 Kensington View Blvd, Winter Haven, FL 33880

    Discover modern living in this stunning newly built 3-bedroom, 2-bath home, where style meets comfort. Bright, spacious bedrooms provides the perfect retreat, while sleek, thoughtfully designed bathrooms add a touch of luxury. The open-concept layout flows effortlessly from the kitchen to the living and dining areas, ideal for entertaining or relaxing. A generous walk-in closet keeps everything

    Christopher Gallon, Pa EXP REALTY LLC

    233 Kensington View Blvd, Winter Haven, FL 33880
  • /15

    $1,650 per month

    • 2 Beds
    • 2 Baths
    • 1,143 Sq Ft
    • House for Rent

    1095 Sunshine Way SW, Winter Haven, FL 33880

    We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home

    1095 Sunshine Way SW, Winter Haven, FL 33880
  • /6

    $1,900 per month

    • 3 Beds
    • 2 Baths
    • 1,484 Sq Ft
    • House for Rent

    3832 Giorgio Dr, Winter Haven, FL 33884

    Appointment Only, Combination Lockbox, See Remarks, Use ShowingTime Button

    Daniela Leal Castro EXP REALTY LLC

    3832 Giorgio Dr, Winter Haven, FL 33884
  • /17

    $1,800 per month

    • 3 Beds
    • 2 Baths
    • 1,950 Sq Ft
    • House for Rent

    3236 Timberline Rd, Winter Haven, FL 33880

    Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening!Take advantage of the incredible location,

    3236 Timberline Rd, Winter Haven, FL 33880
  • /24

    $2,000 per month

    • 4 Beds
    • 2 Baths
    • 1,935 Sq Ft
    • House for Rent

    1498 Austin St, Winter Haven, FL 33884

    One or more photo(s) has been virtually staged. Step into this inviting 4 bedroom, 2 bathroom home in the Peace Creek Reserve community, where comfort meets modern style. The split floor plan gives everyone their own space, while the open living, dining, and kitchen area keeps the heart of the home bright, connected, and perfect for everyday life. You’ll love the modern appliances, clean

    Christin Davis PROPERTY MANAGEMENT OF POLK

    1498 Austin St, Winter Haven, FL 33884
  • /17

    $1,975 per month

    • 4 Beds
    • 2.5 Baths
    • 1,889 Sq Ft
    • House for Rent

    2753 Whispering Trails Dr, Winter Haven, FL 33884

    Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening!Take advantage of the incredible location,

    2753 Whispering Trails Dr, Winter Haven, FL 33884
  • /34

    $1,900 per month

    • 3 Beds
    • 2 Baths
    • 1,268 Sq Ft
    • House for Rent

    2893 Whispering Trails Dr, Winter Haven, FL 33884

    This cozy and well-maintained home offers a warm and inviting layout, ideal for comfortable and easy living. The property features a functional floor plan with a modern kitchen, bright and spacious bedrooms, and low-maintenance living areas designed for convenience. Centrally located with quick access to US-27, US-17, SR-540, and I-4, this home provides easy commutes to Orlando and Tampa, as well

    Jenny Caso LIFESTYLE INTERNATIONAL REALTY

    2893 Whispering Trails Dr, Winter Haven, FL 33884
  • /16

    $1,955 per month

    • 3 Beds
    • 2 Baths
    • 1,431 Sq Ft
    • House for Rent

    92 Lake Daisy Blvd, Winter Haven, FL 33884

    Please note, our homes are available on a first-come, first-serve basis and are not reserved until the lease is signed by all applicants and security deposits are collected.Interested in this home? You clearly have exceptional taste. This charming 3-bedroom, 2.0-bathroom home is not only pet-friendly, but also equipped with smart home features to make everyday life more convenient and

    92 Lake Daisy Blvd, Winter Haven, FL 33884
  • /41

    $2,000 per month

    • 3 Beds
    • 1 Bath
    • 1,602 Sq Ft
    • House for Rent

    3022 Hickory St NW, Winter Haven, FL 33881

    Welcome to this incredible Winter Haven pool home offering the perfect blend of comfort, upgrades, and true Florida lifestyle living. This move-in ready 3-bedroom home sits on a large oversized lot and is ideal for first-time homebuyers, families, or investors looking for a prime Central Florida opportunity. Step inside to find generous living space, a functional layout, and fresh upgrades that

    Ashlee Morrell THE URBAN GROUP, INC.

    3022 Hickory St NW, Winter Haven, FL 33881
  • /16

    $1,700 per month

    • 3 Beds
    • 1 Bath
    • 1,120 Sq Ft
    • House for Rent

    240 16th St NE, Winter Haven, FL 33881

    Beautiful, pet-friendly home coming soon! Apply now, Move-In is available on or after the listed date. Upon approval, $500 reservation deposit to reserve (applied to security deposit and/or refundable). Application fee: $50 per adult. Security Deposit: one month?s rent. Pet fees: $250 + $40/mo per pet. Some homes may include pool ($150/mo), septic ($15/mo), and/or HOA fees; other fees may apply.

    240 16th St NE, Winter Haven, FL 33881
  • /15

    $1,895 per month

    • 4 Beds
    • 2 Baths
    • 1,566 Sq Ft
    • House for Rent

    1341 Avenue S NW, Winter Haven, FL 33881

    4/2 home in Winter Haven available now! Features ceramic tile and laminate flooring, inside laundry room, nice yard, and 2 car carport. Approval subject to credit, income, and rental verification.

    Tracey Crews SUPERIOR PROPERTY MGMT & SALES

    1341 Avenue S NW, Winter Haven, FL 33881
  • /15

    $1,850 per month

    • 4 Beds
    • 2 Baths
    • 1,938 Sq Ft
    • House for Rent

    104 Southern Breeze Lp, Winter Haven, FL 33880

    We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home

    104 Southern Breeze Lp, Winter Haven, FL 33880
  • /11

    $1,700 per month

    • 3 Beds
    • 2 Baths
    • 1,662 Sq Ft
    • House for Rent

    1019 Mockingbird Cir, Winter Haven, FL 33884

    3 bedroom 2 bath home with 2 car garage located in SE Winter Haven near Legoland. Modern custom cabinets throughout the home, open island kitchen design with pantry, bedrooms with plenty of closet space. Large master suite with roomy walk-in closet, spacious tiled master bath, and sliding doors to screened porch. Double pane windows throughout. Fenced yard. Located in a family friendly

    Donna Williams REMAX EXPERTS

    1019 Mockingbird Cir, Winter Haven, FL 33884

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