197

Winter Haven, FL Homes for Rent under $2,200

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  • /19

    $1,925 per month

    • 3 Beds
    • 2 Baths
    • 1,424 Sq Ft
    • House for Rent

    344 Sand Pine Trail, Winter Haven, FL 33880

    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.This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at This home is priced to rent

    344 Sand Pine Trail, Winter Haven, FL 33880
  • /13

    $1,395 per month

    • 2 Beds
    • 1 Bath
    • 800 Sq Ft
    • Apartment for Rent

    140 Avenue W NW Unit 3, Winter Haven, FL 33881

    One or more photo(s) has been virtually staged. HALF OFF FIRST MONTHS RENT! Spacious rental located in the heart of Winter Haven! This updated unit offers comfortable living with generous room sizes and a functional layout. Conveniently located near shopping, dining, schools, and major roadways, making daily commutes a breeze. Public water and sewer, city utilities, and easy access to everything

    David Small KELLER WILLIAMS REALTY SMART 1

    140 Avenue W NW Unit 3, Winter Haven, FL 33881
  • /20

    $2,010 per month

    • 3 Beds
    • 2 Baths
    • 1,723 Sq Ft
    • House for Rent

    104 Lake Daisy Terrace, 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.This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at Coming soon! This home is

    104 Lake Daisy Terrace, Winter Haven, FL 33884
  • /19

    $1,600 per month

    • 2 Beds
    • 2 Baths
    • 1,017 Sq Ft
    • Condo for Rent

    1704 Eagle Pond Dr Unit 1704, Winter Haven, FL 33884

    GROUND FLOOR Eagle Pond condominium in the highly desirable gated community of Cypresswood Golf and Country Club. This professionally-managed condominium has just been partially renovated to include luxury vinyl flooring and fresh paint throughout. Key features are interior laundry, walk-in closets, open concept living space, and so much more. The spacious master bedroom features an en suite

    Kayly Malinas JOHN WOOD REALTY, INC.

    1704 Eagle Pond Dr Unit 1704, Winter Haven, FL 33884
  • /17

    $1,770 per month

    • 3 Beds
    • 2 Baths
    • 1,632 Sq Ft
    • House for Rent

    1405 N Lake Shipp Dr SW, 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,

    1405 N Lake Shipp Dr SW, Winter Haven, FL 33880
  • /25

    $1,850 per month

    • 3 Beds
    • 2 Baths
    • 1,536 Sq Ft
    • Townhouse for Rent

    2727 Rutledge Ct, Winter Haven, FL 33884

    For Rent – 2727 Rutledge Court | $1,950/monthMove-in ready and available now! This end-unit townhome offers 2 bedrooms, 2 bathrooms, plus a flexible office/bonus room that can easily serve as a third bedroom, with 1,536 square feet of bright, low-maintenance Florida living.At $1,950 per month, rent includes internet, cable, lawn care, community pool access, a fishing dock, and a beautiful

    Veronica Bard LA ROSA REALTY PRESTIGE

    2727 Rutledge Ct, Winter Haven, FL 33884
  • /10

    $1,665 per month

    • 3 Beds
    • 1.5 Baths
    • 1,750 Sq Ft
    • House for Rent

    1333 Stately Oaks Dr NW, Winter Haven, FL 33881

    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 $1799.95. That covers your base rent, $1665.00 + our required services designed to make your life easier: Internet & Media ($85), Smart Home with

    1333 Stately Oaks Dr NW, Winter Haven, FL 33881
  • /40

    $1,600 per month

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • Townhouse for Rent

    222 7th St NW Unit 2, Winter Haven, FL 33881

    Charming Furnished Cottages for Rent in the Heart of Winter HavenWelcome to Rose Hill Cottages, a thoughtfully restored collection of furnished cottages nestled in a quiet, established neighborhood just minutes from downtown Winter Haven. These cottages offer the perfect blend of charm, comfort, and convenience — ideal for professionals, relocations, extended stays, or anyone seeking a

    Veronica Bard LA ROSA REALTY PRESTIGE

    222 7th St NW Unit 2, Winter Haven, FL 33881
  • /18

    $2,035 per month

    • 4 Beds
    • 2.5 Baths
    • 2,203 Sq Ft
    • House for Rent

    2069 Whispering Trails Blvd, 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.This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at Coming soon! This home is

    2069 Whispering Trails Blvd, Winter Haven, FL 33884
  • /12

    $2,000 per month

    • 3 Beds
    • 2 Baths
    • 1,390 Sq Ft
    • House for Rent

    137 Woodland Dr, Winter Haven, FL 33881

    Like-new 3 bedroom, 2 bathroom home with only one previous tenant. No carpet throughout—easy-care flooring in every room. Open and functional layout with modern finishes, well-maintained and move-in ready.

    Mindy Hunley TRIBUTE REALTY LLC

    137 Woodland Dr, Winter Haven, FL 33881
  • /16

    $1,925 per month

    • 4 Beds
    • 2 Baths
    • 1,458 Sq Ft
    • House for Rent

    822 Terranova Rd, 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.This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at Coming soon! This home is

    822 Terranova Rd, Winter Haven, FL 33884
  • /20

    $2,150 per month

    • 3 Beds
    • 2 Baths
    • 1,709 Sq Ft
    • House for Rent

    3904 Osprey Pointe Cir, Winter Haven, FL 33884

    Modern design with comfort in mind! Available for Lease April 1, 2026! Spacious 3-Bedroom, 2-Bath Home in a Charming Winter Haven Neighborhood Welcome to this beautifully maintained 3-bedroom, 2-bath home offering over 1,700 square feet of living space in a quaint and friendly community. Conveniently located near downtown Winter Haven, with easy access to theme parks, shopping, and dining, this

    Oswald Carrerou CARREROU ENTERPRISES, LLC

    3904 Osprey Pointe Cir, Winter Haven, FL 33884
  • /18

    $1,845 per month

    • 3 Beds
    • 2 Baths
    • 1,428 Sq Ft
    • House for Rent

    5711 Lakeside Landings Blvd, Winter Haven, FL 33881

    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 $1989.90. That covers your base rent, $1845.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    5711 Lakeside Landings Blvd, Winter Haven, FL 33881
  • /22

    $1,400 per month

    • 1 Bed
    • 1 Bath
    • 1,078 Sq Ft
    • Apartment for Rent

    150 El Dorado Unit 208, Winter Haven, FL 33884

    Comfortable 1BR Apartment in Desirable 55+ Community, well-maintained one-bedroom, one-bath apartment located in a quiet and welcoming 55+ community. Features a functional floor plan with bright living and dining areas, a spacious bedroom with ample closet space, and a clean, well-appointed kitchen. Enjoy community amenities and a peaceful setting designed for active living. Conveniently located

    Elsa Gonzalez LPT REALTY, LLC

    150 El Dorado Unit 208, Winter Haven, FL 33884
  • /15

    $1,945 per month

    • 4 Beds
    • 2 Baths
    • 1,874 Sq Ft
    • House for Rent

    930 Deming Dr, 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,

    930 Deming Dr, Winter Haven, FL 33880
  • /45

    $1,850 per month

    • 4 Beds
    • 2 Baths
    • 1,750 Sq Ft
    • House for Rent

    3993 Warbler Dr, Winter Haven, FL 33880

    Lovely 4 bedroom home, conveniently located at the heart of Winter Haven, minutes from all the stores and restaurants, quick access to Polk Parkway & I-4, & takes less than an hour drive to Orlando or Tampa. This gorgeous home features an elegant ceramic tile flooring, a great open floor plan with 2 spacious living areas, dining room, its' kitchen has plenty of cabinets & counter space, a nice

    Lienyvette Grimaldo MAZELG REALTY

    3993 Warbler Dr, Winter Haven, FL 33880
  • /15

    $2,015 per month

    • 4 Beds
    • 2 Baths
    • 2,110 Sq Ft
    • House for Rent

    171 Southern Breeze Lp, Winter Haven, FL 33880

    From Hwy 17 S - Turn right onto Spirit Lake Rd and continue for 1.6 miles. Turn left onto Grady Polk Rd and destination will be on the right. From Hwy 17 N - Turn left onto Spirit Lake Rd and continue for 1.6 miles. Turn left onto Grady Polk Rd and destination will be on the right.Please note that the advertised price may exclude additional fees. These include a $55 application fee per

    171 Southern Breeze Lp, Winter Haven, FL 33880
  • /17

    $2,095 per month

    • 5 Beds
    • 2 Baths
    • 2,254 Sq Ft
    • House for Rent

    1220 Tyler Loop, Winter Haven, FL 33884

    Pet-Friendly 5-Bedroom Home in Winter Haven, FL!This new construction 5-bedroom, 2.5-bath home combines style and practicality, ideal for modern living.Highlights include:Gourmet kitchen with granite countertops, stainless steel appliances, and elegant cabinetrySpacious living area, perfect for guests or multi-generational livingPrimary suite featuring dual sinks, a walk-in

    Morgan Evans RESZI MANAGEMENT I, LLC

    1220 Tyler Loop, Winter Haven, FL 33884
  • /19

    $1,575 total monthly price

    • 2 Beds
    • 1 Bath
    • 650 Sq Ft
    • Condo for Rent

    650 Ave B SW Unit 650 Avenue B SW, Winter Haven, FL 33880

    650 Ave B SW Unit 650 Avenue B SW, Winter Haven, FL 33880
  • /15

    $1,950 per month

    • 3 Beds
    • 1 Bath
    • 1,160 Sq Ft
    • House for Rent

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

    Wake up to peaceful lakefront views in this inviting Winter Haven home. Designed for comfort and everyday living, this residence offers a warm, functional layout filled with natural light. Step outside to enjoy evenings by the fire pit overlooking the water, creating the perfect setting for relaxing or entertaining. Situated on a generous lot with no HOA, just minutes from downtown Winter Haven,

    Ivet Ortega LAYER 7 GROUP

    922 Martin Luther King Blvd NE, Winter Haven, FL 33881
  • /6

    $1,525 total monthly price

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • House for Rent

    1407 N Lake Shipp Dr SW, Winter Haven, FL 33880

    rent ready 2/1 in Winter Haven Fl. Home has central heat and air, screened front porch and a 1 car carport with attached utility room. Nice size yard with small shed for you yard tools.

    1407 N Lake Shipp Dr SW, Winter Haven, FL 33880
  • /6

    $1,150 per month

    • 1 Bed
    • 1 Bath
    • 500 Sq Ft
    • Townhouse for Rent

    1210 Avenue Z SE Unit A, Winter Haven, FL 33884

    Available! Beautiful and modern 1 BD/1 BA apartment featuring luxury vinyl plank flooring throughout, stainless steel appliances and granite countertops; a tastefully designed interior. Convenient location, so call today, this property won’t last long!

    Pedro Cartagena 1513 REALTY LLC

    1210 Avenue Z SE Unit A, Winter Haven, FL 33884
  • /21

    $1,950 total monthly price

    • 3 Beds
    • 2 Baths
    • 1,444 Sq Ft
    • House for Rent

    336 Kayden Cove, Winter Haven, FL 33884

    “Se están ACEPTANDO todos los programas de asistencia para la vivienda “Se consideran vales de viviendaEsta encantadora casa de 3 dormitorios y 2 baños está lista para recibirte, con una cocina moderna con una amplia isla y electrodomésticos.Disfruta de un garaje para dos autos en la casa y otros dos en el exterior, un hermoso patio y un total de 1444 pies cuadrados de

    336 Kayden Cove, Winter Haven, FL 33884
  • /12

    $1,300 per month

    • 2 Beds
    • 1 Bath
    • 840 Sq Ft
    • Condo for Rent

    900 Avenue Z SE Unit C 6, Winter Haven, FL 33880

    Nice area, closed to Legoland, complex is on a lake, quiet neighborhood

    Mayra Roberto Linked Realty Inc

    900 Avenue Z SE Unit C 6, Winter Haven, FL 33880
  • /9

    $1,600 total monthly price

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

    5626 Struthers Ct, Winter Haven, FL 33884

    2BR / 1BA Duplex • Washer/Dryer • New A/C • $1,600 • Available April 8Clean and well-maintained 2 bedroom / 1 bathroom duplex located in a quiet Winter Haven neighborhood near US-27 and Legoland.Features:• Washer & dryer included• New central A/C• Tile flooring throughout (no carpet)• Bright, open living space• Large shared yard• 2 parking

    5626 Struthers Ct, Winter Haven, FL 33884
  • /9

    $1,000 per month

    • 1 Bed
    • 1 Bath
    • 456 Sq Ft
    • Apartment for Rent

    310 Farnol St SW Unit 3, Winter Haven, FL 33880

    Discover easy downtown living in this bright and inviting studio apartment located in the heart of Winter Haven. The spacious combined living and bedroom area offers plenty of room to relax and make the space your own. A large sliding glass door fills the apartment with natural light and opens to a large, quiet yard. This studio blends comfort, convenience, and simplicity, all within steps of the

    Christin Davis PROPERTY MANAGEMENT OF POLK

    310 Farnol St SW Unit 3, Winter Haven, FL 33880
  • /4

    $1,850 total monthly price

    • 4 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • Condo for Rent

    731 Avenue A SW Unit B, Winter Haven, FL 33880

    It is in a prime area walking distance to restaurant, malls etc. The house contains very large rooms.

    731 Avenue A SW Unit B, Winter Haven, FL 33880
  • /12

    $1,125 per month

    • 2 Beds
    • 1 Bath
    • 700 Sq Ft
    • Townhouse for Rent

    243 Avenue L NE, Winter Haven, FL 33881

    NICE DUPLEX APARTMENT AVAILABLE! Newly renovated, this 2 BD/1 BA has wood-look plank flooring throughout, kitchen and so much more. Just steps from Lake Silver and conveniently located to shopping, dining, medical and downtown Winter Haven! Don’t miss out on a great this rental. Call Today to schedule your showing!!!

    Pedro Cartagena 1513 REALTY LLC

    243 Avenue L NE, Winter Haven, FL 33881
  • /12

    $1,375 total monthly price

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • Condo for Rent

    448 Avenue A NE Unit Cozy Cottage, Winter Haven, FL 33881

    This cozy Cottage is a 1/1 in Winter Haven Fl. Walk to downtowns restaurant and local shops and breweries. Close to Legoland. Short term unit with small kitchenette. Fenced yard with private spa. This home is set up for short term rental and has kitchenette with Convection Microwave, coffee pot, and all dishware. Washer Dryer, queen bed, TVs in the living room and bedroom. This is a duplex

    448 Avenue A NE Unit Cozy Cottage, Winter Haven, FL 33881
  • /30

    $2,000 per month

    • 4 Beds
    • 2 Baths
    • 1,851 Sq Ft
    • House for Rent

    820 Sun Burst Rd, Winter Haven, FL 33880

    Beautiful 4-Bedroom Home in Squires Grove – Built in 2022! Welcome to this stunning 4-bedroom, 2-bathroom single-family home located in the desirable Squires Grove community. Built in 2022, this modern home offers 1,851 sq. ft. of thoughtfully designed living space with a spacious 2-car garage. You'll love the open floor plan, perfect for both everyday living and entertaining. The kitchen flows

    Nicole Torres AZURE REAL ESTATE & PROPERTY MANAGEMENT GROUP LLC

    820 Sun Burst Rd, Winter Haven, FL 33880
  • /118

    $1,260 - $2,215 per month

    Alera at Hunters Glen

    1 - 3 Beds

    3005 Willow Glen Cir, Lake Wales, FL 33859

    Set Your Own Pace at Alera at Hunters GlenDiscover a modern vision for upscale apartment living at Alera at Hunters Glen—where style meets simplicity in Lake Wales, FL. Embrace the freedom of a lock-and-leave lifestyle in a sophisticated community designed for those who live life on their own terms. With a seamless blend of contemporary design and refined elegance, Alera is where your

    3005 Willow Glen Cir, Lake Wales, FL 33859
  • /33

    $1,900 per month

    • 3 Beds
    • 2.5 Baths
    • 1,625 Sq Ft
    • House for Rent

    2521 Pine Place, Winter Haven, FL 33881

    One or more photo(s) has been virtually staged. Welcome to 2521 Pine Pl, where modern elegance meets peaceful lakefront living. This beautifully designed 3-bedroom, 2.5-bath home offers spectacular lake views right from your backyard, creating the perfect backdrop for morning coffee, sunset relaxation, or weekend gatherings. Inside, enjoy a bright open-concept floor plan, a sleek contemporary

    Jacob Hara TRANSCEND REALTY

    2521 Pine Place, Winter Haven, FL 33881
  • /24

    $1,595 per month

    • 2 Beds
    • 2 Baths
    • 1,238 Sq Ft
    • House for Rent

    145 Audubon Rd, Winter Haven, FL 33884

    This inviting 1,238 sq ft home offers the perfect blend of comfort and style with two spacious bedrooms and two full bathrooms. The thoughtfully designed layout maximizes every inch of space with large windows and a well-appointed kitchen. Outside, the surrounding neighborhood offers a peaceful setting, perfect for leisurely strolls and outdoor activities. With its prime location, you're never

    Milton De La Cruz LAKELAND HOMES AND REALTY, LLC

    145 Audubon Rd, Winter Haven, FL 33884
  • /49

    $1,990 per month

    • 3 Beds
    • 2 Baths
    • 1,532 Sq Ft
    • Townhouse for Rent

    36 Enclave Dr, Winter Haven, FL 33884

    One or more photo(s) has been virtually staged. Corner - unfurnished unit @ The Enclave, located within the manned, gated Cypresswood Golf & Country Club in Winter Haven, Florida. This premier community features an 18-hole championship golf course designed by award-winning architect Ron Garl. The course is open 365 days a year, from sunrise to sunset. Residents enjoy access to outstanding

    Jimmy Aguilar 3D TEAM REALTY LLC

    36 Enclave Dr, Winter Haven, FL 33884
  • /12

    $2,200 per month

    • 4 Beds
    • 2 Baths
    • 1,518 Sq Ft
    • House for Rent

    865 Terranova Rd, Winter Haven, FL 33884

    Discover this stunning 4-bedroom, 2-bath home, now available in a highly desirable gated community. Perfectly zoned for the acclaimed A-rated Chain of Lakes Elementary, this residence offers the ideal blend of comfort and convenience for today’s families.Step inside to an expansive open floor plan—ideal for modern living and effortless entertaining. Enjoy a spacious, fully fenced

    Annette Newkirk HOMELIFE REALTY COASTAL PROPERTIES LLC

    865 Terranova Rd, Winter Haven, FL 33884
  • /3

    $1,325 per month

    • 2 Beds
    • 2 Baths
    • 896 Sq Ft
    • Property for Rent

    76 Stebbins Dr Unit 76, Winter Haven, FL 33884

    Find your place in the world at Grove Shores, a well-maintained, professionally managed manufactured home community. Right now, we are offering a 2019 model year, 896 sq. ft., 2 bed/2 bath home for only $55,900! You owe it to yourself to call our representatives and schedule a viewing of this home before someone else snaps it up!

    Tori Coil Grove Shores

    76 Stebbins Dr Unit 76, Winter Haven, FL 33884
  • /31

    $1,950 per month

    • 3 Beds
    • 2 Baths
    • 1,542 Sq Ft
    • House for Rent

    1522 Fuji Ct, Winter Haven, FL 33881

    Move-in ready and brand new, this beautiful corner-lot home offers immediate occupancy and modern comfort with luxury vinyl plank flooring, volume ceilings, and a covered patio perfect for relaxing. At the front of the home are two spacious bedrooms, a full bath, and a dedicated laundry room, leading into an open chef’s kitchen featuring a large island, 36-inch upper cabinets with hardware,

    Sana Butt THE FIRM RE

    1522 Fuji Ct, Winter Haven, FL 33881
  • /6

    $1,800 per month

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • House for Rent

    1669 Teagan Ln, Winter Haven, FL 33884

    READY TO MOVE !!! Imagine life in a home that perfectly blends modern convenience with quiet community charm. This beautiful residence offers 3 bedrooms, 2 bath, and a 1-car garage, providing just the right amount of space to grow, relax, or entertain. The heart of the home is the open kitchen, complete with a handy pantry, which seamlessly overlooks the family room. This creates a fluid,

    Adriana Sanchez WF REALTY CORP.

    1669 Teagan Ln, Winter Haven, FL 33884
  • /23

    $1,650 per month

    • 3 Beds
    • 1 Bath
    • 1,876 Sq Ft
    • House for Rent

    107 Avenue F SW, Winter Haven, FL 33880

    Available for immediate move-in! Experience the perfect blend of historic charm and modern updates in this beautifully remodeled 1928 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

    Christin Davis PROPERTY MANAGEMENT OF POLK

    107 Avenue F SW, Winter Haven, FL 33880
  • /22

    $2,050 per month

    • 4 Beds
    • 2 Baths
    • 1,858 Sq Ft
    • House for Rent

    3543 Evening Star Dr, Winter Haven, FL 33881

    Welcome home to this modern 2025-built single-family residence featuring 4 bedrooms, 2 bathrooms, and 1,858 sq ft of bright, open living space. The open-concept design flows beautifully from the spacious living area into a sleek kitchen finished with stone countertops, contemporary cabinetry, and a clean, modern feel throughout. The oversized tile flooring adds a polished, upscale look and makes

    Felix Ortiz LA ROSA REALTY KISSIMMEE

    3543 Evening Star Dr, Winter Haven, FL 33881

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