Winter Haven, FL Homes for Rent under $2,100

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  /15

  $1,840 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
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  /16

  $1,750 per month

  • 2 Beds
  • 2 Baths
  • 1,490 Sq Ft
  • House for Rent

  14 Lamplight Ln, Winter Haven, FL 33884

  Welcome to 14 Lamplight Lane in beautiful Winter Haven — a delightful 2-bedroom, 2-bath home offering 1,490 square feet of comfortable living space plus a versatile bonus room that adds flexibility to fit your lifestyle. This inviting residence features a bright and open living area filled with natural light, creating a warm and welcoming atmosphere from the moment you step inside. With 1,490

  Leila Torres LA ROSA REALTY PRESTIGE

  14 Lamplight Ln, Winter Haven, FL 33884
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  /14

  $1,952 per month

  • 3 Beds
  • 2 Baths
  • 1,690 Sq Ft
  • House for Rent

  237 St Georges Cir, Eagle Lake, FL 33839

  Property Id: 1568095This 1690 square foot single family home has 3 bedrooms and 2 bathrooms for rent. Completely fenced in neighborhood. Included an attached 2-car garage. Home was built in 2020. NEW LUXURY LAMINATE FLOORS installed before you move in! $1950 per month + $2 ACH transaction fee = $1952 per month for a year contract . Shorter terms are negotiable for a higher

  237 St Georges Cir, Eagle Lake, FL 33839
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  $1,795 per month

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

  3063 Laurel Oak Ln, Winter Haven, FL 33884

  2ND MONTH RENT FREE: Move-In Ready, Pet-Friendly, 2-Car Garage! Available for immediate occupancy! Step into this stunning 2023 Meritage Home in the heart of Winter Haven, Florida—a highly upgraded 3-bedroom, 2-bath single-story home designed to impress. This move-in ready home features neutral tones throughout, a chef-inspired kitchen with stainless steel appliances, quartz countertops, and a

  Katrina Anarumo RENT A FLORIDA HOME

  3063 Laurel Oak Ln, Winter Haven, FL 33884
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  /20

  $2,025 per month

  • 4 Beds
  • 2 Baths
  • 2,004 Sq Ft
  • House for Rent

  613 Sarner Pass Way, Winter Haven, FL 33881

  This property is available. Please inquire on this site to schedule a showing. Limited-Time Offer! Sign a lease by April 15th and enjoy $100 off your first month’s rent a great opportunity to save on your new home! Welcome to 613 Sarner Pass Way, located in the serene and charming community of Winter Haven, FL. This delightful single-story home boasts a modern and inviting open

  613 Sarner Pass Way, Winter Haven, FL 33881
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  $1,295 per month

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

  320 Spirit Landings Cir, Winter Haven, FL 33880

  Fully furnished 1-bedroom apartment available for immediate occupancy. Rent includes all utilities electric, water, internet, and trash providing a truly hassle-free living experience. Well-maintained unit featuring comfortable furnishings, a functional layout, and abundant natural light. Ideal for professionals, traveling nurses, or anyone seeking a turnkey rental. Conveniently located near

  Laura Medina Ruiz RE/MAX HERITAGE PROFESSIONALS

  320 Spirit Landings Cir, Winter Haven, FL 33880
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  /15

  $1,770 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
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  /15

  $1,799 per month

  • 3 Beds
  • 2 Baths
  • 1,718 Sq Ft
  • House for Rent

  Unlisted Address

  Take a look at this beautiful home, Clean and Move-In Ready, featuring 3 bedrooms, 2 bathrooms, 2 car garage and approximately 1,718 heated square feet. Enjoy the freedom of a virtually maintenance free lifestyle while residing in a great community. Smart Home Tech - $21.95/mo; Washer/Dryer - $35/mo; High Speed Cable/Internet (if applicable by 3rd Party user) $55/mo; Renters insurance reqrd, Pool

  Cathy Behe TAH FLORIDA LLC

  Unlisted Address
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  /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
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  /11

  $1,100 per month

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

  102 Oak Crest Dr NW Unit 106, Winter Haven, FL 33881

  HALF OFF FIRST MONTHS RENT! Recently updated apartment available for lease! This bright and comfortable unit features updated cabinets, crown molding, ceiling fans, and modern light fixtures throughout, making it both stylish and easy to maintain. Enjoy private off-street parking. Located on a quiet street with no thru traffic and just minutes from shopping, dining, parks, and everyday

  David Small KELLER WILLIAMS REALTY SMART 1

  102 Oak Crest Dr NW Unit 106, Winter Haven, FL 33881
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  /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
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  /16

  $1,100 per month

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

  118 Oak Crest Dr NW, Winter Haven, FL 33881

  HALF OFF FIRST MONTHS RENT! Recently updated apartment available for lease! This bright and comfortable unit features updated cabinets, crown molding, ceiling fans, and modern light fixtures throughout, making it both stylish and easy to maintain. Enjoy private off-street parking. Located on a quiet street with no thru traffic and just minutes from shopping, dining, parks, and everyday

  David Small KELLER WILLIAMS REALTY SMART 1

  118 Oak Crest Dr NW, Winter Haven, FL 33881
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  /16

  $1,935 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 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

  92 Lake Daisy Blvd, Winter Haven, FL 33884
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  /22

  $2,030 per month

  • 4 Beds
  • 2 Baths
  • 1,824 Sq Ft
  • House for Rent

  2122 Chris Dr, Winter Haven, FL 33884

  Beautiful brand-new 4-bedroom, 2-bathroom home located in a great area of Winter Haven. The property features a charming front porch, perfect for relaxing. Inside, the home offers a spacious open-concept living room seamlessly connected to the dining area and kitchen, creating a modern and functional layout. Sliding glass doors provide access to a large outdoor area, ideal for entertaining and

  Jessyka Dos Santos WRA BUSINESS & REAL ESTATE

  2122 Chris Dr, Winter Haven, FL 33884
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  /19

  $1,695 per month

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

  3634 Queens Cove Blvd, Winter Haven, FL 33880

  We are currently making final preparations for this home to be available. 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

  3634 Queens Cove Blvd, Winter Haven, FL 33880
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  $1,395 per month

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

  140 Avenue W NW Unit 2, 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 2, Winter Haven, FL 33881
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  /16

  $1,740 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
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  /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
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  /15

  $2,000 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
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  /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
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  /16

  $1,785 per month

  • 3 Beds
  • 1 Bath
  • 1,089 Sq Ft
  • House for Rent

  309 Vaniman Ave, 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

  309 Vaniman Ave, Winter Haven, FL 33880
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  $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
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  /15

  $2,060 per month

  • 3 Beds
  • 2 Baths
  • 1,821 Sq Ft
  • House for Rent

  5800 Driftwood Dr, 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

  5800 Driftwood Dr, Winter Haven, FL 33884
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  $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
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  /18

  $1,949 per month

  • 3 Beds
  • 2 Baths
  • 1,961 Sq Ft
  • House for Rent

  914 Whisper Lake Dr, Winter Haven, FL 33880

  Coming soon - this home is currently being enjoyed by another resident but will be available soon. This home is professionally managed by Tricon, dedicated to creating exceptional rental experiences. Featuring 3 bedrooms, 2.0 bathrooms, and approximately 1,961 square feet, this well-maintained home offers a high standard of rental living, supported by a team that puts residents first. As a

  914 Whisper Lake Dr, Winter Haven, FL 33880
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  /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
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  $1,950 per month

  • 3 Beds
  • 2 Baths
  • 1,672 Sq Ft
  • House for Rent

  175 Grove Branch Rd, Winter Haven, FL 33880

  Property Id: 2402477Welcome Home This gorgeous modern 3 bed 2 bath and 2 car garage is located in beautiful Winter Haven. This is very open and spacious split floor plan. Perfect for entertaining. Kitchen is tastefully designed with espresso brown 42" cabinets and features an island overlooking the family room. Large pantry closet. Master bedroom suite offers a large walk-in closet and an

  175 Grove Branch Rd, Winter Haven, FL 33880
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  /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
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  /16

  $1,449 per month

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

  3215 Timberline Rd, Winter Haven, FL 33880

  This home is professionally managed by Tricon, dedicated to creating exceptional rental experiences. Featuring 2 bedrooms, 1.0 bathrooms, and approximately 904 square feet, this well-maintained home offers a high standard of rental living, supported by a team that puts residents first. As a Tricon resident, you'll enjoy access to Tricon Vantage — a program designed to support your rental journey.

  3215 Timberline Rd, Winter Haven, FL 33880
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  $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
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  /17

  $1,815 per month

  • 3 Beds
  • 2.5 Baths
  • 1,320 Sq Ft
  • House for Rent

  669 Lake Dexter Cir, Winter Haven, FL 33884

  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.

  669 Lake Dexter Cir, Winter Haven, FL 33884
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  /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
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  /20

  $1,849 per month

  • 3 Beds
  • 2 Baths
  • 1,442 Sq Ft
  • House for Rent

  509 Kensington View Dr, Winter Haven, FL 33880

  Sign in by April 17, Get 4 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.

  509 Kensington View Dr, Winter Haven, FL 33880
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  $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
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  $1,800 per month

  • 3 Beds
  • 2 Baths
  • 1,177 Sq Ft
  • House for Rent

  2006 34th St NW, Winter Haven, FL 33881

  Property Id: 2400855This beautifully maintained 3-bedroom, 2-bath home is now available for rent! Originally listed for sale, this property offers exceptional space, accessibility, and flexibility for a variety of living needs.Designed with wheelchair accessibility in mind, the home features wide entryways and a fully accessible bathroom while still maintaining a stylish,

  2006 34th St NW, Winter Haven, FL 33881
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  /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
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  /16

  $1,949 per month

  • 4 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • House for Rent

  1532 Wallace Manor Ave, Winter Haven, FL 33880

  Coming soon - this home is currently being enjoyed by another resident but will be available soon. Pre-lease this home now with Tricon Pre-Lease Guarantee. This home is professionally managed by Tricon, dedicated to creating exceptional rental experiences. Featuring 4 bedrooms, 2.0 bathrooms, and approximately 1,300 square feet, this well-maintained home offers a high standard of rental living,

  1532 Wallace Manor Ave, Winter Haven, FL 33880
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  $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
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  /18

  $1,790 per month

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

  637 Sunway Ln, Winter Haven, FL 33880

  We are currently making final preparations for this home to be available. 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

  637 Sunway Ln, Winter Haven, FL 33880
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  /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

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