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

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  $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

  $1,810 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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  /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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  /17

  $2,000 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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  $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

  $1,935 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 Coming soon! This home is

  92 Lake Daisy Blvd, Winter Haven, FL 33884
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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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  /19

  $1,760 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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  /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

  $1,740 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 + $35/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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  $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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  /14

  $1,920 per month

  • 3 Beds
  • 2 Baths
  • 2,018 Sq Ft
  • House for Rent

  2610 Ave N NW, 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 Home$10.95 - Utility ManagementSet in Northwest Winter Haven, this 3-bedroom, 2-bathroom home offers 2,018 square feet of thoughtfully designed living space just minutes from the Chain of Lakes. With convenient access to Downtown

  2610 Ave N NW, Winter Haven, FL 33881
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  /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
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  /2

  $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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  /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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  /16

  $1,479 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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  /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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  /17

  $1,855 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 + $35/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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  $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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  /7

  $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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  $1,900 per month

  • 3 Beds
  • 2 Baths
  • 1,505 Sq Ft
  • House for Rent

  1735 Carnostie Rd, Winter Haven, FL 33884

  Well-maintained 3 bedroom, 2 bathroom home located in the desirable Villa Mar community in Winter Haven, FL. This home offers 1,505 square feet of living space with a functional open layout, a 2-car garage, and a fully fenced backyard. The interior features a combined living and dining area, ideal for everyday living and entertaining. Breakfast bar is perfect for grabbing a quick bite. The

  Jacob Bellamy REMAX EXPERTS

  1735 Carnostie Rd, Winter Haven, FL 33884
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  /18

  $1,845 per month

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

  637 Sunway Ln, 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

  637 Sunway Ln, Winter Haven, FL 33880
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  /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
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  /19

  $1,880 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
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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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  /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
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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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  /10

  $1,699 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 $1833.95. That covers your base rent, $1699.00 + our required services designed to make your life easier: Internet & Media ($85), Smart Home with

  1333 Stately Oaks Dr NW, Winter Haven, FL 33881
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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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  /16

  $1,930 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
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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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  /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
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  $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
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  /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, nestled

  930 Deming Dr, Winter Haven, FL 33880
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  $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
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  /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
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  /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
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  /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
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  $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
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  /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

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