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

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  $1,100 Per Month

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

  1328 37th St NW, Winter Haven, FL 33881

  Enjoy comfort and privacy in this cozy 1-bedroom, 1-bathroom rear unit located in a quiet Winter Haven neighborhood. This home features its own fully fenced private backyard, perfect for relaxing, entertaining, or enjoying outdoor space. Inside, you’ll find a functional layout with a bright living area, a comfortable bedroom, and a well-appointed kitchen. Conveniently located near shopping,

  Francisco Medina RODRIGUEZ PROPERTY MANAGEMENT

  1328 37th St NW, Winter Haven, FL 33881
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  $2,000 Per Month

  • 3 Beds
  • 2 Baths
  • House for Rent

  679 Avenue G SE, Winter Haven, FL 33880

  Spacious 3-bedroom, 2-bathroom rental home located in the heart of Winter Haven! This well-maintained property offers comfortable living with a functional floor plan, generously sized bedrooms, and ample natural light throughout. Water service is included in the monthly rent, providing added value and convenience. Conveniently located near shopping, dining, schools, parks, and major roadways for

  Esmitha Lauriston First World Realty Group,LLC

  679 Avenue G SE, Winter Haven, FL 33880
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  $1,900 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
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  $1,700 Per Month

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

  903 Eagle Pond Dr Unit C9, Winter Haven, FL 33884

  This absolutely gorgeous MOVE-IN READY Eagle Pond condominium on the GROUND FLOOR has been luxuriously remodeled from top to bottom with no expense spared! Located in the highly desirable 24-hour guard gated community of Cypresswood Golf and Country Club, this meticulously-maintained condo features hardwood floors throughout (no carpet!), upgraded light fixtures, interior laundry, and so much

  Kayly Malinas JOHN WOOD REALTY, INC.

  903 Eagle Pond Dr Unit C9, Winter Haven, FL 33884
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  $1,049 Per Month

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

  1507 7th St SW Unit 1507, Winter Haven, FL 33880

  AWESOME CONTEMPORARY HOUSE WITH AN AMAZING KITCHEN, TILE IN ALL HOUSE, APPLIANCES INCLUDED. YOU GOT TO COME AND SEE IT TODAY.

  Adan Ordonez ADAN INVESTMENTS REAL ESTATE GROUP, PLLC

  1507 7th St SW Unit 1507, Winter Haven, FL 33880
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  $1,300 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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  $1,400 Per Month

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

  1100 Martinique Dr Unit 106, Winter Haven, FL 33884

  Virtually Staged. Nestled within the peaceful and highly desirable Orchid Springs Village, this beautifully renovated ground-floor condominium offers the perfect blend of modern style, low-maintenance living, and an unbeatable Winter Haven location. Designed with comfort and functionality in mind, the bright open floor plan seamlessly connects the living and dining areas, creating an inviting

  David Small KELLER WILLIAMS REALTY SMART 1

  1100 Martinique Dr Unit 106, Winter Haven, FL 33884
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  /23

  $1,690 Per Month

  • 2 Beds
  • 1 Bath
  • 1,152 Sq Ft
  • House for Rent

  495 Avenue F SE, Winter Haven, FL 33880

  Virtually Staged. Discover modern comfort and privacy in this fully renovated single-family home just moments from downtown Winter Haven. Thoughtfully updated from top to bottom, the home features a new roof, new A/C, and a beautifully redesigned kitchen and bathroom with granite countertops and sleek finishes. Porcelain tile flooring flows throughout the home, complementing the high ceilings and

  David Small KELLER WILLIAMS REALTY SMART 1

  495 Avenue F SE, Winter Haven, FL 33880
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  /23

  $1,695 Per Month

  • 3 Beds
  • 2 Baths
  • 1,246 Sq Ft
  • House for Rent

  260 Westwood Ave, Winter Haven, FL 33880

  Beautiful and well-maintained 4-bedroom, 2-bathroom home available for rent! This move-in-ready property features ceramic tile flooring throughout, a spacious living area, and a fully fenced backyard. Conveniently located near schools, shopping, restaurants, and major roadways. Don't miss this great rental opportunity-schedule your showing today!

  Tebi Rodriguez La Rosa Realty Kissimmee

  260 Westwood Ave, Winter Haven, FL 33880
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  /19

  $1,595 Per Month

  • 3 Beds
  • 1 Bath
  • 1,234 Sq Ft
  • Townhouse for Rent

  501 Avenue G SE Unit A, Winter Haven, FL 33880

  Welcome to your SPACIOUS and STYLISH abode in the heart of Winter Haven, FL! This stunning front unit of a charming duplex offers the perfect blend of comfort and convenience, boasting THREE BEDROOMS, one bath, and an expansive 1200 SQFT + layout. Step inside to discover the beauty of modern living with newly installed QUARTZ COUNTERTOP gracing the kitchen, complemented by sleek LAMINATE FLOORS

  Nomar Rosa LPT REALTY, LLC

  501 Avenue G SE Unit A, Winter Haven, FL 33880
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  $1,700 Per Month

  • 3 Beds
  • 2 Baths
  • 1,110 Sq Ft
  • House for Rent

  803 Foxboro Ln SW, Winter Haven, FL 33880

  THIS HOME IS A MUST TO SEE AS THE OWNE HAS HAD IT COMPLETELY RE DONE LIKE A NEW HOME. KITCHEN HAS QUARTZ COUNTER TOPS AND NEW WOOD CABINETS, NEW SINK,AND NEW APPLICANCES BOTH STOVE & REFRIGERATOR.NEW SCREEN REAR PORCH.

  William Beasley STAR REALTY OF WINTER HAVEN

  803 Foxboro Ln SW, Winter Haven, FL 33880
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  $1,850 Per Month

  • 2 Beds
  • 2.5 Baths
  • 1,425 Sq Ft
  • House for Rent

  2414 Willow Way, Winter Haven, FL 33881

  One or more photo(s) has been virtually staged. Modern Comfort Meets Style – Beautiful 2-Bed, 2.5-Bath Home in Winter Haven! ***June Move-In Special: Get $500 OFF Your First Month’s Rent — This Month Only!*** Welcome to 2414 Willow Way, a stunning and move-in-ready 2-bedroom, 2.5-bathroom home nestled in one of Winter Haven’s most desirable and fast-growing communities! Step into a bright and

  Jacob Hara TRANSCEND REALTY

  2414 Willow Way, Winter Haven, FL 33881
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  $1,675 Per Month

  • 3 Beds
  • 2 Baths
  • 1,040 Sq Ft
  • Townhouse for Rent

  2318 W Cannon Terrace NW Unit B, Winter Haven, FL 33881

  3 Bedroom, 2 Bath Duplex For Rent in Winter Haven, FL 33881; Range, Refrigerator, D/W, Disposal, Central Heat and A/C.

  Rick Sein REALSOURCE PROPERTY MANGNT LLC

  2318 W Cannon Terrace NW Unit B, Winter Haven, FL 33881
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  $1,400 Per Month

  • 3 Beds
  • 1 Bath
  • 990 Sq Ft
  • House for Rent

  110 Orange Ave, Winter Haven, FL 33880

  FOR RENT - 3/1 Single Family Home with a big, fenced-in backyard. The range and the refrigerator are included. The home is less than 5 minutes away from Highway 17 and the Polk Parkway. Come see this home today.

  Linda Andre COLDWELL BANKER REALTY

  110 Orange Ave, Winter Haven, FL 33880
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  $2,000 Per Month

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

  939 Sun Burst Rd, Winter Haven, FL 33880

  This stunning single-family home offers an inviting open-concept kitchen and living area, perfect for entertaining or relaxing. The modern kitchenfeatures sleek countertops, ample cabinet space, and a seamless flow into the spacious living room. With a two-car garage providing plenty ofparking and storage, this home is as practical as it is beautiful. The large fenced backyard offers

  Jose Solano FUSION FLORIDA REALTY LLC

  939 Sun Burst Rd, Winter Haven, FL 33880
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  $2,000 Per Month

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

  702 Avenue H NE, Winter Haven, FL 33881

  Welcome home to this spacious 3-bedroom, 2-bath duplex in the heart of Winter Haven! This well-maintained home offers an oversized living room with plenty of space to relax or entertain, a separate dining room, and generously sized bedrooms throughout. Enjoy the convenience of a one-car garage, in-unit laundry, and ceiling fans in multiple rooms to keep you comfortable year-round. Step outside to

  Christin Davis PROPERTY MANAGEMENT OF POLK

  702 Avenue H NE, Winter Haven, FL 33881
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  $1,100 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. Move-In Special: Half Off the First Month's Rent for qualified tenants who sign a 12-month lease! 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.

  David Small KELLER WILLIAMS REALTY SMART 1

  140 Avenue W NW Unit 3, Winter Haven, FL 33881
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  $1,275 Per Month

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

  2463 Avenue C SW Unit A, Winter Haven, FL 33880

  1 month free!Welcome home to this charming 2-bedroom duplex in Winter Haven, featuring a fully separate yard perfect for pets, gardening, or outdoor relaxing. This unit offers a comfortable layout with a bright living area, functional kitchen, and two well-sized bedrooms.

  Jordan Clark PALM LEAF PROPERTY MANAGEMENT

  2463 Avenue C SW Unit A, Winter Haven, FL 33880
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  $1,300 Per Month

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

  912 Lake Jessie Dr Unit B, Winter Haven, FL 33881

  Enjoy the beauty of waterfront living in this well-maintained 1-bedroom, 1-bath residence offering approximately 800 square feet of functional and inviting living space. Rent includes utilities, making for easy and convenient monthly budgeting. The kitchen comes equipped with a range and refrigerator, while the home's efficient layout maximizes comfort and usability. Take advantage of scenic

  Tiffani Kline HOUSE OF GLASS REAL ESTATE PM

  912 Lake Jessie Dr Unit B, Winter Haven, FL 33881
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  $1,900 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
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  $1,190 Per Month

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

  955 6th St SE Unit 5, Winter Haven, FL 33880

  The renovated first-floor apartment features laminate floors throughout, beautiful kitchen cabinets, appliances include a stove, microwave, and refrigerator and Washer & Dryer It also features an A/C unit Hight efficiency, modern lighting lamps and blinds. Security cameras on property exteriors. Great location offering walking distance to the bus line, Winter Haven High School, municipal offices,

  Manuel Paredes La Rosa Realty Llc

  955 6th St SE Unit 5, Winter Haven, FL 33880
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  $1,700 Per Month

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

  245 Southern Breeze Loop, Winter Haven, FL 33880

  SUPER SWEET SAVINGS!!! Enjoy ONE MONTH off your first month's rent when you apply by February 14, 2024, move in by February 21, 2024! Concession applied in March. Select homes, subject to change.Adorable home ready for move in! This home offer 3 bedroom and 2 bathrooms located in beautiful place. In addition, this home features vinyl and carpeted floors, a modern kitchen with updated cabinets

  Ethel Gumaru FIRSTKEY HOMES LLC

  245 Southern Breeze Loop, Winter Haven, FL 33880
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  $1,900 Per Month

  • 3 Beds
  • 2 Baths
  • 1,464 Sq Ft
  • House for Rent

  3079 Laurel Oak Ln, Winter Haven, FL 33884

  Beautiful 3-Bedroom Home for Rent in Villamar – Winter Haven, FLWelcome to this beautiful 3-bedroom, 2-bathroom home located in the highly desirable Villamar community in Winter Haven. Built with comfort and modern living in mind, this home features a spacious open-concept layout, a private primary suite with a large walk-in closet and en-suite bathroom, a fully equipped kitchen with all

  Umberto Da Cunha Neto WRA BUSINESS & REAL ESTATE

  3079 Laurel Oak Ln, Winter Haven, FL 33884
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  $1,100 Per Month

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

  1484 32nd St NW, Winter Haven, FL 33881

  Discover this charming duplex in the heart of Winter Haven, FL, offering 2 bedrooms and 1 bathroom in a thoughtfully designed layout. Step inside to find a bright and functional kitchen equipped with essential appliances, including a refrigerator and range, making meal preparation effortless. The kitchen flows seamlessly into the living area, creating an open and welcoming space that combines

  Jordan Leventhal RENTAL AND REALTY GROUP

  1484 32nd St NW, Winter Haven, FL 33881
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  $1,595 Per Month

  • 2 Beds
  • 2 Baths
  • 1,033 Sq Ft
  • House for Rent

  267 Lake Thomas Dr, Winter Haven, FL 33880

  Welcome to this beautiful WATERFRONT VIEW home, where comfort and scenery meet in perfect harmony. The kitchen has just been re done new cabinets, granite counter tops new flooring, adding a fresh touch to the heart of the home. Inside, you’ll find a desirable split floor plan, a huge living room with plenty of space to relax or entertain, and stunning lake views that can be enjoyed right from

  William Beasley STAR REALTY OF WINTER HAVEN

  267 Lake Thomas Dr, Winter Haven, FL 33880
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  $1,850 Per Month

  • 3 Beds
  • 2 Baths
  • 1,405 Sq Ft
  • House for Rent

  122 Jace Way, Winter Haven, FL 33881

  Welcome to this beautifully updated, move-in-ready home with a fresh, modern feel throughout. The home features luxury vinyl plank flooring, updated lighting, ceiling fans, blinds, doors, fresh interior paint, and smart home technology with Alexa. The spacious great room provides an inviting setting for everyday living and entertaining, while the kitchen with brand-new stainless-steel appliances,

  Glory Montalvo PROPERTY OUTLET INTERNATIONAL

  122 Jace Way, Winter Haven, FL 33881
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  /22

  $1,600 Per Month

  • 3 Beds
  • 2 Baths
  • 1,508 Sq Ft
  • Property for Rent

  5320 Laurel Oak Dr, Winter Haven, FL 33880

  Virtually Staged. This welcoming 3 bedroom, 2 bathroom home in the Winter Haven Oaks 55+ community blends comfort, convenience, and an upbeat, easygoing lifestyle. The layout offers three flexible bedrooms along with a bright sun room that quickly becomes the heart of the home — an ideal spot for morning coffee, quiet afternoons, or simply enjoying the peaceful surroundings. An attached carport

  Christin Davis PROPERTY MANAGEMENT OF POLK

  5320 Laurel Oak Dr, Winter Haven, FL 33880

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