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

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  $1,900 per month

  • 3 Beds
  • 2 Baths
  • 1,463 Sq Ft
  • House for Rent

  281 Arbuthnot St, Winter Haven, FL 33881

  NOW AVAILABLE! This like new stunning 3-bedroom, 2-bathroom home is perfectly situated in North Winter Haven within the gated community of Sanctuary by the Lake. Located on the shores of Lake Rochelle and directly adjacent to the Winter Haven Chain-of-Lakes Bike Trail, this property offers a premier location for outdoor enthusiasts. The interior features a spacious open-concept floor plan

  Sheryl Webster VENTURE HOME REALTY

  281 Arbuthnot St, Winter Haven, FL 33881
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  $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
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  $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
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  $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
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  $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
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  $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
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  $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
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  $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
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  $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
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  $1,000 per month

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

  1103 Cypress Gardens Blvd Unit C-106, Winter Haven, FL 33884

  1 bedroom 1 bath ground floor condo with access to Lake Roy on the famous Winter Haven Chain of Lakes.New Luxury Vinyl Plank Flooring and fresh interior paint.

  Steven Smith, PA LOCKHART & ASSOCIATES INC

  1103 Cypress Gardens Blvd Unit C-106, Winter Haven, FL 33884
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  $1,850 per month

  • 4 Beds
  • 2 Baths
  • 1,688 Sq Ft
  • House for Rent

  4819 Summerfield Cir, Winter Haven, FL 33881

  Super Cute Home features 4 bedroom, 2 bath, 2 car garage home, located in Country Club Estates. Freshly painted a neutral color, tile in living areas and brand new LVP in bedroom. Living room kitchen combo, great for family time. Call today for a showing!

  Ronald Gentile ORLANDO REO PROF I INC

  4819 Summerfield Cir, Winter Haven, FL 33881
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  /10

  $1,100 per month

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

  2824 Avenue G NW, Winter Haven, FL 33880

  1 bedroom 1 bath apartment. Beautifully updated apartment home with all ceramic tile, newer cabinets and appliances. Home overlooks Deer Lake. Large backyard with lawn care included. This unit is the right hand side of the home. Separate 3 bedroom home is on the left side.

  Kara Severit REMAX EXPERTS

  2824 Avenue G NW, Winter Haven, FL 33880
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  $1,745 per month

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

  1804 Carnostie Rd, Winter Haven, FL 33884

  House available for rent in the VillaMar condominium – 3 bedrooms and 2 bathrooms Beautiful residence with a veranda at the entrance and a charming garden, perfect for those seeking comfort and practicality. The open-concept layout offers integration between the living room, dining room, and kitchen, providing spaciousness and brightness to the environment. The master suite guarantees total

  Umberto Da Cunha Neto WRA BUSINESS & REAL ESTATE

  1804 Carnostie Rd, Winter Haven, FL 33884
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  $1,790 per month

  • 3 Beds
  • 2.5 Baths
  • 3,654 Sq Ft
  • Townhouse for Rent

  1125 Evergreen Ct, Winter Haven, FL 33881

  This beautiful 3-bedroom, 2.5-bath townhouse is now ready for its next occupants! This home features hardwood flooring in the common areas and a spacious living room perfect for relaxing or entertaining. The kitchen offers wide countertops and comes fully equipped with all the appliances you need for everyday convenience. Upstairs, the master bedroom includes an ensuite with both a bathtub and a

  Mohamed Souissi BULL PROPERTY MANAGEMENT

  1125 Evergreen Ct, Winter Haven, FL 33881
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  $1,350 per month

  • 2 Beds
  • 2 Baths
  • 1,078 Sq Ft
  • Condo for Rent

  2040 San Marcos Dr SE Unit 103, Winter Haven, FL 33880

  Welcome to your new home just off Cypress Gardens Blvd — a spacious and inviting first-floor condo with 2 bedrooms and 2 full bathrooms. This unit features high ceilings in the living room that create an open, airy feel, and the master bedroom includes its own private ensuite for added comfort. Located in a quiet, well-kept community, you’ll also enjoy access to a sparkling pool perfect for

  Christin Davis PROPERTY MANAGEMENT OF POLK

  2040 San Marcos Dr SE Unit 103, Winter Haven, FL 33880
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  $1,095 per month

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

  208 Sears Ave NE, Winter Haven, FL 33881

  Single Family Home. 3 bed, 1 bath, fenced yard. Newer carpet.

  Arnold Austria A+ HOME RENTALS LLC

  208 Sears Ave NE, Winter Haven, FL 33881
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  $1,395 per month

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

  2000 15th Ct NW Unit 15, Winter Haven, FL 33881

  One or more photo(s) has been virtually staged. NOW LEASING - AQUA APARTMENT HOMES! MOVE-IN READY! THIS SECOND (2ND) FLOOR UNIT COMES KITCHEN APPLIANCES, IN UNIT WASHER/DRYER, NEW TILE BACKSPLASH, NEW COUNTERTOPS AND TILE FLOORING THROUGHOUT. THIS UNIT IS FRESHLY PAINTED AND ALL FIXTURES HAVE BEEN REPLACED. UNIT OFFERS A VIEW TO THE INGROUND COMMUNITY POOL. LAUNDRY FACILITIES LOCATED ON SITE.

  Manuel Paredes LA ROSA REALTY LLC

  2000 15th Ct NW Unit 15, Winter Haven, FL 33881
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  $1,000 per month

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

  1480 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

  1480 32nd St NW, Winter Haven, FL 33881
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  $1,395 per month

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

  2000 15th Ct NW Unit 11, Winter Haven, FL 33881

  Now Leasing - Aqua Apartment Homes! Move-in Ready! This 2nd floor unit comes with all stainless steel kitchen appliances, in unit washer/dryer, new tile backsplash, new countertops and tile flooring throughout. This unit is freshly painted and all fixtures have been replaced. Unit offers a view to the inground community pool. Laundry facilities located on site. Property is located a short

  Manuel Paredes LA ROSA REALTY LLC

  2000 15th Ct NW Unit 11, Winter Haven, FL 33881
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  $1,550 per month

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

  403 Avenue J SE, Winter Haven, FL 33880

  Cute and cozy 1/2 duplex. Updated kitchen, bathroom and flooring. Close to major restaurants, shopping and grocery stores.

  Angela Chapman CAPITAL REALTY GROUP FLORIDA

  403 Avenue J SE, Winter Haven, FL 33880
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  $1,900 per month

  • 3 Beds
  • 2 Baths
  • 1,553 Sq Ft
  • House for Rent

  2845 Whispering Trails Dr, Winter Haven, FL 33884

  This beautiful 3-bedroom, 2-bathroom home is nestled in the sought-after Whispering Trails neighborhood of Winter Haven. Inside, you’ll find an open floor plan that creates a bright, airy flow from the living area to the kitchen and dining space—perfect for both everyday living and entertaining. The home comes equipped with a washer and dryer, making move-in easy and convenient. Step outside to

  Christin Davis PROPERTY MANAGEMENT OF POLK

  2845 Whispering Trails Dr, Winter Haven, FL 33884
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  $1,825 per month

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

  2783 Sycamore St, Winter Haven, FL 33881

  One or more photo(s) has been virtually staged. Welcome to this beautiful 3-bedroom, 2.5-bath home perfectly designed for comfort and style! Step inside to an open and airy floor plan featuring a bright living area, a contemporary kitchen with sleek finishes, and a cozy dining space—ideal for family gatherings or entertaining guests. Upstairs, you’ll find spacious bedrooms including a relaxing

  Jacob Hara TRANSCEND REALTY

  2783 Sycamore St, Winter Haven, FL 33881
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  $1,300 per month

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

  1728 Teagan Ln, Winter Haven, FL 33884

  Beautiful studio apartment for a couple or single person, in a new community, with separate entrance, with defined spaces, laundry area, small but very comfortable kitchen, and bedroom with private bathroom. The parking space is shared with the owner. The house comes with its own separate apartment, built directly by the builder, so its spaces are designed with comfort in mind.

  Adriana Sanchez WF REALTY CORP.

  1728 Teagan Ln, Winter Haven, FL 33884
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  $1,750 per month

  • 3 Beds
  • 2 Baths
  • 1,489 Sq Ft
  • House for Rent

  620 Reflections Loop, Winter Haven, FL 33884

  Welcome to this spacious 3/2 near Legoland! Nestled in the heart of Winter Haven, FL, this home boasts three generously sized bedrooms and two full bathrooms. The split bedroom floor plan ensures privacy, while the eat-in kitchen nook provides a cozy space for meals. The master suite is a true retreat, complete with a luxurious garden tub. The entire home is outfitted with ceramic tiled flooring,

  Francisco Nieves-Taranto CT HOMES REALTY CORPORATION

  620 Reflections Loop, Winter Haven, FL 33884
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  $1,850 per month

  • 3 Beds
  • 2 Baths
  • 2,013 Sq Ft
  • House for Rent

  517 Heather Glen Dr, Winter Haven, FL 33884

  Move-In Ready & Minutes from LEGOLAND!Discover the perfect blend of comfort and convenience in this beautifully maintained 3-bedroom, 2-bath home boasting 2,013 sq. ft. of open-concept living space. The light-filled interior features a modern kitchen with a large island, spacious living and dining areas, and in-unit laundry for everyday ease. The split bedroom layout offers privacy, while the

  Raven Mundy GARRISON PROPERTY SERVICES LLC

  517 Heather Glen Dr, Winter Haven, FL 33884
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  $1,150 per month

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

  514 Avenue C NE Unit 4, Winter Haven, FL 33881

  Fantastic 2 bedroom/1.0 bathroom apartment totally renovated and ready for its new occupants. Unit is in close proximity of schools, including Jewett School of the Arts, Fred G. Garner Elementary School, and Frank E. Brigham Academy. 2 minute walk to Rotary Park. 7 minute walk to Kiwanis Park. 14 minute walk to Winter Haven Tennis Center. Water is included in the rent.

  Angela Chapman CAPITAL REALTY GROUP FLORIDA

  514 Avenue C NE Unit 4, Winter Haven, FL 33881
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  $1,995 per month

  • 3 Beds
  • 2.5 Baths
  • 1,722 Sq Ft
  • House for Rent

  434 Avenue C NE, Winter Haven, FL 33881

  Lovely older home with original hardwood flooring located near downtown Winter Haven. Fenced in yard great for kids or animals. Located half way between Tampa and Orlando.

  Steven Baron BARON HOLDINGS REAL ESTATE LLC

  434 Avenue C NE, Winter Haven, FL 33881
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  $1,700 per month

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

  8307 Waterview Way Unit 8307, Winter Haven, FL 33884

  Welcome to your perfect home away from home in beautiful Winter Haven, Florida! This fully furnished rental is located in a private, peaceful community just 5 miles from LEGOLAND® Florida and approximately 45 miles from Orlando. Ideal for traveling professionals or anyone seeking a relaxing retreat, this cozy unit offers access to a community clubhouse, pool, and scenic lake access for added

  Brooke Islas LA ROSA REALTY PRESTIGE

  8307 Waterview Way Unit 8307, Winter Haven, FL 33884
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  $1,000 per month

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

  Unlisted Address

  Furnished Mini Master Bedroom Suite for rent in beautiful private home. Rent includes all utilities and Wi-Fi. Private fridge available for tenant's use. Owner looking for single professional or travel nurse.

  Patricia Townsend MAHOGANY REAL ESTATE GROUP

  Unlisted Address
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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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  $1,700 per month

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

  168 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.Beautiful home offers 3 bedroom and 2 bathroom with ceramic tile type flooring. Home has 2 attached car garage. This home offers a spacious kitchen, updated bathrooms and is located in a beautiful

  Ethel Gumaru FIRSTKEY HOMES LLC

  168 Southern Breeze Loop, Winter Haven, FL 33880
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  $1,350 per month

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

  1100 Martinique Dr Unit 212, Winter Haven, FL 33884

  Beautifully renovated 2/1 in Winter Haven’s Orchid Springs. This community is NOT 55+, although the area is quiet and relaxed. The unit features LVP in the living room, stainless steel appliances, and modern features throughout such as a barn door, black switch plates and black trims in the bedroom area, and black ac vents. The condo is truly a sight to be seen. Water, sewer, trash, and gas ARE

  Alexios McDonald THE K TEAM REAL ESTATE SERVICES LLC

  1100 Martinique Dr Unit 212, Winter Haven, FL 33884
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  $925 per month

  • 1 Bed
  • 1 Bath
  • 4,440 Sq Ft
  • Apartment for Rent

  1890 Lake Mariam Dr, Winter Haven, FL 33884

  This home is part of a complex and comes with a refrigerator, stove, and oven as well as an electric water heater. Full size washer and dryer connections are located in the laundry room. Call today and ask about our move in deal!!

  Nancy Greenwood PALM LEAF PROPERTY MANAGEMENT

  1890 Lake Mariam Dr, Winter Haven, FL 33884
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  $1,800 per month

  • 4 Beds
  • 2 Baths
  • 1,598 Sq Ft
  • House for Rent

  108 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.Charming 4 bedroom and 2 bathroom home updated with ceramic tile type flooring and neutral paint throughout. The inviting living room is spacious and great for entertaining. The modern kitchen

  Ethel Gumaru FIRSTKEY HOMES LLC

  108 Southern Breeze Loop, Winter Haven, FL 33880
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  $1,600 per month

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

  1005 Eagle Pond Dr, Winter Haven, FL 33884

  MOVE-IN READY Eagle Pond condominium in the highly desirable gated community of Cypresswood Golf and Country Club available beginning 12/1/2023. This meticulously-maintained condo features hard floors throughout (no carpet!), new interior paint, NEW kitchen appliances, interior laundry (with brand new front load LG washer/dryer provided), and so much more. The spacious master bedroom features an

  Kayly Malinas JOHN WOOD REALTY, INC.

  1005 Eagle Pond Dr, Winter Haven, FL 33884
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  $1,800 per month

  • 3 Beds
  • 2 Baths
  • 1,852 Sq Ft
  • House for Rent

  1811 5th St SE, Winter Haven, FL 33880

  Ready to move in Three Beds / Two Baths located in the heart of Winter Haven, FL

  Othner Stfleurose OSF REAL ESTATE SERVICE

  1811 5th St SE, Winter Haven, FL 33880
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  $1,850 per month

  • 3 Beds
  • 2.5 Baths
  • 1,463 Sq Ft
  • Townhouse for Rent

  4622 Linda Dr, Lake Wales, FL 33859

  Move-in ready, brand-new 3-bedroom, 2.5-bath townhouse for rent in a quiet Lake Wales neighborhood. Perfect for families or anyone seeking comfort, privacy, and a relaxed lifestyle. Located close to schools and major roadways, this home combines residential tranquility with convenient access to everything you need. Don’t miss the chance to make this charming property your next home!

  Laritza Torres EXP REALTY LLC

  4622 Linda Dr, Lake Wales, FL 33859
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  $1,700 per month

  • 4 Beds
  • 2 Baths
  • 1,674 Sq Ft
  • Property for Rent

  365 Alturas Rd, Bartow, FL 33830

  Don’t miss the opportunity of leasing this spacious 4 BD/ 2 BA manufactured home with screen porch, workshop and carport. The home sits on a large 248'x100' lot (.57 acres) with shade trees, convenient to SR Hwy 60. Relax on the open-air front porch or quiet evenings on the screened in back porch. This property offers many positives for its next tenants.

  Pedro Cartagena 1513 REALTY LLC

  365 Alturas Rd, Bartow, FL 33830

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