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

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  $1,620 Per Month

  • 3 Beds
  • 2 Baths
  • 1,109 Sq Ft
  • House for Rent

  449 Red Hawk Loop, Winter Haven, FL 33880

  Apply now or schedule your self-tour today and take the first step toward getting more than just a place to live. Rent with FirstKey Homes for a home that's right for you, plus professional service and maintenance, innovative resident programs, and more… that's the power of purple!This 3-bedroom, 2-bathroom rental home in Winter Haven, FL, may be the right place for you. The fenced

  (863) 251-6437

  449 Red Hawk Loop, Winter Haven, FL 33880
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  $1,855 Per Month

  • 3 Beds
  • 2 Baths
  • 1,470 Sq Ft
  • House for Rent

  4301 Larrys Lagoon, Winter Haven, FL 33884

  Apply now or schedule your self-tour today and take the first step toward getting more than just a place to live. Rent with FirstKey Homes for a home that's right for you, plus professional service and maintenance, innovative resident programs, and more… that's the power of purple!This 3-bedroom, 2-bathroom rental home in Winter Haven, FL, might be the perfect fit for your lifestyle. See

  (863) 474-9529

  4301 Larrys Lagoon, Winter Haven, FL 33884
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  $1,925 Per Month

  • 3 Beds
  • 2 Baths
  • 1,201 Sq Ft
  • House for Rent

  812 Whisper Lake Ct, Winter Haven, FL 33880

  EXCITING NEWS: WE ARE CURRENTLY RENOVATING THIS HOME! NOTE THAT THE PHOTOS SHOWN REPRESENT THE HOME BEFORE RENOVATION AND DO NOT REFLECT ANY UPDATES. PLANNED IMPROVEMENTS INCLUDE: NEW STAINLESS STEEL APPLIANCES. APPLY TODAY OR ASK YOUR LEASING SPECIALIST FOR MORE DETAILS! Apply now or schedule your self-tour today and take the first step toward getting more than just a place to live. Rent

  (863) 622-9626

  812 Whisper Lake Ct, Winter Haven, FL 33880
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  $1,400 Per Month

  • 2 Beds
  • 2 Baths
  • 1,015 Sq Ft
  • Condo for Rent

  1935 Ave O SW Unit 201, Winter Haven, FL 33880

  Property Id: 2515636Home features: Plank flooring throughout (easy to clean) Wood cabinetry + granite countertops Stainless steel appliances including dishwasher and garbage disposal Ceiling fans in the bedroom and living roomIn-unit washer & dryer Bedroom and living room are cable-readyLocation: Minutes to downtown Winter Haven—close to shopping, restaurants,

  (863) 837-4814

  1935 Ave O SW Unit 201, Winter Haven, FL 33880
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  $1,250 Per Month

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

  1059 Spirit Lake Rd, Winter Haven, FL 33880

  This 900 SqFt unit offers comfort and convenience in a desirable location.- Electric range, microwave, and refrigerator included - Forced air heating and central cooling for year-round comfort - Tile flooring and ceiling fan(s)- Dryer included for ease of laundry - Fenced yard and patio for outdoor enjoyment - On-street parking available Perfectly situated

  (659) 207-5228

  1059 Spirit Lake Rd, Winter Haven, FL 33880
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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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  $1,825

  Total Monthly Price

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

  711 Avenue B NE, Winter Haven, FL 33881

  This is a 3/2 home in Winter Haven Fl. This home is move in ready and had been freshly updated. Call for you're showing today. Close to downtown and convenient to all winter haven has to offer.

  711 Avenue B NE, Winter Haven, FL 33881
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  $1,750

  Total Monthly Price

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Condo for Rent

  330 Avenue G SE Unit Apartment, Winter Haven, FL 33880

  330 Avenue G SE Unit Apartment, Winter Haven, FL 33880
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  $1,450

  Total Monthly Price

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

  5624 Struthers Ct, Winter Haven, FL 33884

  Freshly updated 2 bed, 1 bath duplex in a quiet Winter Haven location near US-27 and Legoland.Available now. Clean, updated unit ready for immediate move-in.• Washer & dryer included• New central A/C• Tile floors throughout (no carpet)• Fresh interior updates• Private parking• Shared yard$1,450/month$1,450 security deposit Available now.

  5624 Struthers Ct, Winter Haven, FL 33884
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  $1,350

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Condo for Rent

  5663 Struthers Ct Unit 5663 Struthers Ct, Winter Haven FL, 33837, Winter Haven, FL 33884

  Spacious condoPeaceful family friendly neighborhoodNear Garden Grove Elementary and LegolandBig yard Ceiling fansCeiling fans in bedroomsPets allowed

  5663 Struthers Ct Unit 5663 Struthers Ct, Winter Haven FL, 33837, Winter Haven, FL 33884
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  $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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  $2,000 Per Month

  • 4 Beds
  • 3 Baths
  • 1,883 Sq Ft
  • House for Rent

  Unlisted Address

  Beautiful 4-bedroom, 3-bath home located in a great family-friendly neighborhood! This spacious home features a desirable 3-way split floor plan, vaulted ceilings, and stylish LVP wood-look plank flooring throughout the main living areas. The open kitchen offers granite countertops, ample cabinet space, and overlooks the bright living and dining areas, creating the perfect space for everyday

  John-Michael Elliott S & D REAL ESTATE SERVICE LLC

  Unlisted Address
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  /2

  $1,595 Per Month

  • 3 Beds
  • 1 Bath
  • 1,296 Sq Ft
  • House for Rent

  876 Crestwood Dr, Winter Haven, FL 33881

  This home located in a quiet and desirable area of Winter Haven. This well-maintained property offers a comfortable layout with plenty of natural light, creating a warm and inviting living space.The home features spacious bedrooms, a cozy living area, and a functional kitchen with ample cabinet space, perfect for everyday living. The property also includes a nice outdoor area, ideal for

  876 Crestwood Dr, Winter Haven, FL 33881
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  $1,425 Per Month

  • 2 Beds
  • 2 Baths
  • 1,030 Sq Ft
  • Condo for Rent

  333 Lake Howard Dr NW Unit 312C, Winter Haven, FL 33880

  FOR RENT - 2 Bedroom/2 Bath Condo at Imperial Harbours. This community is for ages 55+. The unit comes with all of the appliances and faces the garden area. The bedrooms are generously sized, and the porch area is enclosed. The community features a very nice pool with a TIKI Bar area for relaxing and sipping your favorite drinks. In the distance you can watch the sun rise over Lake Howard in the

  Linda Andre COLDWELL BANKER REALTY

  333 Lake Howard Dr NW Unit 312C, Winter Haven, FL 33880
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  $2,000 Per Month

  • 4 Beds
  • 3 Baths
  • 1,883 Sq Ft
  • House for Rent

  3054 Buckeye Point Dr, Winter Haven, FL 33881

  Beautiful 4-bedroom, 3-bath home located in a great family-friendly neighborhood! This spacious home features a desirable 3-way split floor plan, vaulted ceilings, and stylish LVP wood-look plank flooring throughout the main living areas. The open kitchen offers granite countertops, ample cabinet space, and overlooks the bright living and dining areas, creating the perfect space for everyday

  3054 Buckeye Point Dr, Winter Haven, FL 33881
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  $1,100 Per Month

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

  115 Avenue F SW Unit B, Winter Haven, FL 33880

  This brand-new studio apartment in Winter Haven offers efficient, low-maintenance living with an open layout and vinyl flooring throughout. The space features a bright main living area and a bathroom with a walk-in shower. With its fresh construction and easy-care design, the space maintains a straightforward, functional feel ideal for someone seeking a no-frills place to call home.

  Christin Davis PROPERTY MANAGEMENT OF POLK

  115 Avenue F SW Unit B, Winter Haven, FL 33880
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  $1,950 Per Month

  • 4 Beds
  • 2 Baths
  • House for Rent

  1108 Carefree Cove Dr, Winter Haven, FL 33881

  Property Id: 1524046Rent is Negotiable. Looking for responsible, good and clean people. Large House for a family with fenced in large yard, tiles floors, updated kitchen and bathrooms with lots of extras. Available mid July 2024. Please call both contact numbers to get more information on property and terms of rental.

  1108 Carefree Cove Dr, Winter Haven, FL 33881
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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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  $1,700 Per Month

  • 3 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Condo for Rent

  701 Bates Ave SW Unit 202, Winter Haven, FL 33880

  ***BRAND NEW CONSTRUCTION*** Everything is new!! Never lived in 3 bed 2 bath unit. Beautiful kitchen with open eating concept, granite countertops, and stainless steel appliance. The units also come with a stackable washer and dryer included! Great layout with plenty of storage. Your rent also includes your water and trash for convenience and simplicity. Great location near downtown Winter Haven

  701 Bates Ave SW Unit 202, Winter Haven, FL 33880
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  $1,850 Per Month

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

  744 Reggie Rd, Winter Haven, FL 33884

  Step into pure luxury with the Annapolis. This exceptional home is complete with 3 bedrooms and 2 bathrooms. The kitchen has a lovely center island that overlooks an open dining room with a large family room, which is perfect for entertaining. The owner suite features a over-sized bedroom connected to a bathroom with his and her sinks and a roomy walk-in closet. This home comes fully equipped

  Yurisney Alonso Acosta LPT REALTY, LLC

  744 Reggie Rd, Winter Haven, FL 33884
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  /12

  $2,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,373 Sq Ft
  • 3 Bedroom/2 Bath Fully Furnished Pool Home for Rent

  2416 Ave B SW, Winter Haven, FL 33880

  Welcome to this Fully Furnished Pool Home for RentA stunning property located in the beautiful Winter Haven, FL. This home boasts three spacious bedrooms and two full bathrooms, offering ample space for comfortable living. The property is fully furnished, allowing you to move in with ease and start enjoying your new home immediately. The private swimming pool is a standout

  2416 Ave B SW, Winter Haven, FL 33880
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  $700 Per Month

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

  720 6th St NW Unit 3, Winter Haven, FL 33881

  Rent with confidence from a licensed Real Estate Brokerage. We have a quick and simple application process. Contact us through this website or call to set up a tour and apply today! WE PROUDLY WELCOME ALL PETS. Welcome to this cute 2-bed, 1-bath home! Our spacious layout is perfect for comfortable living. Enjoy the yard to unwind after a long day, enjoy the fresh air, and gather for fun-filled

  Erich Spivey ALABAMA LLC

  720 6th St NW Unit 3, Winter Haven, FL 33881
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  $1,399 Per Month

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

  609 Ave G SE, Winter Haven, FL 33880

  Welcome to your new home!This 2-bedroom, 1-bathroom unit offers approximately 875 sq ft of living space, designed for practical and efficient living.Step inside to a functional layout with easy-to-maintain flooring throughout. The kitchen is equipped with a refrigerator, stove/oven, and microwave, along with adequate cabinet space. Washer and dryer hookups are included, with

  609 Ave G SE, Winter Haven, FL 33880
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  $1,550 Per Month

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

  64 Stebbins Dr Unit 64, Winter Haven, FL 33884

  Why keep renting when you can own for less? Step into your own 2 bed / 2 bath home-brand new, spacious, and designed for real living. Located in Grove Shores, a beautifully maintained, professionally managed community, this is your chance to upgrade your lifestyle without increasing your monthly cost. Call today to schedule your tour-opportunities like this don't last.

  Tori Coil Grove Shores

  64 Stebbins Dr Unit 64, Winter Haven, FL 33884
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  $1,375 Per Month

  • 2 Beds
  • 1.5 Baths
  • 995 Sq Ft
  • Two-Bedroom Townhouse near Park

  1860 Ave Q SW, Winter Haven, FL 33880

  You will enjoy a quiet stroll around the park or some outdoor sporting activities with Sertoma Park immediately across the street!The home boasts a private patio in the rear of the home, a downstairs/half bath for guests, washer/dryer hookups, and a walk-in pantry. Pets allowed based on results. Fees/rents based on results.*Tenants are required to sign up for our Resident

  1860 Ave Q SW, Winter Haven, FL 33880
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  $1,998 Per Month

  • 4 Beds
  • 2 Baths
  • 1,845 Sq Ft
  • House for Rent

  1993 Sarah St, Winter Haven, FL 33884

  Welcome to this spacious, modern 4-bedroom, 2-bathroom one-story home in the sought-after Peace Creek Reserve community! Perfectly positioned near Hwy 27, this prime location offers quick access to Legoland, Downtown Winter Haven & Lake Wales, shopping, dining, and the stunning Chain of Lakes—ideal for boating, fishing, and outdoor adventures. Step inside and spoil yourself with the upscale Bloom

  Anna Shi LPT REALTY, LLC

  1993 Sarah St, Winter Haven, FL 33884
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  $1,250 Per Month

  • 2 Beds
  • 1.5 Baths
  • 854 Sq Ft
  • Condo for Rent

  163 Ave a SE Unit 2, Winter Haven, FL 33880

  Downstairs rental near Downtown Winter Haven! Freshly renovated and full of charm. Enjoy hard-surface flooring throughout, generous bedrooms sizes, a spacious living area, and a bonus den perfect for a home office or extra lounge space. Stylish, functional, and in a location that’s hard to beat. Schedule your showing today!Security deposit is $1,300 and pet fees are $250 per pet. No

  163 Ave a SE Unit 2, Winter Haven, FL 33880
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  $2,000 Per Month

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

  910 Sun Burst Rd, Winter Haven, FL 33880

  This charming, move-in-ready home offers a popular open-concept layout with a spacious kitchen island, dining area, and 3 bedrooms/2 bathrooms. The split-bedroom plan provides privacy for the owner’s suite. Enjoy peaceful evenings on the covered screened in porch overlooking the large fenced backyard with neighbors on only one side and none behind.Proximity to downtown Winter Haven, you’ll be

  Pedro Cartagena 1513 REALTY LLC

  910 Sun Burst Rd, Winter Haven, FL 33880
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  $1,625 Per Month

  • 2 Beds
  • 2 Baths
  • 828 Sq Ft
  • House for Rent

  1902 Garden Lake Dr, Winter Haven, FL 33884

  GATED WATERFRONT COMMUNITY! This 2BR/2BA condo is move-in ready and features gorgeous views from a waterfront deck and screened lanai. Water view continues into master suite with 2 closets and walk-in shower! Luxury vinyl flooring throughout, NO CARPET, stainless steel appliances, granite countertops, and washer/dryer in the unit. Community offers lakefront pool and tennis courts with a fabulous

  1902 Garden Lake Dr, Winter Haven, FL 33884
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  $1,800 Per Month

  • 3 Beds
  • 2 Baths
  • 1,147 Sq Ft
  • House for Rent

  1539 Roselawn St SW, Winter Haven, FL 33880

  Beautifully fully remodeled 3-bedroom, 2-bathroom home located at 1539 Roselawn, offering modern comfort and stylish living throughout. This residence features premium waterproof luxury vinyl flooring, a spacious and upgraded kitchen with elegant granite countertops, and stainless steel appliances. The home has been thoughtfully updated to provide both functionality and design, along with a

  Ines Morales LA ROSA REALTY KISSIMMEE

  1539 Roselawn St SW, Winter Haven, FL 33880
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  $1,875 Per Month

  • 4 Beds
  • 2 Baths
  • 1,840 Sq Ft
  • 4-Bedroom, 2.-Bathroom in Winter Haven ***MOVE-IN SPECIAL/50% OFF 2ND MONTH***

  877 Cambridge Dr, Winter Haven, FL 33881

  ****MOVE-IN SPECIAL - 50% OFF 2ND MONTH****This gorgeous 4-bedroom, 2.5-bathroom home is loaded with space and comes with stainless appliances as well as a spacious two-car garage.Call to schedule your showing and come see this beautiful home TODAY!HOA APPROVAL MANDATORYAll residents are enrolled in the Resident Benefits Package (RBP) at a cost of $25/per month,

  877 Cambridge Dr, Winter Haven, FL 33881
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  $1,150 Per Month

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

  710 Avenue C SW Unit 4A, Winter Haven, FL 33880

  This well maintained first floor 1 BD/1 BA apartment is on a quiet street near Lake Howard. Centrally located, approximately 10 min. walking distance to downtown Winter Haven. The apartment has been freshly painted for the new residence and is ready for immediate move in! The building has a free on site laundry facility and off street parking. Call today to schedule your private tour!

  Pedro Cartagena 1513 REALTY LLC

  710 Avenue C SW Unit 4A, Winter Haven, FL 33880
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  $1,275 Per Month

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

  430 Ave B NE Unit A, Winter Haven, FL 33881

  This unit is part of a tri-plex and features a massive open living space, luxury vinyl flooring throughout, washer/dryer hookups in the unit, granite countertops, and NO CARPET throughout. Conveniently located close to food, shopping, medical, and just minutes from Downtown Winter Haven, this is a great place to call home! Call today, don’t miss out!Resident Benefits Package,

  430 Ave B NE Unit A, Winter Haven, FL 33881
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  $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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  $1,300 Per Month

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

  151 Avenue C SE, Winter Haven, FL 33880

  PROFESSIONALLY MANAGED!! This fully renovated 2BR/1BA condominium has been tastefully updated and upgraded throughout. Conveniently located just steps from Winter Haven's beautiful historic downtown, this is a marvelous place to call home. UPDATED EVERYTHING - cabinets, granite counters, ALL APPLIANCES, lighting, bathroom, shelving, floors, paint, water heater and MORE! Long term leases available

  151 Avenue C SE, 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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  $1,600 Per Month

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Condo for Rent

  701 Bates Ave SW Unit 201, Winter Haven, FL 33880

  ***BRAND NEW CONSTRUCTION*** Everything is new!! Never lived in 3 bed 1 bath unit. Beautiful kitchen with open eating concept, granite countertops, and stainless steel appliance. The units also come with a stackable washer and dryer included! Great layout with plenty of storage. Your rent also includes your water and trash for convenience and simplicity. Great location near downtown Winter

  701 Bates Ave SW Unit 201, Winter Haven, FL 33880
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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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  $1,275 Per Month

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

  430 Ave B NE Unit B, Winter Haven, FL 33881

  2 BD/1 BA APARTMENT AVAILABLE FOR LONG-TERM LEASE! This unit is part of a tri-plex and features a massive open living space, luxury vinyl flooring throughout, washer/dryer hookups in the unit, granite countertops, and NO CARPET throughout. Conveniently located close to food, shopping, medical, and just minutes from Downtown Winter Haven, this is a great place to call home! Call today, don’t miss

  430 Ave B NE Unit B, Winter Haven, FL 33881
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  $1,450 Per Month

  • 2 Beds
  • 1.5 Baths
  • 912 Sq Ft
  • Townhouse for Rent

  395 Quentin Ave NW Unit 397, Winter Haven, FL 33881

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

  Adan Ordonez ADAN INVESTMENTS REAL ESTATE GROUP, PLLC

  395 Quentin Ave NW Unit 397, Winter Haven, FL 33881

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