Winter Haven, FL Homes for Rent under $1,800

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  $1,474 per month

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

  3110 Gowan Dr Unit A1, Winter Haven, FL 33884

  Currently offering 1 months free upfront and a 99.00 app/ admin fee which is credited to rental account. Prices, promotions, and availability are subject to change. Multiple floor plans available. Days on market is not specific to this current plan listed. Discover Prose Cypress Pointe and make every day feel like a getaway. Nestled in the heart of Winter Haven and just a short drive from

  

  AJ Rebhan

  THE APARTMENT BROTHERS LLC

  (863) 312-0563

  3110 Gowan Dr Unit A1, Winter Haven, FL 33884
• Explore Winter Haven

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  $1,675 per month

  • 2 Beds
  • 2 Baths
  • 1,180 Sq Ft
  • Apartment for Rent

  3110 Gowan Dr Unit B1, Winter Haven, FL 33884

  Currently offering 1 months free upfront and a 99.00 app/ admin fee which is credited to rental account. Prices, promotions, and availability are subject to change. Multiple floor plans available. Days on market is not specific to this current plan listed. Discover Prose Cypress Pointe and make every day feel like a getaway. Nestled in the heart of Winter Haven and just a short drive from

  

  AJ Rebhan

  THE APARTMENT BROTHERS LLC

  (863) 694-0332

  3110 Gowan Dr Unit B1, Winter Haven, FL 33884
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  $1,300 per month

  • 1 Bed
  • 1 Bath
  • 2,109 Sq Ft
  • House for Rent

  1453 Austin St Unit B, Winter Haven, FL 33884

  Charming PRIVATE ENTRANCE 1 - NEW bedroom apartment available for rent! Welcome to your new home! This beautiful apartment with living room, kitchen, 1 bathroom and 1 bedroom. Located in a quiet and friendly neighborhood in Eagle Lake, this space offers all the comfort and convenience you need. As for the location, it is close to shopping centers, restaurants, parks and public transportation.

  

  Isabel Melin Mora

  MELIN REALTY LLC

  (863) 208-5449

  1453 Austin St Unit B, Winter Haven, FL 33884
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  $1,700 per month

  • 2 Beds
  • 2 Baths
  • 1,572 Sq Ft
  • House for Rent

  4004 Cypress Landing S, Winter Haven, FL 33884

  Discover this beautiful 2-bedroom, 2-bath home with an additional flex room, perfect for a home office, den, or guest space, enclosed with a stylish barn door. Located in the desirable lakefront community of Cypress Landing, this home offers a welcoming and open layout with vaulted ceilings and abundant natural light. The kitchen is designed for both function and style, featuring ample cabinetry,

  

  CarLee Marchetti

  STAR REALTY OF WINTER HAVEN

  (863) 356-8719

  4004 Cypress Landing S, Winter Haven, FL 33884
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  $1,650 per month

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

  715 Magnolia Place, Winter Haven, FL 33884

  Gorgeous sunset views over Lake Winterset... this is the kind of rental you don’t come across often. Located in the gated Winterset community, this well-maintained 2-bedroom, 2-bath upstairs condo with a private one-car garage offers easy, low-maintenance lakeview living. Inside, you’ll find an open and airy layout with vaulted ceilings, skylights, and large sliding glass doors that bring in tons

  

  CarLee Marchetti

  STAR REALTY OF WINTER HAVEN

  (863) 431-3989

  715 Magnolia Place, Winter Haven, FL 33884
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  $1,500 per month

  • 2 Beds
  • 2 Baths
  • 1,073 Sq Ft
  • Condo for Rent

  383 Winter Ridge Blvd Unit 383, Winter Haven, FL 33881

  Thoughtfully remodeled 2-bedroom, 2-bath end unit condo situated on the Canal of Lake Smart/Lake Connie. Step inside to discover new luxury vinyl plank flooring throughout, new kitchen cabinets and beautiful granite countertops in the kitchen and bathrooms. The open-concept great room seamlessly blends the living and dining areas. The galley kitchen is equipped with all appliances, including a

  

  CarLee Marchetti

  STAR REALTY OF WINTER HAVEN

  (863) 270-7153

  383 Winter Ridge Blvd Unit 383, Winter Haven, FL 33881
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  $1,650 per month

  • 2 Beds
  • 2 Baths
  • 930 Sq Ft
  • Condo for Rent

  7903 Waterview Way, Winter Haven, FL 33884

  2BR/2BA Ground Floor Condo in the Gated neighborhood of Winterset. Wood laminate flooring (no carpet) throughout. New granite countertops and appliances in kitchen. Updated bathrooms. Primary bedroom has a very large walk in closet. Full size washer and dryer included. Community features a clubhouse with swimming pool overlooking Lake Winterset, tennis courts, boat ramp, and dock for fishing.

  

  Amy Reynolds

  LOCKHART & ASSOCIATES INC

  (863) 375-7146

  7903 Waterview Way, Winter Haven, FL 33884
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  $1,600 per month

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

  1756 2nd St NE, Winter Haven, FL 33881

  VACANT, MOVE-IN READY & PET FRIENDLY! Lease for just $1,600/month! Located in the lovely and up-and-coming Winter Haven area, this completely remodeled historic 1930s home has been beautifully restored to its former glory. This charming home offers 2 bedrooms and 1 well-appointed full bathroom, perfect for comfortable living. Situated on an oversized, fully fenced corner lot—perfect for pets—the

  

  Daniel Hut

  HUT REALTY, LLC

  (863) 887-8920

  1756 2nd St NE, Winter Haven, FL 33881
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  $1,455 - $2,150 per month

  The Waverly at Winter Haven

  1 - 3 Beds

  1015 Lake Forest Blvd, Winter Haven, FL 33884

  Experience stylish, comfortable living at The Waverly at Winter Haven. Located in the sought-after Cypress Gardens area, our pet-friendly community offers a peaceful lifestyle with convenient access to everything Central Florida has to offer.At The Waverly at Winter Haven, you'll enjoy a host of resort-inspired amenities designed to enhance your lifestyle, from a sparkling pool and

  1015 Lake Forest Blvd, Winter Haven, FL 33884
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  $1,200 per month

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

  2085 Isle Royale Ct SE Unit 189, Winter Haven, FL 33880

  FOR RENT - 1 Bedroom/1 Bathroom Executive Condo in beautiful Park Lake. This ground floor unit has access to Lake Lulu, a community pool, a dock, and a clubhouse/recreational facility. The association fees are included in the rent. If you like skiing, Winter Haven is the Ski Capital of World! Downtown Winter Haven has about a dozen restaurants plus activities for the family every month. These

  Linda Andre COLDWELL BANKER REALTY

  2085 Isle Royale Ct SE Unit 189, Winter Haven, FL 33880
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  $1,350 - $2,328 per month

  The Breeze

  Studio - 2 Beds

  265 Ave E SW, Winter Haven, FL 33880

  Welcome Home to The Breeze!

  265 Ave E SW, Winter Haven, FL 33880
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  $1,775 per month

  • 3 Beds
  • 2 Baths
  • 1,336 Sq Ft
  • House for Rent

  2214 Avenue B SW, Winter Haven, FL 33880

  Available for immediate move-in! Experience the perfect blend of historic charm and modern updates in this beautifully remodeled 1957 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

  Sylvain Sara HOMETRUST REALTY GROUP

  2214 Avenue B SW, Winter Haven, FL 33880
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  $1,441 - $1,841 total monthly price

  Prose Cypress Pointe

  1 - 2 Beds

  3110 Gowan Dr, Winter Haven, FL 33884

  Welcome home to Prose Cypress Pointe, a brand-new multifamily community located in Winter Haven, Florida. Our spacious one- and two-bedroom apartment homes feature modern stainless-steel appliances, walk-in closets, dining-sized kitchen islands, premium plank flooring throughout and full-sized washers and dryers in every apartment home. And with convenient, must-have amenities like a fitness

  3110 Gowan Dr, Winter Haven, FL 33884
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  $1,650 per month

  • 3 Beds
  • 2 Baths
  • 1,520 Sq Ft
  • Apartment for Rent

  2249 9th St SE, Winter Haven, FL 33880

  One or more photo(s) has been virtually staged. Check out this 3 bedroom 2bath townhome. Open floor plan, formal dining room, open lanai, Spacious master bedroom with double walk in closets and vaulted ceilings. 2 car carport.Freshly painted, new carpets upstairs. LVP flooring downstairs. Open lanai. Great community. Close to shopping and grocery store. Washer and dryer hook ups. Administration

  John-Michael Elliott S & D REAL ESTATE SERVICE LLC

  2249 9th St SE, Winter Haven, FL 33880
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  $1,295 - $2,210 per month

  Raindance

  1 - 2 Beds

  200 Avenue C SW, Winter Haven, FL 33880

  Welcome Home to Raindance!

  200 Avenue C SW, Winter Haven, FL 33880
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  $1,400 per month

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

  1101 Eagle Pond Dr, Winter Haven, FL 33884

  Affordability meets Comfort. First Floor unit for easy access in a highly desirable gated community of Cypresswood Golf & Country Club. This rental will include access to community pool, 24-hour security, exterior maintenance, common area taxes, trash service, pest control, and private road upkeep. Residents can also enjoy an 18-hole golf course, on-site restaurant, tennis courts, and a fitness

  Lienyvette Grimaldo MAZELG REALTY

  1101 Eagle Pond Dr, Winter Haven, FL 33884
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  $1,219 - $2,405 per month

  The Carlton at Lake Dexter

  1 - 3 Beds

  1015 Mahaffey Rd, Winter Haven, FL 33884

  A luxury rental lakefront apartment community in Winter Haven, Florida. Accepting leases now.

  1015 Mahaffey Rd, Winter Haven, FL 33884
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  $1,010 per month

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

  1892 Lake Mariam Dr, Winter Haven, FL 33884

  Enjoy peaceful lakefront living right off Dundee Rd in this charming 1-bedroom, 1-bath apartment located in a quiet 7-plex on beautiful Lake Mariam. With Legoland less than 5 miles away, you’re perfectly positioned for convenience and fun.Inside, you’ll find a dedicated utility room with full-size washer/dryer hookups—no laundromat runs needed. The flooring keeps the space cool and easy to

  Jordan Clark PALM LEAF PROPERTY MANAGEMENT

  1892 Lake Mariam Dr, Winter Haven, FL 33884
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  $1,250 - $1,570 per month

  The Jade

  1 Bed

  1150 3rd St SW, Winter Haven, FL 33880

  The Best Amenities in TownThe Jade offers the most comprehensive amenity package in town, offering an unmatched blend of luxury, comfort, and convenience at one inclusive price—no other apartment complex nearby provides such a diverse range of options under one roof.

  1150 3rd St SW, Winter Haven, FL 33880
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  $1,700 per month

  • 3 Beds
  • 2 Baths
  • 1,662 Sq Ft
  • House for Rent

  1019 Mockingbird Cir, Winter Haven, FL 33884

  3 bedroom 2 bath home with 2 car garage located in SE Winter Haven near Legoland. Modern custom cabinets throughout the home, open island kitchen design with pantry, bedrooms with plenty of closet space. Large master suite with roomy walk-in closet, spacious tiled master bath, and sliding doors to screened porch. Double pane windows throughout. Fenced yard. Located in a family friendly

  Donna Williams REMAX EXPERTS

  1019 Mockingbird Cir, Winter Haven, FL 33884
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  $1,395 - $2,050 per month

  Magnolia at Lake Hamilton

  1 - 3 Beds

  2850 W Lake Hamilton Dr, Winter Haven, FL 33881

  Welcome Home to Magnolia at Lake Hamilton!

  2850 W Lake Hamilton Dr, Winter Haven, FL 33881
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  $1,750 per month

  • 3 Beds
  • 2 Baths
  • 1,222 Sq Ft
  • House for Rent

  40 Jefferson Rd, Winter Haven, FL 33884

  Charming 3 Bedroom, 2 Bath Home on a Quiet Street – Available April 1st!Enjoy peaceful Florida living in this adorable home situated on a quiet street with no HOA and a spacious lot—perfect for evening walks and soaking in the sunshine.Inside, you’ll find a freshly painted interior, new vinyl flooring in the bedrooms, and tile flooring in the kitchen and living room for easy maintenance.

  AMIRE PEDRAZA HOME RENTAL FLORIDA

  40 Jefferson Rd, Winter Haven, FL 33884
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  $959 - $1,793 per month

  Carlton Arms Of Winter Haven

  Studio - 3 Beds

  7676 Carlton Arms Blvd, Winter Haven, FL 33884

  Carlton Arms of Winter Haven located on 122 acres of wooded lakefront property, offers country club living at many different rental rates. With its cascading fountains, beautifully landscaped grounds, peaceful woods and 5 freshwater lakes, this resort-style community provides every resident with professional management and maintenance that are trademarks of all Mahaffey planned properties.

  7676 Carlton Arms Blvd, Winter Haven, FL 33884
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  $1,799 per month

  • 3 Beds
  • 2 Baths
  • 1,329 Sq Ft
  • House for Rent

  3032 Spirit Lake Dr, Winter Haven, FL 33880

  One or more photo(s) has been virtually staged. Check out this 3 bedroom 2 bath totally renovated an updated home. The gorgouse home offers so much! Updated kitchen with granite solid surface counter tops, stainless steel applainces and closet pantry. The home offers an open floor plan. Spacious master bedroom with an totally updated ensute master bath that offers a step in glass shower and

  John-Michael Elliott S & D REAL ESTATE SERVICE LLC

  3032 Spirit Lake Dr, Winter Haven, FL 33880
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  $1,299 - $2,099 per month

  Dream Winter Haven

  1 - 3 Beds

  5004 Dream Dr, Winter Haven, FL 33881

  Embrace the art of living fully at Dream Winter Haven, where each day is a masterpiece waiting to be painted. Here, life is about more than just a home—it's about thriving in a community designed to enrich your every experience. Discover the charm of brand-new luxury 1, 2, and 3-bedroom apartments, complemented by resort-style amenities that encourage you to live fully. Set in the heart of Winter

  5004 Dream Dr, Winter Haven, FL 33881
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  $1,675 per month

  • 3 Beds
  • 2 Baths
  • 1,393 Sq Ft
  • House for Rent

  165 Osprey Heights Dr, Winter Haven, FL 33880

  Welcome home to 165 Osprey Heights Drive! This well-maintained 3-bedroom, 2-bath home offers a desirable split floor plan, providing both privacy and functionality. The home features brand-new vinyl flooring in the main living areas and fresh interior paint, giving it a clean, updated feel throughout. The bedrooms are comfortably carpeted, creating a warm and cozy retreat. The kitchen is both

  William Beasley STAR REALTY OF WINTER HAVEN

  165 Osprey Heights Dr, Winter Haven, FL 33880
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  $999 - $1,549 per month

  Haven at Lake Deer

  Studio - 2 Beds

  350 24th St NW, Winter Haven, FL 33880

  Haven at Lake Deer is the retreat you've been looking for in Winter Haven, FL. Our lakeside community features studio, one and two bedroom homes complete with patios, wood-style flooring, and upgraded kitchens. What's more, as a member of the community you'll also have access to our sparkling swimming pools and a 24-hour gym. At Haven at Lake Deer, you're guaranteed to find a place to live with a

  350 24th St NW, Winter Haven, FL 33880
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  $1,795 per month

  • 3 Beds
  • 2 Baths
  • 1,450 Sq Ft
  • House for Rent

  506 Eagle Landing Blvd, Winter Haven, FL 33880

  Make this your new home today! This property will not last long! Live in this 3 Bedroom, 2 Bathroom home for rent in Winter Haven! Located in the Eagle Landing Subdivision. Corner Lot one-story Home. Open Floor Plan. Open Kitchen with Breakfast Bar features granite countertops, and al Stainless Steel Kitchen Appliances are included (Refrigerator, Dishwasher, Range, and Microwave. Living & Dining

  Elizabeth Santiago ALLEGIANT MANAGEMENT GROUP INC

  506 Eagle Landing Blvd, Winter Haven, FL 33880
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  $997 - $1,540 per month

  Briarcrest at Winter Haven

  1 - 3 Beds

  200 Avenue K SE, Winter Haven, FL 33880

  Welcome to Briarcrest at Winter Haven Apartments, ideally located near downtown Winter Haven, FL where convenience meets comfort in a picturesque setting. Choose from our spacious and versatile one, two, and three-bedroom floor plans, each thoughtfully designed to suit diverse lifestyles. Our community boasts not just one, but two sparking pools for residents to unwind and enjoy Florida's

  200 Avenue K SE, Winter Haven, FL 33880
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  $949 per month

  • 1 Bath
  • 600 Sq Ft
  • Apartment for Rent

  2227 9th St SE, Winter Haven, FL 33880

  Check out this waterfront STUDIO apartment. This home boasts tile floors, freshly painted interior. Screen lanai with great views of Lake Lulu. Community includes lawn care. 1 car carport. Great location of chain of lakes. Close to shopping and grocery store. Administration Fee: Upon approval tenants will be subject to a $250 one-time administration fee. This property is proud to offer

  John-Michael Elliott S & D REAL ESTATE SERVICE LLC

  2227 9th St SE, Winter Haven, FL 33880
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  $1,189 - $1,598 per month

  Barrington Place At Winter Haven

  1 - 2 Beds

  1101 Cambridge Square, Winter Haven, FL 33880

  Barrington Place at Winter Haven is an intimate and charming community located in Winter Haven, FL. Our exclusive residences offer a serene retreat for residents seeking comfort and convenience. Discover the perfect balance of tranquility and accessibility, with proximity to Cypress Gardens Blvd., top-rated schools, healthcare facilities, and shopping destinations just moments away. Choose from

  1101 Cambridge Square, Winter Haven, FL 33880
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  $1,800 per month

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

  1661 Teagan Ln, Winter Haven, FL 33884

  3beds,2baths 2024 built. Available immediately.

  Lora Harper Keller Williams Realty of PSL

  1661 Teagan Ln, Winter Haven, FL 33884
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  $1,223 - $2,985 per month

  Vista Lake Ned

  1 - 3 Beds

  4025 Lake Ned Village Cir, Winter Haven, FL 33884

  Flow through the good life at Vista Lake Ned Apartments. The park-like setting, eclectic amenities, and expansive interiors will make you fall in love with our apartments in Winter Haven. Even better, our Cypress Gardens location places you right off Highway 27 and close to Legoland! Add in the top-notch services that have earned us glowing reviews throughout the years, and you know you're in the

  4025 Lake Ned Village Cir, Winter Haven, FL 33884
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  $1,400 per month

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

  2025 San Marcos Dr SE Unit 27, Winter Haven, FL 33880

  Beautiful first-floor apartment, conveniently located near restaurants, shopping, and the hospital. This one-bedroom, one-bathroom home features a granite vanity, a laundry room, and a kitchen with granite countertops. Currently available and a must-see!

  Marisol Padilla CENTURY 21 WATSON & MYERS REALTY

  2025 San Marcos Dr SE Unit 27, Winter Haven, FL 33880
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  $1,160 - $1,575 per month

  Della Vita Apartments

  1 - 3 Beds

  4200 Mahogany Run, Winter Haven, FL 33884

  Della Vita Apartments offers the best in brand new interior finishes, abundant community amenity offerings and quick and easy access to some of the best shopping, entertainment and dining Winter Haven has to offer. We’ve recently started a multi-million dollar renovation that will enhance your everyday lifestyle. Our 1, 2 & 3 bedroom apartment homes include large bedrooms with walk-in closets,

  4200 Mahogany Run, Winter Haven, FL 33884
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  $1,600 per month

  • 2 Beds
  • 2 Baths
  • 1,073 Sq Ft
  • Condo for Rent

  361 Winter Ridge Blvd Unit 361, Winter Haven, FL 33881

  AVAILABLE UNFURNISHED CONDO FOR RENT AT THE CHAIN OF LAKES Community of Winter Ridge Condominiums between Lake Smart and Lake Conine! This corner unit property offers stunning views across Lake Smart and the canal to Lake Conine. The master ensuite offers access to the porch with view to enjoy the panorama of the canal and Lake Smart. This spacious bedroom provides a large walk-in closet with

  Alvaro Molina TWIN HOMES REALTY

  361 Winter Ridge Blvd Unit 361, Winter Haven, FL 33881
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  $1,475 - $2,200 per month

  Lakeshore Club

  1 - 3 Beds

  1300 Lake Howard Dr SW, Winter Haven, FL 33880

  Welcome to luxury living in Winter Haven. Lakeshore Club is located on the Chain of Lakes between Lake Howard and Lake Mary minutes from downtown Winter Haven.

  1300 Lake Howard Dr SW, Winter Haven, FL 33880
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  $1,200 per month

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

  103 4th St SE Unit B, Winter Haven, FL 33880

  Cozy and updated 1 bedroom, 1 bathroom apartment located in the heart of Winter Haven, FL, just minutes from downtown shopping, dining, and the Chain of Lakes. This charming unit offers a bright living space, comfortable bedroom, and convenient access to local parks, restaurants, and major roadways. Perfect for anyone looking for comfortable living in a great location.

  Pedro Cartagena 1513 REALTY LLC

  103 4th St SE Unit B, Winter Haven, FL 33880
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  $1,350 - $1,450 per month

  Apartment for Rent

  2 Beds

  510 Avenue K NW, Winter Haven, FL 33881

  This property features a spacious 2-bed, 2-bath unit offering comfortable living space and thoughtful updates.This apartment includes modern conveniences such as central air conditioning, ceiling fans, and comfortable layouts designed for everyday living. There is also an on-site laundry facility exclusive to tenants for no extra cost. The building sits just minutes from downtown Winter

  510 Avenue K NW, Winter Haven, FL 33881
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  $1,700 per month

  • 2 Beds
  • 2.5 Baths
  • 1,184 Sq Ft
  • Townhouse for Rent

  2500 21st St NW Unit 31, Winter Haven, FL 33881

  Modern 2-Bed, 2.5-Bath Townhome in Desirable Casa del Sol... Step into comfort and convenience in this beautifully designed two-story end unit townhome, perfect for professionals seeking a stylish, low-maintenance lifestyle. Downstairs Living: Formal living room ideal for relaxing or entertaining, Convenient guest half bath, Bright kitchen featuring refrigerator, range, microwave, dishwasher, and

  Dorothea Bogert FL REALTY

  2500 21st St NW Unit 31, Winter Haven, FL 33881

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