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

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  Starting at $1,480 Per Month

  • 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

  The Waverly at Winter Haven

  (863) 591-0648

  

  1015 Lake Forest Blvd, Winter Haven, FL 33884
• Explore Winter Haven

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  /91

  Starting at $1,275 Per Month

  • Studio - 2 Beds

  265 Ave E SW, Winter Haven, FL 33880

  Discover the essence of upscale living at The Breeze, where the vibrant spirit of Winter Haven meets the serenity of a private retreat. Our community was designed for those who demand more from their surroundings. Each residence serves as a masterclass in architectural efficiency, blending high-performance energy standards with "luxury-first" essentials. From gourmet-inspired kitchens to living

  The Breeze

  (863) 356-0906

  

  265 Ave E SW, Winter Haven, FL 33880
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  Starting at $1,441

  Total Monthly Price

  • 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

  Prose Cypress Pointe

  (833) 669-3928

  

  3110 Gowan Dr, Winter Haven, FL 33884
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  Starting at $1,350 Per Month

  • 1 - 2 Beds

  200 Avenue C SW, Winter Haven, FL 33880

  Discover a living experience that moves with you. At Raindance, we have reimagined the modern residence as a sanctuary of light and fluid design. Each floor plan is a masterclass in spatial harmony, meticulously curated to balance expansive windows with intimate, designer-led interiors. Our commitment to excellence is woven into the very bones of the building, exceeding the highest energy

  Raindance

  (863) 356-1136

  

  200 Avenue C SW, Winter Haven, FL 33880
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  Starting at $1,219 Per Month

  • 1 - 3 Beds

  1015 Mahaffey Rd, Winter Haven, FL 33884

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

  The Carlton at Lake Dexter

  (727) 295-2861

  

  1015 Mahaffey Rd, Winter Haven, FL 33884
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  Starting at $1,200 Per Month

  • 1 - 2 Beds

  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.

  The Jade

  (863) 837-4924

  

  1150 3rd St SW, Winter Haven, FL 33880
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  Starting at $1,510 Per Month

  • 1 - 3 Beds

  2850 W Lake Hamilton Dr, Winter Haven, FL 33881

  Welcome Home to Magnolia at Lake Hamilton!

  Magnolia at Lake Hamilton

  (863) 588-7216

  

  2850 W Lake Hamilton Dr, Winter Haven, FL 33881
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  Starting at $959 Per Month

  • 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.

  Carlton Arms Of Winter Haven

  (863) 251-6034

  

  7676 Carlton Arms Blvd, Winter Haven, FL 33884
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  Starting at $1,299 Per Month

  • 1 - 2 Beds

  5004 Dream Dr, Winter Haven, FL 33880

  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

  Dream Winter Haven

  (863) 312-1112

  

  5004 Dream Dr, Winter Haven, FL 33880
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  Starting at $995 Per Month

  • 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

  Haven at Lake Deer

  (863) 356-1158

  

  350 24th St NW, Winter Haven, FL 33880
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  Starting at $997 Per Month

  • 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

  Briarcrest at Winter Haven

  (863) 356-1058

  

  200 Avenue K SE, Winter Haven, FL 33880
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  Starting at $1,130 Per Month

  • 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

  Barrington Place At Winter Haven

  (863) 204-5542

  1101 Cambridge Square, Winter Haven, FL 33880
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  Starting at $1,300 Per Month

  • 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

  Vista Lake Ned

  (863) 216-1915

  

  4025 Lake Ned Village Cir, Winter Haven, FL 33884
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  Starting at $1,160 Per Month

  • 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,

  Della Vita Apartments

  (863) 456-1985

  4200 Mahogany Run, Winter Haven, FL 33884
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  Starting at $1,475 Per Month

  • 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.

  Lakeshore Club

  (863) 356-0860

  

  1300 Lake Howard Dr SW, Winter Haven, FL 33880
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  Starting at $1,310 Per Month

  • 1 - 3 Beds

  4900 Cypress Gardens Rd, Winter Haven, FL 33884

  A variety of spacious and inviting floor plans await you at Arbours at Garden Grove. Choose from one of our three floor plans offering one, two and three bedrooms, designed with your comfort in mind. Enjoy an assortment of amenities such as vaulted ceilings, a wet bar, air conditioning and double vanities to name a few! The Arbours at Garden Grove amenities extend far beyond your doorstep. Take a

  The Arbours at Garden Grove

  (727) 205-8061

  

  4900 Cypress Gardens Rd, Winter Haven, FL 33884
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  Starting at $1,000 Per Month

  • Studio - 2 Beds

  130 Avenue C SE, Winter Haven, FL 33880

  Central Haven Apartments

  (863) 837-4828

  130 Avenue C SE, Winter Haven, FL 33880
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  Starting at $993 Per Month

  • 2 - 3 Beds

  4225 Vista Del Lago Dr, Winter Haven, FL 33881

  You've found your slice of paradise at Villas at Lake Smart in sunny Winter Haven, FL! Our spacious and affordable two and three-bedroom apartment homes offer the perfect sanctuary for you to unwind after a long day. Ensuring you don't have to go far for fun and fitness, our community features a volleyball court, playground, fitness center, clubhouse, pool, and more! Looking for some

  Villas at Lake Smart Apartments

  (863) 269-3488

  

  4225 Vista Del Lago Dr, Winter Haven, FL 33881
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  Starting at $1,250 Per Month

  • 1 - 2 Beds

  101 Parker Ln NE, Winter Haven, FL 33881

  Call for availability! Our apartment complex is nestled back in a residential housing lakeside community, away from busy traffic. Quiet surroundings for families and single professionals to relax in their home. We provide high tech security cameras throughout the whole complex to assure your safety. Lake Buckeye owners want to provide a drug-free and safe environment for your family to call

  Lake Buckeye Apartments

  (863) 269-3501

  101 Parker Ln NE, Winter Haven, FL 33881
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  Starting at $899 Per Month

  • 1 - 2 Beds

  102 Landings Way, Winter Haven, FL 33880

  Welcome to The Landings, a tranquil pet friendly retreat nestled among towering trees and lush greenery in the heart of Winter Haven, Florida. As one of our three Winter Haven locations, The Landings offers upgraded 1 and 2 bedroom apartments designed with spacious layouts that maximize comfort and livability. Each home features modern white cabinets that brighten the space, durable vinyl

  The Landings Apartment Homes

  (863) 251-5637

  102 Landings Way, Winter Haven, FL 33880
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  Starting at $950 Per Month

  • 1 Bed

  745 Avenue A SW, Winter Haven, FL 33880

  Lakeview Tower offers newly remodeled studio and one bedroom apartment homes. It is an exceptional senior living, 62+ and disabled Community. Lakeview Tower sits right on Lake Howard, allowing breath taking views from your window.

  Lakeview Tower

  (863) 877-4288

  

  745 Avenue A SW, Winter Haven, FL 33880
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  Starting at $975 Per Month

  • 1 Bed

  101-123 Oak Crest Dr NW, Winter Haven, FL 33881

  Ideally located with convenient access to US Hwy 17-92, I-4, and the greater Winter Haven and Central Florida area, this community offers both accessibility and comfort.Our cozy one-bedroom apartments feature energy-efficient central A/C, tile flooring, washer/dryer hookups, and newly updated appliances designed for everyday convenience.Residents enjoy scenic surroundings,

  Oakcrest Apartments

  (855) 606-5243

  101-123 Oak Crest Dr NW, Winter Haven, FL 33881
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  Starting at $1,299 Per Month

  • 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

  Alera at Hunters Glen

  (863) 270-4758

  

  3005 Willow Glen Cir, Lake Wales, FL 33859
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  $1,400 Per Month

  • 2 Beds
  • 2 Baths
  • 884 Sq Ft
  • Apartment for Rent

  711 Lake Jessie Dr, Winter Haven, FL 33881

  Well maintained 2BR 2BA apartment (part of triplex). Vaulted ceilings, granite countertops, Washer/Dryer hookups

  

  Steve Lockhart

  LOCKHART & ASSOCIATES INC

  (863) 624-3356

  711 Lake Jessie Dr, Winter Haven, FL 33881
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  $1,295 Per Month

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

  669 Avenue B NW Unit 10, Winter Haven, FL 33881

  Discover the charm of historic Winter Haven in this newly renovated 1-bedroom, 1-bath apartment located just steps from beautiful Lake Howard and within walking distance to downtown Winter Haven. This updated unit blends classic character with modern touches, featuring built-in details, new countertops, updated appliances, a new vanity, and a newly renovated shower. The kitchen includes an

  Lucas Oliveira HAINES AND HAVEN RESIDENTIAL

  669 Avenue B NW Unit 10, Winter Haven, FL 33881
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  /18

  $1,195 Per Month

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

  669 Avenue B NW Unit 4, Winter Haven, FL 33881

  Discover the charm of historic Winter Haven in this newly renovated 1-bedroom, 1-bath apartment located just steps from beautiful Lake Howard and within walking distance to downtown Winter Haven. This updated unit blends classic character with modern touches, featuring built-in details, new countertops, updated appliances, a new vanity, and a newly renovated shower. The kitchen includes an

  Lucas Oliveira HAINES AND HAVEN RESIDENTIAL

  669 Avenue B NW Unit 4, Winter Haven, FL 33881
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  $1,095 Per Month

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

  658 Avenue B NW, Winter Haven, FL 33881

  Enjoy the charm of historic Winter Haven in this newly renovated ground-floor 1-bedroom, 1-bath apartment located just minutes from Lake Howard and downtown Winter Haven. This cozy unit offers a private fenced yard, giving you your own outdoor space to relax, garden, or enjoy the Florida weather. Inside, the apartment features updated countertops, newer appliances, a renovated bathroom with new

  Lucas Oliveira HAINES AND HAVEN RESIDENTIAL

  658 Avenue B NW, Winter Haven, FL 33881
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  $1,600 Per Month

  • 2 Beds
  • 1.5 Baths
  • Apartment for Rent

  117 5th St NE Unit 113, Winter Haven, FL 33881

  REMODELED UNIT IN THE WINTER HAVEN LOCATION NEAR BY LEGOLAND PARK AND ACCESS TO THE CHAIN OF LAKES, EAGLE LAKE, LAKE WALES, HAINES CITY AND MORE. YOU CAN APPLY WITH $50.00 FOR THE BACKGROUND OR BRING YOUR POLICE REPORT. OWNER IS VERY FLEXIBLE WITH CREDIT AND ONLY TWO MONTHS TO MOVE. THE ELECTRIC FEE IS LOW AND THE WATER IS INCLUDED ALSO THE INTERNET IS INCLUDED ON THE RENT. FOR QUESTIONS AND

  Paola ramirez Lifestyle International Realty

  117 5th St NE Unit 113, Winter Haven, FL 33881
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  $2,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,090 Sq Ft
  • Apartment for Rent

  332 Avenue D SE, Winter Haven, FL 33880

  This 2 bedroom 2 bathroom end unit is fully furnished with a modern flair. Renovated with new roof, energy efficient tankless water heater, paint, appliances & more. Featuring luxury vinyl floors throughout, granite countertops in the kitchen, both bathrooms feature renovated showers & tub, vanities & fixtures. This home is turnkey including all linens, electronics and kitchenware. The living

  Kathryn Shevlin THE PROPERTY FIRM

  332 Avenue D SE, Winter Haven, FL 33880
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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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  $1,200 Per Month

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Apartment for Rent

  3601 Cypress Gardens Rd Unit 6, Winter Haven, FL 33884

  Spacious 2-bedroom/2-bathroom apartment in a prime southeast Winter Haven location. New luxury vinyl flooring throughout, minutes from Legoland Florida Resort, tons of convenient restaurant, grocery, shopping, and dining options. Extremely commutable to Highway 27 and the Polk Parkway.

  Kayly Malinas JOHN WOOD REALTY, INC.

  3601 Cypress Gardens Rd Unit 6, Winter Haven, FL 33884
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  $1,100 Per Month

  • 2 Beds
  • 1 Bath
  • 8,232 Sq Ft
  • Apartment for Rent

  730 W Central Ave, Winter Haven, FL 33880

  Charming, updated, and ideally located this recently renovated 2 bedroom,1 bath apartment offers comfortable living just one mile from downtown Winter Haven. The thoughtfully designed layout features a bright and inviting living area, well proportioned bedrooms, and a cozy kitchen equipped with a microwave and dishwasher for everyday convenience. Natural light fills the space, complemented by

  Kelly Lamplugh DENNIS REALTY PROPERTY MGMT.

  730 W Central Ave, Winter Haven, FL 33880
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  $1,000 Per Month

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

  301 Avenue B SE Unit 4, Winter Haven, FL 33880

  Cozy 1 bedroom, 1 bathroom unit located on the second floor. Situated in a calm, residential neighborhood near a local school, with convenient access to downtown just minutes away. Approximately 10–15 minutes from Legoland, offering an ideal central location. No pets allowed. First month’s rent and security deposit required. A great option for comfortable and convenient living.

  Lilhana Masis MASIS ROYALTY REAL ESTATE

  301 Avenue B SE Unit 4, Winter Haven, FL 33880
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  $1,190 Per Month

  • 1 Bed
  • 1 Bath
  • 550 Sq Ft
  • Apartment 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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  $1,395 Per Month

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

  2000 15th Ct NW Unit 23, Winter Haven, FL 33881

  Apartment For Rent - Move In Ready! MOVE IN SPECIALS: Free 1/2 Month Rent, waived Processing Fee and $250 Security Deposit based on approval. This second (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

  Manuel Paredes LA ROSA REALTY LLC

  2000 15th Ct NW Unit 23, Winter Haven, FL 33881
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  $1,000 Per Month

  • 1 Bed
  • 1 Bath
  • 1,052 Sq Ft
  • Apartment for Rent

  301 Avenue B SE Unit 2, Winter Haven, FL 33880

  Cozy 1 bed / 1 bath + den with built-in closet, perfect for a home office or guest space, located on the ground floor for easy access. Freshly painted and offering a functional layout with great natural light. Enjoy a shared backyard and on-site coin laundry for added convenience. Includes 1 assigned parking space. Situated in a quiet, well-kept neighborhood near a local school, just 5 minutes

  Lilhana Masis MASIS ROYALTY REAL ESTATE

  301 Avenue B SE Unit 2, Winter Haven, FL 33880
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  $1,275 Per Month

  • 2 Beds
  • 2 Baths
  • 2,732 Sq Ft
  • Apartment for Rent

  521 20th St SW Unit c, Winter Haven, FL 33880

  Winter Haven.. private home with rental unit. Only mins walk to Food and shopping, Lake Howard and Lake Howard Nature Park This unit is currently available for June 1 .Plenty of windows, enclosed/covered porch, sccond floor unit Only minutes from major shopping and dining, and directly across from Lake Howard. This one bedroom unit is ground floor has large living space. Open floor plan with

  Scott Butts KIMBRIDGE REALTY, LLC

  521 20th St SW Unit c, Winter Haven, FL 33880
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  $800 Per Month

  • 1 Bath
  • 500 Sq Ft
  • Apartment for Rent

  1111 Cypress Gardens Blvd Unit 12, Winter Haven, FL 33884

  A studio apartment with 1 bath for rent off of Lake Roy. Included in the rent is Water, and Lawn service. This property does not have a washer or dryer hook-up. Call soon before this property is gone! Application Fee runs $50 per adult with a onetime $50 Lease Fee. For this home we are asking for First Month's Rent ($800), and Security Deposit ($1000) making total move in cost assuming one adult

  Daniel Gonzalez AT YOUR SERVICE REALTY, LLC

  1111 Cypress Gardens Blvd Unit 12, Winter Haven, FL 33884
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  /23

  $1,200 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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  /16

  $1,100 Per Month

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

  118 Oak Crest Dr NW, Winter Haven, FL 33881

  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 conveniences.

  David Small KELLER WILLIAMS REALTY SMART 1

  118 Oak Crest Dr NW, Winter Haven, FL 33881

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