Winter Haven, FL Homes for Rent under $2,800

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  $2,600 per month

  • 4 Beds
  • 2 Baths
  • 1,933 Sq Ft
  • Townhouse for Rent

  748 Reggie Rd, Winter Haven, FL 33884

  Welcome to this beautiful tranquil home. Prime Location, Beautiful Community many amenities. Highly sought Peace Creek Reserve Community in Winter Haven. Modern Living in today's busy world. High end kitchen, Many architectural features sets this home off from others. Upgraded bathrooms. Very large space for family gatherings. Large bedrooms. Plenty of storage. Two car garage. Credit Score

  

  Donna Galloway

  GOLDEN SANDS S. FLORIDA REALTY

  (863) 340-7767

  748 Reggie Rd, Winter Haven, FL 33884
• Explore Winter Haven

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  $2,250 per month

  • 4 Beds
  • 2 Baths
  • 1,867 Sq Ft
  • House for Rent

  3180 Royal Tern Dr, Winter Haven, FL 33881

  Beautiful 4 bedroom home in the heart of Winter Haven. You'll find tile throughout living areas, spacious bedrooms, an open concept, a covered rear porch and a large yard fully fenced. Lawn maintenance included for a more relaxed living! Quiet community with pool and amenities to enjoy. Close to Davenport, Haines City, and only 28 miles to 192 in Kissimmee! Schedule your tour today and you can

  

  Jennifer Arguello

  MERCEDES INVESTMENTS LLC

  (863) 356-1279

  3180 Royal Tern Dr, Winter Haven, FL 33881
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  $2,200 per month

  • 4 Beds
  • 2.5 Baths
  • 2,370 Sq Ft
  • House for Rent

  6408 Domizio Dr, Winter Haven, FL 33884

  Additional reduction of this 4 bedroom 2.5 Baths is located in Villa Mar in Winter Haven, Florida. Master-planned amenities including a pool with cabana that is walking distance from your home, a playground, and shaded seating area. Highway 27, less than 10 minutes away, has everything you are looking for. Grocery stores, movie theaters, shopping centers, golf courses, restaurants, and so much

  

  Sushama Sharma

  CROWN INVESTMENT BROKERS

  (863) 880-2473

  6408 Domizio Dr, 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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  $1,474 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
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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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  $1,455 - $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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  $1,350 per month

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

  1019 2nd St SE, Winter Haven, FL 33880

  Charmingly renovated 2 bedroom, 1 bathroom duplex in Downtown Winter Haven! Featuring stylish tile floors throughout, modern kitchen with quartz countertops, stainless appliances and washer dryer hookups. Perfect for urban living with contemporary comforts. Call today to schedule a tour!

  Pedro Cartagena 1513 REALTY LLC

  1019 2nd St SE, 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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  $1,817 per month

  • 3 Beds
  • 2 Baths
  • 1,504 Sq Ft
  • House for Rent

  3304 White Indigo Rd, Winter Haven, FL 33884

  WINTER HAVEN NEW BUILD 3 BED/2 BATH HOME FOR RENT! MOVE-IN SPECIAL!Priced Low, Call Now! Very Clean Property, Move-in Ready, 2 Car Garage, Brand New Build—First Tenancy! Huge Master Suite, Eat-In Kitchen, Corian Countertops, Upgraded Kitchen, Brand New Kitchen, Carpeted Bedrooms, Laminate Wood-Look Flooring, COMMUNITY Pool, COMMUNITY Playground, COMMUNITY Multiple Lakes, COMMUNITY Walking &

  Jay Myers ORLANDO REALTY & PROPERTY MGNT

  3304 White Indigo Rd, Winter Haven, FL 33884
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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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  $1,900 per month

  • 2 Beds
  • 2 Baths
  • 1,250 Sq Ft
  • House for Rent

  227 Volusia Dr, Winter Haven, FL 33884

  Located in an established neighborhood this home offers 2 bedrooms and 2 bathrooms. Galley kitchen overlooking large fenced backyard. Inside laundry room and 2 car garage. Available and ready for immediate occupancy.

  Sue Ann Williamon THE HOME COMPANY

  227 Volusia Dr, Winter Haven, FL 33884
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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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  $1,650 per month

  • 3 Beds
  • 2 Baths
  • 1,178 Sq Ft
  • Property for Rent

  5320 Laurel Oak Dr, Winter Haven, FL 33880

  One or more photo(s) has been virtually staged. This welcoming 3 bedroom, 2 bathroom home in the Winter Haven Oaks 55+ community blends comfort, convenience, and an upbeat, easygoing lifestyle. The layout offers three flexible bedrooms along with a bright sun room that quickly becomes the heart of the home — an ideal spot for morning coffee, quiet afternoons, or simply enjoying the peaceful

  Christin Davis PROPERTY MANAGEMENT OF POLK

  5320 Laurel Oak Dr, Winter Haven, FL 33880
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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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  $2,150 per month

  • 4 Beds
  • 2 Baths
  • 1,850 Sq Ft
  • House for Rent

  1063 Michelangelo Ln, Winter Haven, FL 33884

  Immaculate home still feels like brand new construction! 4 bedroom 2 bath home in the Estates of Lake Florence. This home is ideally located in Winter Haven minutes from HWY 17, near I-4 and SR 60, for easy access to the Greater Orlando Area and Lakeland. The living area is bright and open connecting the living room space with the dining area and kitchen. The stylish kitchen showcases a

  Jacob Bellamy REMAX EXPERTS

  1063 Michelangelo Ln, 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
  • 1,194 Sq Ft
  • House for Rent

  606 Holt Cir, Winter Haven, FL 33880

  This 3 bedroom, 2 bathroom home brings a fun mix of comfort and flexibility, featuring a bonus room that’s ready to become whatever you need next — a home office, gaming room, craft space, or an extra spot to unwind. The interior offers an easy, functional flow with bedrooms that make the most of the home’s footprint, and the primary suite includes its own private bath for added

  Christin Davis PROPERTY MANAGEMENT OF POLK

  606 Holt Cir, Winter Haven, FL 33880
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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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  $1,200 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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  $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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  $1,775 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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  $1,299 - $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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  $2,100 per month

  • 4 Beds
  • 2 Baths
  • 1,682 Sq Ft
  • House for Rent

  1174 Haines Dr, Winter Haven, FL 33881

  Beautiful 4 bed / 2 bath home with modern upgrades throughout! This energy-efficient property features solar panels included at no extra cost—helping you save on electricity from day one. Enjoy tile flooring throughout the entire home, a remodeled kitchen and bathrooms, fresh interior paint, and brand-new appliances. Washer and dryer are also included for your convenience. The home offers a

  Maria Cruz Vazquez ONE TEAM REALTY

  1174 Haines Dr, Winter Haven, FL 33881
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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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  $1,650 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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  $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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  $1,900 per month

  • 2 Beds
  • 2 Baths
  • 1,575 Sq Ft
  • House for Rent

  616 Crystals Blvd, Winter Haven, FL 33884

  Spacious and beautifully laid out home now available for rent! This open floor plan features 2 bedrooms, 2 bathrooms, plus a versatile flex space that can easily function as a third bedroom, office, or additional living area. Inside, you’ll find laminate flooring throughout with tile in the bathrooms, along with fresh interior paint and updated finishes that enhance the home’s overall appeal. The

  Jeff Inman FHG REALTY, LLC

  616 Crystals Blvd, Winter Haven, FL 33884
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  $1,165 - $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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  $1,975 per month

  • 3 Beds
  • 2 Baths
  • 1,491 Sq Ft
  • House for Rent

  233 Kensington View Blvd, Winter Haven, FL 33880

  Discover modern living in this stunning newly built 3-bedroom, 2-bath home, where style meets comfort. Bright, spacious bedrooms provides the perfect retreat, while sleek, thoughtfully designed bathrooms add a touch of luxury. The open-concept layout flows effortlessly from the kitchen to the living and dining areas, ideal for entertaining or relaxing. A generous walk-in closet keeps everything

  Christopher Gallon, Pa EXP REALTY LLC

  233 Kensington View Blvd, Winter Haven, FL 33880
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  $1,236 - $1,808 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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  $2,200 per month

  • 4 Beds
  • 3 Baths
  • 2,174 Sq Ft
  • House for Rent

  1116 Tyler Loop, Winter Haven, FL 33884

  Discover modern comfort and thoughtful design in this newly built home at 1116 Tyler Loop in Winter Haven, FL, crafted by Lennar Homes. This residence showcases high-quality construction paired with stylish finishes, including an open-concept layout perfect for both everyday living and entertaining. The home features energy-efficient systems, smart home technology, and a contemporary kitchen

  Julien Silva JOHN SILVA REALTY & ASSOCIATES

  1116 Tyler Loop, Winter Haven, FL 33884
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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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  $2,200 per month

  • 5 Beds
  • 2.5 Baths
  • 2,254 Sq Ft
  • House for Rent

  530 Short Ln, Winter Haven, FL 33881

  LOCATION! LOCATION! LOCATION! This two-story home features a contemporary open space layout in the dining room, kitchen and family room with easy accessibility to the lanai for outdoor relaxing. Upstairs are five bedrooms and a loft as an extra common area. SOLAR SYSTEM IS INCLUDED! SAVE half of your Electricity Bill! The community is close all the major highway, supermarket and restaurant,

  Yukey Hoo U KEY REALTY

  530 Short Ln, 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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