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

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  /20

  $2,150 per month

  • 3 Beds
  • 2 Baths
  • 1,709 Sq Ft
  • House for Rent

  3904 Osprey Pointe Cir, Winter Haven, FL 33884

  Modern design with comfort in mind! Available for Lease April 1, 2026! Spacious 3-Bedroom, 2-Bath Home in a Charming Winter Haven Neighborhood Welcome to this beautifully maintained 3-bedroom, 2-bath home offering over 1,700 square feet of living space in a quaint and friendly community. Conveniently located near downtown Winter Haven, with easy access to theme parks, shopping, and dining, this

  Oswald Carrerou CARREROU ENTERPRISES, LLC

  3904 Osprey Pointe Cir, Winter Haven, FL 33884
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  /15

  $1,945 per month

  • 4 Beds
  • 2 Baths
  • 1,874 Sq Ft
  • House for Rent

  930 Deming Dr, Winter Haven, FL 33880

  Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening!Take advantage of the incredible location,

  930 Deming Dr, Winter Haven, FL 33880
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  /22

  $1,400 per month

  • 1 Bed
  • 1 Bath
  • 1,078 Sq Ft
  • Apartment for Rent

  150 El Dorado Unit 208, Winter Haven, FL 33884

  Comfortable 1BR Apartment in Desirable 55+ Community, well-maintained one-bedroom, one-bath apartment located in a quiet and welcoming 55+ community. Features a functional floor plan with bright living and dining areas, a spacious bedroom with ample closet space, and a clean, well-appointed kitchen. Enjoy community amenities and a peaceful setting designed for active living. Conveniently located

  Elsa Gonzalez LPT REALTY, LLC

  150 El Dorado Unit 208, Winter Haven, FL 33884
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  /15

  $1,830 per month

  • 3 Beds
  • 2 Baths
  • 1,316 Sq Ft
  • House for Rent

  3320 Timberline Rd W, Winter Haven, FL 33880

  Beautiful, pet-friendly home coming soon! Apply now, Move-In is available on or after the listed date. Upon approval, $500 reservation deposit to reserve (applied to security deposit and/or refundable). Application fee: $50 per adult. Security Deposit: one month?s rent. Pet fees: $250 + $40/mo per pet. Some homes may include pool ($150/mo), septic ($15/mo), and/or HOA fees; other fees may apply.

  3320 Timberline Rd W, Winter Haven, FL 33880
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  $1,850 per month

  • 4 Beds
  • 2 Baths
  • 1,750 Sq Ft
  • House for Rent

  3993 Warbler Dr, Winter Haven, FL 33880

  Lovely 4 bedroom home, conveniently located at the heart of Winter Haven, minutes from all the stores and restaurants, quick access to Polk Parkway & I-4, & takes less than an hour drive to Orlando or Tampa. This gorgeous home features an elegant ceramic tile flooring, a great open floor plan with 2 spacious living areas, dining room, its' kitchen has plenty of cabinets & counter space, a nice

  Lienyvette Grimaldo MAZELG REALTY

  3993 Warbler Dr, Winter Haven, FL 33880
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  /15

  $2,400 per month

  • 4 Beds
  • 2.5 Baths
  • 2,400 Sq Ft
  • House for Rent

  2973 Whispering Trails Dr, Winter Haven, FL 33884

  We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home

  2973 Whispering Trails Dr, Winter Haven, FL 33884
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  /10

  $2,300 per month

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft
  • House for Rent

  942 Cattleman St, Winter Haven, FL 33884

  Gorgeous 3BR/2BA Home - AVAILABLE FOR APRIL Looking for a hassle-free rental? This beautifully furnished 3-bedroom, 2-bathroom home in Winter Haven is move-in ready! Just unpack and start living. Features You\'ll Love:-Modern Kitchen - Stainless steel appliances & tons of counter space.-Washer & Dryer In-Unit - Laundry made easy.-Attached Garage - Convenient parking & extra

  Manuel Paredes LA ROSA REALTY LLC

  942 Cattleman St, Winter Haven, FL 33884
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  /16

  $2,160 per month

  • 4 Beds
  • 2 Baths
  • 1,946 Sq Ft
  • House for Rent

  264 Daisy Estates Dr, Winter Haven, FL 33884

  Please note, our homes are available on a first-come, first-serve basis and are not reserved until the lease is signed by all applicants and security deposits are collected.This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at Want to tour on your own? Click the “Self

  264 Daisy Estates Dr, Winter Haven, FL 33884
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  /17

  $2,095 per month

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

  1220 Tyler Loop, Winter Haven, FL 33884

  Pet-Friendly 5-Bedroom Home in Winter Haven, FL!This new construction 5-bedroom, 2.5-bath home combines style and practicality, ideal for modern living.Highlights include:Gourmet kitchen with granite countertops, stainless steel appliances, and elegant cabinetrySpacious living area, perfect for guests or multi-generational livingPrimary suite featuring dual sinks, a walk-in

  Morgan Evans RESZI MANAGEMENT I, LLC

  1220 Tyler Loop, Winter Haven, FL 33884
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  /15

  $2,015 per month

  • 4 Beds
  • 2 Baths
  • 2,110 Sq Ft
  • House for Rent

  171 Southern Breeze Lp, Winter Haven, FL 33880

  From Hwy 17 S - Turn right onto Spirit Lake Rd and continue for 1.6 miles. Turn left onto Grady Polk Rd and destination will be on the right. From Hwy 17 N - Turn left onto Spirit Lake Rd and continue for 1.6 miles. Turn left onto Grady Polk Rd and destination will be on the right.Please note that the advertised price may exclude additional fees. These include a $55 application fee per

  171 Southern Breeze Lp, Winter Haven, FL 33880
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  /21

  $2,500 per month

  • 3 Beds
  • 2 Baths
  • 1,391 Sq Ft
  • House for Rent

  112 Lagoon Rd, Winter Haven, FL 33884

  For Rent – Winter Haven, FL Welcome to this beautifully remodeled home located at 112 Lagoon Rd, Winter Haven, FL 33884. This property offers comfort, convenience, and a prime location. “The property includes an efficient that you can rent out to help cover the rent payment.” Property Features: • 3 spacious bedrooms • 2 updated bathrooms • Modern remodeled kitchen with quality finishes • Indoor

  Zulmy Serrano AGENT TRUST REALTY CORPORATION

  112 Lagoon Rd, Winter Haven, FL 33884
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  /19

  $1,575 total monthly price

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

  650 Ave B SW Unit 650 Avenue B SW, Winter Haven, FL 33880

  650 Ave B SW Unit 650 Avenue B SW, Winter Haven, FL 33880
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  /6

  $2,450 per month

  • 4 Beds
  • 2.5 Baths
  • 1,879 Sq Ft
  • House for Rent

  1433 Austin St, Winter Haven, FL 33884

  Beautiful Two-Story Home in Winter Haven! Welcome to this spacious two-story home located in a desirable Winter Haven community featuring a community pool, dog park, and playground. This fully fenced property offers privacy and comfort for the whole family. The home features 4 bedrooms and 3 full bathrooms, with two separate family rooms, perfect for entertaining or creating flexible living

  Cora Johnson WYNNMORE REALTY LLC

  1433 Austin St, Winter Haven, FL 33884
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  /6

  $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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  /6

  $1,150 per month

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

  1210 Avenue Z SE Unit A, Winter Haven, FL 33884

  Available! Beautiful and modern 1 BD/1 BA apartment featuring luxury vinyl plank flooring throughout, stainless steel appliances and granite countertops; a tastefully designed interior. Convenient location, so call today, this property won’t last long!

  Pedro Cartagena 1513 REALTY LLC

  1210 Avenue Z SE Unit A, Winter Haven, FL 33884
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  /21

  $1,950 total monthly price

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

  336 Kayden Cove, Winter Haven, FL 33884

  “Se están ACEPTANDO todos los programas de asistencia para la vivienda “Se consideran vales de viviendaEsta encantadora casa de 3 dormitorios y 2 baños está lista para recibirte, con una cocina moderna con una amplia isla y electrodomésticos.Disfruta de un garaje para dos autos en la casa y otros dos en el exterior, un hermoso patio y un total de 1444 pies cuadrados de

  336 Kayden Cove, Winter Haven, FL 33884
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  /12

  $1,300 per month

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

  900 Avenue Z SE Unit C 6, Winter Haven, FL 33880

  Nice area, closed to Legoland, complex is on a lake, quiet neighborhood

  Mayra Roberto Linked Realty Inc

  900 Avenue Z SE Unit C 6, Winter Haven, FL 33880
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  $1,550 total monthly price

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

  5626 Struthers Ct, Winter Haven, FL 33884

  2BR / 1BA Duplex • Washer/Dryer • New A/C • $1,550 • Available April 6Clean and well-maintained 2 bedroom / 1 bathroom duplex located in a quiet Winter Haven neighborhood near US-27 and Legoland.Features:• Washer & dryer included• New central A/C• Tile flooring throughout (no carpet)• Bright, open living space• Large shared yard• 2 parking

  5626 Struthers Ct, Winter Haven, FL 33884
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  /9

  $1,000 per month

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

  310 Farnol St SW Unit 3, Winter Haven, FL 33880

  Discover easy downtown living in this bright and inviting studio apartment located in the heart of Winter Haven. The spacious combined living and bedroom area offers plenty of room to relax and make the space your own. A large sliding glass door fills the apartment with natural light and opens to a large, quiet yard. This studio blends comfort, convenience, and simplicity, all within steps of the

  Christin Davis PROPERTY MANAGEMENT OF POLK

  310 Farnol St SW Unit 3, Winter Haven, FL 33880
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  /2

  $2,500 total monthly price

  • 4 Beds
  • 2 Baths
  • 8,624 Sq Ft
  • House for Rent

  558 Reddicks Cir, Winter Haven, FL 33884

  This is a single family property located in a quiet neighborhood but not too far from all necessesities and parks. LegoLand is about 10 minutes away, all shopping but not limited to Walmart and Publix is 5 minutes away. We have great schools in our neighborhood and the house has a lot of space. All new kitchen appliance were installed for our new tenants.

  558 Reddicks Cir, Winter Haven, FL 33884
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  /12

  $1,125 per month

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

  243 Avenue L NE, Winter Haven, FL 33881

  NICE DUPLEX APARTMENT AVAILABLE! Newly renovated, this 2 BD/1 BA has wood-look plank flooring throughout, kitchen and so much more. Just steps from Lake Silver and conveniently located to shopping, dining, medical and downtown Winter Haven! Don’t miss out on a great this rental. Call Today to schedule your showing!!!

  Pedro Cartagena 1513 REALTY LLC

  243 Avenue L NE, Winter Haven, FL 33881
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  $1,850 total monthly price

  • 4 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Condo for Rent

  731 Avenue A SW Unit B, Winter Haven, FL 33880

  It is in a prime area walking distance to restaurant, malls etc. The house contains very large rooms.

  731 Avenue A SW Unit B, Winter Haven, FL 33880
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  /30

  $2,000 per month

  • 4 Beds
  • 2 Baths
  • 1,851 Sq Ft
  • House for Rent

  820 Sun Burst Rd, Winter Haven, FL 33880

  Beautiful 4-Bedroom Home in Squires Grove – Built in 2022! Welcome to this stunning 4-bedroom, 2-bathroom single-family home located in the desirable Squires Grove community. Built in 2022, this modern home offers 1,851 sq. ft. of thoughtfully designed living space with a spacious 2-car garage. You'll love the open floor plan, perfect for both everyday living and entertaining. The kitchen flows

  Nicole Torres AZURE REAL ESTATE & PROPERTY MANAGEMENT GROUP LLC

  820 Sun Burst Rd, Winter Haven, FL 33880
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  /12

  $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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  $1,900 per month

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

  2521 Pine Place, Winter Haven, FL 33881

  One or more photo(s) has been virtually staged. Welcome to 2521 Pine Pl, where modern elegance meets peaceful lakefront living. This beautifully designed 3-bedroom, 2.5-bath home offers spectacular lake views right from your backyard, creating the perfect backdrop for morning coffee, sunset relaxation, or weekend gatherings. Inside, enjoy a bright open-concept floor plan, a sleek contemporary

  Jacob Hara TRANSCEND REALTY

  2521 Pine Place, Winter Haven, FL 33881
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  $1,260 - $2,215 per month

  Alera at Hunters Glen

  1 - 3 Beds

  3005 Willow Glen Cir, Lake Wales, FL 33859

  Set Your Own Pace at Alera at Hunters GlenDiscover a modern vision for upscale apartment living at Alera at Hunters Glen—where style meets simplicity in Lake Wales, FL. Embrace the freedom of a lock-and-leave lifestyle in a sophisticated community designed for those who live life on their own terms. With a seamless blend of contemporary design and refined elegance, Alera is where your

  3005 Willow Glen Cir, Lake Wales, FL 33859
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  $1,990 per month

  • 3 Beds
  • 2 Baths
  • 1,532 Sq Ft
  • Townhouse for Rent

  36 Enclave Dr, Winter Haven, FL 33884

  One or more photo(s) has been virtually staged. Corner - unfurnished unit @ The Enclave, located within the manned, gated Cypresswood Golf & Country Club in Winter Haven, Florida. This premier community features an 18-hole championship golf course designed by award-winning architect Ron Garl. The course is open 365 days a year, from sunrise to sunset. Residents enjoy access to outstanding

  Jimmy Aguilar 3D TEAM REALTY LLC

  36 Enclave Dr, Winter Haven, FL 33884
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  /12

  $2,200 per month

  • 4 Beds
  • 2 Baths
  • 1,518 Sq Ft
  • House for Rent

  865 Terranova Rd, Winter Haven, FL 33884

  Discover this stunning 4-bedroom, 2-bath home, now available in a highly desirable gated community. Perfectly zoned for the acclaimed A-rated Chain of Lakes Elementary, this residence offers the ideal blend of comfort and convenience for today’s families.Step inside to an expansive open floor plan—ideal for modern living and effortless entertaining. Enjoy a spacious, fully fenced

  Annette Newkirk HOMELIFE REALTY COASTAL PROPERTIES LLC

  865 Terranova Rd, Winter Haven, FL 33884
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  /3

  $1,325 per month

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

  76 Stebbins Dr Unit 76, Winter Haven, FL 33884

  Find your place in the world at Grove Shores, a well-maintained, professionally managed manufactured home community. Right now, we are offering a 2019 model year, 896 sq. ft., 2 bed/2 bath home for only $55,900! You owe it to yourself to call our representatives and schedule a viewing of this home before someone else snaps it up!

  Tori Coil Grove Shores

  76 Stebbins Dr Unit 76, Winter Haven, FL 33884
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  /31

  $1,950 per month

  • 3 Beds
  • 2 Baths
  • 1,542 Sq Ft
  • House for Rent

  1522 Fuji Ct, Winter Haven, FL 33881

  Move-in ready and brand new, this beautiful corner-lot home offers immediate occupancy and modern comfort with luxury vinyl plank flooring, volume ceilings, and a covered patio perfect for relaxing. At the front of the home are two spacious bedrooms, a full bath, and a dedicated laundry room, leading into an open chef’s kitchen featuring a large island, 36-inch upper cabinets with hardware,

  Sana Butt THE FIRM RE

  1522 Fuji Ct, Winter Haven, FL 33881
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  /25

  $2,299 per month

  • 4 Beds
  • 2.5 Baths
  • 1,933 Sq Ft
  • House for Rent

  1179 Tyler Loop, Winter Haven, FL 33884

  Beautiful semi-furnished rental home featuring 4 bedrooms, including a primary suite, plus a loft, 2 full bathrooms, and 1 half bath. The first floor offers tile flooring throughout, while the second floor is carpeted. The home comes fully equipped with all appliances, including range, dishwasher, refrigerator, microwave, washer, and dryer. Semi-furnished with dining table and six chairs,

  Viviane de Fraga Kalkmann WRA BUSINESS & REAL ESTATE

  1179 Tyler Loop, Winter Haven, FL 33884
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  /15

  $2,500 per month

  • 4 Beds
  • 2 Baths
  • 1,853 Sq Ft
  • House for Rent

  643 Grove St, Winter Haven, FL 33881

  Spacious and well-maintained 4-bedroom, 2-bath home, functional floor plan with generous living areas, comfortable bedrooms, and abundant natural light throughout. The kitchen offers ample cabinet space and flows seamlessly into the main living area, ideal for everyday living and entertaining. Enjoy outdoor living in the fully fenced yard and relax on the screened patio, perfect for morning

  Martha Leighton MIHOUSE REALTY LLC

  643 Grove St, Winter Haven, FL 33881
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  /11

  $1,000 per month

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

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

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

  Steven Smith, PA LOCKHART & ASSOCIATES INC

  1103 Cypress Gardens Blvd Unit C-106, Winter Haven, FL 33884
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  /22

  $2,050 per month

  • 4 Beds
  • 2 Baths
  • 1,858 Sq Ft
  • House for Rent

  3543 Evening Star Dr, Winter Haven, FL 33881

  Welcome home to this modern 2025-built single-family residence featuring 4 bedrooms, 2 bathrooms, and 1,858 sq ft of bright, open living space. The open-concept design flows beautifully from the spacious living area into a sleek kitchen finished with stone countertops, contemporary cabinetry, and a clean, modern feel throughout. The oversized tile flooring adds a polished, upscale look and makes

  Felix Ortiz La Rosa Realty Kissimmee

  3543 Evening Star Dr, Winter Haven, FL 33881
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  /17

  $1,850 per month

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

  4819 Summerfield Cir, Winter Haven, FL 33881

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

  Ronald Gentile ORLANDO REO PROF I INC

  4819 Summerfield Cir, Winter Haven, FL 33881
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  /10

  $1,100 per month

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

  2824 Avenue G NW, Winter Haven, FL 33880

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

  Kara Severit REMAX EXPERTS

  2824 Avenue G NW, Winter Haven, FL 33880
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  /21

  $1,745 per month

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

  1804 Carnostie Rd, Winter Haven, FL 33884

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

  Umberto Da Cunha Neto WRA BUSINESS & REAL ESTATE

  1804 Carnostie Rd, Winter Haven, FL 33884
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  /19

  $2,250 per month

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

  118 Inman Blvd, Winter Haven, FL 33881

  One or more photo(s) has been virtually staged. Welcome home to this stunning brand-new 5-bedroom, 2.5-bath residence, designed to elevate your lifestyle from the moment you walk in.Step into a bright and open floor plan where the heart of the home—the chef’s kitchen—features expansive counter space, a large island, and a seamless flow into the spacious family room. It’s the perfect setting

  Roxana Sangiorgi KELLER WILLIAMS INTERNATIONAL LIFESTYLES

  118 Inman Blvd, Winter Haven, FL 33881
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  /20

  $2,300 per month

  • 5 Beds
  • 3 Baths
  • 2,447 Sq Ft
  • House for Rent

  4094 Giorgio Dr, Winter Haven, FL 33884

  Welcome home to this newly built, stunning 5-bedroom, 3 FULL bath two-story home! From the moment you step through the modern frosted-glass entry, you’re welcomed into an open and airy layout perfect for families, guests, or anyone who loves space and convenience. The first floor features an open-concept design with a stylish kitchen complete with Silestone countertops, a large center island,

  Vanessa Exil THE KLR GROUP LLC

  4094 Giorgio Dr, Winter Haven, FL 33884
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  /15

  $1,790 per month

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

  1125 Evergreen Ct, Winter Haven, FL 33881

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

  Mohamed Souissi BULL PROPERTY MANAGEMENT

  1125 Evergreen Ct, Winter Haven, FL 33881

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