Winter Haven, FL Homes for Rent under $2,500

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  $2,466

  Total Monthly Price

  • 2 Beds
  • 2 Baths
  • 1,636 Sq Ft
  • Condo for Rent

  1630 17th St NW Unit SI ID1545923P, Winter Haven, FL 33881

  The advertised rate of $2,466/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 1, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

  1630 17th St NW Unit SI ID1545923P, Winter Haven, FL 33881
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  /20

  $2,190 Per Month

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • House for Rent

  1331 11th St NE, Winter Haven, FL 33881

  Property Id: 2117741THIS IS NOT YOUR TYPICAL RENTAL. IT’S YOUR OPPORTUNITY TO OWN!HomeWays makes homeownership accessible to everyone.If you've struggled with qualifying for a traditional home loan, HomeWays' "Homeownership Now" program is designed specifically for you. Low Credit is OKAY, student debt and medical bills, NO PROBLEM. Don’t miss out on this chance to make

  1331 11th St NE, Winter Haven, FL 33881
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  $1,375

  Total Monthly Price

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

  448 Avenue A NE Unit Cozy Cottage, Winter Haven, FL 33881

  This cozy Cottage is a 1/1 in Winter Haven Fl. Walk to downtowns restaurant and local shops and breweries. Close to Legoland. Short term unit with small kitchenette. Fenced yard with private spa. This home is set up for short term rental and has kitchenette with Convection Microwave, coffee pot, and all dishware. Washer Dryer, queen bed, TVs in the living room and bedroom. This is a duplex

  448 Avenue A NE Unit Cozy Cottage, Winter Haven, FL 33881
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  $1,775

  Total Monthly Price

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

  711 Avenue B NE, Winter Haven, FL 33881

  This is a 3/2 home in Winter Haven Fl. This home is move in ready and had been freshly updated. Call for your showing today. Close to downtown and convenient to all winter haven has to offer.Washer Dryer hook upsCentral heat and airScreened porchLong term or short term approved.

  711 Avenue B NE, Winter Haven, FL 33881
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  $1,500

  Total Monthly Price

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

  357 Winter Ridge Blvd Unit 357, Winter Haven, FL 33881

  357 Winter Ridge Blvd Unit 357, Winter Haven, FL 33881
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  $1,750

  Total Monthly Price

  • 3 Beds
  • 2 Baths
  • 1,411 Sq Ft
  • Condo for Rent

  690 Avenue C SE Unit 690, Winter Haven, FL 33880

  690 Avenue C SE Unit 690, Winter Haven, FL 33880
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  $1,199

  Total Monthly Price

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

  399 Ave B Ave SE Unit 399. Ave B, Winter Haven, FL 33880

  Trendy and chic boutique style apartment. If you are looking for something unique, different and trendy look no further. This cute upscale yet affordable apartment has real white marble tile throughout, newly updated shower, kitchen, laundry room with washer and dryer hook ups included, a private fenced in court yard and lots of neat touches you wont find in the "run of the mill" cookie cutter

  399 Ave B Ave SE Unit 399. Ave B, Winter Haven, FL 33880
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  /13

  $2,150

  Total Monthly Price

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

  1108 29th St NW, Winter Haven, FL 33881

  4 bed/2 bath home with a large fenced backyard.Fully renovated for your convenience.Contact me to visit this beautiful property you will soon call home!

  1108 29th St NW, Winter Haven, FL 33881
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  $1,650

  Total Monthly Price

  • 2 Beds
  • 3 Baths
  • 1,400 Sq Ft
  • House for Rent

  103 11th St SE, Winter Haven, FL 33880

  Beautiful home in a quiet neighborhood yet convent to downtown. This 2-bedroom 3 bath home has original hardwood floors large bedrooms and split bedrooms. Kitchen opens up to your large screened in patio that is connected to your garage with full bath and enclosed room. If you are looking for a large yard you found it the home sits on a half-acre lot right in town. call to schedule your showing

  103 11th St SE, Winter Haven, FL 33880
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  $2,000

  Total Monthly Price

  • 3 Beds
  • 2 Baths
  • 2,550 Sq Ft
  • House for Rent

  926 30th St NW, Winter Haven, FL 33881

  Large fully remodeled 3/2 house ( could also be converted to a 4 bedroom ) with huge back yard all fenced in and large screened in patio with washer and dryer hook ups.lots of space

  926 30th St NW, Winter Haven, FL 33881
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  /19

  $900

  Total Monthly Price

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

  1131 5th St SW Unit 4 downstairs, Winter Haven, FL 33880

  Centrally located to restaurants, Aldis, Lowe's and other shopping within walking distance. Small quiet apartments - property has security lights for safety.

  1131 5th St SW Unit 4 downstairs, Winter Haven, FL 33880
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  $1,397 Per Month

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

  3008 Saint Paul Dr Unit 3012, Winter Haven, FL 33880

  Beautiful 2/1 VIEW TODAY!

  Adan Ordonez ADAN INVESTMENTS REAL ESTATE GROUP, PLLC

  3008 Saint Paul Dr Unit 3012, Winter Haven, FL 33880
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  $1,700 Per Month

  • 3 Beds
  • 2 Baths
  • 1,124 Sq Ft
  • House for Rent

  407 Ave a SE, Winter Haven, FL 33880

  Great location! This 3 bedroom 2 bath home is conveniently located in downtown Winter Haven and near the hospital, downtown, doctor offices, restaurants and shopping. Updated Kitchen with granite counter tops, stainless steel appliances, and inside laundry. Owner's recently added a screened back porch with brick pavers and ceiling fan.Administration Fee:Upon approval tenants will be

  407 Ave a SE, Winter Haven, FL 33880
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  /19

  $1,425 Per Month

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

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

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

  Linda Andre COLDWELL BANKER REALTY

  333 Lake Howard Dr NW Unit 312C, Winter Haven, FL 33880
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  /13

  $1,125 Per Month

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

  3039 St Paul Dr, Jan Phyl Village, FL 33880

  Beautiful 2-bedroom unit off of Winter Lake Rd in Winter Haven is move-in ready! Enjoy the vaulted ceiling and exposed beams in the living room. Kitchen features include breakfast bar, granite counters, & custom cabinets. Washer/dryer hookups and lawn care for stress-free living. Up to 2 small pets welcome-30 lbs. or less. Schedule your showing today!Applications do not hold the property

  3039 St Paul Dr, Jan Phyl Village, FL 33880
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  $850 Per Month

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

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

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

  Christin Davis PROPERTY MANAGEMENT OF POLK

  115 Avenue F SW Unit B, Winter Haven, FL 33880
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  $1,075 Per Month

  • 2 Beds
  • 1 Bath
  • Condo for Rent

  3025 St Paul Dr, Winter Haven, FL 33880

  Updated paint 2 bedrooms one bath quad. Kitchen with breakfast bar. Large living room/dining room combo. Two large bedrooms. Inside utility room with washer and dryer hook ups. Yard service is included in the rent. Tenants must carry renters' insurance. $1075.00 per month. Call today for your private showing. Pet free/smoke free.

  3025 St Paul Dr, Winter Haven, FL 33880
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  $1,150 Per Month

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

  514 Avenue C NE Unit 4, Winter Haven, FL 33881

  Fantastic 2 bedroom/1.0 bathroom apartment totally renovated and ready for its new occupants. Unit is in close proximity of schools, including Jewett School of the Arts, Fred G. Garner Elementary School, and Frank E. Brigham Academy. 2 minute walk to Rotary Park. 7 minute walk to Kiwanis Park. 14 minute walk to Winter Haven Tennis Center. Water is included in the rent.

  Angela Chapman CAPITAL REALTY GROUP FLORIDA

  514 Avenue C NE Unit 4, Winter Haven, FL 33881
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  $2,000 Per Month

  • 4 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • House for Rent

  554 Reddicks Cir, Winter Haven, FL 33884

  Welcome to this inviting home located in a quiet neighborhood in Winter Haven! This well-maintained property features a spacious layout with comfortable living areas, perfect for relaxing or entertaining. The home offers multiple bedrooms and bathrooms, providing plenty of space for families or roommates.Conveniently located near shopping, dining, schools, and major roadways, this home

  554 Reddicks Cir, Winter Haven, FL 33884
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  $2,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,312 Sq Ft
  • House for Rent

  1666 Ambar Ct, Winter Haven, FL 33881

  Located on a quiet residential community in Winter Haven, this property offers the perfect blend of comfort, convenience, and quality of life in the heart of Central Florida. Just minutes away from shopping centers, grocery stores, restaurants, hospitals, and schools, the location is ideal for families and anyone seeking everyday convenience. The home also features a spacious fenced backyard,

  Amis Quijada MY REALTY GROUP, LLC.

  1666 Ambar Ct, Winter Haven, FL 33881
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  /18

  $2,345 Per Month

  • 5 Beds
  • 3 Baths
  • 2,601 Sq Ft
  • House for Rent

  668 Squires Grove Dr, Winter Haven, FL 33880

  This home is move-in ready. Schedule your tour now or start your application today.Welcome to 668 Squires Grove Dr in Winter Haven, FL, a 5-bedroom, 3-bath home offering 2,601 square feet of space with an easy, functional flow. The two-story layout and 2-car garage set the tone from the curb, and inside, the mix of soft carpet and tile creates a comfortable feel that works well for

  668 Squires Grove Dr, Winter Haven, FL 33880
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  $1,795 Per Month

  • 2 Beds
  • 2.5 Baths
  • 1,425 Sq Ft
  • House for Rent

  2405 Willow Way, Winter Haven, FL 33881

  Virtually Staged. Brand-New Townhome in Winter Haven | 2 Bed • 2.5 Bath • Modern Living at Its Best! ***Move-In Special: Get $500 OFF Your First Month’s Rent — This Month Only!*** Welcome home to this beautiful brand-new 2-bedroom, 2.5-bath townhome located in one of Winter Haven's growing and convenient communities. Thoughtfully designed with a modern open floor plan, this home offers the

  Jacob Hara TRANSCEND REALTY

  2405 Willow Way, Winter Haven, FL 33881
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  $1,595 Per Month

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

  876 Crestwood Dr, Winter Haven, FL 33881

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

  876 Crestwood Dr, Winter Haven, FL 33881
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  $2,250 Per Month

  • 3 Beds
  • 2 Baths
  • 1,540 Sq Ft
  • House for Rent

  1708 Teagan Ln, Winter Haven, FL 33884

  Beautiful single family house built in 2024 with 3 bedrooms, 2 bathrooms, with open kitchen, Living room and Dining Area, Master Bedroom with attached master bath with double sinks and large walking closet, 2 other bedrooms with hall bath, 2 car garages with appliances Stove, Refrigerator, Dishwasher, Microwave, Washer and Dryer. Amenities include pool, playground etc. in the community. 1st,

  K.C. Thomas CHARLES RUTENBERG REALTY ORLANDO

  1708 Teagan Ln, Winter Haven, FL 33884
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  /23

  $2,200 Per Month

  • 4 Beds
  • 2.5 Baths
  • 2,480 Sq Ft
  • House for Rent

  4450 Rapallo Ave, Winter Haven, FL 33884

  Introducing this 4 bed 2.5 bath home built in 2024 in Winter Haven, FL — a modern four-bedroom, 2.5-bath residence. The property offers a two-car garage and a fenced backyard for privacy and outdoor use. Residents also have access to community amenities including a pool and a play park. Thoughtfully designed spaces and recent construction provide contemporary living in a community-oriented

  4450 Rapallo Ave, Winter Haven, FL 33884
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  $700 Per Month

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

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

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

  Erich Spivey ALABAMA LLC

  720 6th St NW Unit 3, Winter Haven, FL 33881
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  $950 Per Month

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

  663 Ave J NW Unit 2, Winter Haven, FL 33881

  Discover the perfect blend of comfort, privacy, and convenience in this well-maintained Winter Haven residence. Ideally suited for anyone seeking a low-maintenance, independent living space, this cozy 1-bedroom, 1-bathroom apartment delivers a peaceful residential feel with excellent functional perksLease & Move-In Details:Availability: Ready for immediate move-in.Parking:

  663 Ave J NW Unit 2, Winter Haven, FL 33881
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  $1,550 Per Month

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

  64 Stebbins Dr Unit 64, Winter Haven, FL 33884

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

  Tori Coil Grove Shores

  64 Stebbins Dr Unit 64, Winter Haven, FL 33884
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  /15

  $1,350 Per Month

  • 2 Beds
  • 2 Baths
  • 1,003 Sq Ft
  • House for Rent

  2366 Lake Dr NW, Winter Haven, FL 33881

  Welcome to 2366 Lake Dr in Winter Haven — a freshly updated home offering both style and functionality. Inside, you’ll find spacious bedrooms with modern flooring, ceiling fans, and ample natural light. The bathrooms feature clean tile finishes and practical layouts, while the kitchen is equipped with essential appliances including a range oven, range hood, and dishwasher, making everyday living

  2366 Lake Dr NW, Winter Haven, FL 33881
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  $1,750 Per Month

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

  1539 Roselawn St SW, Winter Haven, FL 33880

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

  Ines Morales LA ROSA REALTY KISSIMMEE

  1539 Roselawn St SW, Winter Haven, FL 33880
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  $1,250 Per Month

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

  117 5th St NE, Winter Haven, FL 33881

  All Utilities Included!!! Welcome to this beautiful 1 Bed 1 Bathroom Apartment centrally located on the Main District of Winter Haven. Minutes from downtown Winter Haven, convenience stores, fast foods, gas stations, and more. Enjoy the best of the City of Winter haven and all the new developments happening nearby. All applicants 18 and over must each submit an application, upload copies

  117 5th St NE, Winter Haven, FL 33881
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  $1,100 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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  $2,200 Per Month

  • 4 Beds
  • 2 Baths
  • 1,680 Sq Ft
  • House for Rent

  1816 Carnostie Rd, Winter Haven, FL 33884

  This bright and inviting home offers 4 spacious bedrooms, 2 full bathrooms, and an open-concept floor plan designed for modern living. The living area flows effortlessly into the kitchen, which is equipped with a large island, breakfast bar, stylish cabinetry, quartz countertops, and stainless-steel appliances. Each bedroom features custom closets, providing excellent storage solutions. The Villa

  1816 Carnostie Rd, Winter Haven, FL 33884
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  /15

  $2,190 Per Month

  • 4 Beds
  • 2.5 Baths
  • 1,880 Sq Ft
  • House for Rent

  2154 Chris Dr, Winter Haven, FL 33884

  FOR RENT! Beautiful and move-in ready home located in the heart of Winter Haven! This charming property offers a bright and spacious floor plan with comfortable living areas, generously sized bedrooms, and a welcoming atmosphere perfect for everyday living. Enjoy a functional kitchen, plenty of natural light, and a peaceful neighborhood setting. Conveniently located near shopping, restaurants,

  Daniel Serpa NOSSA REALTY LLC

  2154 Chris Dr, Winter Haven, FL 33884
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  $2,000 Per Month

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

  2416 Ave B SW, Winter Haven, FL 33880

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

  2416 Ave B SW, Winter Haven, FL 33880
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  /15

  $1,700 Per Month

  • 3 Beds
  • 2 Baths
  • 1,407 Sq Ft
  • House for Rent

  168 Southern Breeze Loop, Winter Haven, FL 33880

  SUPER SWEET SAVINGS!!! Enjoy ONE MONTH off your first month's rent when you apply by February 14, 2024, move in by February 21, 2024! Concession applied in March. Select homes, subject to change.Beautiful home offers 3 bedroom and 2 bathroom with ceramic tile type flooring. Home has 2 attached car garage. This home offers a spacious kitchen, updated bathrooms and is located in a beautiful

  Ethel Gumaru FIRSTKEY HOMES LLC

  168 Southern Breeze Loop, Winter Haven, FL 33880
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  /13

  $1,800 Per Month

  • 3 Beds
  • 2 Baths
  • 1,410 Sq Ft
  • House for Rent

  304 Ave P NW, Winter Haven, FL 33881

  This newly built duplex is ready for its next tenants. This unit comes with stainless steel appliances, open living concept, private master bedroom and bathroom, large back yard and so much more. Professionally managed so tenants can be assured their needs are being met. Call us today to set up a showing. All Pro X Property Management The Swain Group. LLC residents are enrolled in the

  304 Ave P NW, Winter Haven, FL 33881
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  /15

  $1,800 Per Month

  • 4 Beds
  • 2 Baths
  • 1,598 Sq Ft
  • House for Rent

  108 Southern Breeze Loop, Winter Haven, FL 33880

  SUPER SWEET SAVINGS!!! Enjoy ONE MONTH off your first month's rent when you apply by February 14, 2024, move in by February 21, 2024! Concession applied in March. Select homes, subject to change.Charming 4 bedroom and 2 bathroom home updated with ceramic tile type flooring and neutral paint throughout. The inviting living room is spacious and great for entertaining. The modern kitchen

  Ethel Gumaru FIRSTKEY HOMES LLC

  108 Southern Breeze Loop, Winter Haven, FL 33880
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  /22

  $2,045 Per Month

  • 4 Beds
  • 2 Baths
  • 1,936 Sq Ft
  • House for Rent

  1482 Austin St, Winter Haven, FL 33884

  Welcome home to 1482 Austin St, nestled in the heart of Winter Haven, FL! This beautifully designed 4-bed, 2-bath home offers the space, comfort, and style your family deserves. Enjoy an open-concept layout filled with natural light, a chef-inspired kitchen perfect for weeknight dinners, and a private backyard ideal for playtime or weekend barbecues. Located near top-rated schools, parks, and

  1482 Austin St, Winter Haven, FL 33884
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  $2,300 Per Month

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

  219 Cloverdale Rd, Winter Haven, FL 33884

  ~Fully Furnished 4/2 Winter Haven Residence Offered for Lease - Just bring your wardrobe and toothbrush!~This resort-style home boasts a fully furnished Florida-themed beautiful interior, ceramic tiling throughout, spacious kitchen with breakfast bar and plenty of cabinetry/counter space, sizeable primary bedroom with large walk-in closet and en-suite bath featuring dual vanities and a garden

  Andrea Muzzy HOUSE OF GLASS REAL ESTATE PM

  219 Cloverdale Rd, Winter Haven, FL 33884

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