Winter Haven, FL Homes 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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  $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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  Starting at $1,365 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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  $1,600 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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  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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  $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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  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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  $1,250 Per Month

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

  630 Pavare Ct, Winter Haven, FL 33884

  Welcome to 630 Pavare Ct, a charming 2-bedroom, 2-bath end-unit condo available for rent in the desirable Orchid Springs community. This second-floor residence offers 823 square feet of comfortable living space with an open floor plan, ceramic tile flooring throughout, with carpet in the bedrooms and neutral paint tones. The spacious great room flows into the dining area and kitchen, creating a

  

  Amy Reynolds

  LOCKHART & ASSOCIATES INC

  (863) 302-9940

  630 Pavare Ct, Winter Haven, FL 33884
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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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  $1,350 Per Month

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

  5667 Struthers Ct, Winter Haven, FL 33884

  Clean and cozy 2-bedroom, 1-bathroom duplex in southeast Winter Haven. Featuring wood laminate flooring in living areas and bedrooms, with ceramic tile flooring in the kitchen and bathroom. Kitchen equipped with newerKitchen cabinets and comes with range/oven, refrigerator, and washer/dryer hookups in utility closet. Both bedrooms of ample size with ceiling fans. Recently remodeled bathroom with

  

  CarLee Marchetti

  STAR REALTY OF WINTER HAVEN

  (863) 265-1579

  5667 Struthers Ct, Winter Haven, FL 33884
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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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  $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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  Starting at $1,499 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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  $1,650 Per Month

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

  715 Magnolia Place Unit 715, 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) 624-3828

  715 Magnolia Place Unit 715, Winter Haven, FL 33884
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  Starting at $985 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 $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 $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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  Starting at $1,326 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 $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 $1,189 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 $1,290 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 $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 $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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  $1,800

  Total Monthly Price

  • 4 Beds
  • 2 Baths
  • 1,368 Sq Ft
  • House for Rent

  3960 Avenue U NW, Winter Haven, FL 33881

  Don't miss out on this 4 bedroom home, at an amazing price. This home has been freshly painted and has ceramic tile throughout. The French doors lead to a paver patio that provides access to a huge backyard. The uncovered gazebo/patio area is perfect for those fire pit evenings. Your front covered patio gives you a Waterview of Lake Blue.

  (863) 281-6376

  3960 Avenue U NW, Winter Haven, FL 33881
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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 $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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  $1,925 Per Month

  • 3 Beds
  • 2 Baths
  • 1,201 Sq Ft
  • House for Rent

  812 Whisper Lake Ct, Winter Haven, FL 33880

  EXCITING NEWS: WE ARE CURRENTLY RENOVATING THIS HOME! NOTE THAT THE PHOTOS SHOWN REPRESENT THE HOME BEFORE RENOVATION AND DO NOT REFLECT ANY UPDATES. PLANNED IMPROVEMENTS INCLUDE: NEW STAINLESS STEEL APPLIANCES. APPLY TODAY OR ASK YOUR LEASING SPECIALIST FOR MORE DETAILS! Apply now or schedule your self-tour today and take the first step toward getting more than just a place to live. Rent

  (863) 622-9626

  812 Whisper Lake Ct, Winter Haven, FL 33880
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  $1,400 Per Month

  • 2 Beds
  • 2 Baths
  • 1,015 Sq Ft
  • Condo for Rent

  1935 Ave O SW Unit 201, Winter Haven, FL 33880

  Property Id: 2515636Home features: Plank flooring throughout (easy to clean) Wood cabinetry + granite countertops Stainless steel appliances including dishwasher and garbage disposal Ceiling fans in the bedroom and living roomIn-unit washer & dryer Bedroom and living room are cable-readyLocation: Minutes to downtown Winter Haven—close to shopping, restaurants,

  (863) 837-4814

  1935 Ave O SW Unit 201, Winter Haven, FL 33880
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  $1,250 Per Month

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

  1059 Spirit Lake Rd, Winter Haven, FL 33880

  This 900 SqFt unit offers comfort and convenience in a desirable location.- Electric range, microwave, and refrigerator included - Forced air heating and central cooling for year-round comfort - Tile flooring and ceiling fan(s)- Dryer included for ease of laundry - Fenced yard and patio for outdoor enjoyment - On-street parking available Perfectly situated

  (659) 207-5228

  1059 Spirit Lake Rd, Winter Haven, FL 33880
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  $1,245 Per Month

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

  3060 St Paul Dr, Jan Phyl Village, FL 33880

  This cozy 2-bedroom, 1-bathroom apartment offers 761.5 square feet of comfortable living space. Enjoy modern conveniences in a practical layout.- Electric range, dishwasher, microwave, and refrigerator included- Garbage disposal for convenience- Efficient forced air heating and central cooling system- Durable tile flooring- Washer and dryer hookups for easy laundry

  (205) 946-1398

  3060 St Paul Dr, Jan Phyl Village, FL 33880
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  $1,819 Per Month

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

  1532 Wallace Manor Ave, Winter Haven, FL 33880

  This home is professionally managed by Tricon, dedicated to creating exceptional rental experiences. Featuring 4 bedrooms, 2.0 bathrooms, and approximately 1,300 square feet, this well-maintained home offers a high standard of rental living, supported by a team that puts residents first. As a Tricon resident, you'll enjoy access to Tricon Vantage — a program designed to support your rental

  (863) 264-5250

  1532 Wallace Manor Ave, Winter Haven, FL 33880
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  $1,945 Per Month

  • 3 Beds
  • 2 Baths
  • 1,340 Sq Ft
  • House for Rent

  502 Glad Rd, 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,

  (863) 588-7104

  502 Glad Rd, Winter Haven, FL 33880
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  $1,750 Per Month

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

  3320 Timberline Rd W, 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,

  (863) 431-4711

  3320 Timberline Rd W, Winter Haven, FL 33880
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  $1,855 Per Month

  • 3 Beds
  • 2 Baths
  • 1,460 Sq Ft
  • House for Rent

  206 Kingshill Ct SE, Winter Haven, FL 33884

  Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.This home is priced to rent and won't be around for long. Apply now, while we make this home ready for you, or call to arrange a meeting with your local Progress Residential leasing specialist

  (863) 343-0941

  206 Kingshill Ct SE, Winter Haven, FL 33884
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  $1,175 Per Month

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

  3074 St Paul Dr, Jan Phyl Village, FL 33880

  Property Id: 13559002 Bedroom / 1 Bathroom Home for Rent - Winter Haven, FLAddress: 3078,3076,3074,3072 Saint Paul Drive, Winter Haven, FL(3076 is currently for rent)Affordable 2-bedroom, 1-bathroom single-family home located in a Winter Haven neighborhood walking distance from the Publix plaza. This home offers a comfortable layout, perfect for small families,

  (239) 208-1520

  3074 St Paul Dr, Jan Phyl Village, FL 33880

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