Homes for Rent in Winter Haven, FL with 2-Bedrooms

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  Starting at $1,505 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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  $1,350 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 $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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  $1,400 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 $1,441

  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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  $1,650 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 $1,400 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 $1,200 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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  $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 $1,510 Per Month

  • 1 - 3 Beds

  2850 W Lake Hamilton Dr, Winter Haven, FL 33881

  Welcome Home to Magnolia at Lake Hamilton!

  Magnolia at Lake Hamilton

  (863) 588-7216

  

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

  • Studio - 3 Beds

  7676 Carlton Arms Blvd, Winter Haven, FL 33884

  Carlton Arms of Winter Haven located on 122 acres of wooded lakefront property, offers country club living at many different rental rates. With its cascading fountains, beautifully landscaped grounds, peaceful woods and 5 freshwater lakes, this resort-style community provides every resident with professional management and maintenance that are trademarks of all Mahaffey planned properties.

  Carlton Arms Of Winter Haven

  (863) 251-6034

  

  7676 Carlton Arms Blvd, Winter Haven, FL 33884
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  Starting at $1,349 Per Month

  • 1 - 2 Beds

  5004 Dream Dr, Winter Haven, FL 33880

  Embrace the art of living fully at Dream Winter Haven, where each day is a masterpiece waiting to be painted. Here, life is about more than just a home—it's about thriving in a community designed to enrich your every experience. Discover the charm of brand-new luxury 1, 2, and 3-bedroom apartments, complemented by resort-style amenities that encourage you to live fully. Set in the heart of Winter

  Dream Winter Haven

  (863) 312-1112

  

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

  • Studio - 2 Beds

  350 24th St NW, Winter Haven, FL 33880

  Haven at Lake Deer is the retreat you've been looking for in Winter Haven, FL. Our lakeside community features studio, one and two bedroom homes complete with patios, wood-style flooring, and upgraded kitchens. What's more, as a member of the community you'll also have access to our sparkling swimming pools and a 24-hour gym. At Haven at Lake Deer, you're guaranteed to find a place to live with a

  Haven at Lake Deer

  (863) 356-1158

  

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

  • 1 - 3 Beds

  200 Avenue K SE, Winter Haven, FL 33880

  Welcome to Briarcrest at Winter Haven Apartments, ideally located near downtown Winter Haven, FL where convenience meets comfort in a picturesque setting. Choose from our spacious and versatile one, two, and three-bedroom floor plans, each thoughtfully designed to suit diverse lifestyles. Our community boasts not just one, but two sparking pools for residents to unwind and enjoy Florida's

  Briarcrest at Winter Haven

  (863) 356-1058

  

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

  • 1 - 2 Beds

  1101 Cambridge Square, Winter Haven, FL 33880

  Barrington Place at Winter Haven is an intimate and charming community located in Winter Haven, FL. Our exclusive residences offer a serene retreat for residents seeking comfort and convenience. Discover the perfect balance of tranquility and accessibility, with proximity to Cypress Gardens Blvd., top-rated schools, healthcare facilities, and shopping destinations just moments away. Choose from

  Barrington Place At Winter Haven

  (863) 204-5542

  1101 Cambridge Square, Winter Haven, FL 33880
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  Starting at $1,249 Per Month

  • 1 - 3 Beds

  4025 Lake Ned Village Cir, Winter Haven, FL 33884

  Flow through the good life at Vista Lake Ned Apartments. The park-like setting, eclectic amenities, and expansive interiors will make you fall in love with our apartments in Winter Haven. Even better, our Cypress Gardens location places you right off Highway 27 and close to Legoland! Add in the top-notch services that have earned us glowing reviews throughout the years, and you know you're in the

  Vista Lake Ned

  (863) 216-1915

  

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

  • 1 - 3 Beds

  4200 Mahogany Run, Winter Haven, FL 33884

  Della Vita Apartments offers the best in brand new interior finishes, abundant community amenity offerings and quick and easy access to some of the best shopping, entertainment and dining Winter Haven has to offer. We’ve recently started a multi-million dollar renovation that will enhance your everyday lifestyle. Our 1, 2 & 3 bedroom apartment homes include large bedrooms with walk-in closets,

  Della Vita Apartments

  (863) 456-1985

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

  • 1 - 3 Beds

  1300 Lake Howard Dr SW, Winter Haven, FL 33880

  Welcome to luxury living in Winter Haven. Lakeshore Club is located on the Chain of Lakes between Lake Howard and Lake Mary minutes from downtown Winter Haven.

  Lakeshore Club

  (863) 356-0860

  

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

  • 1 - 3 Beds

  4900 Cypress Gardens Rd, Winter Haven, FL 33884

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

  The Arbours at Garden Grove

  (727) 205-8061

  

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

  • Studio - 2 Beds

  130 Avenue C SE, Winter Haven, FL 33880

  Central Haven Apartments

  (863) 837-4828

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

  • 2 - 3 Beds

  4225 Vista Del Lago Dr, Winter Haven, FL 33881

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

  Villas at Lake Smart Apartments

  (863) 269-3488

  

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

  • 1 - 2 Beds

  101 Parker Ln NE, Winter Haven, FL 33881

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

  Lake Buckeye Apartments

  (863) 269-3501

  101 Parker Ln NE, Winter Haven, FL 33881
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  $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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  $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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  $1,495 Per Month

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

  23 Kinsmen Dr, Winter Haven, FL 33884

  Property Id: 2572985Move-in-condition and bright/FURNISHED OR UNFURNISHED AVAILABLE/Updated A/C, duct work, vapor barrier, flooring, windows, bathrooms, kitchen, blinds and expanded shed/Near golf courses, hospital, doctors offices, Legoland, shopping and restaurants/Extra parking for guests across the street/Metal roof/Glassed in lanai (east exposure)/Carport

  (863) 238-2552

  23 Kinsmen Dr, Winter Haven, FL 33884
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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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  $2,091

  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 $2,091/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 7, 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

  (863) 328-4815

  1630 17th St NW Unit SI ID1545923P, Winter Haven, FL 33881
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  $1,475 Per Month

  • 2 Beds
  • 1 Bath
  • 1,206 Sq Ft
  • House for Rent

  850 17th Terrace NE, Winter Haven, FL 33881

  MOVE-IN READYThis home is move-in ready. Schedule your tour now or start your application today.Welcome to this 2-bedroom, 1-bathroom home in Winter Haven, Florida, offering a practical layout and inviting living spaces throughout. An attached carport adds everyday convenience, while the enclosed patio provides additional versatile space to enjoy.Inside, hard surface

  (863) 356-8702

  850 17th Terrace NE, Winter Haven, FL 33881
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  $1,450

  Total Monthly Price

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

  5624 Struthers Ct, Winter Haven, FL 33884

  Freshly updated 2 bed, 1 bath duplex in a quiet Winter Haven location near US-27 and Legoland.Available now. Clean, updated unit ready for immediate move-in.• Washer & dryer included• New central A/C• Tile floors throughout (no carpet)• Fresh interior updates• Private parking• Shared yard$1,450/month$1,450 security deposit Available now.

  5624 Struthers Ct, Winter Haven, FL 33884
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  $1,350

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Condo for Rent

  5663 Struthers Ct Unit 5663 Struthers Ct, Winter Haven FL, 33837, Winter Haven, FL 33884

  Spacious condoPeaceful family friendly neighborhoodNear Garden Grove Elementary and LegolandBig yard Ceiling fansCeiling fans in bedroomsPets allowed

  5663 Struthers Ct Unit 5663 Struthers Ct, Winter Haven FL, 33837, Winter Haven, FL 33884
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  $1,495

  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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  $1,185

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Condo for Rent

  501 Avenue L NE, Winter Haven, FL 33881

  This affordable 2 bedroom, 1 bathroom apartment is available now and offers plenty of space, natural light, and a convenient location close to shopping, schools.Apartment Features:2 spacious bedrooms1 full bathroomLarge living area with tile flooringBright kitchen Window A/C unit + ceiling fansPet friendly (ask for details) Rent & Move InFirst Month

  501 Avenue L NE, Winter Haven, FL 33881
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  $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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  $1,235 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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  $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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  $1,399 Per Month

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

  609 Ave G SE, Winter Haven, FL 33880

  Welcome to your new home!This 2-bedroom, 1-bathroom unit offers approximately 875 sq ft of living space, designed for practical and efficient living.Step inside to a functional layout with easy-to-maintain flooring throughout. The kitchen is equipped with a refrigerator, stove/oven, and microwave, along with adequate cabinet space. Washer and dryer hookups are included, with

  609 Ave G SE, Winter Haven, FL 33880

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