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Winter Haven, FL Homes for Rent

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  • /52

    $3,250 per month

    • 3 Beds
    • 3 Baths
    • 2,371 Sq Ft
    • House for Rent

    7358 Bent Grass Dr, Winter Haven, FL 33884

    *EXCLUSIVE SHORT-TERM RENTAL available from September 1, 2025 to April 15, 2026.* Welcome to this stunning lakefront pool home in the gated community of Miller's Landing. Situated on a 0.80-acre lot, this property features a private geothermal pool, newly built dock with a boat lift, oversized fenced/gated backyard, well irrigation, 3-car garage, LVP flooring throughout, and crown molding. Upon

    Agent Photo

    CarLee Marchetti

    STAR REALTY OF WINTER HAVEN

    (863) 356-7683

    7358 Bent Grass Dr, Winter Haven, FL 33884
  • /31

    $2,190 per month

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

    377 Kayden Cove, Winter Haven, FL 33884

    Beautiful Brand new home ready for you and your family , 4 bedrooms 2.5 baths and a loft , quartz counter tops and 42"cabinets washer and dryer included . Call us now

    Agent Photo

    Elaine Garcia

    GARCIA REALTY GROUP

    (863) 445-9573

    377 Kayden Cove, Winter Haven, FL 33884
  • /40

    $2,100 per month

    • 4 Beds
    • 2 Baths
    • 1,820 Sq Ft
    • House for Rent

    2111 Cartgate Ln, Winter Haven, FL 33884

    LOCATION, LOCATION A unique opportunity awaits! This practically new home, located in a prime area, offers a modern and comfortable lifestyle for the whole family. Its open-concept design, elegant countertops, and stainless steel appliances will captivate you. Four spacious bedrooms, two beautiful bathrooms, and an extra space for your home office give you all the space you need. Excellent

    Agent Photo

    Jose Aguilar

    LA ROSA REALTY KISSIMMEE

    (863) 282-2979

    2111 Cartgate Ln, Winter Haven, FL 33884
  • /20

    $1,800 per month

    • 3 Beds
    • 1 Bath
    • 985 Sq Ft
    • House for Rent

    2122 Lake Blvd, Winter Haven, FL 33881

    Welcome to this charming 3-bedroom, 1-bath home located on beautiful Lake Blvd in the heart of Winter Haven. This well-maintained residence offers a perfect blend of comfort, convenience, and natural beauty—ideal for families, couples, or anyone looking to enjoy peaceful Florida living. 3 Spacious Bedrooms 1 Full BathroomBright Kitchen with Plenty of Storage Open Living Area

    Agent Photo

    Catherine Torres

    IAD FLORIDA LLC

    (863) 431-4579

    2122 Lake Blvd, Winter Haven, FL 33881
  • /20

    $1,400 per month

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

    1814 3rd St SE Unit C, Winter Haven, FL 33880

    Experience the comfort of this spacious 2-bedroom, 1-bath unit with durable vinyl plank flooring throughout. Formal dining room situated off the galley kitchen, seamlessly flowing into the open living room. Living room has double sliding glass doors open to a rear patio, providing ample living space for you to relax and unwind. Both bedrooms are generously sized and equipped with ceiling fans,

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    CarLee Marchetti

    STAR REALTY OF WINTER HAVEN

    (863) 342-6745

    1814 3rd St SE Unit C, Winter Haven, FL 33880
  • /44

    $1,500 per month

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

    615 Ridge Terrace, Winter Haven, FL 33881

    Tucked away in the waterfront community with direct access to the Chain of Lakes (Lake Smart), Unit 615 is a charming 2-bedroom, 2-bath home that offers low-maintenance living, convenience, and value! Step inside to discover brand new vinyl plank flooring throughout, with ceramic tile in the kitchen and bathrooms. The open layout seamlessly connects the spacious living and dining areas to a

    Agent Photo

    CarLee Marchetti

    STAR REALTY OF WINTER HAVEN

    (863) 340-7451

    615 Ridge Terrace, Winter Haven, FL 33881
  • /12

    $1,350 per month

    • 2 Beds
    • 2 Baths
    • 1,012 Sq Ft
    • Property for Rent

    6332 Bayberry Blvd NE, Winter Haven, FL 33881

    Beautiful 55 + community .Spacious 2 Bedrooms,2 bathrooms,1 car carport . Large screened in enclosure with view to an open field . Easy access to everything.

    Agent Photo

    Jannette Pena

    JMP REALTY, INC.

    (863) 880-1241

    6332 Bayberry Blvd NE, Winter Haven, FL 33881
  • /22

    $1,699 per month

    • 3 Beds
    • 2 Baths
    • 1,148 Sq Ft
    • House for Rent

    2110 Whispering Trails Blvd, Winter Haven, FL 33884

    GATED COMMUNITY WITH AWESOME POOL waiting for a good tenant. Updated Home Minutes from Legoland! This charming 3/ 2 home / garage blends comfort and convenience. Newer roof and fresh paint inside and out, this is a move-in ready home! Spacious living room perfect for gatherings, a well-equipped kitchen, 3 comfortable bedrooms, including a master suite with a private bathroom. Additional features

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    Silvana Friedel

    The Keyes Company

    (863) 593-8022

    2110 Whispering Trails Blvd, Winter Haven, FL 33884
  • /23

    $1,500 per month

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

    248 Avenue L NE, Winter Haven, FL 33881

    Adorable move-in ready 2-bedroom, 1-bath home! This delightful property features vinyl plank flooring throughout, with ceramic tile in the bathroom for easy maintenance. The open great room is filled with natural light, creating a warm, welcoming atmosphere. The kitchen boasts sleek stainless steel appliances, ample counter space, and a convenient breakfast bar with additional cabinets on the

    Agent Photo

    CarLee Marchetti

    STAR REALTY OF WINTER HAVEN

    (863) 269-3421

    248 Avenue L NE, Winter Haven, FL 33881
  • /38

    $1,500 per month

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

    513 Winter Terrace Unit 513, Winter Haven, FL 33881

    This fully remodeled unit boasts brand new vinyl plank flooring throughout, elegant granite countertops in both the kitchen and bathrooms, as well as updated mirrors and fixtures. The freshly painted interior complements the open great room, which seamlessly blends the living and dining areas. The galley kitchen is equipped with all appliances, including a washer and dryer, ample counter space,

    Agent Photo

    CarLee Marchetti

    STAR REALTY OF WINTER HAVEN

    (863) 722-1224

    513 Winter Terrace Unit 513, Winter Haven, FL 33881
  • /14

    $2,350 per month

    • 5 Beds
    • 3 Baths
    • 2,523 Sq Ft
    • House for Rent

    1404 Axel Cir, Winter Haven, FL 33880

    Spacious & Stylish 5-Bedroom Home for Rent in Winter Haven!Step into over 2,400 sq. ft. of beautifully designed living space in this 5-bedroom, 3-bathroom rental gem located in Winter Haven, FL. With an open-concept layout, this home offers both comfort and flexibility—perfect for families or anyone who loves to entertain. Downstairs features a convenient first-floor bedroom and full bath,

    Agent Photo

    Carlos DeJesus

    EXIT REALTY 4CORNERS

    (863) 343-1856

    1404 Axel Cir, Winter Haven, FL 33880
  • /6

    $900 per month

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

    117 Avenue B NE, Winter Haven, FL 33881

    Convenient location close to downtown, shopping, post office, Winter Haven Hospital. All tile floors. Sorry, but no pets and occupancy limited to TWO persons.

    Agent Photo

    Steve Lockhart

    LOCKHART & ASSOCIATES INC

    (863) 900-9266

    117 Avenue B NE, Winter Haven, FL 33881
  • /30

    $1,480 - $2,150 per month

    The Waverly at Winter Haven

    1 - 3 Beds

    1015 Lake Forest Blvd, Winter Haven, FL 33884

    Experience stylish, comfortable living at The Waverly at Winter Haven. Located in the sought-after Cypress Gardens area, our pet-friendly community offers a peaceful lifestyle with convenient access to everything Central Florida has to offer.At The Waverly at Winter Haven, you'll enjoy a host of resort-inspired amenities designed to enhance your lifestyle, from a sparkling pool and

    1015 Lake Forest Blvd, Winter Haven, FL 33884
  • /14

    $1,400 per month

    • 2 Beds
    • 2 Baths
    • 1,017 Sq Ft
    • Condo for Rent

    1004 Eagle Pond Dr Unit D10, Winter Haven, FL 33884

    FRESH INTERIOR PAINT!Enjoy the convenience of this first-floor corner-unit located in the Eagle Pond neighborhood at Cypresswood Golf and Country Club.Features include 2 bedrooms, 2 bathrooms, open kitchen and living area, inside laundry room, split bedrooms with ample closet space, exterior storage closet and one assigned parking space.Maximum 2 vehicles allowed.No commercial

    Steven Smith, PA LOCKHART & ASSOCIATES INC

    1004 Eagle Pond Dr Unit D10, Winter Haven, FL 33884
  • /49

    $1,450 - $2,405 per month

    The Carlton at Lake Dexter

    1 - 3 Beds

    1015 Mahaffey Rd, Winter Haven, FL 33884

    A luxury rental lakefront apartment community in Winter Haven, Florida. Accepting leases now.

    1015 Mahaffey Rd, Winter Haven, FL 33884
  • /8

    $2,200 per month

    • 4 Beds
    • 2 Baths
    • 1,498 Sq Ft
    • House for Rent

    Unlisted Address

    Don’t miss out on this beautiful 4-bedroom, 2-bath home built in January 2021!Featuring a spacious and well-designed layout, this home offers everything a family needs.From the moment you arrive, you'll notice the inviting curb appeal and the wide concrete driveway leading to a generously sized garage. Inside, enjoy the modern open floor plan with tile flooring throughout the main living areas,

    Amis Quijada MY REALTY GROUP, LLC.

    Unlisted Address
  • /7

    $1,300 - $2,306 per month

    The Breeze

    Studio - 2 Beds

    265 Avenue East SW, Winter Haven, FL 33880

    265 Avenue East SW, Winter Haven, FL 33880
  • /9

    $1,375 per month

    • 3 Beds
    • 1 Bath
    • 915 Sq Ft
    • House for Rent

    1997 5th St NE, Winter Haven, FL 33881

    Discover the perfect blend of tranquility and accessibility in this inviting 3-bedroom home, complete with a spacious carport for easy parking. Nestled just minutes from vibrant shopping centers and serene nature parks, this residence offers the best of both worlds—urban convenience and outdoor escape.CALL TODAY TO VIEW !

    Nancy Greenwood PALM LEAF PROPERTY MANAGEMENT

    1997 5th St NE, Winter Haven, FL 33881
  • /22

    $1,494 - $1,865 per month

    Prose Cypress Pointe

    1 - 2 Beds

    3110 Gowan Dr, Winter Haven, FL 33884

    Welcome home to Prose Cypress Pointe, a brand-new multifamily community located in Winter Haven, Florida. Our spacious one- and two-bedroom apartment homes feature modern stainless-steel appliances, walk-in closets, dining-sized kitchen islands, premium plank flooring throughout and full-sized washers and dryers in every apartment home. And with convenient, must-have amenities like a fitness

    3110 Gowan Dr, Winter Haven, FL 33884
  • /6

    $2,200 per month

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

    912 Lake Jessie Dr Unit 2, Winter Haven, FL 33881

    Be the first to live in this fully renovated 1 bedroom, 1 bath unit on Lake Jessie in Winter Haven! This all-new lakefront home offers boat dock access, perfect for enjoying the Chain of Lakes lifestyle. The interior is bright and modern, with stylish finishes and plenty of natural light. Water, electric, and internet are all included — just move in and start living. Conveniently located in-town,

    Lucy Hinson RE/MAX HERITAGE

    912 Lake Jessie Dr Unit 2, Winter Haven, FL 33881
  • /31

    $1,400 - $2,137 per month

    RainDance

    1 - 2 Beds

    200 Avenue C SW, Winter Haven, FL 33880

    Welcome to Raindance Apartments, located in the beautiful Winter Haven, FL. Our community offers a range of exceptional amenities designed to enhance your lifestyle. Take a dip in our heated pool, perfect for year-round enjoyment and relaxation. Stay active and maintain your fitness goals in our state-of-the-art gym, equipped with modern exercise equipment. We understand that your furry friends

    200 Avenue C SW, Winter Haven, FL 33880
  • /8

    $2,500 per month

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

    912 Lake Jessie Dr Unit 3, Winter Haven, FL 33881

    Beautifully renovated upstairs 1 bedroom, 1 bathroom unit with a sleek, modern design. Enjoy the convenience of in-unit laundry and stunning views of Lake Jessie. This property includes access to a dock, and water, electric, and internet are all included in the rent. Whether you're relaxing indoors or enjoying the lakeside lifestyle, this unit offers comfort and convenience in a serene setting.

    Lucy Hinson RE/MAX HERITAGE

    912 Lake Jessie Dr Unit 3, Winter Haven, FL 33881
  • /42

    $1,300 - $1,425 per month

    The Jade

    1 Bed

    1150 3rd St SW, Winter Haven, FL 33880

    The Best Amenities in TownThe Jade offers the most comprehensive amenity package in town, offering an unmatched blend of luxury, comfort, and convenience at one inclusive price—no other apartment complex nearby provides such a diverse range of options under one roof.

    1150 3rd St SW, Winter Haven, FL 33880
  • /7

    $1,350 per month

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

    Unlisted Address

    Quiet lakefront apartment located in SW Winter Haven. Don't pass up this oprotunity to enjoy this quiet peacful location. Rent includes electricity, water and internet.

    Lamanda Jones CENTURY 21 WATSON & MYERS REALTY

    Unlisted Address
  • /48

    $912 - $1,723 per month

    Carlton Arms of Winter Haven

    Studio - 3 Beds

    7676 Carlton Arms Blvd, Winter Haven, FL 33884

    *Call or email for today’s availabilityConveniently located on SR540/US27, Carlton Arms of Winter Haven offers 122 wooded lakefront acres with beautiful grounds, free amenities and great service! Country club living at great monthly rents.

    7676 Carlton Arms Blvd, Winter Haven, FL 33884
  • /8

    $2,500 per month

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

    912 Lake Jessie Dr Unit 1, Winter Haven, FL 33881

    Enjoy lakefront living in this beautifully upgraded 2 bedroom, 1 bath unit on Lake Jessie — complete with a private boat dock and serene water views. This bright and airy home features modern finishes, updated flooring, and a spacious open layout that invites natural light throughout. Water, electric, and internet are all included, making for stress-free living. Located in-town, you’re just

    Lucy Hinson RE/MAX HERITAGE

    912 Lake Jessie Dr Unit 1, Winter Haven, FL 33881
  • /35

    $1,199 - $1,549 per month

    Haven at Lake Deer

    Studio - 2 Beds

    350 24th St NW, Winter Haven, FL 33880

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

    350 24th St NW, Winter Haven, FL 33880
  • /11

    $1,950 per month

    • 3 Beds
    • 2 Baths
    • 1,120 Sq Ft
    • House for Rent

    427 Lake Daisy Dr, Winter Haven, FL 33884

    Welcome to this well-maintained rental home featuring a spacious open-concept living and dining area, a modern kitchen fully equipped with appliances, and two full bathrooms for added convenience.This property offers in-unit washer and dryer, central A/C, and abundant natural light throughout. A private, fenced backyard provides the perfect space for relaxing, entertaining, or allowing

    Lucas Gonzalez LIFESTYLE INTERNATIONAL REALTY

    427 Lake Daisy Dr, Winter Haven, FL 33884
  • /31

    $1,529 - $1,999 per month

    Dream Winter Haven

    1 - 2 Beds

    5004 Dream Dr, Winter Haven, FL 33881

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

    5004 Dream Dr, Winter Haven, FL 33881
  • /32

    $1,995 per month

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

    2527 Pine Place, Winter Haven, FL 33881

    One or more photo(s) has been virtually staged. Welcome to 2527 Pine Place, where style, space, and convenience come together! This beautiful 3-bedroom, 2.5-bath home is perfectly nestled in a peaceful Winter Haven neighborhood, offering the ideal blend of privacy and accessibility.Step inside to discover a bright and open layout designed for modern living. The spacious kitchen seamlessly

    Jacob Hara TRANSCEND REALTY

    2527 Pine Place, Winter Haven, FL 33881
  • /15

    $1,090 - $1,540 per month

    Briarcrest at Winter Haven

    1 - 3 Beds

    200 Avenue K SE, Winter Haven, FL 33880

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

    200 Avenue K SE, Winter Haven, FL 33880
  • /32

    $1,995 per month

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

    2533 Pine Place, Winter Haven, FL 33881

    One or more photo(s) has been virtually staged. Discover comfort, space, and modern flair at 2533 Pine Place—a beautifully maintained 3-bedroom, 2.5-bath home nestled in a quiet Winter Haven community. From the moment you arrive, you’ll appreciate the inviting curb appeal and smart layout designed for easy living.Enjoy an open-concept living area perfect for entertaining, a spacious

    Jacob Hara TRANSCEND REALTY

    2533 Pine Place, Winter Haven, FL 33881
  • /26

    $1,269 - $1,675 per month

    Della Vita Apartments

    1 - 3 Beds

    4200 Mahogany Run, Winter Haven, FL 33884

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

    4200 Mahogany Run, Winter Haven, FL 33884
  • /32

    $1,950 per month

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

    2562 Pine Place, Winter Haven, FL 33881

    One or more photo(s) has been virtually staged. Welcome to 2562 Pine Pl, a stunning 3-bedroom, 2.5-bath home nestled in the heart of Winter Park, FL—where comfort meets serene waterfront living. Enjoy peaceful water views right from your backyard, perfect for morning coffee or evening relaxation. This beautifully maintained property offers a spacious, open layout, modern kitchen, and a primary

    Jacob Hara TRANSCEND REALTY

    2562 Pine Place, Winter Haven, FL 33881
  • /32

    $1,575 - $2,050 per month

    Lakeshore Club

    1 - 3 Beds

    1300 Lake Howard Dr SW, Winter Haven, FL 33880

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

    1300 Lake Howard Dr SW, Winter Haven, FL 33880
  • /11

    $1,435 per month

    • 3 Beds
    • 1 Bath
    • 1,057 Sq Ft
    • House for Rent

    1311 5th St NE, Winter Haven, FL 33881

    This adorable 3-bedroom home offers cozy living with functional flair. Enjoy a spacious kitchen perfect for cooking and gathering, plus a dedicated laundry/mud room to keep things neat and tidy. The large yard provides ample room for play, pets, or peaceful gardening afternoons. A detached one-car garage adds extra storage or workspace potential. Best of all, you’re just minutes from local parks

    Nancy Greenwood PALM LEAF PROPERTY MANAGEMENT

    1311 5th St NE, Winter Haven, FL 33881
  • /50

    $1,349 - $1,890 per month

    Vista Lake Ned

    1 - 3 Beds

    4025 Lake Ned Village Cir, Winter Haven, FL 33884

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

    4025 Lake Ned Village Cir, Winter Haven, FL 33884
  • /17

    $1,820 per month

    • 2 Beds
    • 2 Baths
    • 1,904 Sq Ft
    • House for Rent

    3217 Timberline 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, nestled

    Nico Silva Vanegas MAIN STREET RENEWAL LLC

    3217 Timberline Rd, Winter Haven, FL 33880
  • /12

    $1,165 - $1,592 per month

    Barrington Place At Winter Haven

    1 - 2 Beds

    1101 Cambridge Square, Winter Haven, FL 33880

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

    1101 Cambridge Square, Winter Haven, FL 33880
  • /32

    $1,895 per month

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

    2607 Tanoak Terrace, Winter Haven, FL 33881

    One or more photo(s) has been virtually staged. Welcome to 2607 Tanoak Terrace, a beautifully designed 3-bedroom, 2.5-bathroom townhome nestled in a peaceful community in Winter Haven, FL. This spacious and modern home offers the perfect blend of comfort and functionality—ideal for families, professionals, or anyone seeking low-maintenance living in a prime location.Step into an

    Jacob Hara TRANSCEND REALTY

    2607 Tanoak Terrace, Winter Haven, FL 33881

Showing Results 1 - 40, Page 1 of 8

Why Live in Winter Haven

Winter Haven is the midpoint between Tampa and Orlando in rapidly growing Polk County. Known for having dozens of lakes, this outdoor paradise has experienced significant growth in recent years, reaching 60,000 in 2024. For years the city was a ...

Frequently Asked Questions

What are the most popular neighborhoods in Winter Haven, FL for renters?
The most popular neighborhoods in Winter Haven, FL for renters are Downtown Winter Haven, Poinsettia Park, Lake Ashton, Southwest Winter Haven and Cypresswood.
What are the most popular zip codes in Winter Haven, FL for renters?
The most popular zip codes in Winter Haven, FL for renters include 33880, 33884, 33881, 33839 and 33859.
How to Rent a Home