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Downtown Winter Haven Homes for Rent

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    $1,725 - $1,794 per month

    RainDance

    1 Bed

    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
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    $1,720 per month

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

    1721 Broxey Ct NE, Winter Haven, FL 33881

    Newly Renovated 3 Bedroom Home – Available Now!Welcome to your fresh start at 1721 Broxey Ct NE, Winter Haven, FL 33881 – a beautifully renovated 3-bedroom, 1-bathroom home listed at $1,720/month. This charming residence has been thoughtfully updated to offer modern comfort and convenience in a quiet Winter Haven neighborhood.Step inside to find a bright, open layout with

    Kelton Wright EXP REALTY LLC

    1721 Broxey Ct NE, Winter Haven, FL 33881
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    $1,325 - $1,650 per month

    The Jade

    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.

    1150 3rd St SW, Winter Haven, FL 33880
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    $1,950 per month

    • 3 Beds
    • 2 Baths
    • 1,364 Sq Ft
    • House for Rent

    836 Avenue N SW, Winter Haven, FL 33880

    Please read full addFOR RENT – 3BR/2BA Home | $1,950/Month | Utilities IncludedNow available in a quiet neighborhood – in renovation 3 bedroom, 2 bathroom home featuring:•? ?Fresh paint (inside & out)•? ?Brand new wood look flooring•? ?Master bedroom with walk-in closet•? ?Washer & dryer included•? ?Stove & refrigerator included•? ?Fully fenced yard –

    Milena Bardales PROPERTY OUTLET INTERNATIONAL

    836 Avenue N SW, Winter Haven, FL 33880
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    $1,080 - $1,530 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
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    $1,800 per month

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

    1539 Roselawn St SW, Winter Haven, FL 33880

    Charming 3-Bedroom, 2-Bathroom Home for Rent Welcome to your new home! This beautiful 3-bedroom, 2-bathroom house offers the perfect blend of comfort and convenience. Located in a friendly neighborhood, this home features luxury vinyl flooring in the living spaces, providing wonderful space to enjoy. The bedrooms are spacious and confortable allowing for a reaxed rest. The kitchen ia beauty

    Ines Morales LA ROSA REALTY KISSIMMEE

    1539 Roselawn St SW, Winter Haven, FL 33880
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    $1,500 - $2,100 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
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    $825 per month

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

    1111 Cypress Gardens Blvd Unit 26, Winter Haven, FL 33884

    1 Bed, 1 bath for rent off of Lake Roy. Included in the rent is Water, and Lawn service. Call soon before this property is gone! Application Fee runs $50 for each adult with a onetime $50 Lease Fee. For this home we are asking for First Month's Rent ($825), and Security Deposit ($1000) making total move in cost assuming one adult to be $1,925. NO PETS ALLOWED. (Service animals are the only

    Daniel Gonzalez AT YOUR SERVICE REALTY, LLC

    1111 Cypress Gardens Blvd Unit 26, Winter Haven, FL 33884
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    $1,105 - $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
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    $1,350 per month

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

    1103 Cypress Gardens Blvd Unit 51, Winter Haven, FL 33884

    Welcome to Lamplighter Village with this one of a kind 2 bedroom/1 bath condo. The property was nicely renovated and features updated vinyl flooring and updated stainless steel kitchen appliances with a gas stove. New solid wood cabinets and granite countertops. The condo was freshly painted and is turn key ready. Property also includes a stand up washer and dryer and new window blinds. The

    MAYOLET BORNAS MAYOLET REALTY LLC

    1103 Cypress Gardens Blvd Unit 51, Winter Haven, FL 33884
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    $1,000 - $1,275 per month

    Georgetown Apartments

    Studio-2 Beds

    130 Avenue C SE, Winter Haven, FL 33880

    130 Avenue C SE, Winter Haven, FL 33880
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    $2,350 per month

    • 5 Beds
    • 3 Baths
    • 2,806 Sq Ft
    • House for Rent

    1501 7th St SE, Winter Haven, FL 33880

    Fantastic rental opportunity calling your name. Welcome Home to this 5 bedroom 3 bath POOL Home on a large corner lot in Winter Haven.Upgrades galore. NEW ROOF, NEW POOL EQUIPMENT, 2 NEW A/C UNITS. The home features luxury vinyl wood flooring throughout. The kitchen has been renovated featuring white wood shaker cabinets, quartz countertops and stainless steel appliances. The bathrooms have

    Laura Auten ELEVATE REALTY LLC

    1501 7th St SE, Winter Haven, FL 33880
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    $950 per month

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

    806 Ave O SW, Winter Haven, FL 33880

    Property Id: 1833123Located just off Lake Shipp and only minutes from downtown Winter Haven, this charming first-floor 2-bedroom, 1-bath unit is nestled in a quiet, well-kept neighborhood. The apartment has been recently updated with fresh paint, offering a clean and comfortable living space that's move-in ready.The property features convenient alley access and ample parking,

    806 Ave O SW, Winter Haven, FL 33880
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    $1,950 per month

    • 3 Beds
    • 2 Baths
    • 1,380 Sq Ft
    • House for Rent

    1204 Lake Elbert Dr SE, Winter Haven, FL 33880

    Beautiful 3 bedrooms and 2 bathrooms single family home with amazing and wide-open lake view!! Everything new from top to bottom: new roof, Impact windows, high traffic laminated floors; new bathrooms and new kitchen with stainless steel appliances and quartz countertops. Huge fenced backyard and new paved driveway. A must see before it is gone!

    Ana Saya Direct Realty Solutions

    1204 Lake Elbert Dr SE, Winter Haven, FL 33880
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    $2,150 per month

    • 4 Beds
    • 2 Baths
    • 1,846 Sq Ft
    • House for Rent

    251 Krenson Bay Loop, Winter Haven, FL 33881

    Property Id: 1397491Security Deposit and first month rent required to move in.if you have can questions please contactReal Estate Agent Rabie Georgey Properties in Town .Se requiere un depósito de seguridad y el primer mes de alquiler para mudarse. Si tiene preguntas, comuníquese con el agente de bienes raíces Rabie Georgey Properties en la ciudad al .

    251 Krenson Bay Loop, Winter Haven, FL 33881
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    $1,795 per month

    • 2 Beds
    • 2 Baths
    • 1,090 Sq Ft
    • Apartment for Rent

    332 Avenue D SE, Winter Haven, FL 33880

    This 2 bedroom 2 bathroom end unit is fully furnished with a modern flair. Renovated with new roof, energy efficient tankless water heater, paint, appliances & more. Featuring luxury vinyl floors throughout, granite countertops in the kitchen, both bathrooms feature renovated showers & tub, vanities & fixtures. This home is turnkey including all linens, electronics and kitchenware. The living

    Kathryn Shevlin THE PROPERTY FIRM

    332 Avenue D SE, Winter Haven, FL 33880
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    $2,380 per month

    • 3 Beds
    • 3 Baths
    • 2,271 Sq Ft
    • House for Rent

    25 Casarena Ct, Winter Haven, FL 33881

    COMING SOONMaymont Homes is committed to clear and upfront pricing. In addition to the advertised rent, residents may have monthly fees, including a $10.95 utility management fee, a $25.00 wastewater fee for homes on septic systems, and an amenity fee for homes with smart home technology, valet trash, or other community amenities. This does not include utilities or optional fees,

    25 Casarena Ct, Winter Haven, FL 33881
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    $1,400 per month

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

    639 Avenue F NW Unit 12, Winter Haven, FL 33881

    Newly remodeled 2 bedroom 1 bathroom condo for rent.. WATER INCLUDED. New appliances, cabinets, counters, fixtures, and paint. Washer and dryer on site.

    Jonathan Turner LAND SOURCE REALTY, LLC

    639 Avenue F NW Unit 12, Winter Haven, FL 33881
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    $1,425 per month

    • 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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    $1,475 per month

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

    2050 San Marcos Dr SE Unit 214, Winter Haven, FL 33880

    Discover a spacious 2-bedroom, 2-bathroom second floor condo nestled in one of the most sought-after complexes in town. This home offers a perfect blend of comfort and convenience, featuring an open floor plan, natural light, and premium finishes throughout. The condo is located right across from the community's office and mailboxes.The two bedrooms provide plenty of space and privacy, with

    Christin Davis PROPERTY MANAGEMENT OF POLK

    2050 San Marcos Dr SE Unit 214, Winter Haven, FL 33880
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    $1,825 per month

    • 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 you're showing today. Close to downtown and convenient to all winter haven has to offer.

    711 Avenue B NE, Winter Haven, FL 33881
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    $1,600 per month

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

    422 22nd St SW, Winter Haven, FL 33880

    FOR RENT - 3 Bedroom/1 Bath Single Family Home - Immaculate cement block home ready for a new tenant. This home has been totally remodeled and comes with beautiful ceiling fans, light fixtures, a range, and a refrigerator. It also features two sheds in the fenced back yard. If you like skiing, Winter Haven is the Ski Capital of the World! Downtown Winter Haven has about a dozen restaurants

    Linda Andre COLDWELL BANKER REALTY

    422 22nd St SW, Winter Haven, FL 33880
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    $1,825 per month

    • 2 Beds
    • 2 Baths
    • 1,162 Sq Ft
    • Condo for Rent

    235 6th St NW Unit 404, Winter Haven, FL 33881

    Beautiful corner unit located in the highly sought after complex known as The Haven. This complex was once a famous hotel featured in the 1953 movie "Easy to Love" starring Ester Williams. It has since been converted into a beautiful condominium full of history. The Haven is located steps away from the historic downtown Winter Haven district with shopping, dining, coffee shops, yoga studio,

    235 6th St NW Unit 404, Winter Haven, FL 33881
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    $1,400 per month

    • 2 Beds
    • 2 Baths
    • 1,347 Sq Ft
    • Condo for Rent

    1776 6th St NW Unit 209, Winter Haven, FL 33881

    Rent this Condo. Conveniently located condominium in LakeRidge Winter Haven, close to downtown entertainment, hospitals, shopping, gas stations, and restaurants. A 55 year old community with a strategic location. What else could you ask for, when you enjoy peace and security of a gated community but yet close to everything. This unit has 2 spacious bedroom and 2 bath with an open concept style a

    Mary Sorrell MAZELG REALTY

    1776 6th St NW Unit 209, Winter Haven, FL 33881
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    $900 per month

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

    390 Quentin Ave, WINTER HAVEN, FL 33881

    2/1 Duplex in Winter Haven WASHER / DRYER includedSection 8 welcomedWelcome to your 500 sq. ft. 2/1 apartment that offers a cozy living. A perfect home for a small family, providing comfort and convenience with close proximity to downtown Winter haven. Washer and dryer are included. Requirements: first month rent and security deposit upfront. verifiable Income must be 3x monthly rent. No

    390 Quentin Ave, WINTER HAVEN, FL 33881
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    $1,875 per month

    • 3 Beds
    • 1.5 Baths
    • 1,744 Sq Ft
    • House for Rent

    1146 W Lake Martha Dr NE, Winter Haven, FL 33881

    Welcome to 1146 W Lake Martha Dr NE, a delightful 3-bedroom, 1.5-bathroom single-family home located in the heart of Winter Haven, Florida. This residence offers 1,744 square feet of living space, featuring beautiful wood floors and abundant built-in shelving that add both charm and functionality. The spacious living room provides a comfortable setting for relaxation, while the dining room is

    Kelton Wright EXP REALTY LLC

    1146 W Lake Martha Dr NE, Winter Haven, FL 33881
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    $900 per month

    • 1-2 Beds
    • 1 Bath
    • 500 Sq Ft
    • Townhouse for Rent

    1715 Broxey Ct NE Unit 3 (RIGHT SIDE), Winter Haven, FL 33881

    1715 Broxey Ct NE Unit 3 (RIGHT SIDE), Winter Haven, FL 33881
  • /20

    $1,950 per month

    • 2 Beds
    • 2 Baths
    • 1,190 Sq Ft
    • Condo for Rent

    700 Mirror Terrace NW Unit 403, Winter Haven, FL 33881

    Winter Haven's premier condominium located directly overlooking the picturesque Lake Spring that is part of the Chain of Lakes. Be the first to enjoy this 4th floor extensively remodeled and upgraded 2BR/2BA unit including brand-new appliances. Completely furnished. Turn-key ready. Exquisitely maintained building and has passed the newly required Florida State Milestone Inspection with flying

    Scott Kline KLINE REAL ESTATE SERVICES

    700 Mirror Terrace NW Unit 403, Winter Haven, FL 33881
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    $1,700 per month

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

    2075 Isle Royale Ct SE Unit 167, Winter Haven, FL 33880

    Centrally located in Winter Haven with easy access to restaurants, shopping, and downtown.Two miles from Winter Haven Hospital and easy to get to the Polk Parkway to get to Lakeland.Outback, Panera, Chik Fil A, Starbucks are all within walking distance of the unit. There is a pool on site as well.

    2075 Isle Royale Ct SE Unit 167, Winter Haven, FL 33880
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    $1,150 per month

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

    2085 Isle Royale Ct SE Unit 280, Winter Haven, FL 33880

    LOCATION-LOCATION-LOCATION. Adorable partially furnished 1 Bedroom/1 Bathroom Executive Condo in beautiful Park Lake. Features all laminate flooring, large open living/dining room combo with vaulted ceilings. Bedroom also has high ceilings with a fan and a plant shelf above the closet. Stackable washer and dryer included. Huge, screened balcony with garden views for relaxing. Park Lake is a

    MAYOLET BORNAS MAYOLET REALTY LLC

    2085 Isle Royale Ct SE Unit 280, Winter Haven, FL 33880
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    $1,350 per month

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

    669 Avenue B NW Unit 2, Winter Haven, FL 33881

    Settled in a quiet neighborhood 1 block from Lake Howard is a spacious 1 bedroom, 1 bath second floor unit. Unit features a claw-foot tub, stove, refrigerator, built-in pantry hardwood floors and large closet. With views of Lake Howard from all windows, this unit makes an excellent home. The property is part of the Pope Historic District which has been undergoing revitalization through

    669 Avenue B NW Unit 2, Winter Haven, FL 33881
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    $2,500 per month

    • 4 Beds
    • 3 Baths
    • 2,135 Sq Ft
    • House for Rent

    202 Lake Howard Dr NW, Winter Haven, FL 33880

    One or more photo(s) has been virtually staged. Escape to this stunning 4-bedroom, 2.5-bathroom lake house perfectly situated on the shores of Lake Howard! This spacious home boasts an open floorplan with a thoughtful split-bedroom layout, offering both comfort and privacy for your family or guests.Step inside and be greeted by tons of natural light streaming through expansive windows

    David Small KELLER WILLIAMS REALTY SMART 1

    202 Lake Howard Dr NW, Winter Haven, FL 33880
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    $950 per month

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

    631 Ave H Ave NW Unit 2, Winter Haven, FL 33881

    Just steps away from Lake Howard, shopping, restaurants and other area amenities. Pets' negotiable with additional deposit. Tenant to pay all utilities. Lawn care provided. 1st & security. Application with background/credit check. Text or Email for more details and access information.

    631 Ave H Ave NW Unit 2, Winter Haven, FL 33881
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    $1,800 per month

    • 3 Beds
    • 1.5 Baths
    • 960 Sq Ft
    • House for Rent

    2217 Avenue A NW, Winter Haven, FL 33880

    Great older home with spacious bedrooms. Must come and see for yourself

    Steven Baron BARON HOLDINGS REAL ESTATE LLC

    2217 Avenue A NW, Winter Haven, FL 33880
  • /2

    $1,200 per month

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

    650 Avenue J NW Unit 202, Winter Haven, FL 33881

    Beautiful 2 Bedroom, 1 Bath home in Kissimmee. Near schools and retail shops. Schedule a viewing today before it's gone!

    maria vega THE EXPERTS TEAM REALTY INC

    650 Avenue J NW Unit 202, Winter Haven, FL 33881
  • /16

    $1,750 per month

    • 4 Beds
    • 2 Baths
    • 1,584 Sq Ft
    • House for Rent

    314 Sears Ave NE, Winter Haven, FL 33881

    Looking for your dream home? Through our seamless leasing process, this beautifully designed home is move-in ready. Our spacious layout is perfect for comfortable living that you can enjoy with your pets too; we’re proud to be pet friendly. Our homes are built using high-quality, eco-friendly materials with neutral paint colors, updated fixtures, and energy-efficient appliances. Enjoy the

    Hunter Fendley BUNGALO

    314 Sears Ave NE, Winter Haven, FL 33881
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    $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.

    Steve Lockhart LOCKHART & ASSOCIATES INC

    117 Avenue B NE, Winter Haven, FL 33881

About Downtown Winter Haven

Downtown Winter Haven is a vibrant neighborhood known for its eclectic dining, cultural attractions, and lakefront recreation. The area boasts a burgeoning dining scene with notable restaurants like Nutwood, Arabellas, Adler’s, and The Smokin’ Ox, alongside new additions such as Bowen Yard and established eateries like Lucille’s American Café. For nightlife, residents can enjoy Social Cocktail Lounge, Grove Roots Brewing Co., and The Union Taproom. The neighborhood is also a cultural hub, featuring Theatre Winter Haven, the Historic Ritz Theatre, and Gram Parsons Derry Down. Annual events, including Taste of Winter Haven and Craft Beer Crawl, along with the weekly Winter Haven Farmers Market, add to the community's lively atmosphere. The neighborhood is surrounded by several lakes, including Lake Howard, May, Shipp, and Cannon, offering ample opportunities for boating, fishing, and water skiing. Parks like South Lake Howard Nature Park and Martin Luther King Park provide green spaces with walking trails and recreational facilities. Housing options range from traditional ranch-style and midcentury homes to contemporary custom homes in gated communities, with lakefront properties being the most expensive. The area is served by top-rated schools such as Chain of Lakes Collegiate High and Frank E. Brigham Academy. Downtown Winter Haven is safer than the national average and is well-connected via U.S. Highway 17, U.S. Highway 27, and Interstate 4, with Tampa and Orlando approximately 50 miles away. Local amenities include Walmart, Publix, Aldi, and Lowe’s, ensuring convenient access to essentials.

Frequently Asked Questions

What are the most popular neighborhoods for renters near Downtown Winter Haven?
The most popular neighborhoods for renters near Downtown Winter Haven are Southwest Winter Haven, Poinsettia Park, Jan Phyl Village, Inwood and Cypresswood.
What are the most popular zip codes for renters near Downtown Winter Haven?
The most popular zip codes for renters near Downtown Winter Haven are 33837, 33896, 34759, 34746 and 34758.
How to Rent a Home