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

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  • /26

    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

    1015 Lake Forest Blvd, Winter Haven, FL 33884
  • /26

    $2,099 Per Month

    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft
    • House for Rent

    172 Inman Blvd, Winter Haven, FL 33881

    Welcome to your LIKE-NEW dream home in the master planned community of INMAN GROVES! This stunning 3-Bedroom, 2-Bath,2 car garage open floorplan, is situated just a short drive from world class theme parks and attractions. Enjoy localrestaurants, golf and shopping that are just a short drive away. Love the outdoors? Slow down the pace and explorenearby parks, farmer's markets and much

    Agent Photo

    Cheryl Rozanski

    JC FLORIDA REALTY LLC

    172 Inman Blvd, Winter Haven, FL 33881
  • /101

    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

    265 Ave E SW, Winter Haven, FL 33880
  • /42

    $2,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,690 Sq Ft
    • House for Rent

    624 Honey Bell Rd, Winter Haven, FL 33880

    Welcome to 624 Honey Bell Road in the desirable Squires Grove community of Winter Haven! Built in 2022, this move-in ready 3-bedroom, 2-bath home offers the perfect blend of modern design, open living spaces, and everyday comfort. Step inside to discover a bright and inviting open-concept floor plan featuring tile flooring in the main living areas, abundant natural light, and a spacious living

    Agent Photo

    David Hartigan

    JASON MITCHELL REAL ESTATE FLO

    624 Honey Bell Rd, Winter Haven, FL 33880
  • /22

    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

    3110 Gowan Dr, Winter Haven, FL 33884
  • /30

    $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

    Agent Photo

    CarLee Marchetti

    STAR REALTY OF WINTER HAVEN

    5667 Struthers Ct, Winter Haven, FL 33884
  • /39

    Starting at $1,295 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

    200 Avenue C SW, Winter Haven, FL 33880
  • /15

    $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

    Agent Photo

    Steve Lockhart

    LOCKHART & ASSOCIATES INC

    711 Lake Jessie Dr, Winter Haven, FL 33881
  • /54

    Starting at $1,397 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

    1015 Mahaffey Rd, Winter Haven, FL 33884
  • /36

    $2,100 Per Month

    • 4 Beds
    • 3 Baths
    • 1,883 Sq Ft
    • House for Rent

    2726 Rochelle Dr, Winter Haven, FL 33881

    Soak in stunning sunsets and views on Lake Rochelle from the spacious great room, primary suite, and backyard. With access to the lake directly behind the home, you'll appreciate the peaceful setting, abundant wildlife, and added privacy with no rear neighbors. Whether you enjoy fishing, kayaking, paddleboarding, water skiing, personal watercraft, or simply relaxing by the water, this property

    Agent Photo

    CarLee Marchetti

    STAR REALTY OF WINTER HAVEN

    2726 Rochelle Dr, Winter Haven, FL 33881
  • /36

    Starting at $1,259 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

    5004 Dream Dr, Winter Haven, FL 33880
  • /44

    $1,400 Per Month

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

    8302 Waterview Way, Winter Haven, FL 33884

    Cute and clean downstairs end unit in Winterset, a gated community. Features wood laminate flooring in living area and bedrooms and ceramic tile in the wet areas. Open floor plan, kitchen with breakfast bar overlooking living room with mirror wall and dining area. Master bedroom has sliding glass doors to a private 6x7 screened in patio. Master suite includes walk-in closet, stackable washer &

    Agent Photo

    CarLee Marchetti

    STAR REALTY OF WINTER HAVEN

    8302 Waterview Way, Winter Haven, FL 33884
  • /47

    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

    1150 3rd St SW, Winter Haven, FL 33880
  • /56

    $2,400 Per Month

    • 4 Beds
    • 2.5 Baths
    • 1,942 Sq Ft
    • House for Rent

    1504 Hummingbird Rd, Winter Haven, FL 33884

    Welcome to your slice of Florida paradise! This almost-new, fully furnished 4-bedroom, 2.5-bath home sits beautifully on a spacious corner lot with a lush yard—perfect for relaxing or entertaining. Designed with modern finishes throughout, every room feels fresh and inviting. The home boasts a large 2-car garage equipped with a Tesla charger, making it ideal for eco-conscious residents. Enjoy the

    Agent Photo

    Matthew Stanley

    The Keyes Company

    1504 Hummingbird Rd, Winter Haven, FL 33884
  • /77

    Starting at $1,350 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

    2850 W Lake Hamilton Dr, Winter Haven, FL 33881
  • /48

    $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

    Agent Photo

    CarLee Marchetti

    STAR REALTY OF WINTER HAVEN

    715 Magnolia Place Unit 715, Winter Haven, FL 33884
  • /65

    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

    7676 Carlton Arms Blvd, Winter Haven, FL 33884
  • /38

    $1,300 Per Month

    • 2 Beds
    • 2 Baths
    • 1,148 Sq Ft
    • Condo for Rent

    1550 11th St NE Unit D7, Winter Haven, FL 33881

    Welcome home to this inviting upstairs condo located in the peaceful Lake Buckeye Condo community, where tranquil lake views and relaxed living come together. Step inside to find laminate and ceramic tile flooring throughout, offering both durability and easy maintenance. The open living and dining area is light and welcoming, seamlessly extending to a private 3x7 balcony, the perfect place to

    Agent Photo

    CarLee Marchetti

    STAR REALTY OF WINTER HAVEN

    1550 11th St NE Unit D7, Winter Haven, FL 33881
  • /35

    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

    350 24th St NW, Winter Haven, FL 33880
  • /6

    $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.

    Agent Photo

    Isabel Melin Mora

    MELIN REALTY LLC

    1453 Austin St Unit B, Winter Haven, FL 33884
  • /127

    Starting at $1,310 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

    3005 Willow Glen Cir, Lake Wales, FL 33859
  • /11

    $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

    Agent Photo

    Daniel Hut

    HUT REALTY, LLC

    1756 2nd St NE, Winter Haven, FL 33881
  • /15

    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

    200 Avenue K SE, Winter Haven, FL 33880
  • /15

    $2,350 Per Month

    • 5 Beds
    • 2.5 Baths
    • 2,280 Sq Ft
    • House for Rent

    6204 Botticella Blvd, Winter Haven, FL 33884

    Brand-New Corner Lakeview Home for Rent in Winter HavenBe the first to live in this stunning two-story home located in one of Winter Haven’s fastest-growing communities.This spacious residence offers 5 bedrooms, 2.5 bathrooms, an upstairs loft ideal for a media room, office, or flex space, a 2-car garage, and 2,112 square feet of living space on a 6,334 square foot corner lot.The home

    Agent Photo

    Yamile Albornoz

    EXP REALTY LLC

    6204 Botticella Blvd, Winter Haven, FL 33884
  • /12

    Starting at $1,165 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

    1101 Cambridge Square, Winter Haven, FL 33880
  • /50

    Starting at $1,301 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

    4025 Lake Ned Village Cir, Winter Haven, FL 33884
  • /26

    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

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

    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

    1300 Lake Howard Dr SW, Winter Haven, FL 33880
  • /14

    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

    4900 Cypress Gardens Rd, Winter Haven, FL 33884
  • /14

    Starting at $1,000 Per Month

    • Studio - 2 Beds

    130 Avenue C SE, Winter Haven, FL 33880

    Central Haven Apartments

    130 Avenue C SE, Winter Haven, FL 33880
  • /31

    $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.

    3960 Avenue U NW, Winter Haven, FL 33881
  • /35

    $2,425 Per Month

    • 4 Beds
    • 2 Baths
    • 1,791 Sq Ft
    • House for Rent

    326 Royal Palm Way, Winter Haven, FL 33881

    **THIS ADDRESS WAS FORMALLY KNOWN AS 326 OXFORD DRIVE. STREET NAME WAS CHANGED TO ROYAL PALM WAY. THE NEW ADDRESS WILL NOT PULL UP ON THE MAP** Private community, energy efficient homes, LOADED with the best finishes. With three different elevations to choose from, you will notice a completely different look and feel. If you have pets, not only do we allow them. Home available that

    326 Royal Palm Way, Winter Haven, FL 33881
  • /16

    $1,995 Per Month

    • 4 Beds
    • 2 Baths
    • 2,138 Sq Ft
    • House for Rent

    608 Terranova Dr, Winter Haven, FL 33884

    Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2139.90. That covers your base rent, $1995.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    608 Terranova Dr, Winter Haven, FL 33884
  • /35

    $2,375 Per Month

    • 4 Beds
    • 2 Baths
    • 1,790 Sq Ft
    • House for Rent

    217 Newcastle Ct, Winter Haven, FL 33881

    Be one of the first to move into these recently built, energy-efficient homes, LOADED with the best finishes. If you have pets, not only do we allow them, but we have homes available that include a fenced-in yard! Landscape is included! All appliances are included! The interior finishes include wood look tile throughout, modern kitchens with quartz appliances and stainless steel appliances, 100%

    217 Newcastle Ct, Winter Haven, FL 33881
  • /23

    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

    4225 Vista Del Lago Dr, Winter Haven, FL 33881
  • /11

    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

    101 Parker Ln NE, Winter Haven, FL 33881
  • /35

    $2,400 Per Month

    • 4 Beds
    • 2 Baths
    • 1,791 Sq Ft
    • House for Rent

    317 Royal Palm Way, Winter Haven, FL 33881

    **THIS ADDRESS WAS FORMALLY KNOWN AS 317 OXFORD DRIVE. STREET NAME WAS CHANGED TO ROYAL PALM WAY. THE NEW ADDRESS WILL NOT PULL UP ON THE MAP**Private community, energy efficient homes, LOADED with the best finishes. With three different elevations to choose from, you will notice a completely different look and feel. If you have pets, not only do we allow them. Home available that

    317 Royal Palm Way, Winter Haven, FL 33881
  • /35

    $2,400 Per Month

    • 4 Beds
    • 2 Baths
    • 1,791 Sq Ft
    • House for Rent

    330 Royal Palm Way, Winter Haven, FL 33881

    **THIS ADDRESS WAS FORMALLY KNOWN AS 326 OXFORD DRIVE. STREET NAME WAS CHANGED TO ROYAL PALM WAY. THE NEW ADDRESS WILL NOT PULL UP ON THE MAP**Private community, energy efficient homes, LOADED with the best finishes. With three different elevations to choose from, you will notice a completely different look and feel. If you have pets, not only do we allow them. Home available that

    330 Royal Palm Way, Winter Haven, FL 33881
  • /18

    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

    102 Landings Way, Winter Haven, FL 33880
  • /20

    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

    745 Avenue A SW, Winter Haven, FL 33880

Showing Results 1 - 40, Page 1 of 8

Rental Home Trends

Number of Homes for Rent
306
Median Rent
$1,800
Median Single Family Home Rent
$1,895
Median Townhouse Rent
$1,350
Median Condo Rent
$1,350
How to Rent a Home