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

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  • /26

    Starting at $1,499 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
  • /24

    $1,550 Per Month

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

    802 Eagle Pond Dr, Winter Haven, FL 33884

    FULLY FURNISHED and EQUIPPED including linens and dishes.Minimum 7 month lease.Enjoy the serene pond front views from this first floor 2 bedroom 2 bathroom condo located in the Eagle Pond Neighborhood in Gated, Cypresswood Golf and Country Club.MOVE IN WITH YOUR SUITCASE!Amenities include 24 hour manned gate, community pool, brand new pickleball and tennis courts, clubhouse with

    Agent Photo

    Steven Smith, PA

    LOCKHART & ASSOCIATES INC

    802 Eagle Pond Dr, Winter Haven, FL 33884
  • /53

    Starting at $1,330 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
  • /26

    $1,895 Per Month

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

    172 Inman Blvd, Winter Haven, FL 33881

    Move-In Special: Receive ½ month's rent off the first month's rent for leases with a move-in date on or before August 31, 2026.Welcome to your LIKE-NEW 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 local restaurants, golf and shopping that

    Agent Photo

    Cheryl Rozanski

    JC FLORIDA REALTY LLC

    172 Inman Blvd, Winter Haven, FL 33881
  • /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
  • /47

    $1,700 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
  • /39

    Starting at $1,605 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

    $1,200 Per Month

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

    8402 Waterview Way Unit 8402, Winter Haven, FL 33884

    2 bedroom 2 bath ground floor condo located in gated Winterset on the Shores of Lake Winterset.Enjoy a community pool, club house, tennis courts and community boat ramp.Partially furnished or furniture can be removed.

    Agent Photo

    Steven Smith, PA

    LOCKHART & ASSOCIATES INC

    8402 Waterview Way Unit 8402, Winter Haven, FL 33884
  • /54

    Starting at $1,455 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
  • /90

    $2,300 Per Month

    • 4 Beds
    • 2 Baths
    • 1,583 Sq Ft
    • House for Rent

    780 Overlook Grove Dr, Winter Haven, FL 33884

    LOCATION! This 4 bedroom 2 bath home is thoughtfully updated and with low cost energy bills, you will delight in this small community! Located minutes away from LegoLand and Highway 27, you will love the convenience of Publix just steps away! Super kitchen with lots of storage and work space. Stone countertops and stainless steel appliance suite. Impeccably maintained. Solar savings benefit

    Agent Photo

    Cyleste Goodson

    FLORIDA REAL ESTATE COMPANY

    780 Overlook Grove Dr, Winter Haven, FL 33884
  • /36

    Starting at $1,249 Per Month

    • 1 - 2 Beds

    5004 Dream Dr, Winter Haven, FL 33880

    Dream Winter Haven offers comfortable, brand-new one-, two-, and three-bedroom apartment homes in Winter Haven, Florida, thoughtfully designed to provide modern convenience, connection, and a welcoming place to call home. Ideally located in Central Florida, our pet-friendly community provides easy access to shopping, dining, entertainment, outdoor recreation, and LEGOLAND Florida. Residents enjoy

    Dream Winter Haven

    5004 Dream Dr, Winter Haven, FL 33880
  • /30

    $1,300 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
  • /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
  • /32

    $1,900 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,320 Sq Ft
    • House for Rent

    687 Lake Dexter Cir, Winter Haven, FL 33884

    What a view! Enjoy pristine lake views from almost every room of this home located directly on Lake Dexter, one of the cleanest lakes in all of Polk County and home to LEGOLAND Beach Resort. This home is ideal for avid water skiers or pontoon cruisers. Enjoy just about any water related activity right from your yard. Kayaking, paddle boarding, water skiing, sailing and of course fishing.

    Agent Photo

    Steven Smith, PA

    LOCKHART & ASSOCIATES INC

    687 Lake Dexter Cir, Winter Haven, FL 33884
  • /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
  • /29

    $1,650 Per Month

    • 3 Beds
    • 2 Baths
    • 1,218 Sq Ft
    • Condo for Rent

    333 Lake Howard Dr NW Unit 211B, Winter Haven, FL 33880

    Remodeled and updated 2nd floor condo with picturesque views of the pool and lush landscaping. This 3 bedroom unit is ready for immediate occupancy. Recent updates include fresh interior paint, new flooring, new kitchen cabinets and solid surface counters.This established 55 and over community is nestled on the shores of Lake Howard on the famous Chain of Lakes and includes a community boat

    Agent Photo

    Steven Smith, PA

    LOCKHART & ASSOCIATES INC

    333 Lake Howard Dr NW Unit 211B, Winter Haven, FL 33880
  • /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
  • /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
  • /35

    Starting at $1,099 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
  • /15

    $1,450 Per Month

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

    407 Eagle Pond Dr Unit 4F, Winter Haven, FL 33884

    Upstairs 2 bedroom 2 bath corner unit condo located in the Eagle Pond neighborhood at Cypresswood Golf and Country Club. The country club amenities include access to the clubhouse with bar and grill, jr. Olympic swimming pool and pickleball/tennis courts. The championship 18 hole golf course is open to the public.As an added bonus, Publix just opened a brand new location just a mile down

    Agent Photo

    Steven Smith, PA

    LOCKHART & ASSOCIATES INC

    407 Eagle Pond Dr Unit 4F, Winter Haven, FL 33884
  • /56

    Starting at $1,380 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
  • /20

    $1,700 Per Month

    • 2 Beds
    • 1 Bath
    • 1,032 Sq Ft
    • House for Rent

    1313 4th St NE, Winter Haven, FL 33881

    Welcome home to this charming 2-bedroom, 1-bathroom rental located in the desirable Chain of Lakes area of Winter Haven! This beautifully renovated home offers a comfortable and inviting space with plenty of room to make it your own. Featuring a newer roof installed in Fall 2023, the home also includes a versatile bonus room that can be used as a home office, guest space, playroom, or additional

    Agent Photo

    Rafael Narvaez

    EXP REALTY LLC

    1313 4th St NE, Winter Haven, FL 33881
  • /50

    Starting at $1,334 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
  • /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
  • /26

    Starting at $1,265 Per Month

    • 2 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
  • /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
  • /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
  • /37

    $1,850 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,407 Sq Ft
    • Townhouse for Rent

    504 Orange Blossom Dr, Winter Haven, FL 33880

    Welcome to unit 504 – this stunning 2-bedroom 2.5 bath Chain-of-Lakes LAKEFRONT townhome is nestled in a serene community of Waters Edge. Downstairs features; spacious great room with a decorative fireplace, 2 access sliding glass doors leading to the screened-in lanai, with convenient storage closet. A wrap-around kitchen with ample counter space and all stainless-steel appliances. Off the

    Agent Photo

    CarLee Marchetti

    STAR REALTY OF WINTER HAVEN

    504 Orange Blossom Dr, Winter Haven, FL 33880
  • /14

    Starting at $1,225 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
  • /26

    $2,175 Per Month

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

    6220 Botticella Blvd, Winter Haven, FL 33884

    Brand-new two-story home located in the sought-after Villamar community of Winter Haven. This residence offers 4 bedrooms, 2.5 bathrooms, a spacious loft, and a 2-car garage with approximately 1,880 square feet of living space.The open-concept floor plan seamlessly connects the living, dining, and kitchen areas, creating a functional layout for everyday living and entertaining. The kitchen

    Agent Photo

    Maritza Monzon

    INTERNATIONAL EXECUTIVE REALTY

    6220 Botticella Blvd, Winter Haven, FL 33884
  • /35

    $2,400 Per Month

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

    330 Royal Palm Way, Winter Haven, FL 33881

    Built in 2022, this 4-bedroom, 2-bath home features wood-look tile throughout, a modern kitchen with quartz countertops and stainless steel appliances, 100% LED lighting, LED-lit tray ceilings, ceiling fans in every room, 2" blinds, energy-efficient doors and windows, a covered porch, and a 2-car garage. A separate office sits off its own hallway and can serve as a fourth bedroom. All appliances

    330 Royal Palm Way, Winter Haven, FL 33881
  • /21

    $1,400 Per Month

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

    5638 Struthers Ct, Winter Haven, FL 33884

    Beautifully renovated 1/2 Duplex for rent in SE Winter Haven. 2BR/1BA with Screened Porch (14x10). Ceramic Tile Flooring throughout with New Luxury Vinyl Flooring in the bedrooms. New kitchen with slow close wood cabinets, granite countertops and stainless appliances. Inside washer/dryer hookup. Lawn Service included with rent. Sorry, NO PETS!

    Agent Photo

    Amy Reynolds

    LOCKHART & ASSOCIATES INC

    5638 Struthers Ct, 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

    Built in 2022, this 4-bedroom, 2-bath home features wood-look tile throughout, a modern kitchen with quartz countertops and stainless steel appliances, 100% LED lighting, LED-lit tray ceilings, ceiling fans in every room, 2" blinds, energy-efficient doors and windows, a covered porch, and a 2-car garage. A separate office sits off its own hallway and can serve as a fourth bedroom. All appliances

    326 Royal Palm Way, 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

    Built in 2022, this 4-bedroom, 2-bath home features wood-look tile throughout, a modern kitchen with quartz countertops and stainless steel appliances, 100% LED lighting, LED-lit tray ceilings, ceiling fans in every room, 2" blinds, energy-efficient doors and windows, a covered porch, and a 2-car garage. A separate office sits off its own hallway and can serve as a fourth bedroom. All appliances

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

    Starting at $1,258 Per Month

    • 1 - 3 Beds

    2850 W Lake Hamilton Dr, Winter Haven, FL 33881

    Brand-New Apartment Homes, Newly Repriced.1 Bed - As low as $11992 Bed - As low as $14993 Bed - As low as $1650PLUS 1 month FREE on 19-24 month lease terms. Schedule your tour TODAY!

    Magnolia at Lake Hamilton

    2850 W Lake Hamilton Dr, Winter Haven, FL 33881
  • /16

    Starting at $1,100 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

Showing Results 1 - 40, Page 1 of 10

Rental Home Trends

Number of Homes for Rent
367
Median Rent
$1,775
Median Single Family Home Rent
$1,893
Median Townhouse Rent
$1,350
Median Condo Rent
$1,385
How to Rent a Home