322

Winter Haven, FL Homes for Rent under $1,500

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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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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 $1,225 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
  • /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
  • /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

    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
  • /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
  • /9

    Starting at $975 Per Month

    • 1 Bed

    101-123 Oak Crest Dr NW, Winter Haven, FL 33881

    Ideally located with convenient access to US Hwy 17-92, I-4, and the greater Winter Haven and Central Florida area, this community offers both accessibility and comfort.Our cozy one-bedroom apartments feature energy-efficient central A/C, tile flooring, washer/dryer hookups, and newly updated appliances designed for everyday convenience.Residents enjoy scenic surroundings,

    Oakcrest Apartments

    101-123 Oak Crest Dr NW, Winter Haven, FL 33881
  • /13

    $1,195 Per Month

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

    669 Avenue B NW Unit 10, Winter Haven, FL 33881

    Get $1000 Off First Full Month’s Rent! Don't miss this opportunity to save big on your new home—limited-time offer. *Disclaimer: These visuals are just artistic representations for marketing. The final build, finishes, and layout may vary. This welcoming apartment offers modern conveniences in a comfortable setting. Enjoy the ease of off-street parking and essential

    669 Avenue B NW Unit 10, Winter Haven, FL 33881
  • /17

    $995 Per Month

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

    3058 St Paul Dr, Jan Phyl Village, FL 33880

    Apply now for free! Don’t miss out on this incredible deal—reach out today to learn more and schedule a tour!Enjoy a comfortable living space with 2 bedrooms and 1 bathroom. Perfect for those seeking convenience and style.- Includes appliances: Refrigerator and Electric Range- Cooling and heating: Central, Heat Pump- Off-street parking available- Flooring: Tile and

    3058 St Paul Dr, Jan Phyl Village, FL 33880
  • /13

    $1,195 Per Month

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

    669 Avenue B NW Unit 9, Winter Haven, FL 33881

    Get $1000 Off First Full Month’s Rent! Don't miss this opportunity to save big on your new home—limited-time offer. Discover this attractive apartment with open living spaces. Featuring a modern kitchen and off-street parking, this unit is perfect for comfortable living.- Electric Range and Refrigerator included- Efficient Forced Air heating- Durable Linoleum flooring-

    669 Avenue B NW Unit 9, Winter Haven, FL 33881
  • /17

    $1,395 Per Month

    • 2 Beds
    • 2 Baths
    • 1,199 Sq Ft
    • House for Rent

    1984 Ave F SW, Winter Haven, FL 33880

    All Bridge Homes listings are pet-friendly and offer easy self-tours schedule yours today! This home comes with high-speed internet at an exclusive group rate. This service includes 24/7 premium support and setup to help you get connected at move-in. This charming two-bedroom, two-bath home offers a delightful blend of comfort, style, and convenience, making it an ideal choice for

    1984 Ave F SW, Winter Haven, FL 33880
  • /16

    $1,199 Per Month

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

    1007 37th St NW Unit 1, Winter Haven, FL 33881

    Property Id: 1919782 This beautifully renovated unit is located in close proximity to Winter Haven Downtown as well as major highways. Unit features new kitchen cabinets with granite countertops and all new stainless steel appliances, with washer and dryer available. More photos coming soon. It’s equipped with new AC - will be able to save on electricity, new tile flooring

    1007 37th St NW Unit 1, Winter Haven, FL 33881
  • /13

    $1,195 Per Month

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

    669 Avenue B NW Unit 10, Winter Haven, FL 33881

    Get $1000 Off First Full Month’s Rent! Don't miss this opportunity to save big on your new home—limited-time offer. *Disclaimer: These visuals are just artistic representations for marketing. The final build, finishes, and layout may vary. This welcoming apartment offers modern conveniences in a comfortable setting. Enjoy the ease of off-street parking and essential

    669 Avenue B NW Unit 10, Winter Haven, FL 33881
  • /16

    $1,199 Per Month

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

    1007 37th St NW Unit 1, Winter Haven, FL 33881

    Property Id: 1919782 This beautifully renovated unit is located in close proximity to Winter Haven Downtown as well as major highways. Unit features new kitchen cabinets with granite countertops and all new stainless steel appliances, with washer and dryer available. More photos coming soon. It’s equipped with new AC - will be able to save on electricity, new tile flooring

    1007 37th St NW Unit 1, Winter Haven, FL 33881
  • /6

    $1,200 Per Month

    • 1 Bed
    • 1 Bath
    • House for Rent

    4320 Dundee Rd, Winter Haven, FL 33884

    Property Id: 2768547 This 1/1 is a brand new park model - manufactured up to 2025 building codes for environmental resistance - comes complete with all new appliances. Located in an up-and-coming part of Winter Haven, right across the street from a newly built Publix and a ton of new business development, within 5 miles of Legoland! Water and sewage is included, alongside the usual

    4320 Dundee Rd, Winter Haven, FL 33884
  • /12

    $1,300

    Total Monthly Price

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

    357 Winter Ridge Blvd Unit 357, Winter Haven, FL 33881

    Available NowLakefront Condo on Lake Smart. The community of Winter Ridge Condos offer a community swimming pool, club house, and private boat dock. This Lakefront inviting condo features 2 large bedrooms and 2 bathrooms and covered car-port. An open layout living/dinning combo and abundant natural light. No Smoking. $1300 rent per month plus one month security deposit and utilities

    357 Winter Ridge Blvd Unit 357, Winter Haven, FL 33881
  • /12

    $1,300

    Total Monthly Price

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

    357 Winter Ridge Blvd Unit 357, Winter Haven, FL 33881

    Available NowLakefront Condo on Lake Smart. The community of Winter Ridge Condos offer a community swimming pool, club house, and private boat dock. This Lakefront inviting condo features 2 large bedrooms and 2 bathrooms and covered car-port. An open layout living/dinning combo and abundant natural light. No Smoking. $1300 rent per month plus one month security deposit and utilities

    357 Winter Ridge Blvd Unit 357, Winter Haven, FL 33881
  • /2

    $1,400

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • House for Rent

    1308 3rd St NE, Winter Haven, FL 33881

    Beautiful and spacious 2/1 for rent. Located at 1308 3rd st ne, Winter Haven, FL 33881.Freshly painted, newer kitchen cabinets, large backyard space.House is located across from an older community residence on a very quiet street.Requirements:-Show proof of income-First month and deposit to move in

    1308 3rd St NE, Winter Haven, FL 33881
  • /20

    $850

    Total Monthly Price

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

    1131 5th St SW Unit 4 downstairs, Winter Haven, FL 33880

    Centrally located to restaurants, Aldis, Lowe's and other shopping within walking distance. Small quiet apartments - property has security lights for safety.

    1131 5th St SW Unit 4 downstairs, Winter Haven, FL 33880
  • /20

    $850

    Total Monthly Price

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

    1131 5th St SW Unit 4 downstairs, Winter Haven, FL 33880

    Centrally located to restaurants, Aldis, Lowe's and other shopping within walking distance. Small quiet apartments - property has security lights for safety.

    1131 5th St SW Unit 4 downstairs, Winter Haven, FL 33880

Showing Results 1 - 40, Page 1 of 3

Rental Home Trends

Number of Homes for Rent
117
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