226

Winter Haven, FL Homes for Rent under $2,400

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  • /2

    $1,950 per month

    • 3 Beds
    • 2 Baths
    • 1,672 Sq Ft
    • House for Rent

    175 Grove Branch Rd, Winter Haven, FL 33880

    Property Id: 2402477Welcome Home This gorgeous modern 3 bed 2 bath and 2 car garage is located in beautiful Winter Haven. This is very open and spacious split floor plan. Perfect for entertaining. Kitchen is tastefully designed with espresso brown 42" cabinets and features an island overlooking the family room. Large pantry closet. Master bedroom suite offers a large walk-in closet and an

    175 Grove Branch Rd, Winter Haven, FL 33880
  • /26

    $2,390 per month

    • 6 Beds
    • 3 Baths
    • 2,463 Sq Ft
    • House for Rent

    2142 Chris Dr, Winter Haven, FL 33884

    Brand new, never-lived-in house for rent in Winter Haven! Beautiful two-story, brand new, never-lived-in house featuring 6 bedrooms and 3 full bathrooms, ideal for families seeking comfort, space, and modern living. The home offers a modern open-concept layout with spacious, bright interiors. At the entrance, a welcoming porch with a garden adds charm and curb appeal. The main living area

    Jessyka Dos Santos WRA BUSINESS & REAL ESTATE

    2142 Chris Dr, Winter Haven, FL 33884
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    $1,449 per month

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

    3215 Timberline Rd, Winter Haven, FL 33880

    This home is professionally managed by Tricon, dedicated to creating exceptional rental experiences. Featuring 2 bedrooms, 1.0 bathrooms, and approximately 904 square feet, this well-maintained home offers a high standard of rental living, supported by a team that puts residents first. As a Tricon resident, you'll enjoy access to Tricon Vantage — a program designed to support your rental journey.

    3215 Timberline Rd, Winter Haven, FL 33880
  • /11

    $1,100 per month

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

    102 Oak Crest Dr NW Unit 106, Winter Haven, FL 33881

    HALF OFF FIRST MONTHS RENT! Recently updated apartment available for lease! This bright and comfortable unit features updated cabinets, crown molding, ceiling fans, and modern light fixtures throughout, making it both stylish and easy to maintain. Enjoy private off-street parking. Located on a quiet street with no thru traffic and just minutes from shopping, dining, parks, and everyday

    David Small KELLER WILLIAMS REALTY SMART 1

    102 Oak Crest Dr NW Unit 106, Winter Haven, FL 33881
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    $1,815 per month

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

    669 Lake Dexter Cir, Winter Haven, FL 33884

    Beautiful, pet-friendly home coming soon! Apply now, Move-In is available on or after the listed date. Upon approval, $500 reservation deposit to reserve (applied to security deposit and/or refundable). Application fee: $50 per adult. Security Deposit: one month?s rent. Pet fees: $250 + $40/mo per pet. Some homes may include pool ($150/mo), septic ($15/mo), and/or HOA fees; other fees may apply.

    669 Lake Dexter Cir, Winter Haven, FL 33884
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    $1,100 per month

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

    118 Oak Crest Dr NW, Winter Haven, FL 33881

    HALF OFF FIRST MONTHS RENT! Recently updated apartment available for lease! This bright and comfortable unit features updated cabinets, crown molding, ceiling fans, and modern light fixtures throughout, making it both stylish and easy to maintain. Enjoy private off-street parking. Located on a quiet street with no thru traffic and just minutes from shopping, dining, parks, and everyday

    David Small KELLER WILLIAMS REALTY SMART 1

    118 Oak Crest Dr NW, Winter Haven, FL 33881
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    $1,849 per month

    • 3 Beds
    • 2 Baths
    • 1,442 Sq Ft
    • House for Rent

    509 Kensington View Dr, Winter Haven, FL 33880

    Sign in by April 17, Get 4 Weeks Free! Discover spacious homes for rent at Kensington View in Winter Haven, FL. Pet-friendly living with access to Lakeland and Tampa Bay. Professionally managed by ARK Homes.

    509 Kensington View Dr, Winter Haven, FL 33880
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    $2,030 per month

    • 4 Beds
    • 2 Baths
    • 1,824 Sq Ft
    • House for Rent

    2122 Chris Dr, Winter Haven, FL 33884

    Beautiful brand-new 4-bedroom, 2-bathroom home located in a great area of Winter Haven. The property features a charming front porch, perfect for relaxing. Inside, the home offers a spacious open-concept living room seamlessly connected to the dining area and kitchen, creating a modern and functional layout. Sliding glass doors provide access to a large outdoor area, ideal for entertaining and

    Jessyka Dos Santos WRA BUSINESS & REAL ESTATE

    2122 Chris Dr, Winter Haven, FL 33884
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    $1,800 per month

    • 3 Beds
    • 2 Baths
    • 1,177 Sq Ft
    • House for Rent

    2006 34th St NW, Winter Haven, FL 33881

    Property Id: 2400855This beautifully maintained 3-bedroom, 2-bath home is now available for rent! Originally listed for sale, this property offers exceptional space, accessibility, and flexibility for a variety of living needs.Designed with wheelchair accessibility in mind, the home features wide entryways and a fully accessible bathroom while still maintaining a stylish,

    2006 34th St NW, Winter Haven, FL 33881
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    $2,220 per month

    • 5 Beds
    • 2.5 Baths
    • 2,112 Sq Ft
    • House for Rent

    2134 Chris Dr, Winter Haven, FL 33884

    Brand New Two-Story Home for Rent in Winter Haven Welcome to this stunning brand new two-story home located in the heart of Winter Haven, offering the perfect combination of space, style, and convenience. Designed with modern living in mind, this beautiful property is ideal for families or anyone looking for comfort and quality in a prime location. The home features 5 spacious bedrooms, including

    Jessyka Dos Santos WRA BUSINESS & REAL ESTATE

    2134 Chris Dr, Winter Haven, FL 33884
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    $1,949 per month

    • 4 Beds
    • 2 Baths
    • 1,300 Sq Ft
    • House for Rent

    1532 Wallace Manor Ave, Winter Haven, FL 33880

    Coming soon - this home is currently being enjoyed by another resident but will be available soon. Pre-lease this home now with Tricon Pre-Lease Guarantee. This home is professionally managed by Tricon, dedicated to creating exceptional rental experiences. Featuring 4 bedrooms, 2.0 bathrooms, and approximately 1,300 square feet, this well-maintained home offers a high standard of rental living,

    1532 Wallace Manor Ave, Winter Haven, FL 33880
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    $1,395 per month

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

    140 Avenue W NW Unit 2, Winter Haven, FL 33881

    One or more photo(s) has been virtually staged. HALF OFF FIRST MONTHS RENT! Spacious rental located in the heart of Winter Haven! This updated unit offers comfortable living with generous room sizes and a functional layout. Conveniently located near shopping, dining, schools, and major roadways, making daily commutes a breeze. Public water and sewer, city utilities, and easy access to everything

    David Small KELLER WILLIAMS REALTY SMART 1

    140 Avenue W NW Unit 2, Winter Haven, FL 33881
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    $1,790 per month

    • 4 Beds
    • 2 Baths
    • 1,874 Sq Ft
    • House for Rent

    637 Sunway Ln, Winter Haven, FL 33880

    We are currently making final preparations for this home to be available. We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be

    637 Sunway Ln, Winter Haven, FL 33880
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    $2,250 per month

    • 5 Beds
    • 2.5 Baths
    • 2,254 Sq Ft
    • House for Rent

    Unlisted Address

    Located in the Peace Creek Reserve community, this well-maintained home offers modern living with serene pond views. The two-story residence features 5 bedrooms, 2 full bathrooms, and 1 half bath, providing ample space for families or those needing extra room for work or guests. The open-concept main floor includes a spacious living area that flows seamlessly into the dining space and

    Don Tilack EXP REALTY LLC

    Unlisted Address
  • /19

    $1,930 per month

    • 3 Beds
    • 2 Baths
    • 1,424 Sq Ft
    • House for Rent

    344 Sand Pine Trail, Winter Haven, FL 33880

    Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at This home is priced to rent

    344 Sand Pine Trail, Winter Haven, FL 33880
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    $2,150 per month

    • 4 Beds
    • 3 Baths
    • 2,093 Sq Ft
    • House for Rent

    1192 Normandy Heights Cir, Winter Haven, FL 33880

    Welcome to this beautifully renovated 4-bedroom, 3-bath single-family home located at 1192 Normandy Heights Cir, Winter Haven, FL 33880, just minutes from Lake Shipp. This spacious residence features fresh interior paint, brand-new tile flooring, and thoughtful updates throughout. The open kitchen flows seamlessly into a formal dining area, making it ideal for entertaining. Enjoy ample space with

    Carissa Lawhun FLORIDA REALTY INVESTMENTS

    1192 Normandy Heights Cir, Winter Haven, FL 33880
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    $2,270 per month

    • 4 Beds
    • 2 Baths
    • 1,938 Sq Ft
    • House for Rent

    159 Southern Breeze Lp, Winter Haven, FL 33880

    We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home

    159 Southern Breeze Lp, Winter Haven, FL 33880
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    $2,290 per month

    • 5 Beds
    • 2.5 Baths
    • 2,326 Sq Ft
    • House for Rent

    1547 Jessica Blvd, Winter Haven, FL 33884

    Stunning New Construction Home for Rent in Winter HavenBe the first to live in this beautiful new construction home located in a desirable Winter Haven neighborhood. Designed with comfort and style in mind, this spacious residence offers a modern open floorplan that is perfect for both everyday living and entertaining.The home features 5 generously sized bedrooms, including a luxurious

    Jessyka Dos Santos WRA BUSINESS & REAL ESTATE

    1547 Jessica Blvd, Winter Haven, FL 33884
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    $2,010 per month

    • 3 Beds
    • 2 Baths
    • 1,723 Sq Ft
    • House for Rent

    104 Lake Daisy Terrace, Winter Haven, FL 33884

    Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at Coming soon! This home is

    104 Lake Daisy Terrace, Winter Haven, FL 33884
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    $1,395 per month

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

    140 Avenue W NW Unit 3, Winter Haven, FL 33881

    One or more photo(s) has been virtually staged. HALF OFF FIRST MONTHS RENT! Spacious rental located in the heart of Winter Haven! This updated unit offers comfortable living with generous room sizes and a functional layout. Conveniently located near shopping, dining, schools, and major roadways, making daily commutes a breeze. Public water and sewer, city utilities, and easy access to everything

    David Small KELLER WILLIAMS REALTY SMART 1

    140 Avenue W NW Unit 3, Winter Haven, FL 33881
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    $1,770 per month

    • 3 Beds
    • 2 Baths
    • 1,632 Sq Ft
    • House for Rent

    1405 N Lake Shipp Dr SW, 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,

    1405 N Lake Shipp Dr SW, Winter Haven, FL 33880
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    $2,300 per month

    • 4 Beds
    • 2 Baths
    • 1,696 Sq Ft
    • House for Rent

    263 Sunfish Dr, Winter Haven, FL 33881

    Now available for rent in the Lake Lucerne community—this well-maintained 4-bedroom, 2-bathroom home features a spacious and open floor plan.Newly fenced yard. The kitchen is equipped with granite countertops, stainless steel appliances, and a center island that overlooks the living and dining areas. The primary suite offers a walk-in closet and private bath. Tile flooring is featured in the main

    Leslie Soto HONEST EXPERTS REAL ESTATE LLC

    263 Sunfish Dr, Winter Haven, FL 33881
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    $2,400 per month

    • 3 Beds
    • 2 Baths
    • 1,433 Sq Ft
    • House for Rent

    733 Oleander Dr SE, Winter Haven, FL 33880

    Property Id: 2417966Welcome to your own Florida poolside retreat at 733 Oleander Ave in Winter Haven. This beautifully renovated 3-bedroom, 2-bath home is completely turn-key and move-in ready, featuring bright living spaces, modern updates, and a private backyard pool perfect for relaxing or entertaining. Even better, pool and lawn maintenance are included, so you can enjoy the sunshine

    733 Oleander Dr SE, Winter Haven, FL 33880
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    $1,600 per month

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

    1704 Eagle Pond Dr Unit 1704, Winter Haven, FL 33884

    GROUND FLOOR Eagle Pond condominium in the highly desirable gated community of Cypresswood Golf and Country Club. This professionally-managed condominium has just been partially renovated to include luxury vinyl flooring and fresh paint throughout. Key features are interior laundry, walk-in closets, open concept living space, and so much more. The spacious master bedroom features an en suite

    Kayly Malinas JOHN WOOD REALTY, INC.

    1704 Eagle Pond Dr Unit 1704, Winter Haven, FL 33884
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    $1,665 per month

    • 3 Beds
    • 1.5 Baths
    • 1,750 Sq Ft
    • House for Rent

    1333 Stately Oaks Dr NW, Winter Haven, FL 33881

    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 $1799.95. That covers your base rent, $1665.00 + our required services designed to make your life easier: Internet & Media ($85), Smart Home with

    1333 Stately Oaks Dr NW, Winter Haven, FL 33881
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    $1,850 per month

    • 3 Beds
    • 2 Baths
    • 1,536 Sq Ft
    • Townhouse for Rent

    2727 Rutledge Ct, Winter Haven, FL 33884

    For Rent – 2727 Rutledge Court | $1,950/monthMove-in ready and available now! This end-unit townhome offers 2 bedrooms, 2 bathrooms, plus a flexible office/bonus room that can easily serve as a third bedroom, with 1,536 square feet of bright, low-maintenance Florida living.At $1,950 per month, rent includes internet, cable, lawn care, community pool access, a fishing dock, and a beautiful

    Veronica Bard LA ROSA REALTY PRESTIGE

    2727 Rutledge Ct, Winter Haven, FL 33884
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    $2,040 per month

    • 4 Beds
    • 2.5 Baths
    • 2,203 Sq Ft
    • House for Rent

    2069 Whispering Trails Blvd, Winter Haven, FL 33884

    Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at Coming soon! This home is

    2069 Whispering Trails Blvd, Winter Haven, FL 33884
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    $1,600 per month

    • 1 Bed
    • 1 Bath
    • 600 Sq Ft
    • Townhouse for Rent

    222 7th St NW Unit 2, Winter Haven, FL 33881

    Charming Furnished Cottages for Rent in the Heart of Winter HavenWelcome to Rose Hill Cottages, a thoughtfully restored collection of furnished cottages nestled in a quiet, established neighborhood just minutes from downtown Winter Haven. These cottages offer the perfect blend of charm, comfort, and convenience — ideal for professionals, relocations, extended stays, or anyone seeking a

    Veronica Bard LA ROSA REALTY PRESTIGE

    222 7th St NW Unit 2, Winter Haven, FL 33881
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    $1,925 per month

    • 4 Beds
    • 2 Baths
    • 1,458 Sq Ft
    • House for Rent

    822 Terranova Rd, Winter Haven, FL 33884

    Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at Coming soon! This home is

    822 Terranova Rd, Winter Haven, FL 33884
  • /12

    $2,000 per month

    • 3 Beds
    • 2 Baths
    • 1,390 Sq Ft
    • House for Rent

    137 Woodland Dr, Winter Haven, FL 33881

    Like-new 3 bedroom, 2 bathroom home with only one previous tenant. No carpet throughout—easy-care flooring in every room. Open and functional layout with modern finishes, well-maintained and move-in ready.

    Mindy Hunley TRIBUTE REALTY LLC

    137 Woodland Dr, Winter Haven, FL 33881
  • /18

    $1,845 per month

    • 3 Beds
    • 2 Baths
    • 1,428 Sq Ft
    • House for Rent

    5711 Lakeside Landings Blvd, Winter Haven, FL 33881

    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 $1989.90. That covers your base rent, $1845.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    5711 Lakeside Landings Blvd, Winter Haven, FL 33881
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    $2,150 per month

    • 3 Beds
    • 2 Baths
    • 1,709 Sq Ft
    • House for Rent

    3904 Osprey Pointe Cir, Winter Haven, FL 33884

    Modern design with comfort in mind! Available for Lease April 1, 2026! Spacious 3-Bedroom, 2-Bath Home in a Charming Winter Haven Neighborhood Welcome to this beautifully maintained 3-bedroom, 2-bath home offering over 1,700 square feet of living space in a quaint and friendly community. Conveniently located near downtown Winter Haven, with easy access to theme parks, shopping, and dining, this

    Oswald Carrerou CARREROU ENTERPRISES, LLC

    3904 Osprey Pointe Cir, Winter Haven, FL 33884
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    $2,080 per month

    • 3 Beds
    • 2 Baths
    • 1,871 Sq Ft
    • House for Rent

    819 Reflections Loop E, 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 $2224.90. That covers your base rent, $2080.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    819 Reflections Loop E, Winter Haven, FL 33884
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    $1,400 per month

    • 1 Bed
    • 1 Bath
    • 1,078 Sq Ft
    • Apartment for Rent

    150 El Dorado Unit 208, Winter Haven, FL 33884

    Comfortable 1BR Apartment in Desirable 55+ Community, well-maintained one-bedroom, one-bath apartment located in a quiet and welcoming 55+ community. Features a functional floor plan with bright living and dining areas, a spacious bedroom with ample closet space, and a clean, well-appointed kitchen. Enjoy community amenities and a peaceful setting designed for active living. Conveniently located

    Elsa Gonzalez LPT REALTY, LLC

    150 El Dorado Unit 208, Winter Haven, FL 33884
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    $1,945 per month

    • 4 Beds
    • 2 Baths
    • 1,874 Sq Ft
    • House for Rent

    930 Deming Dr, 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,

    930 Deming Dr, Winter Haven, FL 33880
  • /45

    $1,850 per month

    • 4 Beds
    • 2 Baths
    • 1,750 Sq Ft
    • House for Rent

    3993 Warbler Dr, Winter Haven, FL 33880

    Lovely 4 bedroom home, conveniently located at the heart of Winter Haven, minutes from all the stores and restaurants, quick access to Polk Parkway & I-4, & takes less than an hour drive to Orlando or Tampa. This gorgeous home features an elegant ceramic tile flooring, a great open floor plan with 2 spacious living areas, dining room, its' kitchen has plenty of cabinets & counter space, a nice

    Lienyvette Grimaldo MAZELG REALTY

    3993 Warbler Dr, Winter Haven, FL 33880
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    $2,275 per month

    • 4 Beds
    • 2 Baths
    • 1,946 Sq Ft
    • House for Rent

    264 Daisy Estates Dr, Winter Haven, FL 33884

    Please note, our homes are available on a first-come, first-serve basis and are not reserved until the lease is signed by all applicants and security deposits are collected.This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at Want to tour on your own? Click the “Self

    264 Daisy Estates Dr, Winter Haven, FL 33884
  • /10

    $2,300 per month

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

    942 Cattleman St, Winter Haven, FL 33884

    Gorgeous 3BR/2BA Home - AVAILABLE FOR APRIL Looking for a hassle-free rental? This beautifully furnished 3-bedroom, 2-bathroom home in Winter Haven is move-in ready! Just unpack and start living. Features You\'ll Love:-Modern Kitchen - Stainless steel appliances & tons of counter space.-Washer & Dryer In-Unit - Laundry made easy.-Attached Garage - Convenient parking & extra

    Manuel Paredes LA ROSA REALTY LLC

    942 Cattleman St, Winter Haven, FL 33884
  • /15

    $2,015 per month

    • 4 Beds
    • 2 Baths
    • 2,110 Sq Ft
    • House for Rent

    171 Southern Breeze Lp, Winter Haven, FL 33880

    From Hwy 17 S - Turn right onto Spirit Lake Rd and continue for 1.6 miles. Turn left onto Grady Polk Rd and destination will be on the right. From Hwy 17 N - Turn left onto Spirit Lake Rd and continue for 1.6 miles. Turn left onto Grady Polk Rd and destination will be on the right.Please note that the advertised price may exclude additional fees. These include a $55 application fee per

    171 Southern Breeze Lp, Winter Haven, FL 33880
  • /17

    $2,095 per month

    • 5 Beds
    • 2 Baths
    • 2,254 Sq Ft
    • House for Rent

    1220 Tyler Loop, Winter Haven, FL 33884

    Pet-Friendly 5-Bedroom Home in Winter Haven, FL!This new construction 5-bedroom, 2.5-bath home combines style and practicality, ideal for modern living.Highlights include:Gourmet kitchen with granite countertops, stainless steel appliances, and elegant cabinetrySpacious living area, perfect for guests or multi-generational livingPrimary suite featuring dual sinks, a walk-in

    Morgan Evans RESZI MANAGEMENT I, LLC

    1220 Tyler Loop, Winter Haven, FL 33884

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