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

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  /13

  $2,045 Per Month

  • 3 Beds
  • 2 Baths
  • 1,628 Sq Ft
  • House for Rent

  1881 N Lake Eloise 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 $2189.90. That covers your base rent, $2045.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  1881 N Lake Eloise Dr, Winter Haven, FL 33884
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  /18

  $1,945 Per Month

  • 4 Beds
  • 2 Baths
  • 1,598 Sq Ft
  • House for Rent

  196 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. Apply now or schedule your self-tour today and take the first step toward getting more than just a place to

  196 Southern Breeze Lp, Winter Haven, FL 33880
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  /15

  $2,025 Per Month

  • 4 Beds
  • 2 Baths
  • 1,598 Sq Ft
  • House for Rent

  211 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. Welcome to South Haven, Winter Haven's newest build-to-rent community where luxury and convenience

  211 Southern Breeze Lp, Winter Haven, FL 33880
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  /15

  $2,155 Per Month

  • 3 Beds
  • 2 Baths
  • 1,407 Sq Ft
  • House for Rent

  228 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. Apply now or schedule your self-tour today and take the first step toward getting more than just a place to

  228 Southern Breeze Lp, Winter Haven, FL 33880
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  /16

  $1,700 Per Month

  • 3 Beds
  • 2 Baths
  • 1,142 Sq Ft
  • House for Rent

  3810 High St NE, Winter Haven, FL 33881

  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,

  3810 High St NE, Winter Haven, FL 33881
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  /16

  $1,990 Per Month

  • 4 Beds
  • 2 Baths
  • 1,670 Sq Ft
  • House for Rent

  839 Cinnamon Dr, Winter Haven, FL 33880

  Beautiful, pet-friendly home coming soon! Apply now — available date is tentative and move-in will be scheduled within 5–10 days of the home being ready. Upon approval, $500 reservation deposit to reserve (applied to security deposit and/or refundable). Application fee: $55 per adult. Security Deposit: one month's rent. Pet fees: $250 + $40/mo per pet. Some homes may include pool ($150/mo),

  839 Cinnamon Dr, Winter Haven, FL 33880
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  /16

  $2,100 Per Month

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • House for Rent

  1506 Kaylor Ct NE, Winter Haven, FL 33881

  Beautiful, pet-friendly home coming soon! Apply now — available date is tentative and move-in will be scheduled within 5–10 days of the home being ready. Upon approval, $500 reservation deposit to reserve (applied to security deposit and/or refundable). Application fee: $55 per adult. Security Deposit: one month's rent. Pet fees: $250 + $40/mo per pet. Some homes may include pool ($150/mo),

  1506 Kaylor Ct NE, Winter Haven, FL 33881
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  /2

  $1,950 Per Month

  • 4 Beds
  • 2 Baths
  • 1,304 Sq Ft
  • House for Rent

  1916 Wallace Manor Dr, Winter Haven, FL 33880

  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.Interested in this home? You clearly have exceptional taste. This charming 4.0-bedroom, 2.0-bathroom home is not only pet-friendly, but also equipped with smart home features to make everyday life more convenient and

  1916 Wallace Manor Dr, Winter Haven, FL 33880
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  /16

  $1,950 Per Month

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

  1501 7th St SE, Winter Haven, FL 33880

  This spacious single-story ranch in Winter Haven offers 5 bedrooms and 3 bathrooms across 2,806 square feet of thoughtfully updated living space. The fresh interior paint and wood-look flooring create a bright and modern atmosphere, while multiple ceiling fans with lights keep the rooms comfortable year-round.An open-concept kitchen with white cabinetry, light countertops, and a mosaic

  1501 7th St SE, Winter Haven, FL 33880
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  /16

  $2,025 Per Month

  • 4 Beds
  • 2 Baths
  • 1,797 Sq Ft
  • House for Rent

  4736 Summerfield Cir, Winter Haven, FL 33881

  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.Interested in this home? You clearly have exceptional taste. This charming 4-bedroom, 2.0-bathroom home is not only pet-friendly, but also equipped with smart home features to make everyday life more convenient and

  4736 Summerfield Cir, Winter Haven, FL 33881
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  /18

  $2,345 Per Month

  • 5 Beds
  • 3 Baths
  • 2,601 Sq Ft
  • House for Rent

  668 Squires Grove Dr, Winter Haven, FL 33880

  This home is move-in ready. Schedule your tour now or start your application today.Welcome to 668 Squires Grove Dr in Winter Haven, FL, a 5-bedroom, 3-bath home offering 2,601 square feet of space with an easy, functional flow. The two-story layout and 2-car garage set the tone from the curb, and inside, the mix of soft carpet and tile creates a comfortable feel that works well for

  668 Squires Grove Dr, Winter Haven, FL 33880
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  /15

  $2,160 Per Month

  • 3 Beds
  • 2 Baths
  • 1,567 Sq Ft
  • House for Rent

  4736 Mandolin Loop, Winter Haven, FL 33884

  Apply now or schedule your self-tour today and take the first step toward getting more than just a place to live. Rent with FirstKey Homes for a home that's right for you, plus professional service and maintenance, innovative resident programs, and more; that's the power of purple! This 3-bedroom, 2-bathroom rental home in Winter Haven, FL, might be the perfect fit for your lifestyle. See

  4736 Mandolin Loop, Winter Haven, FL 33884
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  /16

  $2,099 Per Month

  • 3 Beds
  • 2 Baths
  • 1,340 Sq Ft
  • House for Rent

  3111 Buckeye Point Dr, Winter Haven, FL 33881

  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 3 bedrooms, 2 bathrooms, and approximately 1,340 square feet, this well-maintained home offers a high standard of rental living,

  3111 Buckeye Point Dr, Winter Haven, FL 33881
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  /18

  $1,685 Per Month

  • 3 Beds
  • 2 Baths
  • 1,407 Sq Ft
  • House for Rent

  163 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. Welcome to South Haven, Winter Haven's newest build-to-rent community where luxury and convenience come together

  163 Southern Breeze Lp, Winter Haven, FL 33880
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  /16

  $2,285 Per Month

  • 4 Beds
  • 2 Baths
  • 2,284 Sq Ft
  • House for Rent

  557 Reddicks Cir, Winter Haven, FL 33884

  EXCITING NEWS: WE ARE CURRENTLY RENOVATING THIS HOME! NOTE THAT THE PHOTOS SHOWN REPRESENT THE HOME BEFORE RENOVATION AND DO NOT REFLECT ANY UPDATES. PLANNED IMPROVEMENTS INCLUDE: NEW HARD SURFACE COUNTERTOPS. APPLY TODAY OR ASK YOUR LEASING SPECIALIST FOR MORE DETAILS! Apply now or schedule your self-tour today and take the first step toward getting more than just a place to live. Rent

  557 Reddicks Cir, Winter Haven, FL 33884
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  /15

  $2,250 Per Month

  • 4 Beds
  • 3 Baths
  • 2,576 Sq Ft
  • House for Rent

  3637 Queens Cove Blvd, Winter Haven, FL 33880

  EXCITING NEWS: WE RECENTLY RENOVATED THIS HOME! IMPROVEMENTS INCLUDE: NEW STAINLESS STEEL APPLIANCES. Apply now or schedule your self-tour today and take the first step toward getting more than just a place to live. Rent with FirstKey Homes for a home that's right for you, plus professional service and maintenance, innovative resident programs, and more; that's the power of purple!

  3637 Queens Cove Blvd, Winter Haven, FL 33880
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  /19

  $2,049 Per Month

  • 3 Beds
  • 2 Baths
  • 1,630 Sq Ft
  • House for Rent

  495 Majestic Gardens Blvd, 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 3 bedrooms, 2.0 bathrooms, and approximately 1,630 square feet, this well-maintained home offers a high standard of rental living,

  495 Majestic Gardens Blvd, Winter Haven, FL 33880
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  /16

  $1,730 Per Month

  • 3 Beds
  • 2 Baths
  • 1,286 Sq Ft
  • House for Rent

  3702 Imperial Dr, Winter Haven, FL 33880

  Beautiful, pet-friendly home coming soon! Apply now — available date is tentative and move-in will be scheduled within 5–10 days of the home being ready. Upon approval, $500 reservation deposit to reserve (applied to security deposit and/or refundable). Application fee: $55 per adult. Security Deposit: one month's rent. Pet fees: $250 + $40/mo per pet. Some homes may include pool ($150/mo),

  3702 Imperial Dr, Winter Haven, FL 33880
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  /15

  $2,030 Per Month

  • 3 Beds
  • 2 Baths
  • 1,645 Sq Ft
  • House for Rent

  505 Reddicks Cir, 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.Coming soon! This home is currently being enjoyed by another resident but will be available soon. Please respect their privacy and do not disturb. You can complete the application process and reserve

  505 Reddicks Cir, Winter Haven, FL 33884
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  /20

  $2,025

  Total Monthly Price

  • 4 Beds
  • 2 Baths
  • 1,981 Sq Ft
  • House for Rent

  4766 Osprey Way, Winter Haven, FL 33881

  Now offering 19-month leases. Sign today and lock in today’s low rate for the next 19 months! Offer valid for new applicants who sign a 19-month lease and move-in by August 31, 2026. Base rent will remain at the 12-month lease rate for the duration of the 19-month term. Offer is contingent on application approval and execution of a lease agreement. Other terms and conditions may apply. This home,

  4766 Osprey Way, Winter Haven, FL 33881
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  /16

  $2,145 Per Month

  • 3 Beds
  • 2 Baths
  • 2,056 Sq Ft
  • House for Rent

  878 Terranova Rd, 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 $2409.90. That covers your base rent, $2145.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  878 Terranova Rd, Winter Haven, FL 33884
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  /16

  $2,060 Per Month

  • 4 Beds
  • 2 Baths
  • 2,088 Sq Ft
  • House for Rent

  436 Fish Hawk Dr, 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 is priced to rent and won't be around for long. Apply now, while we make this home ready for you, or call to arrange a meeting with your local Progress Residential leasing specialist

  436 Fish Hawk Dr, Winter Haven, FL 33884
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  /7

  $1,000

  Total Monthly Price

  • 1 Bed
  • 1 Bath
  • 1,111 Sq Ft
  • House for Rent

  101 Lake Sears Dr, Winter Haven, FL 33880

  Nice and clean 3 bedroom house shared bathroom. I have a cat but mostly outside

  101 Lake Sears Dr, Winter Haven, FL 33880
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  /11

  $1,750

  Total Monthly Price

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • House for Rent

  711 Avenue B NE, Winter Haven, FL 33881

  This is a 3/2 home in Winter Haven Fl. This home is move in ready and had been freshly updated. Call for your showing today. Close to downtown and convenient to all winter haven has to offer.Washer Dryer hook upsCentral heat and airScreened porchLong term or short term approved.

  711 Avenue B NE, Winter Haven, FL 33881
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  /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
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  /9

  $2,300

  Total Monthly Price

  • 4 Beds
  • 2 Baths
  • 1,828 Sq Ft
  • House for Rent

  1341 Daisy Field Dr, Winter Haven, FL 33884

  Pond View | NEW Washer & Dryer Included | Pet Friendly | 4BR/2BA 2024 New Construction | Smart Home | Resort-Style Pool 2 minute walkWelcome to this beautiful 4-bedroom, 2-bathroom home located in the desirable Harmony at Lake Eloise community. Offering 1,828 square feet of living space, this owner-occupied home features an open-concept layout, modern finishes, and a peaceful pond

  1341 Daisy Field Dr, Winter Haven, FL 33884
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  /26

  $2,300

  Total Monthly Price

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

  6224 Botticella Blvd, Winter Haven, FL 33884

  The first floor of this new two-story home is host to an open-concept layout that combines the kitchen with the living and dining areas, and an outdoor patio is easily reached off the main living space. Upstairs, five bedrooms surround a versatile loft, including the luxe owner’s suite, complete with a generous walk-in closet and en-suite bathroom.

  6224 Botticella Blvd, Winter Haven, FL 33884
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  /20

  $1,875

  Total Monthly Price

  • 4 Beds
  • 2 Baths
  • 1,821 Sq Ft
  • House for Rent

  1536 Axel Cir, Winter Haven, FL 33880

  - Beautiful 4-Bedroom 2-Bathroom Home for Rent in Winter Haven, FL- NEW BUILT IN 2023- 1536 Axel Cir, Winter Haven, FL 33880- Monthly Rent: $1,875- Available Immediately- Pets Welcome!Welcome home! This inviting rental property offers a comfortable and convenient place to call home in Winter Haven. With a great location and a welcoming atmosphere, this home is a

  1536 Axel Cir, Winter Haven, FL 33880
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  /12

  $2,250 Per Month

  • 4 Beds
  • 2.5 Baths
  • 2,200 Sq Ft
  • House for Rent

  437 Fish Hawk Dr, Winter Haven, FL 33884

  Welcome to this beautiful 4 bedroom, 2.5 bath home. located in a highly desirable community. This spacious home offers a functional floor plan with generous living areas, modern kitchen, and comfortable bedroom, making perfect for families or professionals. Enjoy a private backyard and all the benefits of living in well maintained neighborhood close to school, shopping, dinning, parks and major

  Mike Coicou LA ROSA REALTY PRESTIGE

  437 Fish Hawk Dr, Winter Haven, FL 33884
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  /11

  $1,650 Per Month

  • 3 Beds
  • 2 Baths
  • 1,124 Sq Ft
  • House for Rent

  407 Ave a SE, Winter Haven, FL 33880

  Great location! This 3 bedroom 2 bath home is conveniently located in downtown Winter Haven and near the hospital, downtown, doctor offices, restaurants and shopping. Updated Kitchen with granite counter tops, stainless steel appliances, and inside laundry. Owner's recently added a screened back porch with brick pavers and ceiling fan.Administration Fee:Upon approval tenants will be

  407 Ave a SE, Winter Haven, FL 33880
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  /41

  $1,750 Per Month

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

  204 6th Jpv St, Winter Haven, FL 33880

  Three bedroom, one bathroom home located in Winter Haven. This property features a roof installed in 2025 and an AC system installed in 2025 for energy efficiency and year round comfort. The interior floor plan includes a remodeled kitchen, a remodeled bathroom, and low maintenance ceramic tile flooring throughout with no carpet. Enjoy a functional layout with bright living spaces and a spacious

  Juan Corrales DALTON WADE INC

  204 6th Jpv St, Winter Haven, FL 33880
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  /20

  $1,600 Per Month

  • 2 Beds
  • 2 Baths
  • 1,074 Sq Ft
  • House for Rent

  204 Chaucer Ln, Winter Haven, FL 33884

  Centrally located 2 bedroom 2 bath. This home has been updated with new flooring and paint throughout. 2 car garage, screen lanai, fenced yard.**This home comes with high speed internet up to 1 Gig at an exclusive group rate of $60/month (In addition to advertised rent), and includes 24/7 premium support and setup to help get you connected at move-in**Administration Fee:Upon

  204 Chaucer Ln, Winter Haven, FL 33884
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  /21

  $1,800 Per Month

  • 3 Beds
  • 2 Baths
  • 1,312 Sq Ft
  • House for Rent

  1666 Ambar Ct, Winter Haven, FL 33881

  Located on a quiet residential community in Winter Haven, this property offers the perfect blend of comfort, convenience, and quality of life in the heart of Central Florida. Just minutes away from shopping centers, grocery stores, restaurants, hospitals, and schools, the location is ideal for families and anyone seeking everyday convenience. The home also features a spacious fenced backyard,

  Amis Quijada MY REALTY GROUP, LLC.

  1666 Ambar Ct, Winter Haven, FL 33881
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  /2

  $1,595 Per Month

  • 3 Beds
  • 1 Bath
  • 1,296 Sq Ft
  • House for Rent

  876 Crestwood Dr, Winter Haven, FL 33881

  This home located in a quiet and desirable area of Winter Haven. This well-maintained property offers a comfortable layout with plenty of natural light, creating a warm and inviting living space.The home features spacious bedrooms, a cozy living area, and a functional kitchen with ample cabinet space, perfect for everyday living. The property also includes a nice outdoor area, ideal for

  876 Crestwood Dr, Winter Haven, FL 33881
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  /21

  $2,250 Per Month

  • 3 Beds
  • 2 Baths
  • 1,540 Sq Ft
  • House for Rent

  1708 Teagan Ln, Winter Haven, FL 33884

  Beautiful single family house built in 2024 with 3 bedrooms, 2 bathrooms, with open kitchen, Living room and Dining Area, Master Bedroom with attached master bath with double sinks and large walking closet, 2 other bedrooms with hall bath, 2 car garages with appliances Stove, Refrigerator, Dishwasher, Microwave, Washer and Dryer. Amenities include pool, playground etc. in the community. 1st,

  K.C. Thomas CHARLES RUTENBERG REALTY ORLANDO

  1708 Teagan Ln, Winter Haven, FL 33884
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  /12

  $1,890 Per Month

  • 3 Beds
  • 2 Baths
  • 1,373 Sq Ft
  • House for Rent

  2416 Ave B SW, Winter Haven, FL 33880

  Welcome to this Fully Furnished Pool Home for RentA stunning property located in the beautiful Winter Haven, FL. This home boasts three spacious bedrooms and two full bathrooms, offering ample space for comfortable living. The property is fully furnished, allowing you to move in with ease and start enjoying your new home immediately. The private swimming pool is a standout

  2416 Ave B SW, Winter Haven, FL 33880
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  /9

  $1,320 Per Month

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

  403 8th St NE, Winter Haven, FL 33881

  1 month free !This charming home offers a unique loft space upstairs, perfect for an office, extra living area, or creative nook. Sitting on a large yard, this property gives you plenty of outdoor room to enjoy.Located just minutes from Winter Haven Hospital, shopping, dining, and everyday conveniences, you’ll love the easy access to everything you need. The home includes a one-car garage,

  Jordan Clark PALM LEAF PROPERTY MANAGEMENT

  403 8th St NE, Winter Haven, FL 33881
• 

  

  /19

  $1,675 Per Month

  • 2 Beds
  • 2 Baths
  • 1,230 Sq Ft
  • House for Rent

  415 Laurel Cove Way, Winter Haven, FL 33884

  Lovely second floor 2-Bedroom, 2-Bath in gated Winterset community.Living room has stacked stone wall, no carpet, and screened lanai with a lakeview.Updated appliances in the kitchen that boast a large walk-in pantry.primary walk-in closet is built-out with closet organization.Small pets allowed based on PetScreening results. Fees/rents based on

  415 Laurel Cove Way, Winter Haven, FL 33884
• 

  

  /16

  $2,100 Per Month

  • 3 Beds
  • 2 Baths
  • 1,516 Sq Ft
  • House for Rent

  2375 Brassie Ct, Winter Haven, FL 33884

  Beautiful 3-bedroom, 2-bathroom home for rent in Winter Haven! This newer home features an open floor plan, modern kitchen, spacious bedrooms, and a 2-car garage. Enjoy community amenities including a pool and park. Plus, the home is equipped with solar panels, helping keep electricity costs exceptionally low—typically around $15–$20/month depending on usage. Great location and move-in ready!

  Karina Turcios LPT REALTY, LLC

  2375 Brassie Ct, Winter Haven, FL 33884
• 

  

  /15

  $1,250 Per Month

  • 2 Beds
  • 2 Baths
  • 1,003 Sq Ft
  • House for Rent

  2366 Lake Dr NW, Winter Haven, FL 33881

  Welcome to 2366 Lake Dr in Winter Haven — a freshly updated home offering both style and functionality. Inside, you’ll find spacious bedrooms with modern flooring, ceiling fans, and ample natural light. The bathrooms feature clean tile finishes and practical layouts, while the kitchen is equipped with essential appliances including a range oven, range hood, and dishwasher, making everyday living

  2366 Lake Dr NW, Winter Haven, FL 33881

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