704

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

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  • /12

    $1,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,366 Sq Ft
    • Condo for Rent

    400 El Camino Dr Unit 203, Winter Haven, FL 33884

    Property Id: 2712857***55+ Senior Community***Amazing 2 bedroom, 2 bathroom apartment in Winter Haven. Amenities included: balcony, central air, central heat, and dishwasher. No Utilities included. Is pet friendly. Date Available: Jun 27th 2026. $1,500/month rent. $1,500 security deposit required. Please submit the form on this page or contact Oscar at to learn more. This property is

    400 El Camino Dr Unit 203, Winter Haven, FL 33884
  • /15

    $2,210 Per Month

    • 4 Beds
    • 2 Baths
    • 1,758 Sq Ft
    • House for Rent

    112 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

    112 Southern Breeze Lp, Winter Haven, FL 33880
  • /20

    $2,180

    Total Monthly Price

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

    4766 Osprey Way, Winter Haven, FL 33881

    Now offering 20-month leases. Sign today and lock in today’s low rate for the next 20 months! Offer valid for new applicants who sign a 20-month lease by July 31st, 2026. Base rent will remain at the 12-month lease rate for the duration of the 20-month term. Offer is contingent on application approval and execution of a lease agreement. Other terms and conditions may apply. This home, constructed

    4766 Osprey Way, Winter Haven, FL 33881
  • /15

    $1,775 Per Month

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

    502 Glad Rd, 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,

    502 Glad Rd, Winter Haven, FL 33880
  • /14

    $1,599 Per Month

    • 4 Beds
    • 1 Bath
    • 1,900 Sq Ft
    • House for Rent

    3627 Ave S NW, Winter Haven, FL 33881

    Property Id: 1605345 4 Bed • 1 Bath Brick House for Rent - Winter Haven, FL3627 Ave S NW, Winter Haven, FL 33881$1,599 / MonthMove-in Ready (March 1st) & Pet Friendly! ($50/month per pet)Discover your next home in Winter Haven! This charming 4-bed, 1-bath brick house features a huge shaded backyard with large mature oak trees — perfect for relaxing, gardening, or

    3627 Ave S NW, Winter Haven, FL 33881
  • /15

    $1,915 Per Month

    • 3 Beds
    • 2 Baths
    • 1,515 Sq Ft
    • House for Rent

    838 Summer Glen Dr, Winter Haven, FL 33880

    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 $2059.90. That covers your base rent, $1915.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    838 Summer Glen Dr, Winter Haven, FL 33880
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    $2,100 Per Month

    • 3 Beds
    • 2 Baths
    • 1,504 Sq Ft
    • House for Rent

    835 Summer Glen Dr, Winter Haven, FL 33880

    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, may be the right place for you. Enjoy the privacy

    835 Summer Glen Dr, Winter Haven, FL 33880
  • /14

    $1,395 Per Month

    • 2 Beds
    • 1 Bath
    • 1,206 Sq Ft
    • House for Rent

    850 17th Terrace NE, Winter Haven, FL 33881

    This home is move-in ready. Schedule your tour now or start your application today.Welcome to this 2-bedroom, 1-bathroom home in Winter Haven, Florida, offering a practical layout and inviting living spaces throughout. An attached carport adds everyday convenience, while the enclosed patio provides additional versatile space to enjoy.Inside, hard surface flooring runs through the

    850 17th Terrace NE, Winter Haven, FL 33881
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    $2,015 Per Month

    • 3 Beds
    • 2 Baths
    • 1,862 Sq Ft
    • House for Rent

    6033 Live Oak Dr, 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.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

    6033 Live Oak Dr, Winter Haven, FL 33880
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    $1,870 Per Month

    • 3 Beds
    • 2 Baths
    • 1,310 Sq Ft
    • House for Rent

    2520 Ave a SW, Winter Haven, FL 33880

    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.

    2520 Ave a SW, Winter Haven, FL 33880
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    $2,100 Per Month

    • 4 Beds
    • 2 Baths
    • 1,850 Sq Ft
    • House for Rent

    1336 Axel Cir, Winter Haven, FL 33880

    Property Id: 8361694 bedroom 2 Bathroom Single Family HomeEasy commute to either Tampa or Orlando. Large kitchen granite countertops, large pantry, stainless steel appliances,Washer and Dryer included,vaulted ceiling, 2-car garage. Security deposit due at signing. $21001st and Last and security due at move in. Well qualified applicants may be

    1336 Axel Cir, Winter Haven, FL 33880
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    $2,045 Per Month

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

    192 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

    192 Southern Breeze Lp, Winter Haven, FL 33880
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    $1,820 Per Month

    • 3 Beds
    • 2 Baths
    • 1,694 Sq Ft
    • House for Rent

    3211 Timberline Rd, Jan Phyl Village, 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,

    3211 Timberline Rd, Jan Phyl Village, FL 33880
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    $2,220 Per Month

    • 4 Beds
    • 2 Baths
    • 1,758 Sq Ft
    • House for Rent

    308 S Haven Ct, 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

    308 S Haven Ct, Winter Haven, FL 33880
  • /15

    $2,000 Per Month

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

    220 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

    220 Southern Breeze Lp, Winter Haven, FL 33880
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    $1,895 Per Month

    • 3 Beds
    • 2 Baths
    • 1,593 Sq Ft
    • House for Rent

    584 Lake Smart Blvd, Winter Haven, FL 33881

    This home is move-in ready. Schedule your tour now or start your application today.Welcome to 584 Lake Smart Blvd in Winter Haven, FL, offering 3 bedrooms, 2 bathrooms, and 1,593 square feet. The single-level floor plan opens from the entry into a spacious living room and dining area, with the kitchen placed nearby for easy day-to-day flow. The primary suite is set apart from the

    584 Lake Smart Blvd, Winter Haven, FL 33881
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    $1,575 Per Month

    • 3 Beds
    • 1 Bath
    • 1,050 Sq Ft
    • House for Rent

    3823 Ave J NW, Winter Haven, FL 33881

    This home is move-in ready. Schedule your tour now or start your application today.Welcome to 3823 Avenue J NW, a refreshed 3-bedroom, 1-bathroom home offering 1,050 square feet of comfortable living space in Winter Haven. Surrounded by mature greenery and set behind a gated front entry, this home combines practical everyday living with convenient access to local shopping, dining, parks,

    3823 Ave J NW, Winter Haven, FL 33881
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    $1,850 Per Month

    • 3 Beds
    • 2 Baths
    • 1,852 Sq Ft
    • House for Rent

    144 Shelley 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.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

    144 Shelley Dr, Winter Haven, FL 33884
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    $2,049 Per Month

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

    991 Summer Glen Dr, Winter Haven, FL 33880

    Coming soon - this home is currently being enjoyed by another resident but will be available soon. This home is professionally managed by Tricon, dedicated to creating exceptional rental experiences. Featuring 3 bedrooms, 2.0 bathrooms, and approximately 1,672 square feet, this well-maintained home offers a high standard of rental living, supported by a team that puts residents first. As a

    991 Summer Glen Dr, Winter Haven, FL 33880
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    $2,205 Per Month

    • 3 Beds
    • 2 Baths
    • 2,315 Sq Ft
    • House for Rent

    40 St Kitts Cir, 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, may be the right place for you. Enjoy the privacy

    40 St Kitts Cir, Winter Haven, FL 33884
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    $1,860 Per Month

    • 3 Beds
    • 2 Baths
    • 1,249 Sq Ft
    • House for Rent

    3414 Cove Ct W, Winter Haven, FL 33880

    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 STAINLESS STEEL APPLIANCES. 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

    3414 Cove Ct W, Winter Haven, FL 33880
  • /15

    $1,975 Per Month

    • 4 Beds
    • 2 Baths
    • 1,770 Sq Ft
    • House for Rent

    850 Terranova Rd, 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 4-bedroom, 2-bathroom rental home in Winter Haven, FL, has a lot to offer; does it check all your boxes?

    850 Terranova Rd, Winter Haven, FL 33884
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    $2,170 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
  • /15

    $2,225 Per Month

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

    1054 Summer Glen Dr, Winter Haven, FL 33880

    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.

    1054 Summer Glen Dr, Winter Haven, FL 33880
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    $2,115 Per Month

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

    5603 Lake Fox 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.

    5603 Lake Fox Cir, Winter Haven, FL 33884
  • /20

    $2,095

    Total Monthly Price

    • 4 Beds
    • 3 Baths
    • 1,936 Sq Ft
    • House for Rent

    3941 Warbler Dr, Winter Haven, FL 33880

    Now offering 20-month leases. Sign today and lock in today’s low rate for the next 20 months! Offer valid for new applicants who sign a 20-month lease by July 31st, 2026. Base rent will remain at the 12-month lease rate for the duration of the 20-month term. Offer is contingent on application approval and execution of a lease agreement. Other terms and conditions may apply. This property is

    3941 Warbler Dr, Winter Haven, FL 33880
  • /16

    $2,010 Per Month

    • 4 Beds
    • 2 Baths
    • 1,994 Sq Ft
    • House for Rent

    1167 Sophia Blvd, Winter Haven, FL 33881

    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

    1167 Sophia Blvd, Winter Haven, FL 33881
  • /16

    $2,025 Per Month

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

    6025 Live Oak Dr, 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.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

    6025 Live Oak Dr, Winter Haven, FL 33880
  • /16

    $2,155 Per Month

    • 4 Beds
    • 2 Baths
    • 1,844 Sq Ft
    • House for Rent

    918 Summer Glen Dr, Winter Haven, FL 33880

    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.

    918 Summer Glen Dr, Winter Haven, FL 33880
  • /16

    $1,799 Per Month

    • 3 Beds
    • 2 Baths
    • 1,642 Sq Ft
    • House for Rent

    569 Cody Caleb Dr, Winter Haven, FL 33884

    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 1,642 square feet, this well-maintained home offers a high standard of rental living,

    569 Cody Caleb Dr, Winter Haven, FL 33884
  • /16

    $1,600 Per Month

    • 3 Beds
    • 2 Baths
    • 1,201 Sq Ft
    • House for Rent

    812 Whisper Lake Ct, Winter Haven, FL 33880

    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 STAINLESS STEEL APPLIANCES. 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

    812 Whisper Lake Ct, Winter Haven, FL 33880
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    $1,895 Per Month

    • 3 Beds
    • 2 Baths
    • 1,432 Sq Ft
    • House for Rent

    959 Sunrise Ct, Winter Haven, FL 33880

    This home is move-in ready. Schedule your tour now or start your application today.Welcome to 959 Sunrise Court in Winter Haven, a 3-bedroom, 2-bath home offering 1,432 square feet of comfortable living space. A clean exterior, long driveway, and inviting front approach set the tone, while inside, fresh interior paint gives the home a bright, refreshed feel from the start.The main

    959 Sunrise Ct, Winter Haven, FL 33880
  • /2

    $1,965 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 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

    1916 Wallace Manor Dr, Winter Haven, FL 33880
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    $1,925 Per Month

    • 4 Beds
    • 3 Baths
    • 2,067 Sq Ft
    • House for Rent

    292 Cloverdale Rd, 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.Interested in this home? You clearly have exceptional taste. This charming 4-bedroom, 3.0-bathroom home is not only pet-friendly, but also equipped with smart home features to make everyday life more convenient and

    292 Cloverdale Rd, Winter Haven, FL 33884
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    $1,400 Per Month

    • 2 Beds
    • 2 Baths
    • 1,015 Sq Ft
    • Condo for Rent

    1935 Ave O SW Unit 201, Winter Haven, FL 33880

    Property Id: 2515636MOVE IN SPECIAL-$500 OFF FIRST MONTHHome features: Plank flooring throughout (easy to clean) Wood cabinetry + granite countertops Stainless steel appliances including dishwasher and garbage disposal Ceiling fans in the bedroom and living roomIn-unit washer & dryer Bedroom and living room are cable-readyLocation: Minutes to downtown

    1935 Ave O SW Unit 201, Winter Haven, FL 33880
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    $1,850 Per Month

    • 4 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • Condo for Rent

    731 Ave a SW Unit B, Winter Haven, FL 33880

    Welcome to your new home in the heart of Winter Haven, Florida! This property offers the perfect blend of comfort and convenience, situated near a variety of department stores and beautiful parks, including Trailhead Park Playground and South Lake Howard Nature Park—ideal for leisurely afternoons.Key property features include inviting central heating and cooling, ensuring year-round

    731 Ave a SW Unit B, Winter Haven, FL 33880
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    $1,899 Per Month

    • 3 Beds
    • 2 Baths
    • 1,930 Sq Ft
    • House for Rent

    2112 Jonathan Ln, 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 $2043.90. That covers your base rent, $1899.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    2112 Jonathan Ln, Winter Haven, FL 33884
  • /15

    $1,855 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
  • /16

    $1,975 Per Month

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • House for Rent

    110 7th Jpv St, 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.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

    110 7th Jpv St, Winter Haven, FL 33880
  • /15

    $1,949 Per Month

    • 3 Beds
    • 2 Baths
    • 1,432 Sq Ft
    • House for Rent

    2065 Whispering Trails Blvd, Winter Haven, FL 33884

    Welcome to your future home in beautiful Winter Haven, Florida! This charming property is conveniently located near an array of delightful restaurants and department stores, making it an ideal spot for both leisure and shopping.Key property features include a spacious layout thoughtfully designed for comfort. Enjoy the benefits of central heating and cooling, alongside air conditioning

    2065 Whispering Trails Blvd, Winter Haven, FL 33884

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