$1,700 Per Month
- 2 Beds
- 1 Bath
- 1,032 Sq Ft
- House for Rent
1313 4th St NE, Winter Haven, FL 33881
1313 4th St NE, Winter Haven, FL 33881
193
Winter Haven, FL Houses for Rent under $2,500
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$2,425 Per Month
- 4 Beds
- 2 Baths
- 1,791 Sq Ft
- House for Rent
326 Royal Palm Way, Winter Haven, FL 33881
326 Royal Palm Way, Winter Haven, FL 33881**THIS ADDRESS WAS FORMALLY KNOWN AS 326 OXFORD DRIVE. STREET NAME WAS CHANGED TO ROYAL PALM WAY. THE NEW ADDRESS WILL NOT PULL UP ON THE MAP** Private community, energy efficient homes, LOADED with the best finishes. With three different elevations to choose from, you will notice a completely different look and feel. If you have pets, not only do we allow them. Home available that
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$1,300 Per Month
- 1 Bed
- 1 Bath
- 2,109 Sq Ft
- House for Rent
1453 Austin St Unit B, Winter Haven, FL 33884
1453 Austin St Unit B, Winter Haven, FL 33884 -
$2,400 Per Month
- 4 Beds
- 2 Baths
- 1,791 Sq Ft
- House for Rent
317 Royal Palm Way, Winter Haven, FL 33881
317 Royal Palm Way, Winter Haven, FL 33881**THIS ADDRESS WAS FORMALLY KNOWN AS 317 OXFORD DRIVE. STREET NAME WAS CHANGED TO ROYAL PALM WAY. THE NEW ADDRESS WILL NOT PULL UP ON THE MAP**Private community, energy efficient homes, LOADED with the best finishes. With three different elevations to choose from, you will notice a completely different look and feel. If you have pets, not only do we allow them. Home available that
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$1,600 Per Month
- 2 Beds
- 1 Bath
- 626 Sq Ft
- House for Rent
1756 2nd St NE, Winter Haven, FL 33881
1756 2nd St NE, Winter Haven, FL 33881 -
$2,400 Per Month
- 4 Beds
- 2 Baths
- 1,791 Sq Ft
- House for Rent
330 Royal Palm Way, Winter Haven, FL 33881
330 Royal Palm Way, Winter Haven, FL 33881**THIS ADDRESS WAS FORMALLY KNOWN AS 326 OXFORD DRIVE. STREET NAME WAS CHANGED TO ROYAL PALM WAY. THE NEW ADDRESS WILL NOT PULL UP ON THE MAP**Private community, energy efficient homes, LOADED with the best finishes. With three different elevations to choose from, you will notice a completely different look and feel. If you have pets, not only do we allow them. Home available that
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$2,295 Per Month
- 4 Beds
- 2.5 Baths
- 1,880 Sq Ft
- House for Rent
6220 Botticella Blvd, Winter Haven, FL 33884
6220 Botticella Blvd, Winter Haven, FL 33884 -
$1,700 Per Month
- 3 Beds
- 2 Baths
- 1,142 Sq Ft
- House for Rent
3810 High St NE, Winter Haven, FL 33881
3810 High St NE, Winter Haven, FL 33881Welcome 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,
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$1,950 Per Month
- 3 Beds
- 2 Baths
- 1,560 Sq Ft
- House for Rent
172 Inman Blvd, Winter Haven, FL 33881
172 Inman Blvd, Winter Haven, FL 33881 -
$1,990 Per Month
- 4 Beds
- 2 Baths
- 1,670 Sq Ft
- House for Rent
839 Cinnamon Dr, Winter Haven, FL 33880
839 Cinnamon Dr, Winter Haven, FL 33880Beautiful, 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),
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$2,000 Per Month
- 3 Beds
- 2 Baths
- 1,690 Sq Ft
- House for Rent
624 Honey Bell Rd, Winter Haven, FL 33880
624 Honey Bell Rd, Winter Haven, FL 33880 -
$2,100 Per Month
- 3 Beds
- 2 Baths
- 1,800 Sq Ft
- House for Rent
1506 Kaylor Ct NE, Winter Haven, FL 33881
1506 Kaylor Ct NE, Winter Haven, FL 33881Beautiful, 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),
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$2,300 Per Month
- 4 Beds
- 2 Baths
- 1,583 Sq Ft
- House for Rent
780 Overlook Grove Dr, Winter Haven, FL 33884
780 Overlook Grove Dr, Winter Haven, FL 33884 -
$1,950 Per Month
- 4 Beds
- 2 Baths
- 1,304 Sq Ft
- House for Rent
1916 Wallace Manor Dr, Winter Haven, FL 33880
1916 Wallace Manor Dr, Winter Haven, FL 33880Please 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
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$1,950 Per Month
- 4 Beds
- 3 Baths
- 2,806 Sq Ft
- House for Rent
1501 7th St SE, Winter Haven, FL 33880
1501 7th St SE, Winter Haven, FL 33880This 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
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$2,085 Per Month
- 4 Beds
- 2 Baths
- 1,797 Sq Ft
- House for Rent
4736 Summerfield Cir, Winter Haven, FL 33881
4736 Summerfield Cir, Winter Haven, FL 33881Please 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
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$2,345 Per Month
- 5 Beds
- 3 Baths
- 2,601 Sq Ft
- House for Rent
668 Squires Grove Dr, Winter Haven, FL 33880
668 Squires Grove Dr, Winter Haven, FL 33880This 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
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$2,160 Per Month
- 3 Beds
- 2 Baths
- 1,567 Sq Ft
- House for Rent
4736 Mandolin Loop, Winter Haven, FL 33884
4736 Mandolin Loop, Winter Haven, FL 33884Apply 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
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$2,149 Per Month
- 3 Beds
- 2 Baths
- 1,340 Sq Ft
- House for Rent
3111 Buckeye Point Dr, Winter Haven, FL 33881
3111 Buckeye Point Dr, Winter Haven, FL 33881Coming 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 1,340 square feet, this well-maintained home offers a high standard of rental living,
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$1,685 Per Month
- 3 Beds
- 2 Baths
- 1,407 Sq Ft
- House for Rent
163 Southern Breeze Lp, Winter Haven, FL 33880
163 Southern Breeze Lp, Winter Haven, FL 33880From 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
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$2,285 Per Month
- 4 Beds
- 2 Baths
- 2,284 Sq Ft
- House for Rent
557 Reddicks Cir, Winter Haven, FL 33884
557 Reddicks Cir, Winter Haven, FL 33884EXCITING 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
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$2,250 Per Month
- 4 Beds
- 3 Baths
- 2,576 Sq Ft
- House for Rent
3637 Queens Cove Blvd, Winter Haven, FL 33880
3637 Queens Cove Blvd, Winter Haven, FL 33880EXCITING 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
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$2,049 Per Month
- 3 Beds
- 2 Baths
- 1,630 Sq Ft
- House for Rent
495 Majestic Gardens Blvd, Winter Haven, FL 33880
495 Majestic Gardens Blvd, Winter Haven, FL 33880Coming 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,
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$1,730 Per Month
- 3 Beds
- 2 Baths
- 1,286 Sq Ft
- House for Rent
3702 Imperial Dr, Winter Haven, FL 33880
3702 Imperial Dr, Winter Haven, FL 33880Beautiful, 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),
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$2,030 Per Month
- 3 Beds
- 2 Baths
- 1,645 Sq Ft
- House for Rent
505 Reddicks Cir, Winter Haven, FL 33884
505 Reddicks Cir, Winter Haven, FL 33884Please 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
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$2,055
Total Monthly Price
- 4 Beds
- 2 Baths
- 1,981 Sq Ft
- House for Rent
4766 Osprey Way, Winter Haven, FL 33881
4766 Osprey Way, Winter Haven, FL 33881Now 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,
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$2,145 Per Month
- 3 Beds
- 2 Baths
- 2,056 Sq Ft
- House for Rent
878 Terranova Rd, Winter Haven, FL 33884
878 Terranova Rd, Winter Haven, FL 33884Lease 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
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$2,060 Per Month
- 4 Beds
- 2 Baths
- 2,088 Sq Ft
- House for Rent
436 Fish Hawk Dr, Winter Haven, FL 33884
436 Fish Hawk Dr, Winter Haven, FL 33884Please 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
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$2,249 Per Month
- 3 Beds
- 2 Baths
- 1,821 Sq Ft
- House for Rent
112 Waterside Cir, Winter Haven, FL 33880
112 Waterside Cir, Winter Haven, FL 33880Coming 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 1,821 square feet, this well-maintained home offers a high standard of rental living, supported by a team that puts residents first. As a
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$1,700 Per Month
- 3 Beds
- 2 Baths
- 1,340 Sq Ft
- House for Rent
502 Glad Rd, Winter Haven, FL 33880
502 Glad Rd, Winter Haven, FL 33880Welcome 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,
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$1,200 Per Month
- 1 Bed
- 1 Bath
- House for Rent
4320 Dundee Rd, Winter Haven, FL 33884
4320 Dundee Rd, Winter Haven, FL 33884Property 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
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$1,730 Per Month
- 3 Beds
- 2 Baths
- 1,475 Sq Ft
- House for Rent
2024 10th St NW, Winter Haven, FL 33881
2024 10th St NW, Winter Haven, FL 33881Beautiful, 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),
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$2,280 Per Month
- 4 Beds
- 2 Baths
- 1,999 Sq Ft
- House for Rent
4753 Osprey Way, Winter Haven, FL 33881
4753 Osprey Way, Winter Haven, FL 33881Apply 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, may be the right place for you. See the pictures to
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$1,700 Per Month
- 3 Beds
- 2.5 Baths
- 1,356 Sq Ft
- House for Rent
5850 Cypress Gardens Blvd, Winter Haven, FL 33884
5850 Cypress Gardens Blvd, Winter Haven, FL 33884Property Id: 987474 Spacious 3BR / 2.5BA Townhome in Cypress Gardens Area Welcome to this well maintained 3-bedroom, 2.5-bath townhome located in a convenient and desirable area of Cypress Gardens. This home features a bright, open living space, a functional kitchen, and a comfortable layout ideal for everyday living. All three bedrooms are generously sized, with the primary suite
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$2,155 Per Month
- 3 Beds
- 2 Baths
- 1,621 Sq Ft
- House for Rent
4693 Osprey Way, Winter Haven, FL 33881
4693 Osprey Way, Winter Haven, FL 33881Apply 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
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$1,895 Per Month
- 3 Beds
- 2 Baths
- 1,504 Sq Ft
- House for Rent
835 Summer Glen Dr, Winter Haven, FL 33880
835 Summer Glen Dr, Winter Haven, FL 33880Apply 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
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$2,220 Per Month
- 3 Beds
- 2 Baths
- 1,830 Sq Ft
- House for Rent
444 Lanham Dr, Winter Haven, FL 33881
444 Lanham Dr, Winter Haven, FL 33881Apply 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 outdoor
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$2,195 Per Month
- 4 Beds
- 2 Baths
- 1,851 Sq Ft
- House for Rent
397 Corso Loop, Winter Haven, FL 33884
397 Corso Loop, Winter Haven, FL 33884Property Id: 1220815 Beautiful and spacious 4-bedroom, 2-bath single-family home located in the highly desirable Villamar community in Winter Haven. Built in 2020, this modern home features an open-concept floor plan with a bright living area, spacious kitchen, stainless steel appliances, laminate floor throughout, and a large island perfect for entertaining. The split-bedroom layout offers
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$1,780 Per Month
- 4 Beds
- 2 Baths
- 1,758 Sq Ft
- House for Rent
175 Southern Breeze Lp, Winter Haven, FL 33880
175 Southern Breeze Lp, Winter Haven, FL 33880From 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
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$1,730 Per Month
- 3 Beds
- 2 Baths
- 1,310 Sq Ft
- House for Rent
3740 Imperial Dr, Winter Haven, FL 33880
3740 Imperial Dr, Winter Haven, FL 33880Please 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
Showing Results 1 - 40, Page 1 of 5
Rental Home Trends in Winter Haven, FL
There are currently 193 single-family homes available for rent in Winter Haven, FL. The median rent is $1,895 per month, with 3-bedroom houses renting at $1,800, 4-bedroom houses at $2,000 and 5-bedroom houses at $2,220.
Rental Home Trends
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Number of Houses for Rent
193
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Median Single Family Home Rent
$1,895
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Median 3 Bedroom Single Family Home Rent
$1,800
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Median 4 Bedroom Single Family Home Rent
$2,000
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Median 5 Bedroom Single Family Home Rent
$2,220
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Houses for Rent by Price in Winter Haven
Rentals in Winter Haven
Houses for Rent by Bedrooms in Winter Haven
More About Living in Winter Haven
Houses for Rent in Nearby Neighborhoods
- East Winter Haven Houses for Rent
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- Downtown Winter Haven Houses for Rent
- Cypresswood Houses for Rent
- North Winter Haven Houses for Rent
- Southeast Winterhaven Houses for Rent
- Inwood Houses for Rent
- Lake Lucerne Houses for Rent
- Jan Phyl Village Houses for Rent
- Sun Ridge Houses for Rent
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