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Winter Haven, FL Homes for Rent under $2,000

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  • /16

    $1,760 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 lease is signed by all applicants and security deposits are collected.Interested in this home? You clearly have exceptional taste. This charming 3.0-bedroom, 2.0-bathroom home is not only pet-friendly, but also equipped with smart home features to make everyday life more convenient and

    144 Shelley Dr, Winter Haven, FL 33884
  • /18

    $1,849 Per Month

    • 3 Beds
    • 2 Baths
    • 2,035 Sq Ft
    • House for Rent

    1599 Lemon Ave, Winter Haven, FL 33881

    This home is professionally managed by Tricon, dedicated to creating exceptional rental experiences. Featuring 3 bedrooms, 2.0 bathrooms, and approximately 2,035 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

    1599 Lemon Ave, Winter Haven, FL 33881
  • /18

    $1,795 Per Month

    • 4 Beds
    • 3 Baths
    • 2,101 Sq Ft
    • House for Rent

    3638 Queens Cove Blvd, 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 4-bedroom, 3-bathroom rental home in Winter Haven, FL, could be just what you’re looking for. See the

    3638 Queens Cove Blvd, Winter Haven, FL 33880
  • /18

    $1,690 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. Outdoor fun is just

    40 St Kitts Cir, Winter Haven, FL 33884
  • /14

    $1,695 Per Month

    • 3 Beds
    • 1 Bath
    • House for Rent

    14-26 26th St NW, Winter Haven, FL 33881

    Property Id: 2817555 Nice yard Large 3 Bedroom 1 Bathroom house, nice yard, carport for rent. Taking applications. Asking $1775 can leave it at $1695* per month. Outside showing and Driving at the moment. Area of Lake Cannon Winter Haven NW 26 ST Havendale Blvd. One block from Lake Cannon and Park. If interested and for more information please call. Please leave a message if no answer

    14-26 26th St NW, Winter Haven, FL 33881
  • /17

    $1,849 Per Month

    • 4 Beds
    • 2 Baths
    • 1,851 Sq Ft
    • House for Rent

    217 Kensington View Blvd, Winter Haven, FL 33880

    Welcome to 217 Kensington View Boulevard in the desirable Kensington View community, offering 4 bedrooms, 2 full bathrooms, and 1,851 square feet of living space on the first floor. The home features stainless appliances throughout. The primary bedroom includes dual sinks and a walk-in closet. Washer and dryer hookups are available for your convenience. An individual 2-car garage provides ample

    217 Kensington View Blvd, Winter Haven, FL 33880
  • /18

    $1,820 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
  • /13

    $1,195 Per Month

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

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

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

    669 Avenue B NW Unit 9, Winter Haven, FL 33881
  • /15

    $1,575 Per Month

    • 2 Beds
    • 2 Baths
    • 898 Sq Ft
    • Condo for Rent

    311 Ave Y NE Unit 311 Avenue Y NE Unit B, Winter Haven, FL 33881

    Property Id: 1444878 For Rent: Cozy 2-Bedroom Rent: $1,575/month Deposit: $1,575 Lawn Service is included. Lease Term: 1 year minimum Utilities: Tenant responsible for all utilities. Small Pets Only - Pet Fee $50 a Month, per pet. 2 Pet Max No Smoking Background & Credit Check Every individual aged 18 or older residing at the property and/or any

    311 Ave Y NE Unit 311 Avenue Y NE Unit B, Winter Haven, FL 33881
  • /17

    $1,395 Per Month

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

    1984 Ave F SW, Winter Haven, FL 33880

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

    1984 Ave F SW, Winter Haven, FL 33880
  • /15

    $1,849 Per Month

    • 3 Beds
    • 2 Baths
    • 1,678 Sq Ft
    • House for Rent

    465 Kensington View Dr, Winter Haven, FL 33880

    **MOVE-IN SPECIAL! 4 WEEKS FREE OFF FIRST FULL MONTH WITH MOVE IN BY 8/31/2026**Welcome to 465 Kensington View Dr, a spacious 3-bedroom, 2-bath single-family home offering 1,678 square feet of comfortable living space in Winter Haven, FL.Step inside to an inviting layout with plenty of room to relax, entertain, and make the space your own. The kitchen comes equipped with a

    465 Kensington View Dr, Winter Haven, FL 33880
  • /16

    $1,680 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
  • /16

    $1,940 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
  • /16

    $1,199 Per Month

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

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

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

    1007 37th St NW Unit 1, Winter Haven, FL 33881
  • /16

    $1,850 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
  • /13

    $1,195 Per Month

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

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

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

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

    $1,759 Per Month

    • 3 Beds
    • 2 Baths
    • 1,678 Sq Ft
    • House for Rent

    304 Kensington View Dr, Winter Haven, FL 33880

    This home is professionally managed by Tricon, dedicated to creating exceptional rental experiences. Featuring 3 bedrooms, 2.0 bathrooms, and approximately 1,678 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

    304 Kensington View Dr, Winter Haven, FL 33880
  • /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
  • /15

    $1,575 Per Month

    • 2 Beds
    • 2 Baths
    • 898 Sq Ft
    • Condo for Rent

    311 Ave Y NE Unit 311 Avenue Y NE Unit B, Winter Haven, FL 33881

    Property Id: 1444878 For Rent: Cozy 2-Bedroom Rent: $1,575/month Deposit: $1,575 Lawn Service is included. Lease Term: 1 year minimum Utilities: Tenant responsible for all utilities. Small Pets Only - Pet Fee $50 a Month, per pet. 2 Pet Max No Smoking Background & Credit Check Every individual aged 18 or older residing at the property and/or any

    311 Ave Y NE Unit 311 Avenue Y NE Unit B, Winter Haven, FL 33881
  • /16

    $1,199 Per Month

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

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

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

    1007 37th St NW Unit 1, Winter Haven, FL 33881
  • /20

    $1,995

    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
  • /15

    $1,600 Per Month

    • 1 Bed
    • 1.5 Baths
    • 807 Sq Ft
    • Condo for Rent

    235 6th St NW Unit 608, Winter Haven, FL 33881

    Property Id: 2808642 Charming Downtown Winter Haven Condo with Lake Views Experience the perfect blend of historic charm and modern comfort in this beautiful newly renovated one-bedroom, one-and-a-half-bath condominium located in The Haven Condominiums, a landmark building dating back to 1924 in the heart of downtown Winter Haven. Situated on the 6th floor, this inviting residence

    235 6th St NW Unit 608, Winter Haven, FL 33881
  • /15

    $1,665 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
  • /6

    $1,200 Per Month

    • 1 Bed
    • 1 Bath
    • House for Rent

    4320 Dundee Rd, Winter Haven, FL 33884

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

    4320 Dundee Rd, Winter Haven, FL 33884
  • /16

    $1,779 Per Month

    • 3 Beds
    • 2 Baths
    • 1,764 Sq Ft
    • House for Rent

    518 Squires Grove Dr, 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 1,764 square feet, this well-maintained home offers a high standard of rental living,

    518 Squires Grove Dr, Winter Haven, FL 33880
  • /16

    $1,730 Per Month

    • 3 Beds
    • 2 Baths
    • 1,475 Sq Ft
    • House for Rent

    2024 10th St NW, 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),

    2024 10th St NW, Winter Haven, FL 33881
  • /15

    $1,600 Per Month

    • 1 Bed
    • 1.5 Baths
    • 807 Sq Ft
    • Condo for Rent

    235 6th St NW Unit 608, Winter Haven, FL 33881

    Property Id: 2808642 Charming Downtown Winter Haven Condo with Lake Views Experience the perfect blend of historic charm and modern comfort in this beautiful newly renovated one-bedroom, one-and-a-half-bath condominium located in The Haven Condominiums, a landmark building dating back to 1924 in the heart of downtown Winter Haven. Situated on the 6th floor, this inviting residence

    235 6th St NW Unit 608, Winter Haven, FL 33881
  • /14

    $1,549 Per Month

    • 4 Beds
    • 1 Bath
    • 1,128 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, FL 3627 Ave S NW, Winter Haven, FL 33881 $1,549 / Month Move-in Ready & 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 play. The

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

    $1,735 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
  • /15

    $1,740 Per Month

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

    175 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

    175 Southern Breeze Lp, Winter Haven, FL 33880
  • /16

    $1,690 Per Month

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

    3740 Imperial 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 3.0-bedroom, 2.0-bathroom home is not only pet-friendly, but also equipped with smart home features to make everyday life more convenient and

    3740 Imperial Dr, Winter Haven, FL 33880
  • /17

    $1,849 Per Month

    • 3 Beds
    • 2 Baths
    • 1,541 Sq Ft
    • House for Rent

    417 Kensington View Dr, Winter Haven, FL 33880

    **MOVE IN SPECIAL! 2 WEEKS OFF FIRST FULL MONTH! Must pay deposit by 8/31/26!**This 3-bedroom, 2-bath home offers 1,541 square feet of thoughtfully designed, single-story living space. The open floor plan keeps the main living areas feeling connected, while the kitchen features granite countertops and stainless-steel appliances for a polished, modern look.The spacious living area

    417 Kensington View Dr, Winter Haven, FL 33880
  • /13

    $1,195 Per Month

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

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

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

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

    $995 Per Month

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

    3058 St Paul Dr, Jan Phyl Village, FL 33880

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

    3058 St Paul Dr, Jan Phyl Village, FL 33880
  • /16

    $1,790 Per Month

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

    2520 Ave a 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,

    2520 Ave a SW, Winter Haven, FL 33880
  • /20

    $1,800 Per Month

    • 4 Beds
    • 2 Baths
    • House for Rent

    1108 Carefree Cove Dr, Winter Haven, FL 33881

    Property Id: 1524046 Large House for a family with fenced in large yard, tiles floors, updated kitchen and bathrooms with lots of extras. Available July 2025. Please call both contact numbers to get more information on property and terms of rental.

    1108 Carefree Cove Dr, Winter Haven, FL 33881
  • /15

    $1,775 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
  • /3

    $1,550 Per Month

    • 3 Beds
    • 2 Baths
    • 1,242 Sq Ft
    • Condo for Rent

    2007 9th St NE, Winter Haven, FL 33881

    Welcome to your perfect rental in Winter Haven, Florida! This charming property offers a comfortable living space in a vibrant community, just minutes away from delightful dining options and major department stores. The Winter Haven Hospital is also conveniently located just six minutes from your doorstep, ensuring your peace of mind.Key property features include central heating and

    2007 9th St NE, Winter Haven, FL 33881
  • /15

    $1,855 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
  • /16

    $1,965 Per Month

    • 3 Beds
    • 2 Baths
    • 1,864 Sq Ft
    • House for Rent

    7172 Summit 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

    7172 Summit Dr, Winter Haven, FL 33884

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