896

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

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  • /20

    Starting at $950 Per Month

    • 1 Bed

    745 Avenue A SW, Winter Haven, FL 33880

    Lakeview Tower offers newly remodeled studio and one bedroom apartment homes. It is an exceptional senior living, 62+ and disabled Community. Lakeview Tower sits right on Lake Howard, allowing breath taking views from your window.

    Lakeview Tower

    745 Avenue A SW, Winter Haven, FL 33880
  • /9

    Starting at $975 Per Month

    • 1 Bed

    101-123 Oak Crest Dr NW, Winter Haven, FL 33881

    Ideally located with convenient access to US Hwy 17-92, I-4, and the greater Winter Haven and Central Florida area, this community offers both accessibility and comfort.Our cozy one-bedroom apartments feature energy-efficient central A/C, tile flooring, washer/dryer hookups, and newly updated appliances designed for everyday convenience.Residents enjoy scenic surroundings,

    Oakcrest Apartments

    101-123 Oak Crest Dr NW, 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
  • /12

    $2,050 Per Month

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

    1336 Axel Cir, Winter Haven, FL 33880

    Property Id: 836169 4 bedroom 2 Bathroom Single Family Home Easy 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. $2000 1st and Last and security due at move in. Well qualified applicants may be

    1336 Axel Cir, Winter Haven, FL 33880
  • /17

    $2,100 Per Month

    • 3 Beds
    • 2 Baths
    • 1,393 Sq Ft
    • House for Rent

    4651 Magnolia Ave, Winter Haven, FL 33880

    Property Id: 2816201 Welcome to this beautiful and well-maintained 3-bedroom, 2-bathroom home located in the Magnolia Preserve community of Winter Haven. Offering 1,393 sq. ft. of comfortable living space, this home features a desirable split-bedroom floor plan, providing added privacy with the primary suite located separately from the additional bedrooms. The home features newer

    4651 Magnolia Ave, 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
  • /17

    $2,489

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,636 Sq Ft
    • Condo for Rent

    1630 17th St NW Unit SI ID1545923P, Winter Haven, FL 33881

    The advertised rate of $2,490/month is the lowest available price, based on a 1 month(s) stay with a move-in date of November 1, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

    1630 17th St NW Unit SI ID1545923P, Winter Haven, FL 33881
  • /15

    $1,940 Per Month

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

    207 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

    207 Southern Breeze Lp, Winter Haven, FL 33880
  • /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
  • /15

    $2,115 Per Month

    • 5 Beds
    • 3 Baths
    • 2,566 Sq Ft
    • House for Rent

    957 Gotthard Pass Dr, Winter Haven, FL 33881

    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 5-bedroom, 3-bathroom rental home in Winter Haven, FL, may be the right place for you. Find hours of peace

    957 Gotthard Pass Dr, Winter Haven, FL 33881
  • /19

    $1,795 Per Month

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

    409 Kensington View Dr, Winter Haven, FL 33880

    Welcome to 409 Kensington View Dr., a newer 3-bedroom, 2-bathroom home in Winter Haven offering 1,541 square feet of comfortable living space. This inviting home features a bright, open-concept layout with a spacious living area and a modern kitchen equipped with a refrigerator and dishwasher. The thoughtfully designed floor plan provides comfortable bedrooms and two full bathrooms, creating a

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

    $1,870 Per Month

    • 3 Beds
    • 2 Baths
    • 1,942 Sq Ft
    • House for Rent

    536 Haines Trail, Winter Haven, FL 33881

    EXCITING NEWS: WE RECENTLY RENOVATED THIS HOME! IMPROVEMENTS INCLUDE: NEW LVP FLOORING IN COMMON LIVING AREAS OF THE HOME. 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

    536 Haines Trail, Winter Haven, FL 33881
  • /2

    $1,835 Per Month

    • 2 Beds
    • 1 Bath
    • 1,209 Sq Ft
    • House for Rent

    624 Lake Elizabeth 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

    624 Lake Elizabeth Dr, Winter Haven, FL 33884
  • /13

    $2,000 Per Month

    • 4 Beds
    • 2 Baths
    • 1,900 Sq Ft
    • House for Rent

    456 Adriel Ave, Winter Haven, FL 33880

    Property Id: 2814794 You can rent the entire 4 bedroom 2 bath. Or you can rent per room. 850 per room utilities included if renting per room. $950 for the master bedroom.

    456 Adriel Ave, Winter Haven, FL 33880
  • /15

    $2,025 Per Month

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

    349 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

    349 S Haven Ct, Winter Haven, FL 33880
  • /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
  • /16

    $1,969 Per Month

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

    991 Summer Glen 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 1,672 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

    991 Summer Glen Dr, Winter Haven, FL 33880
  • /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
  • /15

    $2,099 Per Month

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

    393 Kensington View Dr, Winter Haven, FL 33880

    ** MOVE IN SPECIAL! Get 4 Weeks FREE off 2nd Full Month with Deposit Paid by 8/31/26**This 3-bedroom, 2-bath home offers 1,678 square feet of living space with a layout designed for easy everyday living. The main living areas provide plenty of room to gather and unwind, while the kitchen keeps everything connected for casual meals and time spent at home.Three bedrooms give you

    393 Kensington View Dr, Winter Haven, FL 33880
  • /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
  • /20

    $2,495 Per Month

    • 2 Beds
    • 2 Baths
    • 1,162 Sq Ft
    • Condo for Rent

    235 6th St NW Unit 606, Winter Haven, FL 33881

    Property Id: 742061 Welcome to this beautifully renovated and professionally furnished top-floor 2-bedroom, 2-bath condo in The Haven, one of downtown Winter Haven's most distinctive historic buildings. The spacious living area features an 85" smart TV, comfortable seating, sleeper sofa and a striking custom feature wall. Original vintage Cypress Gardens water skis from the 1950s-60s

    235 6th St NW Unit 606, Winter Haven, FL 33881
  • /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
  • /13

    $1,899 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 $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

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

    $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
  • /15

    $2,050 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
  • /20

    $2,450 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,340 Sq Ft
    • House for Rent

    1273 Zambrana Ct, Winter Haven, FL 33884

    Property Id: 2739644 Welcome to your dream home in the Villa Mar community. The property is located at 1273 Zambrana Ct in Winter haven, FL! This stunning 4-bed, 2 1/2bath single-family home is available starting 7/27/2026 for $2450 a month. Enjoy modern amenities, stainless steel appliances, granite countertops, vinyl flooring upstairs, and tile downstairs. There is a playground and

    1273 Zambrana Ct, Winter Haven, FL 33884
  • /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
  • /15

    $2,225 Per Month

    • 4 Beds
    • 2 Baths
    • 1,774 Sq Ft
    • House for Rent

    1947 Bretton Ridge Dr, 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, could be just what you’re looking for. Enjoy

    1947 Bretton Ridge Dr, Winter Haven, FL 33884

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How to Rent a Home