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

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  $1,919 per month

  • 4 Beds
  • 2 Baths
  • 1,707 Sq Ft
  • House for Rent

  Unlisted Address

  Take a look at this beautiful home, Clean and Move-In Ready, featuring 4 bedrooms, 2 bathrooms, 2 car garage and approximately 1,707 heated square feet. Enjoy the freedom of a virtually maintenance free lifestyle while residing in a great community. Smart Home Tech - $21.95/mo; Washer/Dryer - $35/mo; High Speed Cable/Internet (if applicable by 3rd Party user) $55/mo; Renters insurance reqrd, Pool

  Cathy Behe TAH FLORIDA LLC

  Unlisted Address
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  /17

  $2,249 per month

  • 4 Beds
  • 2 Baths
  • 2,240 Sq Ft
  • House for Rent

  1008 Talon Ln, Winter Haven, FL 33880

  This home is professionally managed by Tricon, dedicated to creating exceptional rental experiences. Featuring 4 bedrooms, 2.5 bathrooms, and approximately 2,240 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

  1008 Talon Ln, Winter Haven, FL 33880
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  $1,800 per month

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

  5202 Waterview Way, Winter Haven, FL 33884

  A comfortable first-floor 2 bed, 2 bath condo in the gated Winterset community, this home offers an easy, open layout with plenty of natural light and convenient ground-level access. Each bedroom has its own full bathroom, giving you a setup that works well for roommates, guests, or anyone who wants a little extra privacy. The condo can be leased furnished for a turnkey move-in or unfurnished if

  Christin Davis PROPERTY MANAGEMENT OF POLK

  5202 Waterview Way, Winter Haven, FL 33884
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  /18

  $1,955 per month

  • 4 Beds
  • 2 Baths
  • 1,715 Sq Ft
  • House for Rent

  851 Orleans Dr, Eagle Lake, FL 33839

  Some photos may feature virtual furniture staging, which is intended to help visualize the space and potential designs. The rental home does not come with any furniture shown in the images and these virtual images do not represent actual furnishings. Residents must furnish their own home.Please note that the advertised price may exclude additional fees. These include a $55 application fee per

  851 Orleans Dr, Eagle Lake, FL 33839
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  $2,200 per month

  • 5 Beds
  • 2.5 Baths
  • 2,254 Sq Ft
  • House for Rent

  1454 Austin St, Winter Haven, FL 33884

  Located in Peace Creek Reserve, one of Winter Haven's most peaceful and well-connected residential areas, this property is back on the market and represents a rare opportunity. If you're looking for space, functionality, and quality of life in a natural setting with immediate access to lakes, trails, shopping, and major roads, this is your best option for your next home. This spacious 5-bedroom

  Carla Moreno Pineda EXP REALTY LLC

  1454 Austin St, Winter Haven, FL 33884
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  $1,820 per month

  • 3 Beds
  • 2 Baths
  • 1,252 Sq Ft
  • House for Rent

  3728 Imperial 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 + $35/mo per pet. Some homes may include pool ($150/mo), septic ($15/mo), and/or HOA fees; other fees may apply.

  3728 Imperial Dr, Winter Haven, FL 33880
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  $1,800 per month

  • 4 Beds
  • 2 Baths
  • 1,822 Sq Ft
  • House for Rent

  2363 Twin Lake View Rd, Winter Haven, FL 33881

  MOVE-IN READY in Winter Haven!? Looking for a remodeled home with space, style, and a fenced yard? This 4BR/2BA beauty in Eagle Crest checks every box! Fresh + Updated Vaulted ceilings & wood-look floors Bright kitchen w/ stainless steel appliances Open living & dining leading to a covered lanai Spacious primary suite w/ dual vanities + soaking tub Interior laundry 2-car garage. Fully fenced

  Maria Villacis AVANTI WAY REALTY LLC

  2363 Twin Lake View Rd, Winter Haven, FL 33881
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  /15

  $2,265 per month

  • 3 Beds
  • 2 Baths
  • 1,444 Sq Ft
  • House for Rent

  437 Kensington View Dr, Winter Haven, FL 33880

  We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home

  437 Kensington View Dr, Winter Haven, FL 33880
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  $1,500 per month

  • 1 Bed
  • 1 Bath
  • 2,093 Sq Ft
  • House for Rent

  1313 Diego Terrace Unit In-Law Suite, Winter Haven, FL 33884

  One or more photo(s) has been virtually staged. For Rent: Charming In-Law Suite in Winter Haven, FL – $1,500/Month Looking for a cozy and private living space in a beautiful community? This in-law suite in Winter Haven, FL offers comfort, convenience, and access to great amenities. Key Features: Monthly Rent: $1,500 Lease Term: Minimum 12 months Security Deposit: $1,500 Requirements: First

  Andrea Jastemski DALTON WADE INC

  1313 Diego Terrace Unit In-Law Suite, Winter Haven, FL 33884
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  /15

  $2,090 per month

  • 4 Beds
  • 2 Baths
  • 1,786 Sq Ft
  • House for Rent

  107 Fall Glo Rd, Winter Haven, FL 33880

  Please note that the advertised price may exclude additional fees. These include a $55 application fee per applicant; a one-time $75 admin fee; a $11 monthly utility management fee; other mandatory fees, if applicable, for pool maintenance, pet fees/rent, smart home, internet service, and propane refilling; and optional fees for services like self-guided tours with third-party provider Rently

  107 Fall Glo Rd, Winter Haven, FL 33880
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  $1,975 per month

  • 4 Beds
  • 2 Baths
  • 2,150 Sq Ft
  • House for Rent

  2702 Rochelle Dr, Winter Haven, FL 33881

  HOME IS REALTY BEAUTIFUL WIDE OPEN FLOOR PLAN. VAULTED CEILING IN PART OF HOME. A MUST TO SEE.

  William Beasley STAR REALTY OF WINTER HAVEN

  2702 Rochelle Dr, Winter Haven, FL 33881
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  /15

  $1,935 per month

  • 4 Beds
  • 2 Baths
  • 1,989 Sq Ft
  • House for Rent

  948 Gotthard Pass Dr, Winter Haven, FL 33881

  We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home

  948 Gotthard Pass Dr, Winter Haven, FL 33881
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  $1,595 per month

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

  113 Avenue C SE, Winter Haven, FL 33880

  Welcome to 113 Avenue C SE, Winter Haven – a freshly updated and cozy 3-bedroom, 1-bathroom home perfect for a new family! This home boasts gorgeous hardwood floors throughout, a beautifully updated kitchen and bathroom, and central air for year-round comfort. A washer and dryer are conveniently included, (tenant is responsible for ALL UTILITIES INCLUDING Water, electric and cable/internet). The

  Nomar Rosa LPT REALTY, LLC

  113 Avenue C SE, Winter Haven, FL 33880
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  $1,952 per month

  • 3 Beds
  • 2 Baths
  • 1,690 Sq Ft
  • House for Rent

  237 St Georges Cir, Eagle Lake, FL 33839

  Property Id: 1568095This 1690 square foot single family home has 3 bedrooms and 2 bathrooms for rent. Completely fenced in neighborhood. Included an attached 2-car garage. Home was built in 2020. NEW LUXURY LAMINATE FLOORS installed before you move in! $1950 per month + $2 ACH transaction fee = $1952 per month for a year contract . Shorter terms are negotiable for a higher

  237 St Georges Cir, Eagle Lake, FL 33839
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  $1,750 per month

  • 2 Beds
  • 2 Baths
  • 1,490 Sq Ft
  • House for Rent

  14 Lamplight Ln, Winter Haven, FL 33884

  Welcome to 14 Lamplight Lane in beautiful Winter Haven — a delightful 2-bedroom, 2-bath home offering 1,490 square feet of comfortable living space plus a versatile bonus room that adds flexibility to fit your lifestyle. This inviting residence features a bright and open living area filled with natural light, creating a warm and welcoming atmosphere from the moment you step inside. With 1,490

  Leila Torres LA ROSA REALTY PRESTIGE

  14 Lamplight Ln, Winter Haven, FL 33884
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  /20

  $2,025 per month

  • 4 Beds
  • 2 Baths
  • 2,004 Sq Ft
  • House for Rent

  613 Sarner Pass Way, Winter Haven, FL 33881

  This property is available. Please inquire on this site to schedule a showing. Welcome to 613 Sarner Pass Way, located in the serene and charming community of Winter Haven, FL. This delightful single-story home boasts a modern and inviting open floor plan, perfect for both relaxation and entertaining. The expansive living area is adorned with beautiful wood-look flooring and flows

  613 Sarner Pass Way, Winter Haven, FL 33881
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  $2,172 per month

  • 4 Beds
  • 2.5 Baths
  • 1,880 Sq Ft
  • House for Rent

  6424 Domizio Dr, Winter Haven, FL 33884

  One or more photo(s) has been virtually staged. Welcome to this brand-new 2025-built home located in the highly desirable Villa Mar community in Winter Haven. Offering 4 bedrooms, 2 full bathrooms, and 1 half bath, this modern residence combines style, functionality, and comfort in one beautifully designed floor plan. Step inside to an open-concept layout filled with natural light, creating the

  Rodrigo Araujo Machado WRA BUSINESS & REAL ESTATE

  6424 Domizio Dr, Winter Haven, FL 33884
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  /15

  $1,915 per month

  • 2 Beds
  • 2 Baths
  • 1,143 Sq Ft
  • House for Rent

  1095 Sunshine Way SW, Winter Haven, FL 33880

  We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home

  1095 Sunshine Way SW, Winter Haven, FL 33880
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  $1,795 per month

  • 3 Beds
  • 2 Baths
  • 1,269 Sq Ft
  • House for Rent

  3063 Laurel Oak Ln, Winter Haven, FL 33884

  2ND MONTH RENT FREE: Move-In Ready, Pet-Friendly, 2-Car Garage! Available for immediate occupancy! Step into this stunning 2023 Meritage Home in the heart of Winter Haven, Florida—a highly upgraded 3-bedroom, 2-bath single-story home designed to impress. This move-in ready home features neutral tones throughout, a chef-inspired kitchen with stainless steel appliances, quartz countertops, and a

  Katrina Anarumo RENT A FLORIDA HOME

  3063 Laurel Oak Ln, Winter Haven, FL 33884
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  /17

  $1,810 per month

  • 3 Beds
  • 2 Baths
  • 1,950 Sq Ft
  • House for Rent

  3236 Timberline 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,

  3236 Timberline Rd, Winter Haven, FL 33880
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  $1,295 per month

  • 1 Bed
  • 1 Bath
  • 900 Sq Ft
  • House for Rent

  320 Spirit Landings Cir, Winter Haven, FL 33880

  Fully furnished 1-bedroom apartment available for immediate occupancy. Rent includes all utilities electric, water, internet, and trash providing a truly hassle-free living experience. Well-maintained unit featuring comfortable furnishings, a functional layout, and abundant natural light. Ideal for professionals, traveling nurses, or anyone seeking a turnkey rental. Conveniently located near

  Laura Medina Ruiz RE/MAX HERITAGE PROFESSIONALS

  320 Spirit Landings Cir, Winter Haven, FL 33880
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  /19

  $2,139 per month

  • 4 Beds
  • 2 Baths
  • 1,714 Sq Ft
  • House for Rent

  1016 15th St NE, Winter Haven, FL 33881

  Coming soon - this home is currently being enjoyed by another resident but will be available soon. Pre-lease this home now with Tricon Pre-Lease Guarantee. This home is professionally managed by Tricon, dedicated to creating exceptional rental experiences. Featuring 4 bedrooms, 2.0 bathrooms, and approximately 1,714 square feet, this well-maintained home offers a high standard of rental living,

  1016 15th St NE, Winter Haven, FL 33881
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  $2,250 per month

  • 4 Beds
  • 2 Baths
  • 1,811 Sq Ft
  • House for Rent

  5465 San Pietro Dr, Winter Haven, FL 33884

  Be the first to live in this brand new 4 bedroom, 2 bath home located in the highly desirable Villa Mar community in Winter Haven. Featuring 1,811 sq ft of thoughtfully designed living space with an open-concept floor plan, this home is perfect for modern family living or entertaining guests. The spacious kitchen showcases contemporary finishes, ample cabinetry, and an island that flows into the

  Veronica Martinez MY REALTY GROUP, LLC.

  5465 San Pietro Dr, Winter Haven, FL 33884
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  /17

  $2,000 per month

  • 4 Beds
  • 2.5 Baths
  • 1,889 Sq Ft
  • House for Rent

  2753 Whispering Trails Dr, Winter Haven, FL 33884

  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,

  2753 Whispering Trails Dr, Winter Haven, FL 33884
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  $2,150 per month

  • 4 Beds
  • 2 Baths
  • 1,848 Sq Ft
  • House for Rent

  724 Grove St, Winter Haven, FL 33884

  Modern 4-Bedroom Home for Rent – Winter Haven, FLWelcome to 724 Grove Street, Winter Haven, FL 33881, a beautiful single-story home built in 2023 and located in the desirable Inman Groves Phase 2 community. This spacious residence offers 4 bedrooms, 2 bathrooms, and 1,848 sq ft of comfortable living space with a modern, open layout designed for everyday convenience. Property

  Maria Carolina Lopez LOKATION

  724 Grove St, Winter Haven, FL 33884
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  /18

  $2,140 per month

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

  5882 Windridge Dr, Winter Haven, FL 33881

  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 $2284.90. That covers your base rent, $2140.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  5882 Windridge Dr, Winter Haven, FL 33881
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  $1,749 per month

  • 3 Beds
  • 2 Baths
  • 1,718 Sq Ft
  • House for Rent

  Unlisted Address

  Take a look at this beautiful home, Clean and Move-In Ready, featuring 3 bedrooms, 2 bathrooms, 2 car garage and approximately 1,718 heated square feet. Enjoy the freedom of a virtually maintenance free lifestyle while residing in a great community. Smart Home Tech - $21.95/mo; Washer/Dryer - $35/mo; High Speed Cable/Internet (if applicable by 3rd Party user) $55/mo; Renters insurance reqrd, Pool

  Cathy Behe TAH FLORIDA LLC

  Unlisted Address
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  /16

  $1,935 per month

  • 3 Beds
  • 2 Baths
  • 1,431 Sq Ft
  • House for Rent

  92 Lake Daisy Blvd, 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 features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at Coming soon! This home is

  92 Lake Daisy Blvd, Winter Haven, FL 33884
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  $1,425 per month

  • 2 Beds
  • 2 Baths
  • 1,148 Sq Ft
  • Condo for Rent

  1550 11th St NE Unit B6, Winter Haven, FL 33881

  Enjoy this modern, remodeled 2/2 condo. This condo features granite countertops and has a washer/dryer inside the unit. Enjoy the most peaceful views of the lake and pool from the back porch. Renters insurance is required.

  Mindy Hunley TRIBUTE REALTY LLC

  1550 11th St NE Unit B6, Winter Haven, FL 33881
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  /19

  $1,760 per month

  • 3 Beds
  • 2 Baths
  • 1,632 Sq Ft
  • House for Rent

  3634 Queens Cove Blvd, Winter Haven, FL 33880

  We are currently making final preparations for this home to be available. We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be

  3634 Queens Cove Blvd, Winter Haven, FL 33880
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  $2,390 per month

  • 6 Beds
  • 3 Baths
  • 2,463 Sq Ft
  • House for Rent

  2142 Chris Dr, Winter Haven, FL 33884

  Brand new, never-lived-in house for rent in Winter Haven! Beautiful two-story, brand new, never-lived-in house featuring 6 bedrooms and 3 full bathrooms, ideal for families seeking comfort, space, and modern living. The home offers a modern open-concept layout with spacious, bright interiors. At the entrance, a welcoming porch with a garden adds charm and curb appeal. The main living area

  Jessyka Dos Santos WRA BUSINESS & REAL ESTATE

  2142 Chris Dr, Winter Haven, FL 33884
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  /16

  $1,740 per month

  • 3 Beds
  • 1 Bath
  • 1,120 Sq Ft
  • House for Rent

  240 16th St NE, Winter Haven, FL 33881

  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 + $35/mo per pet. Some homes may include pool ($150/mo), septic ($15/mo), and/or HOA fees; other fees may apply.

  240 16th St NE, Winter Haven, FL 33881
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  $1,100 per month

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • Apartment for Rent

  102 Oak Crest Dr NW Unit 106, Winter Haven, FL 33881

  HALF OFF FIRST MONTHS RENT! Recently updated apartment available for lease! This bright and comfortable unit features updated cabinets, crown molding, ceiling fans, and modern light fixtures throughout, making it both stylish and easy to maintain. Enjoy private off-street parking. Located on a quiet street with no thru traffic and just minutes from shopping, dining, parks, and everyday

  David Small KELLER WILLIAMS REALTY SMART 1

  102 Oak Crest Dr NW Unit 106, Winter Haven, FL 33881
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  /20

  $2,490 total monthly price

  • 5 Beds
  • 3 Baths
  • 2,387 Sq Ft
  • House for Rent

  4890 St James Ln, Winter Haven, FL 33881

  Special security deposit offer: Pay just 50% of your base rent as your security deposit (taxes and fees not included), valid for new applicants who sign a 12-month lease by April 30, 2026. Offer is contingent on application approval and execution of a lease agreement. Other terms and conditions may apply. This home, constructed in 2017, is located in the St James Crossing community. This property

  4890 St James Ln, Winter Haven, FL 33881
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  $1,100 per month

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • Apartment for Rent

  118 Oak Crest Dr NW, Winter Haven, FL 33881

  HALF OFF FIRST MONTHS RENT! Recently updated apartment available for lease! This bright and comfortable unit features updated cabinets, crown molding, ceiling fans, and modern light fixtures throughout, making it both stylish and easy to maintain. Enjoy private off-street parking. Located on a quiet street with no thru traffic and just minutes from shopping, dining, parks, and everyday

  David Small KELLER WILLIAMS REALTY SMART 1

  118 Oak Crest Dr NW, Winter Haven, FL 33881
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  $1,920 per month

  • 3 Beds
  • 2 Baths
  • 2,018 Sq Ft
  • House for Rent

  2610 Ave N NW, Winter Haven, FL 33881

  MOVE-IN READYThis home is move-in ready. Schedule your tour now or start your application today.Monthly Recurring Fees:$25.00 - Smart Home$10.95 - Utility ManagementSet in Northwest Winter Haven, this 3-bedroom, 2-bathroom home offers 2,018 square feet of thoughtfully designed living space just minutes from the Chain of Lakes. With convenient access to Downtown

  2610 Ave N NW, Winter Haven, FL 33881
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  /22

  $2,030 per month

  • 4 Beds
  • 2 Baths
  • 1,824 Sq Ft
  • House for Rent

  2122 Chris Dr, Winter Haven, FL 33884

  Beautiful brand-new 4-bedroom, 2-bathroom home located in a great area of Winter Haven. The property features a charming front porch, perfect for relaxing. Inside, the home offers a spacious open-concept living room seamlessly connected to the dining area and kitchen, creating a modern and functional layout. Sliding glass doors provide access to a large outdoor area, ideal for entertaining and

  Jessyka Dos Santos WRA BUSINESS & REAL ESTATE

  2122 Chris Dr, Winter Haven, FL 33884
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  /15

  $2,165 per month

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

  104 Southern Breeze Lp, Winter Haven, FL 33880

  We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home

  104 Southern Breeze Lp, Winter Haven, FL 33880
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  $2,220 per month

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

  2134 Chris Dr, Winter Haven, FL 33884

  Brand New Two-Story Home for Rent in Winter Haven Welcome to this stunning brand new two-story home located in the heart of Winter Haven, offering the perfect combination of space, style, and convenience. Designed with modern living in mind, this beautiful property is ideal for families or anyone looking for comfort and quality in a prime location. The home features 5 spacious bedrooms, including

  Jessyka Dos Santos WRA BUSINESS & REAL ESTATE

  2134 Chris Dr, Winter Haven, FL 33884
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  /17

  $2,299 per month

  • 3 Beds
  • 2 Baths
  • 2,136 Sq Ft
  • House for Rent

  443 Sandestin Dr SE, Winter Haven, FL 33884

  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 2,136 square feet, this well-maintained home offers a high standard of rental living, supported by a team that puts residents first. As a

  443 Sandestin Dr SE, Winter Haven, FL 33884

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