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

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  $1,900 per month

  • 3 Beds
  • 2 Baths
  • 1,268 Sq Ft
  • House for Rent

  2893 Whispering Trails Dr, Winter Haven, FL 33884

  This cozy and well-maintained home offers a warm and inviting layout, ideal for comfortable and easy living. The property features a functional floor plan with a modern kitchen, bright and spacious bedrooms, and low-maintenance living areas designed for convenience. Centrally located with quick access to US-27, US-17, SR-540, and I-4, this home provides easy commutes to Orlando and Tampa, as well

  Jenny Caso LIFESTYLE INTERNATIONAL REALTY

  2893 Whispering Trails Dr, Winter Haven, FL 33884
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  $1,785 per month

  • 3 Beds
  • 1 Bath
  • 1,089 Sq Ft
  • House for Rent

  309 Vaniman Ave, Winter Haven, FL 33880

  Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.This home 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 This home is priced to rent

  309 Vaniman Ave, Winter Haven, FL 33880
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  $2,000 per month

  • 3 Beds
  • 1 Bath
  • 1,602 Sq Ft
  • House for Rent

  3022 Hickory St NW, Winter Haven, FL 33881

  Welcome to this incredible Winter Haven pool home offering the perfect blend of comfort, upgrades, and true Florida lifestyle living. This move-in ready 3-bedroom home sits on a large oversized lot and is ideal for first-time homebuyers, families, or investors looking for a prime Central Florida opportunity. Step inside to find generous living space, a functional layout, and fresh upgrades that

  Ashlee Morrell THE URBAN GROUP, INC.

  3022 Hickory St NW, Winter Haven, FL 33881
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  $1,950 per month

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

  175 Grove Branch Rd, Winter Haven, FL 33880

  Property Id: 2402477Welcome Home This gorgeous modern 3 bed 2 bath and 2 car garage is located in beautiful Winter Haven. This is very open and spacious split floor plan. Perfect for entertaining. Kitchen is tastefully designed with espresso brown 42" cabinets and features an island overlooking the family room. Large pantry closet. Master bedroom suite offers a large walk-in closet and an

  175 Grove Branch Rd, Winter Haven, FL 33880
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  /15

  $1,895 per month

  • 4 Beds
  • 2 Baths
  • 1,566 Sq Ft
  • House for Rent

  1341 Avenue S NW, Winter Haven, FL 33881

  4/2 home in Winter Haven available now! Features ceramic tile and laminate flooring, inside laundry room, nice yard, and 2 car carport. Approval subject to credit, income, and rental verification.

  Tracey Crews SUPERIOR PROPERTY MGMT & SALES

  1341 Avenue S NW, Winter Haven, FL 33881
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  /17

  $1,815 per month

  • 3 Beds
  • 2.5 Baths
  • 1,320 Sq Ft
  • House for Rent

  669 Lake Dexter Cir, Winter Haven, FL 33884

  Beautiful, pet-friendly home coming soon! Apply now, Move-In is available on or after the listed date. Upon approval, $500 reservation deposit to reserve (applied to security deposit and/or refundable). Application fee: $50 per adult. Security Deposit: one month?s rent. Pet fees: $250 + $40/mo per pet. Some homes may include pool ($150/mo), septic ($15/mo), and/or HOA fees; other fees may apply.

  669 Lake Dexter Cir, Winter Haven, FL 33884
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  $1,700 per month

  • 3 Beds
  • 2 Baths
  • 1,662 Sq Ft
  • House for Rent

  1019 Mockingbird Cir, Winter Haven, FL 33884

  3 bedroom 2 bath home with 2 car garage located in SE Winter Haven near Legoland. Modern custom cabinets throughout the home, open island kitchen design with pantry, bedrooms with plenty of closet space. Large master suite with roomy walk-in closet, spacious tiled master bath, and sliding doors to screened porch. Double pane windows throughout. Fenced yard. Located in a family friendly

  Donna Williams REMAX EXPERTS

  1019 Mockingbird Cir, Winter Haven, FL 33884
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  /20

  $1,849 per month

  • 3 Beds
  • 2 Baths
  • 1,442 Sq Ft
  • House for Rent

  509 Kensington View Dr, Winter Haven, FL 33880

  Sign in by April 17, Get 4 Weeks Free! Discover spacious homes for rent at Kensington View in Winter Haven, FL. Pet-friendly living with access to Lakeland and Tampa Bay. Professionally managed by ARK Homes.

  509 Kensington View Dr, Winter Haven, FL 33880
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  $1,900 per month

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

  235 Hayley St, Winter Haven, FL 33884

  Beautiful 3-bedroom, 2-bathroom home located at 235 Hayley St, Winter Haven, FL 33884. This well-maintained property offers a comfortable and functional layout, perfect for families or anyone seeking a peaceful living environment. Enjoy a bright and inviting interior, with spacious living areas and a practical floor plan designed for everyday living. The home provides a great balance of comfort

  Djanira Puyosa LA ROSA REALTY LLC

  235 Hayley St, Winter Haven, FL 33884
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  $1,800 per month

  • 3 Beds
  • 2 Baths
  • 1,177 Sq Ft
  • House for Rent

  2006 34th St NW, Winter Haven, FL 33881

  Property Id: 2400855This beautifully maintained 3-bedroom, 2-bath home is now available for rent! Originally listed for sale, this property offers exceptional space, accessibility, and flexibility for a variety of living needs.Designed with wheelchair accessibility in mind, the home features wide entryways and a fully accessible bathroom while still maintaining a stylish,

  2006 34th St NW, Winter Haven, FL 33881
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  $1,749 per month

  • 3 Beds
  • 2 Baths
  • 1,329 Sq Ft
  • House for Rent

  3032 Spirit Lake Dr, Winter Haven, FL 33880

  One or more photo(s) has been virtually staged. Check out this 3 bedroom 2 bath totally renovated an updated home. The gorgouse home offers so much! Updated kitchen with granite solid surface counter tops, stainless steel applainces and closet pantry. The home offers an open floor plan. Spacious master bedroom with an totally updated ensute master bath that offers a step in glass shower and

  John-Michael Elliott S & D REAL ESTATE SERVICE LLC

  3032 Spirit Lake Dr, Winter Haven, FL 33880
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  $1,790 per month

  • 4 Beds
  • 2 Baths
  • 1,874 Sq Ft
  • House for Rent

  637 Sunway Ln, Winter Haven, FL 33880

  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

  637 Sunway Ln, Winter Haven, FL 33880
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  $1,675 per month

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

  165 Osprey Heights Dr, Winter Haven, FL 33880

  Welcome home to 165 Osprey Heights Drive! This well-maintained 3-bedroom, 2-bath home offers a desirable split floor plan, providing both privacy and functionality. The home features brand-new vinyl flooring in the main living areas and fresh interior paint, giving it a clean, updated feel throughout. The bedrooms are comfortably carpeted, creating a warm and cozy retreat. The kitchen is both

  William Beasley STAR REALTY OF WINTER HAVEN

  165 Osprey Heights Dr, Winter Haven, FL 33880
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  $1,745 per month

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

  1405 N Lake Shipp Dr 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,

  1405 N Lake Shipp Dr SW, Winter Haven, FL 33880
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  $1,750 per month

  • 3 Beds
  • 2 Baths
  • 1,450 Sq Ft
  • House for Rent

  506 Eagle Landing Blvd, Winter Haven, FL 33880

  Make this your new home today! This property will not last long! Live in this 3 Bedroom, 2 Bathroom home for rent in Winter Haven! Located in the Eagle Landing Subdivision. Corner Lot one-story Home. Open Floor Plan. Open Kitchen with Breakfast Bar features granite countertops, and al Stainless Steel Kitchen Appliances are included (Refrigerator, Dishwasher, Range, and Microwave. Living & Dining

  Elizabeth Santiago ALLEGIANT MANAGEMENT GROUP INC

  506 Eagle Landing Blvd, Winter Haven, FL 33880
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  $1,795 per month

  • 3 Beds
  • 2 Baths
  • 1,358 Sq Ft
  • House for Rent

  329 Gretna Ln, Winter Haven, FL 33880

  All Bridge Homes listings are pet-friendly and offer easy self-toursschedule 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. Introducing 329 Gretna -This open-concept home features: Bright, modern kitchen with tiled floors, a breakfast nook,

  329 Gretna Ln, Winter Haven, FL 33880
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  $2,000 per month

  • 4 Beds
  • 2 Baths
  • 1,717 Sq Ft
  • House for Rent

  213 Lake Lucerne Way, Winter Haven, FL 33881

  Welcome to your next home! This well-maintained 4-bedroom, 2-bathroom home offers 1,701 sq. ft. of comfortable living space with an open-concept layout that creates a bright and inviting atmosphere—perfect for relaxing or entertaining family and friends.Located in a friendly and welcoming community, residents enjoy access to the community pool and playground, providing great options for

  Yashira Arroyo UNITED REALTY GROUP INC

  213 Lake Lucerne Way, Winter Haven, FL 33881
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  $1,665 per month

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

  1333 Stately Oaks Dr NW, 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 $1799.95. That covers your base rent, $1665.00 + our required services designed to make your life easier: Internet & Media ($85), Smart Home with

  1333 Stately Oaks Dr NW, Winter Haven, FL 33881
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  /21

  $1,600 per month

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • House for Rent

  1661 Teagan Ln, Winter Haven, FL 33884

  3beds,2baths 2024 built. Available immediately.

  Lora Harper Keller Williams Realty of PSL

  1661 Teagan Ln, Winter Haven, FL 33884
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  /19

  $1,900 per month

  • 4 Beds
  • 2 Baths
  • 1,458 Sq Ft
  • House for Rent

  822 Terranova Rd, 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

  822 Terranova Rd, Winter Haven, FL 33884
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  $1,950 per month

  • 3 Beds
  • 2 Baths
  • 2,080 Sq Ft
  • House for Rent

  855 Turner Ln, Winter Haven, FL 33884

  Amazing location! In this beautiful house you will find a 3 bedroom 2 full bath and a bonus room (use it as an extra bedroom, office, etc.) This modern house sits on a corner lot, spacious living area, very sunny and inviting, ceramic tiles, stainless steal appliances, quartz counter tops, walking closet and a 2 car garage. Call to schedule a showing and move in to this lovely community.

  Britzeida Pichardo LA ROSA REALTY CENTRAL FLORIDA LLC

  855 Turner Ln, Winter Haven, FL 33884
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  /15

  $1,945 per month

  • 4 Beds
  • 2 Baths
  • 1,874 Sq Ft
  • House for Rent

  930 Deming Dr, 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,

  930 Deming Dr, Winter Haven, FL 33880
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  $1,850 per month

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

  44 Saint Kitts Cir, Winter Haven, FL 33884

  Now available for rent in desirable Planter’s Walk! This beautifully updated 3-bedroom, 2-bath home features ceramic tile flooring throughout, a remodeled kitchen with quartz countertops and new cabinets, vaulted ceilings, and a spacious open layout filled with natural light. Enjoy a large Florida room, screened porch, and a fully fenced backyard with shed—perfect for relaxing or entertaining.

  Manny Quiros RE/MAX HERITAGE PROFESSIONALS

  44 Saint Kitts Cir, Winter Haven, FL 33884
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  $1,780 per month

  • 3 Beds
  • 2 Baths
  • 1,316 Sq Ft
  • House for Rent

  3320 Timberline Rd W, Winter Haven, FL 33880

  Beautiful, pet-friendly home coming soon! Apply now, Move-In is available on or after the listed date. Upon approval, $500 reservation deposit to reserve (applied to security deposit and/or refundable). Application fee: $50 per adult. Security Deposit: one month?s rent. Pet fees: $250 + $40/mo per pet. Some homes may include pool ($150/mo), septic ($15/mo), and/or HOA fees; other fees may apply.

  3320 Timberline Rd W, Winter Haven, FL 33880
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  $1,475 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 Lease: Private In-Law Suite in Winter Haven, FL – $1,500/Month Looking for a clean, private rental in Winter Haven? This 450 sq. ft. in-law suite offers comfortable living in a quiet, well-located neighborhood. Important: This is a separate in-law suite attached to the main home. The main house is owner-occupied. This listing is not for the full

  Andrea Jastemski DALTON WADE INC

  1313 Diego Terrace Unit In-Law Suite, Winter Haven, FL 33884
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  $1,910 per month

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

  171 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.Please note that the advertised price may exclude additional fees. These include a $55 application fee per

  171 Southern Breeze Lp, Winter Haven, FL 33880
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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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  $1,525 total monthly price

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • House for Rent

  1407 N Lake Shipp Dr SW, Winter Haven, FL 33880

  rent ready 2/1 in Winter Haven Fl. Home has central heat and air, screened front porch and a 1 car carport with attached utility room. Nice size yard with small shed for you yard tools.

  1407 N Lake Shipp Dr 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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  $1,950 total monthly price

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

  336 Kayden Cove, Winter Haven, FL 33884

  “Se están ACEPTANDO todos los programas de asistencia para la vivienda “Se consideran vales de viviendaEsta encantadora casa de 3 dormitorios y 2 baños está lista para recibirte, con una cocina moderna con una amplia isla y electrodomésticos.Disfruta de un garaje para dos autos en la casa y otros dos en el exterior, un hermoso patio y un total de 1444 pies cuadrados de

  336 Kayden Cove, Winter Haven, FL 33884
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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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  $1,550 total monthly price

  • 2 Beds
  • 1 Bath
  • 780 Sq Ft
  • House for Rent

  5626 Struthers Ct, Winter Haven, FL 33884

  2BR / 1BA Duplex • Washer/Dryer • New A/C • $1,550 • Available April 6Clean and well-maintained 2 bedroom / 1 bathroom duplex located in a quiet Winter Haven neighborhood near US-27 and Legoland.Features:• Washer & dryer included• New central A/C• Tile flooring throughout (no carpet)• Bright, open living space• Large shared yard• 2 parking

  5626 Struthers Ct, Winter Haven, FL 33884
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  $1,799 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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  $1,930 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,420 Sq Ft
  • House for Rent

  1435 Axel Cir, Winter Haven, FL 33880

  1435 Axel Cir, Winter Haven, FL 33880
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  $2,000 per month

  • 3 Beds
  • 2 Baths
  • 1,390 Sq Ft
  • House for Rent

  137 Woodland Dr, Winter Haven, FL 33881

  Like-new 3 bedroom, 2 bathroom home with only one previous tenant. No carpet throughout—easy-care flooring in every room. Open and functional layout with modern finishes, well-maintained and move-in ready.

  Mindy Hunley TRIBUTE REALTY LLC

  137 Woodland Dr, Winter Haven, FL 33881
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  $1,900 per month

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

  820 Sun Burst Rd, Winter Haven, FL 33880

  Beautiful 4-Bedroom Home in Squires Grove – Built in 2022! Welcome to this stunning 4-bedroom, 2-bathroom single-family home located in the desirable Squires Grove community. Built in 2022, this modern home offers 1,851 sq. ft. of thoughtfully designed living space with a spacious 2-car garage. You'll love the open floor plan, perfect for both everyday living and entertaining. The kitchen flows

  Nicole Torres AZURE REAL ESTATE & PROPERTY MANAGEMENT GROUP LLC

  820 Sun Burst Rd, Winter Haven, FL 33880
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  $1,900 per month

  • 3 Beds
  • 2.5 Baths
  • 1,625 Sq Ft
  • House for Rent

  2521 Pine Place, Winter Haven, FL 33881

  One or more photo(s) has been virtually staged. Welcome to 2521 Pine Pl, where modern elegance meets peaceful lakefront living. This beautifully designed 3-bedroom, 2.5-bath home offers spectacular lake views right from your backyard, creating the perfect backdrop for morning coffee, sunset relaxation, or weekend gatherings. Inside, enjoy a bright open-concept floor plan, a sleek contemporary

  Jacob Hara TRANSCEND REALTY

  2521 Pine Place, Winter Haven, FL 33881
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  /17

  $1,850 per month

  • 4 Beds
  • 2 Baths
  • 1,688 Sq Ft
  • House for Rent

  4819 Summerfield Cir, Winter Haven, FL 33881

  Super Cute Home features 4 bedroom, 2 bath, 2 car garage home, located in Country Club Estates. Freshly painted a neutral color, tile in living areas and brand new LVP in bedroom. Living room kitchen combo, great for family time. Call today for a showing!

  Ronald Gentile ORLANDO REO PROF I INC

  4819 Summerfield Cir, Winter Haven, FL 33881
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  $1,745 per month

  • 3 Beds
  • 2 Baths
  • 1,464 Sq Ft
  • House for Rent

  1804 Carnostie Rd, Winter Haven, FL 33884

  House available for rent in the VillaMar condominium – 3 bedrooms and 2 bathrooms Beautiful residence with a veranda at the entrance and a charming garden, perfect for those seeking comfort and practicality. The open-concept layout offers integration between the living room, dining room, and kitchen, providing spaciousness and brightness to the environment. The master suite guarantees total

  Umberto Da Cunha Neto WRA BUSINESS & REAL ESTATE

  1804 Carnostie Rd, Winter Haven, FL 33884
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  $1,395 per month

  • 2 Beds
  • 1 Bath
  • 750 Sq Ft
  • House for Rent

  2000 15th Ct NW Unit 15, Winter Haven, FL 33881

  One or more photo(s) has been virtually staged. NOW LEASING - AQUA APARTMENT HOMES! MOVE-IN READY! THIS SECOND (2ND) FLOOR UNIT COMES KITCHEN APPLIANCES, IN UNIT WASHER/DRYER, NEW TILE BACKSPLASH, NEW COUNTERTOPS AND TILE FLOORING THROUGHOUT. THIS UNIT IS FRESHLY PAINTED AND ALL FIXTURES HAVE BEEN REPLACED. UNIT OFFERS A VIEW TO THE INGROUND COMMUNITY POOL. LAUNDRY FACILITIES LOCATED ON SITE.

  Manuel Paredes

  2000 15th Ct NW Unit 15, Winter Haven, FL 33881

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