26

Winter Haven, FL Houses for Rent with Community Pool

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  • /17

    $2,400 per month

    • 3 Beds
    • 2 Baths
    • 1,433 Sq Ft
    • House for Rent

    733 Oleander Dr SE, Winter Haven, FL 33880

    Property Id: 2417966Welcome to your own Florida poolside retreat at 733 Oleander Ave in Winter Haven. This beautifully renovated 3-bedroom, 2-bath home is completely turn-key and move-in ready, featuring bright living spaces, modern updates, and a private backyard pool perfect for relaxing or entertaining. Even better, pool and lawn maintenance are included, so you can enjoy the sunshine

    733 Oleander Dr SE, Winter Haven, FL 33880
  • /29

    $2,200 per month

    • 4 Beds
    • 3 Baths
    • 1,988 Sq Ft
    • House for Rent

    2772 San Marco Way, Winter Haven, FL 33884

    Welcome to the desirable Villamar community in Winter Haven, where comfort, convenience, and modern living come together in one of the area’s fastest-growing neighborhoods. This FULLY FENCED like-new 4-bedroom, 3-bathroom home offers a thoughtfully designed layout that perfectly balances functionality and style, making it ideal for families, entertaining, or simply enjoying everyday life.

    Fanny Stollmeyer LIFESTYLE INTERNATIONAL REALTY

    2772 San Marco Way, Winter Haven, FL 33884
  • /18

    $2,015 per month

    • 4 Beds
    • 2.5 Baths
    • 2,203 Sq Ft
    • House for Rent

    2069 Whispering Trails 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

    2069 Whispering Trails Blvd, Winter Haven, FL 33884
  • /22

    $1,817 per month

    • 3 Beds
    • 2 Baths
    • 1,504 Sq Ft
    • House for Rent

    3304 White Indigo Rd, Winter Haven, FL 33884

    WINTER HAVEN NEW BUILD 3 BED/2 BATH HOME FOR RENT! MOVE-IN SPECIAL!Priced Low, Call Now! Very Clean Property, Move-in Ready, 2 Car Garage, Brand New Build—First Tenancy! Huge Master Suite, Eat-In Kitchen, Corian Countertops, Upgraded Kitchen, Brand New Kitchen, Carpeted Bedrooms, Laminate Wood-Look Flooring, COMMUNITY Pool, COMMUNITY Playground, COMMUNITY Multiple Lakes, COMMUNITY Walking &

    Jay Myers ORLANDO REALTY & PROPERTY MGNT

    3304 White Indigo Rd, Winter Haven, FL 33884
  • /21

    $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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    $2,200 per month

    • 4 Beds
    • 3 Baths
    • 2,174 Sq Ft
    • House for Rent

    1116 Tyler Loop, Winter Haven, FL 33884

    Discover modern comfort and thoughtful design in this newly built home at 1116 Tyler Loop in Winter Haven, FL, crafted by Lennar Homes. This residence showcases high-quality construction paired with stylish finishes, including an open-concept layout perfect for both everyday living and entertaining. The home features energy-efficient systems, smart home technology, and a contemporary kitchen

    Julien Silva JOHN SILVA REALTY & ASSOCIATES

    1116 Tyler Loop, Winter Haven, FL 33884
  • /24

    $2,000 per month

    • 4 Beds
    • 2 Baths
    • 1,935 Sq Ft
    • House for Rent

    1498 Austin St, Winter Haven, FL 33884

    One or more photo(s) has been virtually staged. Step into this inviting 4 bedroom, 2 bathroom home in the Peace Creek Reserve community, where comfort meets modern style. The split floor plan gives everyone their own space, while the open living, dining, and kitchen area keeps the heart of the home bright, connected, and perfect for everyday life. You’ll love the modern appliances, clean

    Christin Davis PROPERTY MANAGEMENT OF POLK

    1498 Austin St, Winter Haven, FL 33884
  • /41

    $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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    $2,900 per month

    • 4 Beds
    • 3 Baths
    • 2,008 Sq Ft
    • House for Rent

    341 Sterling Dr, Winter Haven, FL 33884

    One or more photo(s) has been virtually staged. Experience refined living in this beautifully renovated residence designed for both elegance and comfort. This exceptional 4-bedroom, 3-bath home has a newer roof and AC as well as featuring a desirable split floor plan, soaring ceilings in select areas, and an abundance of natural light that enhances the home’s open, airy feel. The designer kitchen

    David Small KELLER WILLIAMS REALTY SMART 1

    341 Sterling Dr, Winter Haven, FL 33884
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    $2,150 per month

    • 4 Beds
    • 2.5 Baths
    • 1,879 Sq Ft
    • House for Rent

    312 Kayden Cove, Winter Haven, FL 33884

    Welcome to this beautiful and spacious rental home located in the heart of Winter Haven, just minutes away from LEGOLAND Florida and top-rated shopping centers. This residence features a bright, open-concept floor plan with modern finishes, perfect for comfortable family living and entertaining. The property boasts a large, private backyard and is situated in a quiet, well-maintained community.

    Ashley Porto GLASSTONE GROUP INC

    312 Kayden Cove, Winter Haven, FL 33884
  • /17

    $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
  • /27

    $2,100 per month

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

    1019 Gotthard Pass Dr, Winter Haven, FL 33881

    Prime location! Just minutes from malls, shopping centers, restaurants, and with easy access to major highways — perfect for commuting and daily convenience.Vacant and move-in ready. Easy to show. Exceptional value for the areaThis home won’t last long!Schedule your private showing today and secure this amazing rental before it’s gone!

    Maria Villacis AVANTI WAY REALTY LLC

    1019 Gotthard Pass Dr, Winter Haven, FL 33881
  • /24

    $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
  • /22

    $4,500 per month

    • 3 Beds
    • 3 Baths
    • 2,266 Sq Ft
    • House for Rent

    236 Ruby Lake Ln, Winter Haven, FL 33884

    One or more photo(s) has been virtually staged. Wake up every morning to the most breath taking views imaginable. Almost every room in the home overlooks the spectacular private Lake Ruby & Lake Bess. Upon entering the home you will find yourself captivated with the spacious and luxurious open floor plan and high degree of natural light that envelops you. Besides having the exquisite view, this

    Scott Kline KLINE REAL ESTATE SERVICES

    236 Ruby Lake Ln, Winter Haven, FL 33884
  • /36

    $2,100 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
  • /41

    $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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    $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
  • /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
  • /27

    $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
  • /27

    $2,150 per month

    • 5 Beds
    • 2.5 Baths
    • 2,326 Sq Ft
    • House for Rent

    1547 Jessica Blvd, Winter Haven, FL 33884

    Stunning New Construction Home for Rent in Winter HavenBe the first to live in this beautiful new construction home located in a desirable Winter Haven neighborhood. Designed with comfort and style in mind, this spacious residence offers a modern open floorplan that is perfect for both everyday living and entertaining.The home features 5 generously sized bedrooms, including a luxurious

    Jessyka Dos Santos WRA BUSINESS & REAL ESTATE

    1547 Jessica Blvd, Winter Haven, FL 33884
  • /16

    $2,495 per month

    • 3 Beds
    • 2 Baths
    • 2,116 Sq Ft
    • House for Rent

    252 Santa Rosa Dr, Winter Haven, FL 33884

    Great location. Perfect place to call home. 3 bedroom 2 bath spa/pool home with garage. Located in gated community-overlook estates. Minutes from lego-land. Home offers a kitchen, dining room and a formal dining room. 3rd bedroom has a Murphy bed and built in desk/office area. Master features french doors leading to the pool &spa. Offers walk in closets throughout home. Mature landscaping. Lots

    Jennifer Geiger PRESTIGE LIFESTYLES REALTY

    252 Santa Rosa Dr, Winter Haven, FL 33884
  • /21

    $2,500 per month

    • 3 Beds
    • 2 Baths
    • 1,391 Sq Ft
    • House for Rent

    112 Lagoon Rd, Winter Haven, FL 33884

    For Rent – Winter Haven, FL Welcome to this beautifully remodeled home located at 112 Lagoon Rd, Winter Haven, FL 33884. This property offers comfort, convenience, and a prime location. “The property includes an efficient that you can rent out to help cover the rent payment.” Property Features: • 3 spacious bedrooms • 2 updated bathrooms • Modern remodeled kitchen with quality finishes • Indoor

    Zulmy Serrano AGENT TRUST REALTY CORPORATION

    112 Lagoon Rd, Winter Haven, FL 33884
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    $2,299 per month

    • 4 Beds
    • 2.5 Baths
    • 1,933 Sq Ft
    • House for Rent

    1179 Tyler Loop, Winter Haven, FL 33884

    Beautiful semi-furnished rental home featuring 4 bedrooms, including a primary suite, plus a loft, 2 full bathrooms, and 1 half bath. The first floor offers tile flooring throughout, while the second floor is carpeted. The home comes fully equipped with all appliances, including range, dishwasher, refrigerator, microwave, washer, and dryer. Semi-furnished with dining table and six chairs,

    Viviane de Fraga Kalkmann WRA BUSINESS & REAL ESTATE

    1179 Tyler Loop, Winter Haven, FL 33884
  • /37

    $2,399 per month

    • 4 Beds
    • 2 Baths
    • 1,820 Sq Ft
    • House for Rent

    904 Vienna Dr, Winter Haven, FL 33884

    Beautiful Newly Built Rental 4/2 fully Furnished In the Community of Villamar in Winter Haven with community pool and playground. Minutes from Legoland shops and restaurants as well as all Disney Parks. This is the home you are looking for with open floor plan.

    Ivis Suarez CENTURY 21 MYERS REALTY

    904 Vienna Dr, Winter Haven, FL 33884
  • /2

    $2,000 per month

    • 3 Beds
    • 2.5 Baths
    • 1,568 Sq Ft
    • House for Rent

    4458 Rapallo Ave, Winter Haven, FL 33884

    Brand New 3BR + Loft Home | Modern Finishes | Be the First to Live Here! Be the first to occupy this stunning, never-lived-in two-story home. Offering 1,568 sq. ft. of bright, open living space, this property features a designer kitchen with Silestone countertops, Samsung stainless steel appliances, and a massive island perfect for entertaining. The layout includes a versatile upstairs loft—ideal

    Shirley Gomez Dalton Wade, Inc.

    4458 Rapallo Ave, Winter Haven, FL 33884
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