25

Winter Haven, FL Houses for Rent with Community Pool

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  • /56

    $2,599 Per Month

    • 4 Beds
    • 2.5 Baths
    • 1,942 Sq Ft
    • House for Rent

    1504 Hummingbird Rd, Winter Haven, FL 33884

    Welcome to your slice of Florida paradise! This almost-new, fully furnished 4-bedroom, 2.5-bath home sits beautifully on a spacious corner lot with a lush yard—perfect for relaxing or entertaining. Designed with modern finishes throughout, every room feels fresh and inviting. The home boasts a large 2-car garage equipped with a Tesla charger, making it ideal for eco-conscious residents. Enjoy the

    Agent Photo

    Matthew Stanley

    The Keyes Company

    (863) 281-6200

    1504 Hummingbird Rd, Winter Haven, FL 33884
  • /16

    $2,200 Per Month

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

    5603 Lake Fox 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.

    (863) 375-7008

    5603 Lake Fox Cir, Winter Haven, FL 33884
  • /20

    $2,065 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.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

    (863) 334-2782

    2069 Whispering Trails Blvd, Winter Haven, FL 33884
  • /20

    $2,595 Per Month

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

    397 Corso Loop, Winter Haven, FL 33884

    Property Id: 1220815Beautiful and spacious 4-bedroom, 2-bath single-family home located in the highly desirable Villamar community in Winter Haven. Built in 2020, this modern home features an open-concept floor plan with a bright living area, spacious kitchen, stainless steel appliances, laminate floor throughout, and a large island perfect for entertaining. The split-bedroom layout

    (424) 688-3903

    397 Corso Loop, Winter Haven, FL 33884
  • /15

    $2,190 Per Month

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

    2154 Chris Dr, Winter Haven, FL 33884

    FOR RENT! Beautiful and move-in ready home located in the heart of Winter Haven! This charming property offers a bright and spacious floor plan with comfortable living areas, generously sized bedrooms, and a welcoming atmosphere perfect for everyday living. Enjoy a functional kitchen, plenty of natural light, and a peaceful neighborhood setting. Conveniently located near shopping, restaurants,

    Daniel Serpa NOSSA REALTY LLC

    2154 Chris Dr, Winter Haven, FL 33884
  • /33

    $2,100 Per Month

    • 4 Beds
    • 2 Baths
    • 1,842 Sq Ft
    • House for Rent

    3711 Julius Estates Blvd, Winter Haven, FL 33881

    Welcome home to this beautifully maintained 4-bedroom, 2-bath rental located in the desirableLake Smart Estates community of Winter Haven! This spacious home features an open and functionalfloor plan with high ceilings, a large living and dining area, and a bright kitchen complete withbreakfast bar and ample cabinet space. Enjoy laminate flooring throughout, generously

    Stephanie Florez CENTURY 21 WOLF'S CROSSING REALTY

    3711 Julius Estates Blvd, Winter Haven, FL 33881
  • /41

    $2,400 Per Month

    • 2 Beds
    • 2 Baths
    • 1,517 Sq Ft
    • House for Rent

    2872 Attwater Loop, Winter Haven, FL 33884

    Beautifully furnished and move-in ready, this pristine residence in the highly desirable 55+ gated community of Traditions at Lake Ruby offers comfort, style, and an easy Florida lifestyle. Available for occupancy June 1, this home has been thoughtfully maintained and is offered fully furnished, making it ideal for tenants looking for a turnkey rental in one of Winter Haven’s premier active-adult

    Mike Daquino DOUGLAS ELLIMAN

    2872 Attwater Loop, 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
  • /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
  • /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
  • /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
  • /47

    $1,900 Per Month

    • 3 Beds
    • 2 Baths
    • 1,483 Sq Ft
    • House for Rent

    3912 Giorgio Dr, Winter Haven, FL 33884

    Brand new, energy-efficient home available NOW for rent! Retreat to your primary suite located in the back of the home for plenty of privacy and offers a huge walk-in closet. This is a split floor plan allowing everyone their privacy. The square footage is the perfect size so you don't feel crowded, but you won't spend an eternity trying to keep it clean. Enjoy the easy clean up in your spacious

    Rick Scott KEY PREMIER REALTY

    3912 Giorgio 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
  • /9

    $2,200 Per Month

    • 3 Beds
    • 2.5 Baths
    • House for Rent

    4056 Giorgio Dr, Winter Haven, FL 33884

    Welcome to Villamar in beautiful Winter Haven — a perfect place for families looking for comfort, space, and the opportunity to enjoy a brand-new home in a peaceful community.This beautiful new construction home offers the independence and privacy families are searching for, with modern finishes, open living spaces, and a warm neighborhood atmosphere designed for everyday living.Residents of

    Maria del Pilar Padilla Olivera My Realty Group, LLC.

    4056 Giorgio Dr, Winter Haven, FL 33884
  • /14

    $1,395 Per Month

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

    2000 15th Ct NW Unit 23, Winter Haven, FL 33881

    Apartment For Rent - Move In Ready! MOVE IN SPECIALS: Free 1/2 Month Rent, waived Processing Fee and $250 Security Deposit based on approval. This second (2nd) floor unit comes with all stainless steel 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

    Manuel Paredes

    2000 15th Ct NW Unit 23, Winter Haven, FL 33881
  • /28

    $1,900 Per Month

    • 3 Beds
    • 2 Baths
    • 1,597 Sq Ft
    • House for Rent

    3927 Palazzo Place, Winter Haven, FL 33884

    MOVE-IN READY and available now! Rare opportunity to lease the FINAL Amarylis model in the community—a beautifully maintained 2023-built home offering modern comfort, style, and convenience. Featuring 3 bedrooms, 2 bathrooms, soaring ceilings, a bright open-concept layout, luxury vinyl flooring throughout the main living areas, and an inviting walk-in foyer. The spacious primary suite includes a

    Iliana Perez MAINFRAME REAL ESTATE

    3927 Palazzo Place, Winter Haven, FL 33884
  • /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
  • /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
  • /41

    $1,900 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
  • /27

    $2,300 Per Month

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

    6472 Domizio Dr, Winter Haven, FL 33884

    Brand-New 5-Bedroom Home for Rent in Winter Haven Be the first to live in this stunning new construction two-story home located in the desirable area of Winter Haven. Designed with comfort, style, and functionality in mind, this spacious property offers 5 bedrooms, 2 full bathrooms, and 1 half bathroom, making it the perfect home for families or tenants looking for extra space and modern living.

    Jessyka Dos Santos WRA BUSINESS & REAL ESTATE

    6472 Domizio Dr, Winter Haven, FL 33884
  • /41

    $1,695 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
  • /36

    $2,290 Per Month

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

    368 Kayden Cove, Winter Haven, FL 33884

    Welcome to 368 Kayden Cove, a beautifully designed home offering a spacious and functional open-concept floor plan perfect for modern living. The layout features a bright living area that flows seamlessly into the kitchen and dining space, ideal for entertaining and everyday comfort. The kitchen is equipped with ample cabinetry, modern appliances, and a central island that adds both style and

    Ashley Porto GLASSTONE GROUP INC

    368 Kayden Cove, Winter Haven, FL 33884
  • /70

    $2,200 Per Month

    • 4 Beds
    • 2 Baths
    • 1,943 Sq Ft
    • House for Rent

    279 Sunfish Dr, Winter Haven, FL 33881

    4 bedrooms 2 baths for rent in lovely Winter Haven, spacious home with open concept family room, dining and fully equiped kitchen. Home has a laundry room with washer and Dryer. Spacious yard for entertaining family and friends. No neighbors in the back. New tile floors. Bedrooms are carpeted, Community pool.

    Maria C Diaz LA ROSA REALTY CENTRAL FLORIDA LLC

    279 Sunfish Dr, Winter Haven, FL 33881
  • /17

    $2,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,709 Sq Ft
    • House for Rent

    612 Heather Glen Loop, Winter Haven, FL 33884

    This is the ONLY rental in Winter Haven that has a pool!! This cute 3 bedroom 2 bath home 2 garage screened pool home has a fully PVC fenced in back yard, perfect for kids to play or aminals to run free. Located in a quiet neighborhood. Clean freshly painted interior and ready for a tenant!

    Amy Riggleman SIGNATURE PROPERTIES OF CENTRAL FLORIDA LLC

    612 Heather Glen Loop, Winter Haven, FL 33884

Rental Home Trends in Winter Haven, FL

Rental Home Trends

Number of Houses for Rent
25
Median Single Family Home Rent
$1,895
Median 3 Bedroom Single Family Home Rent
$1,824
Median 4 Bedroom Single Family Home Rent
$2,000
Median 5 Bedroom Single Family Home Rent
$2,200
How to Rent a Home