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Cypresswood Homes for Rent

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  • /15

    $2,140 per month

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • House for Rent

    2920 Whispering Trails Dr, Winter Haven, FL 33884

    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

    2920 Whispering Trails Dr, Winter Haven, FL 33884
  • /12

    $2,200 per month

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

    3240 Country Walk Club Cir, Winter Haven, FL 33881

    Brochure Available, Docs Available, Floor Plan Available

    Moises Dominguez, LLC LOKATION

    3240 Country Walk Club Cir, Winter Haven, FL 33881
  • /18

    $1,975 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 This home is priced to rent

    2069 Whispering Trails Blvd, Winter Haven, FL 33884
  • /28

    $1,800 per month

    • 2 Beds
    • 2 Baths
    • 1,746 Sq Ft
    • House for Rent

    579 Saint Andrews Rd, Winter Haven, FL 33884

    For rent or for sale! Enjoy unobstructed fairway views from this well maintained and updated 2 bedroom 2 bath home located on the 11th Fairway at Cypresswood Golf and Country Club in Southeast Winter Haven. Enjoy your morning coffee in the air conditioned Florida room as the sun rises over the golf course along with an occasional visit from the Sandhill Cranes. Features include ceramic tile

    Steven Smith, PA LOCKHART & ASSOCIATES INC

    579 Saint Andrews Rd, Winter Haven, FL 33884
  • /3

    $3,400 per month

    • 5 Beds
    • 3 Baths
    • 2,845 Sq Ft
    • House for Rent

    740 Grove St, Winter Haven, FL 33881

    Nestled in the serene location of Winter Haven; beautiful house conveniently located near Lego Land. 5 bedrooms, 3 bathrooms, 2-car garage, stainless steel appliances. Fenced-in backyard offering space and privacy. Includes smart home technology so that you can connect to your home via smartphone. Enjoy Winter Haven's main attractions and sights such as boating on the Chain of Lakes and Antique

    Claudia Pulgarin Capital Nest Realty, LLC

    740 Grove St, Winter Haven, FL 33881
  • /35

    $1,875 per month

    • 2 Beds
    • 2 Baths
    • 1,435 Sq Ft
    • House for Rent

    429 Greenfield Rd, Winter Haven, FL 33884

    This beautiful renovated 2/2 is in the gated community of Cypresswood. The home is a notch above the typical rental. It is a masterpiece of modern luxury and comfort. Step inside and experience a harmonious blend of style and functionality that defines this stunning property. It has many updated features including luxurious vinyl flooring throughout creating a contemporary and low-maintenance

    Lamanda Jones CENTURY 21 WATSON & MYERS REALTY

    429 Greenfield Rd, Winter Haven, FL 33884
  • /25

    $1,700 per month

    • 2 Beds
    • 2 Baths
    • 1,017 Sq Ft
    • Condo for Rent

    903 Eagle Pond Dr Unit C9, Winter Haven, FL 33884

    This absolutely gorgeous MOVE-IN READY Eagle Pond condominium has been luxuriously remodeled from top to bottom with no expense spared! Located in the highly desirable gated community of Cypresswood Golf and Country Club, this meticulously-maintained condo features hardwood floors throughout (no carpet!), upgraded light fixtures, interior laundry, and so much more. Entertain friends and family

    Kayly Malinas JOHN WOOD REALTY, INC.

    903 Eagle Pond Dr Unit C9, Winter Haven, FL 33884
  • /22

    $1,700 per month

    • 2 Beds
    • 2 Baths
    • 1,017 Sq Ft
    • Condo for Rent

    306 Eagle Pond Dr, Winter Haven, FL 33884

    This gorgeous Eagle Pond condominium in the highly desirable gated community of Cypresswood Golf and Country Club is now available for lease. Luxuriously updated, it features tile flooring throughout (no carpet!), marble kitchen countertops with an extended breakfast bar, mathcing marble on both bathroom vanities, upgraded light fixtures/ceiling fans, interior laundry with washer and dryer, pond

    Kayly Malinas JOHN WOOD REALTY, INC.

    306 Eagle Pond Dr, Winter Haven, FL 33884
  • /4

    $1,900 per month

    • 4 Beds
    • 2 Baths
    • 1,701 Sq Ft
    • House for Rent

    3862 Fieldstone Cir, Winter Haven, FL 33881

    This charming newer home sits on a corner lot and is 4-bedroom, 2 bath, located in Country Club Estates. Featuring a kitchen and family room combo, great for family gatherings. Freshly painter interior. BRAND NEW LVP in all bedrooms. Call today for a private showing.

    Ronald Gentile ORLANDO REO PROF I INC

    3862 Fieldstone Cir, Winter Haven, FL 33881
  • /17

    $2,285 per month

    • 4 Beds
    • 2.5 Baths
    • 2,629 Sq Ft
    • House for Rent

    609 Lyndsey Ln, Winter Haven, FL 33884

    Looking for your dream home? Through our seamless leasing process, this beautifully designed home is move-in ready. Our spacious layout is perfect for comfortable living that you can enjoy with your pets too; we’re proud to be pet friendly. Our homes are built using high-quality, eco-friendly materials with neutral paint colors, updated fixtures, and energy-efficient appliances. Enjoy the

    Nico Silva Vanegas MAIN STREET RENEWAL LLC

    609 Lyndsey Ln, Winter Haven, FL 33884
  • /33

    $2,200 per month

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

    686 Augusta Rd, Winter Haven, FL 33884

    Welcome to your new sanctuary! Nestled in a serene neighborhood, this beautifully renovated 2-bedroom/2-bathroom home offers the perfect blend of modern comfort and cozy charm. Step inside to discover an inviting living space, adorned with modern finishes and ample natural light. The heart of the home boasts a spacious living room with a stone wood-burning fireplace, ideal for relaxation or

    Kayly Malinas JOHN WOOD REALTY, INC.

    686 Augusta Rd, Winter Haven, FL 33884
  • /32

    $1,995 per month

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

    193 Inman Blvd, Winter Haven, FL 33881

    Like new home ready for immediate occupancy! This is a lovely 3 bedroom 2 bath 2 car garage home in a newer community. The home has bright open floor plan. Kitchen features granite countertops, wood cabinets and stainless appliances. Primary suite has 2 closets, dual vanities and private water closet. Bedrooms 2 and 3 are located at the front of the house and have hall access to the 2nd bathroom.

    Jacob Bellamy REMAX EXPERTS

    193 Inman Blvd, Winter Haven, FL 33881
  • /26

    $1,450 per month

    • 2 Beds
    • 2 Baths
    • 1,017 Sq Ft
    • Condo for Rent

    706 Eagle Pond Dr, Winter Haven, FL 33884

    Introducing this 2 Bed, 2 Bath upstairs condo located in the highly desirable man-gated Eagle Pond community in the Cypresswood Golf & Country Club. MOVE-IN READY. Well-maintained. Featuring a spacious living room, with each bedroom having their own walk-in closet, and an open kitchen with a breakfast bar and pantry. Plenty of storage space with a convenient Outside STORAGE closet. Beautiful view

    Connie Kim BHHS FLORIDA REALTY

    706 Eagle Pond Dr, Winter Haven, FL 33884
  • /37

    $2,700 per month

    • 5 Beds
    • 3 Baths
    • 2,601 Sq Ft
    • House for Rent

    420 Chance Ave, Winter Haven, FL 33881

    FOR RENT! 5 BEDROOMS + FORMAL DINING + FAMILY ROOM AMD 3 FULL BATHROOMS, ONE BEDROOM AND FULL BATHROOM ON THE FIRST FLOOR. KITCHEN HAS A LARGE ISLAND WITH GRANITE , APPLIANCES INC. DISHWASHER, STOVE AND RANGE. SPACIOUS LIVING & DINING ROOM GREAT FOR ENTERTAINING, AND SO MUCH MORE. EXTRA LARGE BACKYARD. Find everything you need in Winter Haven! Located just minutes from world class theme parks and

    Alaina Edmondson COAST TO COAST REAL ESTATE PRO

    420 Chance Ave, Winter Haven, FL 33881
  • /24

    $1,600 per month

    • 2 Beds
    • 2 Baths
    • 1,017 Sq Ft
    • Condo for Rent

    1005 Eagle Pond Dr, Winter Haven, FL 33884

    MOVE-IN READY Eagle Pond condominium in the highly desirable gated community of Cypresswood Golf and Country Club available beginning 12/1/2023. This meticulously-maintained condo features hard floors throughout (no carpet!), new interior paint, NEW kitchen appliances, interior laundry (with brand new front load LG washer/dryer provided), and so much more. The spacious master bedroom features an

    Kayly Malinas JOHN WOOD REALTY, INC.

    1005 Eagle Pond Dr, Winter Haven, FL 33884

About Cypresswood

Cypresswood in Winter Haven is a master-planned community known for its golf courses and country club amenities. With over 1,000 residential units and 14 neighborhood associations, it offers diverse housing options, primarily ranch-style homes from the 1980s to early 2000s, with new custom builds still emerging. The Cypresswood Golf & Country Club, featuring the best golf course in Winter Haven for 2023, is a central attraction. Residents enjoy country club amenities, including pools, gyms, and tennis courts, with plans to add pickleball courts. The neighborhood is close to shopping and dining, with a Winn-Dixie within 2 miles and a Walmart Supercenter under 6 miles away. Local dining includes the Cypresswood Pub, Legacy Craft BBQ, and Dundee Diner. For outdoor activities, the nearby Michael V. Lewis Arboretum and Parrott Trail offer 42 acres of native and exotic plants. Cypresswood is under 5 miles from Legoland and less than 30 minutes from Disney World, with both east and west coast beaches about 2 hours away. The neighborhood is zoned for Polk County Public Schools, one of the top 50 districts in Florida. Public transportation is not available, so residents rely on cars or golf carts, with major routes like US Highway 27 and Florida State Road 60 nearby. Orlando International Airport is about 45 miles away.

Frequently Asked Questions

What are the most popular neighborhoods for renters near Cypresswood?
The most popular neighborhoods for renters near Cypresswood are Lake Fox, Poinsettia Park, Lake Ashton, Downtown Winter Haven and Lake Lucerne.
What are the most popular zip codes for renters near Cypresswood?
The most popular zip codes for renters near Cypresswood are 33837, 33896, 34759, 34746 and 34758.
How to Rent a Home