23

Cypresswood Homes for Rent

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  • /15

    $1,500 per month

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

    680 Grove St, Winter Haven, FL 33881

    Welcome to 680 Grove St in Winter Haven! This charming 1-bedroom apartment offers a comfortable living room upon entry, a practical kitchenette, a convenient laundry closet, and a spacious bedroom with a full bathroom. Rent includes water, electricity, and internet, providing amazing value and stress-free living. Perfect for one person or a couple, this cozy home is centrally located near

    Vicky Torres Rodriguez RE/MAX HERITAGE PROFESSIONALS

    680 Grove St, Winter Haven, FL 33881
  • /10

    $1,395 per month

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

    505 Eagle Pond Dr, Winter Haven, FL 33884

    Second-floor two-bedroom, two-bathroom condo located in the gated golf community of Cypresswoods. Enjoy the numerous HOA amenities, including private gated entrance with 24/7 guard, pool, gym, tennis courts, and golf. Condo features inside laundry, stainless steel appliances, a storage room, a spacious living room, and walk-in closets in the bedrooms. Home available immediately. 12-month lease.

    Sharon Billups SKYELINE REALTY LLC

    505 Eagle Pond Dr, Winter Haven, FL 33884
  • /28

    $1,995 per month

    • 4 Beds
    • 2 Baths
    • 1,867 Sq Ft
    • House for Rent

    223 Inman Blvd, Winter Haven, FL 33881

    Welcome to your dream rental in the heart of Winter Haven! This beautiful 4-bedrooms, 2-bathroom single family home with an attached 2 car garage offers an open and airy floor plan perfect for modern living. Step inside to find elegant tile flooring throughout the main living areas, a kitchen featuring granite countertops, stainless steel appliances, and the added convenience of an in-home washer

    Annia Torres PA RE/MAX VANTAGE

    223 Inman Blvd, Winter Haven, FL 33881
  • /19

    $2,000 per month

    • 2 Beds
    • 2 Baths
    • House for Rent

    205 Lake Region Blvd S, Winter Haven, FL 33881

    Property Id: 2232592This is a two bedroom two bath house in a gated Comunity. Very safe and close to Lego land and Orlando. Great for working families who want to commute to save money. Also a great home for retired individuals. Very clean and spacious and plenty of room. Has walk in closest and lots of cabinet space.

    205 Lake Region Blvd S, Winter Haven, FL 33881
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    $1,300 per month

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

    905 Eagle Pond Dr Unit 9E, Winter Haven, FL 33884

    MOVE-IN READY upstairs Eagle Pond condominium in the highly desirable gated community of Cypresswood Golf and Country Club. This professionally-managed condominium includes interior laundry, walk-in closets, open concept living space, and so much more. The spacious master bedroom features an en suite bathroom while both bedrooms offer walk-in closets. Additional linen storage exists in the main

    Kayly Malinas JOHN WOOD REALTY, INC.

    905 Eagle Pond Dr Unit 9E, Winter Haven, FL 33884
  • /15

    $2,020 per month

    • 3 Beds
    • 2 Baths
    • 1,303 Sq Ft
    • House for Rent

    3134 Whispering Trails St, 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

    3134 Whispering Trails St, Winter Haven, FL 33884
  • /25

    $1,900 per month

    • 3 Beds
    • 2 Baths
    • 1,553 Sq Ft
    • House for Rent

    2845 Whispering Trails Dr, Winter Haven, FL 33884

    This beautiful 3-bedroom, 2-bathroom home is nestled in the sought-after Whispering Trails neighborhood of Winter Haven. Inside, you’ll find an open floor plan that creates a bright, airy flow from the living area to the kitchen and dining space—perfect for both everyday living and entertaining. The home comes equipped with a washer and dryer, making move-in easy and convenient. Step outside to

    Christin Davis PROPERTY MANAGEMENT OF POLK

    2845 Whispering Trails Dr, Winter Haven, FL 33884
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    $1,500 per month

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

    507 Eagle Pond Dr Unit 507, Winter Haven, FL 33884

    New appliances: stove, refrigerator, dishwasher, microwave, and water heater. Excellent condition 2 bedroom-2 bathroom, 1,017 sqft Eagle Pond Condominium on the second floor. 2 parking spots. Located within the Cypresswood Golf and Country Club gated community, this unit features spacious rooms with beautiful water views, walk-in closets, a neutral color scheme, inside laundry, a generous amount

    507 Eagle Pond Dr Unit 507, Winter Haven, FL 33884
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    $2,250 per month

    • 5 Beds
    • 2.5 Baths
    • 2,215 Sq Ft
    • House for Rent

    640 Grove St, 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, nestled

    Daniel Reyes MAIN STREET RENEWAL LLC

    640 Grove St, Winter Haven, FL 33884
  • /16

    $1,855 per month

    • 3 Beds
    • 2 Baths
    • 1,303 Sq Ft
    • House for Rent

    2768 Whispering Trails Dr, Winter Haven, FL 33884

    Special offer: Pay just $500 of your base rent (taxes and fees not included) as your security deposit, valid for new applicants who sign a 12-month lease by November 30, 2025. Offer is contingent on application approval and execution of a lease agreement. Other terms and conditions may apply. This property is professionally managed by AMH, a leading single-family rental company. We work to

    2768 Whispering Trails Dr, Winter Haven, FL 33884
  • /8

    $950 per month

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

    2924 Whispering Trails Dr, Winter Haven, FL 33884

    Property Id: 2161810Studio with Private Entrance for RentIncludes walk-in closet, private bathroom, electricity, water, YouTube channel and internet.Ready for immediate occupancy.Monthly payment $1200Single occupancy! Gate community!Deposit $1200Application fee $50.00

    2924 Whispering Trails Dr, Winter Haven, FL 33884
  • /19

    $2,100 per month

    • 3 Beds
    • 2 Baths
    • 1,526 Sq Ft
    • House for Rent

    13 Enclave Dr, Winter Haven, FL 33884

    Well maintained 3 bedroom end unit villa located in the Enclave Neighborhood at Cypresswood golf and Country Club.

    Steven Smith, PA LOCKHART & ASSOCIATES INC

    13 Enclave Dr, Winter Haven, FL 33884
  • /13

    $1,600 per month

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

    201 Eagle Pond Dr, Winter Haven, FL 33884

    GROUND FLOOR Eagle Pond condominium in the highly desirable gated community of Cypresswood Golf and Country Club. This professionally-managed condominium includes interior laundry, walk-in closets, open concept living space, and so much more. The spacious master bedroom features an en suite bathroom while both bedrooms offer walk-in closets. Additional linen storage exists in the main bedroom and

    Kayly Malinas JOHN WOOD REALTY, INC.

    201 Eagle Pond Dr, Winter Haven, FL 33884
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    $2,020 per month

    • 5 Beds
    • 3 Baths
    • 2,150 Sq Ft
    • House for Rent

    2037 Whispering Trails Blvd, 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, nestled

    Breana Matviak MAIN STREET RENEWAL LLC

    2037 Whispering Trails Blvd, Winter Haven, FL 33884
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    $2,200 per month

    • 3 Beds
    • 2 Baths
    • 1,937 Sq Ft
    • House for Rent

    677 Augusta Rd, Winter Haven, FL 33884

    Welcome to your dream rental home in the prestigious guard-gated community of Cypresswood Golf and Country Club, where luxury living meets resort-style amenities. Nestled within this exclusive enclave, this meticulously crafted 3-bedroom, 2-bathroom home offers an unparalleled lifestyle experience. Upon entering, you're greeted by an inviting ambiance accentuated by high-end finishes and tasteful

    Kayly Malinas JOHN WOOD REALTY, INC.

    677 Augusta Rd, Winter Haven, FL 33884
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    $2,600 per month

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

    930 Cattleman St, Winter Haven, FL 33884

    Welcome to 930 Cattleman St, located in the charming community of Inman Groves in Winter Haven, FL. This spacious Boston model by Lennar offers an ideal blend of comfort, functionality, and modern living. Boasting 5 generously sized bedrooms and 2.5 baths, this two-story home is perfect for families seeking space to grow or investors looking for strong rental potential. The thoughtfully designed

    Carlos Lopez EXP REALTY LLC

    930 Cattleman St, Winter Haven, FL 33884
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    $1,745 per month

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

    4907 Summerfield Cir, Winter Haven, FL 33881

    Welcome to your new home at 4907 Summerfield Circle Winter Haven, FL 33881! Walk into this 3 bed 2 bath charming home and the first thing you'll notice is the abundance of natural light shining into the kitchen-to-family room combo. The kitchen offers ease & accessibility with all the major appliances including a dishwasher. The master suite is a dream come true with all the storage space and

    Marilyn Kuczynski FLORIDA HOMES SALES & MANAGEMENT LLC

    4907 Summerfield Cir, Winter Haven, FL 33881
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    $2,300 per month

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

    1454 Austin Terrace, Winter Haven, FL 33884

    Discover the charm of Winter Haven! Located in Peace Creek Reserve, a thoughtfully planned community surrounded by nature and a scenic creek, this beautiful Edison model home offers a bright open-concept layout that seamlessly connects the kitchen, living room, and dining area, extending outdoors to a covered patio perfect for relaxation or entertaining. Upstairs, you’ll find five spacious

    Carla Moreno Pineda EXP REALTY LLC

    1454 Austin Terrace, Winter Haven, FL 33884
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    $1,800 per month

    • 3 Beds
    • 2 Baths
    • 1,511 Sq Ft
    • House for Rent

    2700 Crump Rd, Winter Haven, FL 33881

    Lakefront Living at Its Finest!Discover the perfect blend of comfort, convenience, and stunning natural beauty with this 3-bedroom, 2-bath home located on the highly sought-after Lake Hamilton. This property offers unbeatable location — just minutes from shopping, dining, and entertainment, yet far enough to enjoy peace and privacy away from the city bustle.Recently updated, this

    Lamanda Jones CENTURY 21 WATSON & MYERS REALTY

    2700 Crump Rd, Winter Haven, FL 33881
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    $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 TBO REAL ESTATE PARTNERS INC

    3240 Country Walk Club Cir, Winter Haven, FL 33881
  • /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
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    $1,670 per month

    • 3 Beds
    • 2 Baths
    • 1,303 Sq Ft
    • House for Rent

    3119 Whispering Trails St, Winter Haven, FL 33884

    Please note, our homes are available on a first-come, first-serve basis and are not reserved until the lease is signed by all applicants and security deposits are collected.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 Want to tour on your own? Click the “Self

    3119 Whispering Trails St, Winter Haven, FL 33884
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    $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

Frequently Asked Questions

What are the most popular neighborhoods for renters near Cypresswood?
The most popular neighborhoods for renters near Cypresswood are Cypress Gardens, Lake Fox, Southeast Winterhaven, East Winter Haven and North Winter Haven.
What are the most popular zip codes for renters near Cypresswood?
The most popular zip codes for renters near Cypresswood are 33884, 33881, 33844, 33880 and 33838.
How to Rent a Home