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Cypresswood Homes for Rent

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  • /22

    $1,699 per month

    • 3 Beds
    • 2 Baths
    • 1,148 Sq Ft
    • House for Rent

    2110 Whispering Trails Blvd, Winter Haven, FL 33884

    GATED COMMUNITY WITH AWESOME POOL waiting for a good tenant. Updated Home Minutes from Legoland! This charming 3/ 2 home / garage blends comfort and convenience. Newer roof and fresh paint inside and out, this is a move-in ready home! Spacious living room perfect for gatherings, a well-equipped kitchen, 3 comfortable bedrooms, including a master suite with a private bathroom. Additional features

    Agent Photo

    Silvana Friedel

    The Keyes Company

    (863) 593-8022

    2110 Whispering Trails Blvd, Winter Haven, FL 33884
  • /19

    $1,999 per month

    • 4 Beds
    • 2 Baths
    • 2,237 Sq Ft
    • House for Rent

    3013 Whispering Trails Dr, Winter Haven, FL 33884

    Featuring sparkling pool!Coming soon - this home is currently being enjoyed by another resident but will be available soon. Pre-lease this home now with Tricon Pre-Lease Guarantee. This home is professionally managed by Tricon Residential, dedicated to creating exceptional rental experiences. Featuring 4 bedrooms, 2.5 bathrooms, and approximately 2,237 square feet, this well-maintained

    3013 Whispering Trails Dr, Winter Haven, FL 33884
  • /40

    $1,800 per month

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

    2956 Whispering Trails Dr, Winter Haven, FL 33884

    Charming 3 Bedroom, 2 Bathroom Home for rent in a Gated Community, just minutes from Legoland! This 1,500 sq. ft. rental home is ready for its new tenant(s)! Nestled in the highly desirable Whispering Trails community, this property offers a spacious open layout with a split floorplan, spacious living room, and a large kitchen featuring an oversized island and breakfast bar with plenty of

    Kim Connahey HOUSE OF GLASS REAL ESTATE PM

    2956 Whispering Trails Dr, Winter Haven, FL 33884
  • /18

    $1,759 per month

    • 4 Beds
    • 2 Baths
    • 1,728 Sq Ft
    • House for Rent

    2936 Whispering Trails Dr, Winter Haven, FL 33884

    Coming soon - this home is currently being enjoyed by another resident but will be available soon. Pre-lease this home now with Tricon Pre-Lease Guarantee. This home is professionally managed by Tricon Residential, dedicated to creating exceptional rental experiences. Featuring 4 bedrooms, 2 bathrooms, and approximately 1,728 square feet, this well-maintained home offers a high standard of

    2936 Whispering Trails Dr, Winter Haven, FL 33884
  • /45

    $1,900 per month

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

    2900 Whispering Trails Dr, Winter Haven, FL 33884

    Welcome to this beautifully maintained 3-bedroom, 2-bathroom home located in the desirable gated community of Whispering Trails. Built in 2017 and ideally situated just minutes from Hwy 27, this home offers both comfort and convenience.Step inside to a spacious open floorplan featuring sleek, low-maintenance contemporary concrete flooring and a large kitchen with stainless steel appliances

    Patricia de Graaff RE/MAX HERITAGE PROFESSIONALS

    2900 Whispering Trails Dr, Winter Haven, FL 33884
  • /16

    $1,765 per month

    • 3 Beds
    • 2 Baths
    • 1,384 Sq Ft
    • House for Rent

    2968 Whispering Trails Dr, 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

    2968 Whispering Trails Dr, Winter Haven, FL 33884
  • /15

    $2,200 per month

    • 3 Beds
    • 2 Baths
    • 1,998 Sq Ft
    • House for Rent

    553 Saint Andrews Rd, Winter Haven, FL 33884

    This three bedroom, two bathroom home is located in the gated Cypresswood golf subdivision. Enjoy the numerous HOA amenities, including a private gated community entrance with 24/7 guard, pool, fitness center, tennis courts, and golf. Home features a split floor plan, updated kitchen with stainless steel appliances and a gas range, brand new carpet in bedrooms, an enclosed sunroom that overlooks

    Sharon Billups SKYELINE REALTY LLC

    553 Saint Andrews Rd, Winter Haven, FL 33884
  • /19

    $2,295 per month

    • 4 Beds
    • 2.5 Baths
    • 2,733 Sq Ft
    • House for Rent

    552 Cody Caleb Dr, Winter Haven, FL 33884

    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 $2439.90. That covers your base rent, $2295.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    552 Cody Caleb Dr, Winter Haven, FL 33884
  • /8

    $1,475 per month

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

    1105 Eagle Pond Dr Unit 11E, 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 community entrance with 24/7 guard, pool, gym, tennis courts, and golf. Condo features inside laundry, brand new carpet, storage room and spacious living room. Home available immediately. 12-month lease. No smoking. One small pet under 25

    Sharon Billups SKYELINE REALTY LLC

    1105 Eagle Pond Dr Unit 11E, Winter Haven, FL 33884
  • /31

    $2,195 per month

    • 3 Beds
    • 2 Baths
    • 1,785 Sq Ft
    • House for Rent

    692 Augusta Rd, Winter Haven, FL 33884

    Modern, open concept, 3/2 home for rent. This home has NEW TILE ROOF (2023), NEW AC (2022), NEW WATER HEATER (2024), new kitchen and bathrooms (2022). Beautiful 3 bedroom 2 baths plus office. Located in the sought after gated and guarded Cypresswood Golf and Country Club Subdivision, one of the best communities in Winter Haven, with views of the 18th hole. Gourmet kitchen offers new shaker style

    692 Augusta Rd, Winter Haven, FL 33884
  • /13

    $2,000 per month

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

    13 Enclave Dr, Winter Haven, FL 33884

    Welcome to this maintained 3 bedroom, 2 bath one-story villa/townhouse located in Enclave, a quiet and desirable neighborhood within the gated golf community of Cypresswood Golf & Country Club. This spacious end-unit features a functional split-bedroom floor plan, generous living and dining areas, and an inviting Florida room that adds to the overall living space. The kitchen offers ample cabinet

    Suzanna Rudd KELLER WILLIAMS REALTY SMART 1

    13 Enclave Dr, Winter Haven, FL 33884
  • /14

    $1,950 per month

    • 3 Beds
    • 2 Baths
    • 2,087 Sq Ft
    • House for Rent

    500 Cody Caleb Dr, Winter Haven, FL 33884

    BEAUTIFULLY RENOVATED HOME IN THE SAVANNAH ESTATES SUBDIVISIONCLOSE TO DUNDEE ROAD AND MANY SHOPS AND SCHOOLS

    Nell Nelson FLORIDA LAND OFFICE LLC

    500 Cody Caleb Dr, Winter Haven, FL 33884
  • /26

    $1,500 per month

    • 2 Beds
    • 2 Baths
    • 1,172 Sq Ft
    • Apartment for Rent

    2254 Firestone Place, Winter Haven, FL 33884

    Welcome home to this spacious 2-bedroom/2-bathroom Golf Villa located in the highly-sought-after Cypresswood Golf and Country Club community of Winter Haven. This SINGLE STORY villa offers TWO outdoor spaces in both the front and the rear, covered parking (golf carts allowed, too!), a huge heated/cooled lanai overlooking the 8th fairway, and your very own WET BAR in the living room! The

    Kayly Malinas JOHN WOOD REALTY, INC.

    2254 Firestone Place, Winter Haven, FL 33884
  • /2

    $2,000 per month

    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft
    • House for Rent

    672 Grove St, Winter Haven, FL 33884

    Welcome to your new home in beautiful Winter Haven! This charming single-story residence offers 3 spacious bedrooms and 2 full bathrooms, perfect for comfortable family living. Featuring an open-concept floor plan, this home provides a bright and airy living space that seamlessly connects the living room, dining area, and kitchen—ideal for entertaining and everyday life.Step outside to

    Carlos Lopez Cadena EXP REALTY LLC

    672 Grove St, Winter Haven, FL 33884
  • /23

    $2,000 per month

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

    Unlisted Address

    Stunning home built in 2020, 4 Bedrooms and 2 bathrooms! This breathtaking home features an open floor plan with espresso color kitchen cabinets, granite counters and stainless-steel appliances such as refrigerator, dishwasher, microwave and range and vinyl fence

    Humberto Cuevas LA ROSA REALTY LLC

    Unlisted Address
  • /33

    $1,975 per month

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

    4844 Summerfield Cir, Winter Haven, FL 33881

    Welcome to your new home in beautiful Winter Haven, Florida!Property Highlights:This meticulously maintained 4-bedroom, 2-bathroom home offers a serene living experience in the desirable Country Club Estates neighborhood. Built in 2016, the residence boasts a split-bedroom floor plan, providing privacy and comfort for all occupants.Master Suite: Overlooks a tranquil

    Marilyn Kuczynski FLORIDA HOMES SALES & MANAGEMENT LLC

    4844 Summerfield Cir, Winter Haven, FL 33881
  • /25

    $1,500 per month

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

    1003 Eagle Pond Dr Unit 1003, 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 with washer/dryer included, walk-in closets, open concept living space, all hard flooring throughout (no carpet anywhere!), and so much more. The spacious master bedroom features an en suite bathroom while both bedrooms

    Kayly Malinas JOHN WOOD REALTY, INC.

    1003 Eagle Pond Dr Unit 1003, Winter Haven, FL 33884
  • /50

    $4,000 per month

    • 4 Beds
    • 3 Baths
    • 2,549 Sq Ft
    • House for Rent

    1793 Lake Hill Dr, Winter Haven, FL 33884

    NEW CONSTRUCTION home in established Woodpointe gated community of SE Winter Haven. Quality construction and finishes. Floorplan attached. Special Builder Features included: Sealed energy efficient foam insulation system (Living Area) and ventilated energy efficient foam insulation system (Garage and Lanai), brick paver driveway and lanai tongue-and-groove stained wood ceiling (Front Entry and

    Kayly Malinas JOHN WOOD REALTY, INC.

    1793 Lake Hill Dr, Winter Haven, FL 33884
  • /47

    $2,650 per month

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

    934 Cattleman St, Winter Haven, FL 33884

    Stunning 5BR/2.5BA single family home on an oversized lot in the sought-after Inman Groves community. Move-in-ready home offers 2,215sq. ft. of thoughtfully designed living space with high ceilings, tile/carpet floors, and an open-concept layout. The kitchen features a spacious island and flows into the expansive family room. Upstairs, the owner’s suite includes a large walk-in closet and private

    Cristina de Oliveira Miami New Realty

    934 Cattleman St, Winter Haven, FL 33884
  • /14

    $2,200 per month

    • 3 Beds
    • 2 Baths
    • 2,066 Sq Ft
    • House for Rent

    361 Greenfield Rd, Winter Haven, FL 33884

    Great 3bd / 2ba pool home, interior pictures will be posted soon. This wonderful house is situated in Cypresswood Golf & Country Club that offers a community clubhouse, pool, tennis courts, dining rooms and bar plus an 18 hole championship golf course. The great location is just minutes to Winter Haven and convenient to US Hwy. 27, with a short 20 min. drive to I-4.Conveniently located in Central

    Joseph Bowden EXP REALTY LLC

    361 Greenfield Rd, Winter Haven, FL 33884
  • /43

    $2,300 per month

    • 3 Beds
    • 2 Baths
    • 1,940 Sq Ft
    • House for Rent

    204 Lake Region Blvd S, Winter Haven, FL 33881

    This beautiful 3 bedroom, 2 Baths Single-Family House for rent in a private community of Gates of Lake Region. This house has a Range, Refrigerator, D/W, Disposal, Central A/C.

    Rick Sein REALSOURCE PROPERTY MANGNT LLC

    204 Lake Region Blvd S, Winter Haven, FL 33881
  • /16

    $2,200 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 home delivers

    Lamanda Jones CENTURY 21 WATSON & MYERS REALTY

    2700 Crump Rd, Winter Haven, FL 33881
  • /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 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
  • /24

    $1,675 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
  • /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
  • /21

    $1,450 per month

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

    706 Eagle Pond Dr, Winter Haven, FL 33884

    All NEW FLOORING, No Carpets. New Water heater. 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. All NEW FLOORING, No Carpets. New Water heater. Well-maintained. Featuring a spacious living room, with each bedroom having their own walk-in closet, and an open kitchen with a breakfast

    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

Why Live in 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 33884, 33881, 33844, 33838 and 33880.
How to Rent a Home