923

Winter Haven, FL Homes for Rent under $3,000

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  • /15

    $2,280 Per Month

    • 4 Beds
    • 2 Baths
    • 1,999 Sq Ft
    • House for Rent

    4753 Osprey Way, Winter Haven, FL 33881

    Apply now or schedule your self-tour today and take the first step toward getting more than just a place to live. Rent with FirstKey Homes for a home that's right for you, plus professional service and maintenance, innovative resident programs, and more; that's the power of purple! This 4-bedroom, 2-bathroom rental home in Winter Haven, FL, may be the right place for you. See the pictures to

    4753 Osprey Way, Winter Haven, FL 33881
  • /16

    $1,700 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,356 Sq Ft
    • House for Rent

    5850 Cypress Gardens Blvd, Winter Haven, FL 33884

    Property Id: 987474 Spacious 3BR / 2.5BA Townhome in Cypress Gardens Area Welcome to this well maintained 3-bedroom, 2.5-bath townhome located in a convenient and desirable area of Cypress Gardens. This home features a bright, open living space, a functional kitchen, and a comfortable layout ideal for everyday living. All three bedrooms are generously sized, with the primary suite

    5850 Cypress Gardens Blvd, Winter Haven, FL 33884
  • /15

    $1,895 Per Month

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

    835 Summer Glen Dr, Winter Haven, FL 33880

    Apply now or schedule your self-tour today and take the first step toward getting more than just a place to live. Rent with FirstKey Homes for a home that's right for you, plus professional service and maintenance, innovative resident programs, and more; that's the power of purple! This 3-bedroom, 2-bathroom rental home in Winter Haven, FL, may be the right place for you. Enjoy the privacy

    835 Summer Glen Dr, Winter Haven, FL 33880
  • /15

    $2,220 Per Month

    • 3 Beds
    • 2 Baths
    • 1,830 Sq Ft
    • House for Rent

    444 Lanham Dr, Winter Haven, FL 33881

    Apply now or schedule your self-tour today and take the first step toward getting more than just a place to live. Rent with FirstKey Homes for a home that's right for you, plus professional service and maintenance, innovative resident programs, and more; that's the power of purple! This 3-bedroom, 2-bathroom rental home in Winter Haven, FL, may be the right place for you. Enjoy outdoor

    444 Lanham Dr, Winter Haven, FL 33881
  • /20

    $2,195 Per Month

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

    397 Corso Loop, Winter Haven, FL 33884

    Property Id: 1220815 Beautiful 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 offers

    397 Corso Loop, Winter Haven, FL 33884
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    $1,730 Per Month

    • 3 Beds
    • 2 Baths
    • 1,310 Sq Ft
    • House for Rent

    3740 Imperial Dr, Winter Haven, FL 33880

    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 is priced to rent and won't be around for long. Apply now, while we make this home ready for you, or call to arrange a meeting with your local Progress Residential leasing specialist

    3740 Imperial Dr, Winter Haven, FL 33880
  • /16

    $1,820 Per Month

    • 3 Beds
    • 2 Baths
    • 1,310 Sq Ft
    • House for Rent

    2520 Ave a SW, Winter Haven, FL 33880

    Beautiful, pet-friendly home coming soon! Apply now — available date is tentative and move-in will be scheduled within 5–10 days of the home being ready. Upon approval, $500 reservation deposit to reserve (applied to security deposit and/or refundable). Application fee: $55 per adult. Security Deposit: one month's rent. Pet fees: $250 + $40/mo per pet. Some homes may include pool ($150/mo),

    2520 Ave a SW, Winter Haven, FL 33880
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    $2,050 Per Month

    • 4 Beds
    • 2 Baths
    • 1,850 Sq Ft
    • House for Rent

    1336 Axel Cir, Winter Haven, FL 33880

    Property Id: 836169 4 bedroom 2 Bathroom Single Family Home Easy commute to either Tampa or Orlando. Large kitchen granite countertops, large pantry, stainless steel appliances, Washer and Dryer included, vaulted ceiling, 2-car garage. Security deposit due at signing. $2000 1st and Last and security due at move in. Well qualified applicants may be

    1336 Axel Cir, Winter Haven, FL 33880
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    $1,100

    Total Monthly Price

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

    836 Lake Martha Dr NE Unit B, Winter Haven, FL 33881

    This 1 bedroom 1 bath is located close to downtown Winter Haven area walking distance to restaurants and the local Farmer's Market. Very close to a jogging track and several sports fields for fun recreation. Water, washer and dryer, Wi-Fii, trash and water included. Close by a lake to enjoy beautiful sunsets at the lake. The neighborhood is very nice and quiet but walking distance to museums

    836 Lake Martha Dr NE Unit B, Winter Haven, FL 33881
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    $1,400

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,073 Sq Ft
    • Condo for Rent

    357 Winter Ridge Blvd Unit 357, Winter Haven, FL 33881

    Available NowLakefront Condo on Lake Smart. The community of Winter Ridge Condos offer a community swimming pool, club house, and private boat dock. This Lakefront inviting condo features 2 large bedrooms and 2 bathrooms and covered car-port. An open layout living/dinning combo and abundant natural light. No Smoking. $1400 rent per month plus one month security deposit and utilities

    357 Winter Ridge Blvd Unit 357, Winter Haven, FL 33881
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    $1,600

    Total Monthly Price

    • 3 Beds
    • 2 Baths
    • 1,411 Sq Ft
    • Condo for Rent

    690 Avenue C SE Unit 690, Winter Haven, FL 33880

    690 Avenue C SE Unit 690, Winter Haven, FL 33880
  • /18

    $1,500

    Total Monthly Price

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

    901 Eagle Pond Dr Unit 901 Eagle Pond, Winter Haven, FL 33884

    Beautifully Renovated First-Floor Apartment in prestigious Cypresswood Gated Golf Course CommunityWelcome home to this beautifully fully renovated 1,017-square-foot first-floor apartment, located in a highly desirable gated golf course community. This move-in-ready home features 2 spacious bedrooms with walk-in closets, 2 full bathrooms, 2 linen closets, and a convenient laundry closet

    901 Eagle Pond Dr Unit 901 Eagle Pond, Winter Haven, FL 33884
  • /31

    $1,800

    Total Monthly Price

    • 4 Beds
    • 2 Baths
    • 1,368 Sq Ft
    • House for Rent

    3960 Avenue U NW, Winter Haven, FL 33881

    Don't miss out on this 4 bedroom home, at an amazing price. This home has been freshly painted and has ceramic tile throughout. The French doors lead to a paver patio that provides access to a huge backyard. The uncovered gazebo/patio area is perfect for those fire pit evenings. Your front covered patio gives you a Waterview of Lake Blue.

    3960 Avenue U NW, Winter Haven, FL 33881
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    $2,300

    Total Monthly Price

    • 4 Beds
    • 2 Baths
    • 1,828 Sq Ft
    • House for Rent

    1341 Daisy Field Dr, Winter Haven, FL 33884

    Pond View | NEW Washer & Dryer Included | Pet Friendly | 4BR/2BA 2024 New Construction | Smart Home | Resort-Style Pool 2 minute walkWelcome to this beautiful 4-bedroom, 2-bathroom home located in the desirable Harmony at Lake Eloise community. Offering 1,828 square feet of living space, this owner-occupied home features an open-concept layout, modern finishes, and a peaceful pond

    1341 Daisy Field Dr, Winter Haven, FL 33884
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    $2,350

    Total Monthly Price

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

    6224 Botticella Blvd, Winter Haven, FL 33884

    The first floor of this new two-story home is host to an open-concept layout that combines the kitchen with the living and dining areas, and an outdoor patio is easily reached off the main living space. Upstairs, five bedrooms surround a versatile loft, including the luxe owner’s suite, complete with a generous walk-in closet and en-suite bathroom.

    6224 Botticella Blvd, Winter Haven, FL 33884
  • /20

    $850

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 450 Sq Ft
    • Condo for Rent

    1131 5th St SW Unit 4 downstairs, Winter Haven, FL 33880

    Centrally located to restaurants, Aldis, Lowe's and other shopping within walking distance. Small quiet apartments - property has security lights for safety.

    1131 5th St SW Unit 4 downstairs, Winter Haven, FL 33880
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    $1,475

    Total Monthly Price

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

    448 Avenue A NE Unit Cozy Cottage, Winter Haven, FL 33881

    This cozy Cottage is a 1/1 in Winter Haven Fl. Walk to downtowns restaurant and local shops and breweries. Close to Legoland and major medical. Short term unit with small kitchenette. Fenced yard with private spa. This home is set up for short term rental and has kitchenette with Convection Microwave, coffee pot, and all dishware. Washer Dryer, queen bed, TVs in the living room and bedroom.

    448 Avenue A NE Unit Cozy Cottage, Winter Haven, FL 33881
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    $1,000

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 1,111 Sq Ft
    • House for Rent

    101 Lake Sears Dr, Winter Haven, FL 33880

    Nice and clean 3 bedroom house shared bathroom. I have a cat but mostly outside

    101 Lake Sears Dr, Winter Haven, FL 33880
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    $1,750

    Total Monthly Price

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

    711 Avenue B NE, Winter Haven, FL 33881

    This is a 3/2 home in Winter Haven Fl. This home is move in ready and had been freshly updated. Call for your showing today. Close to downtown and convenient to all winter haven has to offer.Washer Dryer hook upsCentral heat and airScreened porchLong term or short term approved.

    711 Avenue B NE, Winter Haven, FL 33881
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    $1,295

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 500 Sq Ft
    • Condo for Rent

    320 Spirit Landings Cir Unit New Apartment, Winter Haven, FL 33880

    - New Beautiful, Spacious Apartment - Great location, near restaurants, hospitals, and highways.- New development in quiet neighbourhood

    320 Spirit Landings Cir Unit New Apartment, Winter Haven, FL 33880
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    $1,400

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 1,260 Sq Ft
    • Condo for Rent

    5850 Cypress Gardens Blvd Unit 607, Winter Haven, FL 33884

    This property at 5850 Cypress Gardens Blvd unit #607 features 2 bedrooms and 1 bathroom within a total of 1,260 square feet. The living room offers ample space for relaxation and entertainment, while the bedrooms provide comfortable accommodations. The bathroom is equipped with standard fixtures. Amenities include air conditioning for climate control, a washer and dryer for laundry convenience,

    5850 Cypress Gardens Blvd Unit 607, Winter Haven, FL 33884
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    $1,425 Per Month

    • 2 Beds
    • 2 Baths
    • 1,030 Sq Ft
    • Condo for Rent

    333 Lake Howard Dr NW Unit 312C, Winter Haven, FL 33880

    FOR RENT - 2 Bedroom/2 Bath Condo at Imperial Harbours. This community is for ages 55+. The unit comes with all of the appliances and faces the garden area. The bedrooms are generously sized, and the porch area is enclosed. The community features a very nice pool with a TIKI Bar area for relaxing and sipping your favorite drinks. In the distance you can watch the sun rise over Lake Howard in the

    Linda Andre COLDWELL BANKER REALTY

    333 Lake Howard Dr NW Unit 312C, Winter Haven, FL 33880
  • /15

    $1,780 Per Month

    • 4 Beds
    • 2 Baths
    • 1,758 Sq Ft
    • House for Rent

    175 Southern Breeze Lp, Winter Haven, FL 33880

    From Hwy 17 S - Turn right onto Spirit Lake Rd and continue for 1.6 miles. Turn left onto Grady Polk Rd and destination will be on the right. From Hwy 17 N - Turn left onto Spirit Lake Rd and continue for 1.6 miles. Turn left onto Grady Polk Rd and destination will be on the right. Apply now or schedule your self-tour today and take the first step toward getting more than

    175 Southern Breeze Lp, Winter Haven, FL 33880
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    $2,250 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,200 Sq Ft
    • House for Rent

    437 Fish Hawk Dr, Winter Haven, FL 33884

    Welcome to this beautiful 4 bedroom, 2.5 bath home. located in a highly desirable community. This spacious home offers a functional floor plan with generous living areas, modern kitchen, and comfortable bedroom, making perfect for families or professionals. Enjoy a private backyard and all the benefits of living in well maintained neighborhood close to school, shopping, dinning, parks and major

    Mike Coicou LA ROSA REALTY PRESTIGE

    437 Fish Hawk Dr, Winter Haven, FL 33884
  • /20

    $1,600 Per Month

    • 2 Beds
    • 2 Baths
    • 1,074 Sq Ft
    • House for Rent

    204 Chaucer Ln, Winter Haven, FL 33884

    Centrally located 2 bedroom 2 bath. This home has been updated with new flooring and paint throughout. 2 car garage, screen lanai, fenced yard.Administration Fee:Upon approval tenants will be subject to a $250 one-time administration fee.**This home comes with high speed internet up to 1 Gig at an exclusive group rate of $60/month (In addition to advertised rent), and includes

    204 Chaucer Ln, Winter Haven, FL 33884
  • /42

    $1,450 Per Month

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

    704 Eagle Pond Dr Unit 7D, Winter Haven, FL 33884

    Lovely GROUND FLOOR Eagle Pond condominium in the highly sought-after gated community of Cypresswood Golf and Country Club. 10-foot high ceilings, complimenting the open concept living area complete with expansive living and dining areas, including a kitchen breakfast bar. All NEW luxury vinyl flooring, NEW windows and sliding glass patio door, NEW kitchen countertops, and fresh interior paint.

    Kayly Malinas JOHN WOOD REALTY, INC.

    704 Eagle Pond Dr Unit 7D, Winter Haven, FL 33884
  • /12

    $1,075 Per Month

    • 2 Beds
    • 1 Bath
    • Condo for Rent

    3025 St Paul Dr, Winter Haven, FL 33880

    Updated paint 2 bedrooms one bath quad. Kitchen with breakfast bar. Large living room/dining room combo. Two large bedrooms. Inside utility room with washer and dryer hook ups. Yard service is included in the rent. Tenants must carry renters' insurance. $1075.00 per month. Call today for your private showing. Pet free/smoke free.

    3025 St Paul Dr, Winter Haven, FL 33880
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    $1,450 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 Eagle Pond condominium in the highly desirable 24-hour guard-gated community of Cypresswood Golf and Country Club. High ceilings, breakfast bar, and open-concept living area are just a few features this property offers. The spacious primary bedroom features an en suite bathroom while both bedrooms offer walk-in closets. Additional linen storage exists in the main bedroom and hallway,

    Kayly Malinas JOHN WOOD REALTY, INC.

    1105 Eagle Pond Dr Unit 11E, Winter Haven, FL 33884
  • /3

    $1,850 Per Month

    • 4 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • Condo for Rent

    731 Ave a SW Unit Apartment 2nd floor, Winter Haven, FL 33880

    Welcome to your new home in Winter Haven, FL! This charming property is ideally situated near excellent dining options and several department stores, making it a vibrant place to live. You'll appreciate the convenience of Winter Haven Hospital just five minutes away, as well as the nearby Trailhead Park Playground and South Lake Howard Nature Park, perfect for outdoor enthusiasts.Key

    731 Ave a SW Unit Apartment 2nd floor, Winter Haven, FL 33880
  • /41

    $1,750 Per Month

    • 3 Beds
    • 1 Bath
    • 1,100 Sq Ft
    • House for Rent

    204 6th Jpv St, Winter Haven, FL 33880

    Three bedroom, one bathroom home located in Winter Haven. This property features a roof installed in 2025 and an AC system installed in 2025 for energy efficiency and year round comfort. The interior floor plan includes a remodeled kitchen, a remodeled bathroom, and low maintenance ceramic tile flooring throughout with no carpet. Enjoy a functional layout with bright living spaces and a spacious

    Juan Corrales DALTON WADE INC

    204 6th Jpv St, Winter Haven, FL 33880
  • /13

    $1,450 Per Month

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • House for Rent

    1734 35th St NW, Winter Haven, FL 33881

    Comfortable 3-Bedroom 2-Bath in Winter Haven is ready for you to call this home! Lawn care is included with the rent on this large lot for stress-free living. Kitchen features stainless steel appliances with built-in microwave. Washer/dryer hookups for your convenience. Pets up to 50 lbs. are welcome with associated fees, 2 pet max. Schedule your tour today!Applications do not hold the

    1734 35th St NW, Winter Haven, FL 33881
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    $1,550 Per Month

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

    802 Eagle Pond Dr, Winter Haven, FL 33884

    FULLY FURNISHED and EQUIPPED including linens and dishes.Minimum 7 month lease.Enjoy the serene pond front views from this first floor 2 bedroom 2 bathroom condo located in the Eagle Pond Neighborhood in Gated, Cypresswood Golf and Country Club.MOVE IN WITH YOUR SUITCASE!Amenities include 24 hour manned gate, community pool, brand new pickleball and tennis courts, clubhouse with

    Steven Smith, PA LOCKHART & ASSOCIATES INC

    802 Eagle Pond Dr, Winter Haven, FL 33884
  • /15

    $2,025 Per Month

    • 4 Beds
    • 2 Baths
    • 1,598 Sq Ft
    • House for Rent

    211 Southern Breeze Lp, Winter Haven, FL 33880

    From Hwy 17 S - Turn right onto Spirit Lake Rd and continue for 1.6 miles. Turn left onto Grady Polk Rd and destination will be on the right. From Hwy 17 N - Turn left onto Spirit Lake Rd and continue for 1.6 miles. Turn left onto Grady Polk Rd and destination will be on the right. Welcome to South Haven, Winter Haven's newest build-to-rent community where luxury and convenience

    211 Southern Breeze Lp, Winter Haven, FL 33880
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    $1,800 Per Month

    • 3 Beds
    • 2 Baths
    • 1,312 Sq Ft
    • House for Rent

    1666 Ambar Ct, Winter Haven, FL 33881

    Located on a quiet residential community in Winter Haven, this property offers the perfect blend of comfort, convenience, and quality of life in the heart of Central Florida. Just minutes away from shopping centers, grocery stores, restaurants, hospitals, and schools, the location is ideal for families and anyone seeking everyday convenience. The home also features a spacious fenced backyard,

    Amis Quijada MY REALTY GROUP, LLC.

    1666 Ambar Ct, Winter Haven, FL 33881
  • /15

    $2,160 Per Month

    • 3 Beds
    • 2 Baths
    • 1,567 Sq Ft
    • House for Rent

    4736 Mandolin Loop, Winter Haven, FL 33884

    Apply now or schedule your self-tour today and take the first step toward getting more than just a place to live. Rent with FirstKey Homes for a home that's right for you, plus professional service and maintenance, innovative resident programs, and more; that's the power of purple! This 3-bedroom, 2-bathroom rental home in Winter Haven, FL, might be the perfect fit for your lifestyle. See

    4736 Mandolin Loop, Winter Haven, FL 33884
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    $2,250 Per Month

    • 3 Beds
    • 2 Baths
    • 1,540 Sq Ft
    • House for Rent

    1708 Teagan Ln, Winter Haven, FL 33884

    Beautiful single family house built in 2024 with 3 bedrooms, 2 bathrooms, with open kitchen, Living room and Dining Area, Master Bedroom with attached master bath with double sinks and large walking closet, 2 other bedrooms with hall bath, 2 car garages with appliances Stove, Refrigerator, Dishwasher, Microwave, Washer and Dryer. Amenities include pool, playground etc. in the community. 1st,

    K.C. Thomas CHARLES RUTENBERG REALTY ORLANDO

    1708 Teagan Ln, Winter Haven, FL 33884
  • /2

    $1,595 Per Month

    • 3 Beds
    • 1 Bath
    • 1,296 Sq Ft
    • House for Rent

    876 Crestwood Dr, Winter Haven, FL 33881

    This home located in a quiet and desirable area of Winter Haven. This well-maintained property offers a comfortable layout with plenty of natural light, creating a warm and inviting living space.The home features spacious bedrooms, a cozy living area, and a functional kitchen with ample cabinet space, perfect for everyday living. The property also includes a nice outdoor area, ideal for

    876 Crestwood Dr, Winter Haven, FL 33881
  • /25

    $1,650 Per Month

    • 2 Beds
    • 2 Baths
    • 1,213 Sq Ft
    • House for Rent

    253 W Lake Ina Dr, Winter Haven, FL 33884

    No HOA! Pet Friendly!Welcome to this beautifully updated 2-bedroom, 2-bathroom single-family home featuring a spacious driveway, an open floor plan, and an oversized Florida room that's perfect for relaxing or entertaining year-round.This home boasts luxury vinyl flooring throughout and tastefully upgraded bathrooms. The bright and inviting living area flows seamlessly into the dining

    Katrina Anarumo RENT A FLORIDA HOME

    253 W Lake Ina Dr, Winter Haven, FL 33884
  • /15

    $1,949 Per Month

    • 3 Beds
    • 2 Baths
    • 1,432 Sq Ft
    • House for Rent

    2065 Whispering Trails Blvd, Winter Haven, FL 33884

    Welcome to your future home in beautiful Winter Haven, Florida! This charming property is conveniently located near an array of delightful restaurants and department stores, making it an ideal spot for both leisure and shopping.Key property features include a spacious layout thoughtfully designed for comfort. Enjoy the benefits of central heating and cooling, alongside air conditioning

    2065 Whispering Trails Blvd, Winter Haven, FL 33884
  • /11

    $1,550 Per Month

    • 2 Beds
    • 2 Baths
    • 896 Sq Ft
    • Property for Rent

    64 Stebbins Dr Unit 64, Winter Haven, FL 33884

    Why keep renting when you can own for less? Step into your own 2 bed / 2 bath home-brand new, spacious, and designed for real living. Located in Grove Shores, a beautifully maintained, professionally managed community, this is your chance to upgrade your lifestyle without increasing your monthly cost. Call today to schedule your tour-opportunities like this don't last.

    Tori Coil Grove Shores

    64 Stebbins Dr Unit 64, Winter Haven, FL 33884

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