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Houses for Rent in Downtown Winter Haven, Winter Haven, FL

Average rent

$1,745

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107 Avenue F Sw - Photo 1 of 1

5d+ ago

South College house for rent in Winter Haven

Single Family Residence - WINTER HAVEN, FL

107 Avenue F Sw, Winter Haven, FL 33880

In-unit laundry | Fireplace | Business center

3 beds

1 bath

$1,700

House for rent

Description

Property Status: Active Experience the perfect blend of historic charm and modern updates in this beautifully remodeled 1928 home, ideally located in the heart of Winter Haven. This property can be leased as a home or commercially!! Bring your business an update with a new office space! Just off First Street and minutes from shopping, public transportation, and major roadways, this home offers both convenience and character. Inside, you'll find a contemporary interior with brand-new flooring and crisp paint that highlights the home's timeless features. With three generousl

495 Avenue F Se - Photo 1 of 1

5d+ ago

House for rent in Winter Haven

Single Family Residence - WINTER HAVEN, FL

495 Avenue F Se, Winter Haven, FL 33880

Air conditioning | High ceilings | Fireplace

2 beds

1 bath

$1,690

House for rent

Description

Property Status: Active One or more photo(s) has been virtually staged. Discover modern comfort and privacy in this fully renovated single-family home just moments from downtown Winter Haven. Thoughtfully updated from top to bottom, the home features a new roof, new A/C, and a beautifully redesigned kitchen and bathroom with granite countertops and sleek finishes. Porcelain tile flooring flows throughout the home, complementing the high ceilings and large windows that fill the space with natural light. The open-concept living area centers around a cozy fireplace, creating

Listings within 5 miles
754 Avenue N Se - Photo 1 of 1

1d ago

House for rent in Winter Haven

Spacious 3-Bedroom Home with Screened Pool Retreat

754 Avenue N Se, Winter Haven, FL 33880

Outdoor space | Swimming pool | On-site management

3 beds

2 baths

$1,800

House for rent

Description

MOVE-IN READY This home is move-in ready. Schedule your tour now or start your application today. Monthly Recurring Fees: $175.00 - Pool Service $10.95 - Utility Management Set in a well-established Winter Haven neighborhood, this 3-bedroom, 2-bath home offering 1,563 square feet blends open living spaces with standout outdoor features. Mature trees frame the property, creating a welcoming approach that leads into a layout designed for both everyday comfort and flexible living. Inside, LVP flooring flows through the main living areas, complemented by fresh interior pai

1405 N Lake Shipp Dr Sw - Photo 1 of 1

5d+ ago

Tranquility Park house for rent in Winter Haven

3 Bedroom Pet-Friendly Home in WINTER HAVEN, FL with Main Street Renewal

1405 N Lake Shipp Dr Sw, Winter Haven, FL 33880

Outdoor space | Storage | Swimming pool

3 beds

2 baths

$1,800

House for rent

Description

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 in a great neighborhood with access to schools, parks, dining and more. Don't miss a chance to make this house your next home! Beyond the home, experience the ease of our technolog

412 Orange Blossom Dr - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Haven

412 Orange Blossom Dr, Winter Haven, FL 33880

In-unit laundry | Garage parking | Swimming pool

2 beds

2 baths

$1,875

House for rent

Description

Welcome to the 2 bed 2.5 bath Lake Front Townhouse, a stunning property located in the heart of Winter Haven, FL. This home boasts two spacious bedrooms and two and a half bathrooms, offering ample space for comfort and relaxation. The property comes with a one-car garage, providing secure parking and additional storage. The townhouse is situated right on the lakefront, offering breathtaking sunsets and easy access to water activities. For those who enjoy outdoor leisure, the property also features a pool, perfect for cooling off on those warm Florida days. The location is

Nearby rental good for eco-living

Nearby rental good for pet owners

1744 Wallace Manor Loop - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

1744 Wallace Manor Loop, Winter Haven, FL 33880

On-site laundry | Outdoor space | Garage parking

3 beds

2 baths

$1,960

House for rent

Available Feb 16

Description

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 rentprogress com smarthome 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 to

1961 9th St Se - Photo 1 of 1

4h ago

Our team has verified this company

Verified

1961 9th St Se, Winter Haven, FL 33880

On-site laundry | Swimming pool | On-site management

4 beds

3 baths

$2,735

House for rent

Available Feb 16

Description

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 is currently occupied and coming soon; please respect the current resident’s privacy and do not disturb. Please note that the advertised price may exclude additional fees. These in

124 Hampden Rd - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

124 Hampden Rd, Cypress Gardens, FL 33884

On-site laundry | Swimming pool | On-site management

2 beds

2 baths

$1,830

House for rent

Available Mar 18

Description

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 is currently occupied and coming soon; please respect the current resident’s privacy and do not disturb. Please note that the advertised price may exclude additional fees. These in

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708 17th St Ne - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

708 17th St Ne, Winter Haven, FL 33881

On-site laundry | Swimming pool | On-site management

3 beds

2 baths

$1,925

$1,690

Price drop

House for rent

Available Jan 16

Description

Please note that the advertised price may exclude additional fees. These include a $55 application fee per applicant; a one-time $75 admin fee; a $11 monthly utility management fee; other mandatory fees, if applicable, for pool maintenance, pet fees/rent, smart home, internet service, and propane refilling; and optional fees for services like self-guided tours with third-party provider Rently ($1.99 to $11.99). HOAs may also charge mandatory application and amenity fees, where applicable, which must be paid directly to the HOA. For a comprehensive overview of all potentia

4202 Roberta Dr - Photo 1 of 1

1d ago

Our team has verified this company

Verified

4202 Roberta Dr Winter Haven, FL 33881

4202 Roberta Dr, Winter Haven, FL 33881

Garage parking

4 beds

2 baths

$2,099

House for rent

Available Jan 16

Description

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 $2243.90. That covers your base rent, $2099.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet & Media ($85), Smart Home with video doorbell ($40), and Utility Billing Service Fee ($9.95). Base rent varies based on selected lease term. This is the house you've been looking

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1112 Sophia Blvd - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

1112 Sophia Blvd Winter Haven, FL 33881

1112 Sophia Blvd, Winter Haven, FL 33881

Garage parking

3 beds

2 baths

$1,930

$1,785

Price drop

House for rent

Available Nov 20

Description

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 $1929.90. That covers your base rent, $1785.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet & Media ($85), Smart Home with video doorbell ($40), and Utility Billing Service Fee ($9.95). Base rent varies based on selected lease term. This is the house where needs and want

913 W Lake Cannon Dr Nw - Photo 1 of 1

1d ago

Our team has verified this company

Verified

913 W Lake Cannon Dr NW Winter Haven, FL 33881

913 W Lake Cannon Dr Nw, Winter Haven, FL 33881

Outdoor space | Garage parking

3 beds

2 baths

$1,749

House for rent

Available Dec 11

Description

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 $1893.90. That covers your base rent, $1749.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet & Media ($85), Smart Home with video doorbell ($40), and Utility Billing Service Fee ($9.95). Base rent varies based on selected lease term. This is the house where needs and want

966 Sunshine Way Sw - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

966 Sunshine Way SW Winter Haven, FL 33880

966 Sunshine Way Sw, Winter Haven, FL 33880

Outdoor space | Garage parking

3 beds

2 baths

$1,595

House for rent

Available Oct 3

Description

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 $1739.90. That covers your base rent, $1595.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet & Media ($85), Smart Home with video doorbell ($40), and Utility Billing Service Fee ($9.95). Base rent varies based on selected lease term. You deserve a quality home that you ca

107 Lake Elizabeth Dr - Photo 1 of 1

5d+ ago

Eloise Woods house for rent in Cypress Gardens

3 Bedroom Pet-Friendly Home in WINTER HAVEN, FL with Main Street Renewal

107 Lake Elizabeth Dr, Cypress Gardens, FL 33884

Outdoor space | Storage | Swimming pool

3 beds

1 bath

$1,505

House for rent

Description

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 in a great neighborhood with access to schools, parks, dining and more. Don't miss a chance to make this house your next home! Beyond the home, experience the ease of our technolog

319 Avenue P Ne - Photo 1 of 1

1d ago

House for rent in Winter Haven

Single Family Residence - WINTER HAVEN, FL

319 Avenue P Ne, Winter Haven, FL 33881

In-unit laundry | Outdoor space | Ceiling fan

3 beds

2 baths

$1,850

House for rent

Description

Property Status: Active Welcome home to this beautifully updated, move-in-ready residence that blends modern finishes with easy, everyday living. Inside, you’ll find a bright, refreshed interior featuring durable new flooring, fresh paint throughout, and a thoughtfully updated kitchen with sleek quartz countertops, new cabinetry, and stainless steel appliances—perfect for both daily use and entertaining. The open, functional layout offers comfortable living spaces and convenient washer/dryer hookups, while the backyard provides a private outdoor retreat ideal for relaxi

1502 Buckeye Rd Ne #3 - Photo 1 of 1

5d+ ago

Lake Buckeye Estates townhouse for rent in Winter Haven

Townhouse - WINTER HAVEN, FL

1502 Buckeye Rd Ne #3, Winter Haven, FL 33881

In-unit laundry | Garage parking | Walk-in closets

2 beds

2 baths

$1,400

House for rent

Description

Property Status: Active Discover comfort, and style in this beautifully remodeled lakefront 2 bedroom, 2 bath home in Winter Haven. This inviting townhome features an open layout, modern finished, updated flooring, and a freshly renovated kitchen and bathroom giving the entire home a clean and contemporary feel. Enjoy spacious bedrooms, plenty of natural light, and a cozy living area perfect for relaxing and entertaining. Step outside and embrace serene waterviews and peaceful surroundings right from your doorstep. Conveniently located near shopping, dining, parks, and Win

2521 Pine Pl - Photo 1 of 1

5d+ ago

House for rent in Winter Haven

2521 Pine Pl, Winter Haven, FL 33881

Swimming pool | Fitness center | Controlled access

3 beds

2 baths

$1,950

House for rent

Description

Welcome to 2521 Pine Pl, where modern elegance meets peaceful lakefront living. This beautifully designed 3-bedroom, 2.5-bath home offers spectacular lake views right from your backyard, creating the perfect backdrop for morning coffee, sunset relaxation, or weekend gatherings. Inside, enjoy a bright open-concept floor plan, a sleek contemporary kitchen, and a luxurious primary suite built for comfort and retreat. Nestled in one of Winter Park’s most desirable communities, you’re just minutes from top-rated schools, upscale dining, shopping, and local attractions. Lake-vie

4222 Roberta Dr - Photo 1 of 1

5d+ ago

House for rent in Winter Haven

4222 Roberta Dr, Winter Haven, FL 33881

In-unit laundry | Outdoor space | Storage

4 beds

2 baths

$1,850

House for rent

Available Jan 7

Description

Say hello to your next family favorite! This 4-bedroom, 2-bath home is full of space, sunshine, and good vibes, all tucked inside a friendly community you’ll love coming home to. Tile floors throughout mean easy cleanups, while plenty of storage keeps everything right where it belongs. Enjoy peaceful water views, unwind in the private primary suite, and appreciate the everyday wins like a washer and dryer and a 2-car garage. From busy mornings to cozy nights, this home is ready for laughter, memories, and a whole lot of living. LOCATION: Scores a 10/10 by us! Convenientl

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2265 3rd St Ne - Photo 1 of 1

5d+ ago

House for rent in Winter Haven

2265 3rd St Ne, Winter Haven, FL 33881

In-unit laundry | Outdoor space | Storage

3 beds

1 bath

$1,695

House for rent

Available Jan 5

Description

Available the first week of January, this well-maintained 3-bedroom home is tucked away on a quiet dead-end street, offering privacy and a peaceful setting. The interior features a functional and efficient layout designed to make the most of every square foot, with a welcoming living area ideal for everyday comfort and casual entertaining. The kitchen is thoughtfully updated with stainless steel appliances and ample cabinetry, providing a practical space for daily meals. A front bonus room adds flexibility and can easily accommodate a home office, playroom, or workout are

Turtle Bay Ave #214 - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Haven

Winter Haven Townhouse

Turtle Bay Ave #214, Winter Haven, FL 33881

In-unit laundry | Assigned parking | Carpet

3 beds

2 baths

$1,850

House for rent

Available Jan 1

Description

Be the first to live in this brand new townhouse in the development of Harborside at Lake Henry. This 2 story townhouse and has all the 3 bedrooms and 2 bathrooms upstairs. There is a communal 1/2 bath downstairs close to the family area. Downstairs there is a family area, kitchen and just off the kitchen there is a flex space. The bottom floor has laminate flooring through out. Going upstairs you will find grey carpet throughout. There is a hookup for washer and dryer upstairs. To schedule a viewing please respond to this post.

3543 Evening Star Dr - Photo 1 of 1
New construction

5d+ ago

House for rent in Winter Haven

Single Family Residence - WINTER HAVEN, FL

3543 Evening Star Dr, Winter Haven, FL 33881

In-unit laundry | Outdoor space | Garage parking

4 beds

2 baths

$2,050

House for rent

Description

Property Status: Active Welcome home to this modern 2025-built single-family residence featuring 4 bedrooms, 2 bathrooms, and 1,858 sq ft of bright, open living space. The open-concept design flows beautifully from the spacious living area into a sleek kitchen finished with stone countertops, contemporary cabinetry, and a clean, modern feel throughout. The oversized tile flooring adds a polished, upscale look and makes everyday living effortless. Step outside and enjoy the covered rear lanai, perfect for relaxing mornings or weekend gatherings. Sitting on a spacious

25 Casarena Ct - Photo 1 of 1
3D tour

1d ago

House for rent in Winter Haven

Retro Charm in Winter Haven, FL!

25 Casarena Ct, Winter Haven, FL 33881

Storage | Garage parking | High ceilings

3 beds

3 baths

$1,975

House for rent

Description

COMING SOON This home is coming soon. Please check maymonthomes. com to see the estimated availability date. Monthly Recurring Fees: $25.00 - Smart Home $10.95 - Utility Management Step into style and character with this inviting 3-bedroom, 3-bathroom end-unit home in Winter Haven. With its distinctive exterior and bold architectural details, this residence stands out with unique charm from the moment you arrive. Inside, the living room features sleek hard-surface flooring that adds a clean and modern feel. The adjoining den offers plush carpeting, vaulted ceilings, an

511 511 Ave B NW - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Haven

2 beds

2 baths

$1,849

House for rent

Description

This rare treasure is now available for a new tenant to call it home! This two-bedroom, two-and-a-half-bathroom home was designed and built by the highly sought after Gene Leedy; everywhere you turn you see his signature touches that have brought him notoriety, the world over. The newly updated kitchen features new cabinets, countertops, sink fixture and stainless-steel appliance package. The unit boasts large windows that overlook the two private courtyards below and lots of closet space. A stackable washer/dryer is included in the townhouse as well. Each bedroom feat

807 Ware Ave Ne #NA - Photo 1 of 1

5d+ ago

House for rent in Winter Haven

3BR/2BA/2 CAR GARAGE

807 Ware Ave Ne #NA, Winter Haven, FL 33881

In-unit laundry | Outdoor space | Garage parking

3 beds

2 baths

$1,750

House for rent

Available Oct 1

Description

Amazing 3 bedroom, 2 bathroom house in Winter Haven, FL. Amenities included: central air, central heat, dishwasher, hardwood floors, stainless steel appliance, laundry area in home, and yard. No Utilities included. Is not pet friendly. Date Available: January 1, 2026 $1,750/month rent. $1,750 security deposit required. All residents are enrolled in the Resident Benefits Package (RBP) at a cost of $25/per month, which includes HVAC air filter delivery (for applicable properties), credit reporting. More details upon application. Lessee(s) are required to provide proof of lia

1995 5th St Ne #10 - Photo 1 of 1

5d+ ago

House for rent in Winter Haven

1995 5th Street NE - 10

1995 5th St Ne #10, Winter Haven, FL 33881

3 beds

1 bath

$995

House for rent

Available Feb 9

Description

Rent with confidence from a licensed Real Estate Brokerage. We have a quick and simple application process. Contact us through this website or call to set up a tour and apply today! WE PROUDLY WELCOME ALL PETS. Welcome to this charming 3-bed, 1-bath home! Our spacious layout is perfect for comfortable living. Enjoy the yard to unwind after a long day, enjoy the fresh air, and gather for fun-filled activities. Approaching the home, you will find a fenced-in backyard with enough space for chairs to enjoy the outdoors and family gatherings. As you enter the home, you will

Showing 1 - 25 of 25 results
Home > House Rentals in Winter Haven > Downtown Winter Haven Houses For Rent
Updated: January 29, 2026

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Discover houses for rent in Downtown Winter Haven, Winter Haven, FL

🌇Available house rentals25 houses
💰Best rent deal495 Avenue F Se
Popular amenities, ,