Displaying: For Rent
Location: Winter Haven
Property Type(s): Single Family
Price: $1,500 to $1,999
Do Not Show Listings
Winter Haven - 47 properties found
509 KENSINGTON VIEW DR, WINTER HAVEN, FL 33880
$1,79930 Days on yellowkey MLS ID: TB8512014
REDUCED by $10 (0.6%) on 06/24/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1604 Built: 2021Community: Kensington ViewSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: Eagle Lake Elem
High School: Lake Region High
Tax Year:
Middle School: Westwood Middle
Remarks: Beautiful 3 Bedroom home welcomes you with spacious, sunlit retreats for restful nights. 2 Bathrooms: Convenience for all with two well-appointed baths. Walk-In Closet: A roomy haven for your wardrobe and accessories. Open Floor Plan: Seamless living, dining, and kitchen spaces for gatherings. Pets Welcome: Furry friends thrive in the pet-friendly backyard.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Kevin Watson (813-777-3586)
1539 ROSELAWN ST SW, WINTER HAVEN, FL 33880
$1,77533 Days on yellowkey MLS ID: S5149633
REDUCED by $25 (1.4%) on 06/24/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1147 Built: 1957Community: Tranquility Park 02 RepSingle Family
Elementary School: None
High School: None
Middle School: None
Remarks: Beautifully fully remodeled 3-bedroom, 2-bathroom home located at 1539 Roselawn, offering modern comfort and stylish living throughout. This residence features premium waterproof luxury vinyl flooring, a spacious and upgraded kitchen with elegant granite countertops, and stainless steel appliances. The home has been thoughtfully updated to provide both functionality and design, along with a reliable AC system updated in 2018 for added comfort and efficiency. Located in a desirable area with no HOA restrictions, this property offers flexibility and convenience. Ideal for tenants seeking a move-in ready home with quality finishes and modern upgrades. A true rental opportunity combining comfort, style, and value.
Listing is courtesy of: LA ROSA REALTY KISSIMMEE (407-930-3530)
Listing Agent: Ines Morales (863-738-8794)
218 DENNIS AVE, WINTER HAVEN, FL 33880
$1,6501 Day on yellowkey MLS ID: P4939135
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1174 Built: 1962Community: Jan Phyl Village Unit 03 ASpa: NoSingle Family
Remarks: Available for immediate occupancy, this charming 3-bedroom, 1-bath block home offers a spacious lot with no rear neighbors, providing added privacy and a peaceful setting. Inside, you'll find updated flooring in the bedrooms and bathroom, giving the home a fresh and welcoming feel. The flexible floor plan includes two bonus rooms that can be used as a home office, playroom, hobby space, guest area, or additional storage—offering plenty of options to fit your lifestyle. Step outside to enjoy the screened lanai, perfect for relaxing, enjoying the Florida weather, or entertaining friends and family year-round. The large yard provides ample outdoor space while maintaining privacy with no rear neighbors. Conveniently located and move-in ready, this home combines comfort, versatility, and outdoor enjoyment. Schedule your showing today!
Listing is courtesy of: HAINES AND HAVEN RESIDENTIAL (863-443-8845)
Listing Agent: Lucas Oliveira (863-443-8845)
2192 ROSE BLVD, WINTER HAVEN, FL 33881
$1,8501 Day on yellowkey MLS ID: O6419209
Bed: 4 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1828 Built: 2019Community: Buckeye Ridge Pb 145 Pg 47-49 Lot 108Spa: NoSingle Family
Remarks: Available from 27 June,2026 No large upfront security deposit needed—"Obligo" lets you secure your home with a safe, flexible, deposit-free option. Welcome to 2192 Rose Blvd, Winter Haven, a charming home nestled in one of the most desirable neighborhoods! This beautiful property offers a perfect blend of modern amenities and classic appeal. Step inside to find spacious living areas bathed in natural light, featuring an open floor plan that seamlessly connects the living room, dining area, and kitchen. The gourmet kitchen is a chef's dream, complete with sleek countertops, stainless steel appliances, and ample storage. The master suite is a serene retreat with a luxurious ensuite bathroom and walk-in closet. Outside, enjoy a private backyard perfect for entertaining or relaxing. Located just minutes from local schools, parks, and shopping, this home offers the ideal combination of comfort and convenience. Don’t miss your chance to own a piece of Winter Haven's charm.
Listing is courtesy of: SAFETYNET REALTY (317-603-8743)
Listing Agent: Avihai Sela (317-603-8743)
3408 COSTELLO CIR, WINTER HAVEN, FL 33884
$1,80019 Days on yellowkey MLS ID: O6414344
0 Days Off yellowkey (back on 6/23/2026)
REDUCED by $100 (5.3%) on 06/08/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1713 Built: 2025Community: Villamar Ph 6 & Ph 6DSpa: NoSingle Family
Remarks: RECENTLY REDUCED !! 4-bedroom 2-bathrooms home for RENT ! A Craftsman-style front porch welcomes you into the fully open living area featuring airy volume ceilings and sunny natural lighting. Unwind in your private owner's suite complete with a large walk-in wardrobe and a private en-suite bath with dual vanities, a tiled glass-enclosed shower, private toilet, and a linen closet. This meticulously designed residence combines modern convenience with timeless elegance, showcasing quartz and tile floors throughout. As you step inside, you are greeted by an inviting foyer that leads you into the heart of the home. The open-concept layout seamlessly connects the living room, dining area, and kitchen, creating a perfect space for entertaining family and friends. The spacious living room features abundant natural light, thanks to large windows that provide picturesque views of the surrounding landscape. With ample room for seating, it's an ideal spot for relaxation and gatherings. The chef's kitchen is a true highlight, boasting quartz countertops, sleek stainless steel appliances, and an oversized island with a breakfast bar. Whether you're preparing a casual meal or hosting a formal dinner, this kitchen is well-equipped to meet your culinary needs. Located seven minutes from Legoland, five minutes from Publix, and third-teen minutes away from Lake Wales Shopping Mall. Water softener and Landscaping is included with the rent. Let’s schedule a showing today !
Listing is courtesy of: BEACH REALTORS (407-201-6300)
Listing Agent: Rachel Reyes (407-201-6300)
1701 36TH ST NW, WINTER HAVEN, FL 33881
$1,8009 Days on yellowkey MLS ID: S5151961
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1815 Built: 1960Community: InwoodSingle Family
Remarks: Spacious and move-in ready! This beautifully updated 4-bedroom, 2-bath rental home offers over 1,800 square feet of comfortable living space and sits on a rare 0.40-acre corner lot with NO HOA restrictions. Inside, you'll find a bright and functional floor plan featuring modern flooring, an updated kitchen with stylish cabinetry and stainless-steel appliances, and refreshed bathrooms with contemporary finishes. Recent improvements to the HVAC, electrical, and plumbing systems provide added comfort and peace of mind. The oversized lot offers plenty of outdoor space and ample parking for multiple vehicles. Whether you need room for work trucks, recreational equipment, or simply enjoy having extra outdoor space, this property delivers flexibility that is hard to find. Conveniently located near shopping, restaurants, schools, medical facilities, and major roadways, this home combines small-town comfort with easy access to everything Winter Haven has to offer. Property Features: • 4 Bedrooms • 2 Full Bathrooms • Over 1,800 Sq. Ft. of Living
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Jose Hooker-Gomez (407-272-6986)
2005 N LAKE ELOISE DR, WINTER HAVEN, FL 33884
$1,95013 Days on yellowkey MLS ID: P4938854
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1513 Built: 2005Community: Eloise Woods Lake Roy UnitSpa: NoSingle Family
Remarks: 3 Bedroom 2 bath home for lease: Ideally located near the Lake Summit Boat Ramp and Park, 2005 N Lake Eloise is a beautifully maintained and spacious single-family home offering comfort, convenience, and charm. Enjoy relaxing evenings, morning coffee, or peaceful outdoor living from the private screened-in patio overlooking the fully fenced backyard. The patio also features a convenient pet door and can be accessed directly from both the vaulted-ceiling living room and the private primary suite. The primary suite offers an ensuite bathroom complete with a beautifully tiled walk-in shower, while the guest bathroom includes a tub and shower combination. A full-size two-car garage provides secure entry and ample additional storage space. All kitchen appliances are included, along with a washer and dryer for added convenience. Availability Available October 2026 Amenities Include: Tile Flooring throughout living areas Carpet in Primary Bedroom 2 car garage Fenced in back yard Appliances include: Full Size Washer and Dryer Oven/Stove Dishwasher Refrigerator and Freezer with Water Dispenser and Ice Maker Microwave Pricing: $1,950/month Tenant Pays: electric, internet, water/sewer, lawn/landscaping, and telephone
Listing is courtesy of: CARREROU ENTERPRISES, LLC (863-294-2384)
Listing Agent: Ozzie Carrerou (863-294-2384)
2409 WILLOW WAY, WINTER HAVEN, FL 33881
$1,8952 Days on yellowkey MLS ID: S5152319
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1625 Built: 2024Community: Bount & Whitledge SubSingle Family
Remarks: Virtually Staged. Stylish 3-Bed, 2.5-Bath Home in Winter Haven – Comfort, Space & Modern Living! *** Move-In Special: Get $500 OFF Your First Month’s Rent — This Month Only!*** Welcome to 2409 Willow Way, a beautifully designed 3-bedroom, 2.5-bathroom home located in one of Winter Haven’s most desirable communities. This property offers the perfect blend of style, function, and comfort—ideal for families, professionals, or anyone looking for spacious modern living. Step inside to an open-concept layout with a bright and airy living space, perfect for entertaining or relaxing. The kitchen features contemporary finishes, ample counter space, and a convenient island—making every meal a joy to prepare. Upstairs, you'll find a generous primary suite with a private en-suite bath, along with two additional bedrooms and a second full bath. Enjoy the convenience of a half-bath downstairs, a 2-car garage, and a low-maintenance backyard—perfect for weekend gatherings or peaceful evenings at home. Located just minutes from shopping, dining, schools, and parks, this home offers easy access to everything Winter Haven has to offer.
Listing is courtesy of: TRANSCEND REALTY (407-518-7653)
Listing Agent: Jacob Hara (407-933-5478)
2515 PINE PL, WINTER HAVEN, FL 33881
$1,8502 Days on yellowkey MLS ID: S5152335
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1425 Built: 2024Community: Bount & Whitledge SubSingle Family
Remarks: Virtually Staged. Modern Comfort Living in Winter Haven | 2 Bed • 2.5 Bath Townhome! *** Move-In Special: Get $500 OFF Your First Month’s Rent — This Month Only!*** Welcome to this beautifully designed 2-bedroom, 2.5-bathroom townhome located in the heart of Winter Haven! Perfectly blending comfort and convenience, this home offers a smart layout ideal for professionals, small families, or anyone seeking low-maintenance living in a prime location. Step inside to a bright and open living space designed for both relaxation and entertaining. The kitchen flows seamlessly into the main living area, creating a welcoming atmosphere perfect for everyday living. Each bedroom features its own private bathroom setup, offering ultimate comfort and privacy, while a convenient half bath downstairs adds extra functionality for guests. Enjoy the ease of modern living with well-planned interiors, ample storage, and a layout that maximizes space and comfort. Located in a quiet and accessible community, this home puts you just minutes away from shopping, dining, schools, and major roadways in Winter Haven. Whether you're relaxing at home or heading out for the day, this property delivers the perfect balance of style, convenience, and location. Don’t miss out—schedule your private tour today and make 2515 Pine Place your next home!
2608 TANOAK TER, WINTER HAVEN, FL 33881
$1,8952 Days on yellowkey MLS ID: S5152333
Remarks: Virtually Staged. Modern Comfort & Style in Winter Haven | 3BR + 2.5BA Beautiful Home! *** Move-In Special: Get $500 OFF Your First Month’s Rent — This Month Only!*** Welcome to this beautifully designed 3-bedroom, 2.5-bath home located in the desirable community of Winter Haven. Offering the perfect blend of comfort, space, and modern living, this home is ideal for families or professionals seeking a peaceful yet convenient lifestyle. Step inside to a bright and open layout that creates an inviting atmosphere from the moment you enter. The main living areas are designed for both relaxation and entertaining, with a seamless flow into a well-appointed kitchen and dining space perfect for everyday living or hosting guests. Upstairs, you’ll find generously sized bedrooms including a spacious primary suite with a private bathroom, providing a comfortable retreat at the end of the day. The additional bedrooms offer flexibility for family, guests, or a home office setup. With 2 full bathrooms plus a convenient half bath, daily routines are made easy and efficient. Located in a growing and accessible area, this home provides quick access to schools, shopping, dining, and major roadways, making everyday commuting and errands simple and stress-free. Don’t miss the opportunity to make this well-maintained home yours—schedule a showing today and experience comfortable Florida living at its best!
2604 TANOAK TER, WINTER HAVEN, FL 33881
$1,7952 Days on yellowkey MLS ID: S5152331
Remarks: Virtually Staged. Stylish & Spacious Townhome Living in Winter Haven | 2 Bed • 2.5 Bath | Modern Comfort ! *** Move-In Special: Get $500 OFF Your First Month’s Rent — This Month Only!*** Welcome home to this beautifully designed 2-bedroom, 2.5-bath townhome located at 2604 Tanoak Ter, Winter Haven, FL 33881—offering the perfect blend of comfort, convenience, and modern living. Step inside to an inviting open-concept layout designed for everyday ease and entertaining. The spacious living area flows seamlessly into a well-appointed kitchen with ample cabinetry and functional counter space, making meal prep and hosting a breeze. Each bedroom features generous space and privacy, with two full bathrooms upstairs plus a convenient half bath downstairs for guests. Enjoy low-maintenance living in a quiet, well-located community close to shopping, dining, schools, and major roadways—putting everything you need just minutes away. Whether you're a working professional, small family, or anyone seeking a comfortable and modern rental, this home delivers both style and practicality in one great package. Don’t miss out—schedule your showing today and experience easy living in the heart of Winter Haven!
2511 PINE PL, WINTER HAVEN, FL 33881
$1,9952 Days on yellowkey MLS ID: S5152326
Remarks: Virtually Staged. Brand-New 3-Bedroom Home with Modern Finishes in Winter Haven | 2.5 Baths & Move-In Ready! *** Move-In Special: Get $500 OFF Your First Month’s Rent — This Month Only!*** Welcome home to 2511 Pine Place, Winter Haven, FL 33881—a beautifully designed 3-bedroom, 2.5-bathroom home that combines modern style, comfort, and convenience in one exceptional package. Step inside and enjoy a bright, open-concept layout with spacious living areas perfect for relaxing or entertaining. The contemporary kitchen features sleek cabinetry, ample counter space, and modern appliances, making meal preparation both easy and enjoyable. The adjoining dining and living areas create a welcoming atmosphere for family gatherings or quiet evenings at home. Upstairs, you'll find three generously sized bedrooms, including a spacious primary suite with a private en-suite bathroom and plenty of closet space. The additional bedrooms gives flexibility for family, guests, or a home office, while the convenient half bath downstairs is perfect for visitors. Located in a growing Winter Haven community, you'll enjoy easy access to shopping, dining, schools, parks, and major highways, making your daily commute and weekend adventures effortless. Whether you're relocating or simply looking for a fresh start, this beautiful home offers the perfect blend of space, style, and location. Don't miss this opportunity—schedule your private tour today and make 2511 Pine Place your next home before it's gone!
2405 WILLOW WAY, WINTER HAVEN, FL 33881
$1,7952 Days on yellowkey MLS ID: S5152325
Remarks: Virtually Staged. Brand-New Townhome in Winter Haven | 2 Bed • 2.5 Bath • Modern Living at Its Best! ***Move-In Special: Get $500 OFF Your First Month’s Rent — This Month Only!*** Welcome home to this beautiful brand-new 2-bedroom, 2.5-bath townhome located in one of Winter Haven's growing and convenient communities. Thoughtfully designed with a modern open floor plan, this home offers the perfect blend of style, comfort, and functionality for professionals, couples, roommates, or small families. The spacious main living area features abundant natural light and flows seamlessly into a contemporary kitchen complete with sleek cabinetry, quality appliances, ample counter space, and a breakfast bar that's perfect for everyday meals or entertaining guests. Upstairs, you'll find two generously sized bedrooms, each with its own private en-suite bathroom, providing maximum privacy and comfort. A convenient half bath on the first floor is ideal for visitors. Enjoy the convenience of an in-home laundry area, modern finishes throughout, energy-efficient construction, and low-maintenance living in a welcoming neighborhood. Located just minutes from shopping, dining, schools, medical facilities, and major highways, you'll have easy access to everything Winter Haven has to offer while enjoying a peaceful residential setting. Don't miss your opportunity to make this stunning new townhome your next home. Schedule your private tour today and ask about our current move-in specials before it's gone!
1200 6TH ST NE, WINTER HAVEN, FL 33881
$1,58523 Days on yellowkey MLS ID: TB8514467
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1224 Built: 1944Community: Shepard & Acree AddSingle Family
Remarks: Ask about our move in special ! Charming 3 bedroom home in Winter Haven featuring a large yard perfect for outdoor living, play, or weekend gatherings. Call today to view
Listing is courtesy of: PALM LEAF PROPERTY MANAGEMENT (813-616-6000)
Listing Agent: Jordan Clark (813-616-6000)
1407 28TH ST NW, WINTER HAVEN, FL 33881
$1,70044 Days on yellowkey MLS ID: P4938674
REDUCED by $100 (5.6%) on 06/22/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1709 Built: 1955Community: InwoodSingle Family
Remarks: List Agent is Related to Owner. Please call if interested in seeing it. Detached garage and shop building combo has limited access. Please talk to property manager. Home has wood, tile and vinyl flooring; cabinets are only 3 years old with granite counter tops and stainless steel appliances. Large pantry & dining area. Large primary bed room has extra large closet and big Wilkin shower bath. Near elementary schools. Ideal for tenant who needs lots of storage or work shop.
Listing is courtesy of: STAR REALTY OF WINTER HAVEN (863-299-7827)
Listing Agent: William Beasley (863-299-1256)
267 LAKE THOMAS DR, WINTER HAVEN, FL 33880
$1,70044 Days on yellowkey MLS ID: P4938588
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1033 Built: 1984Community: Timber WoodSingle Family
Remarks: Welcome to this beautiful WATERFRONT VIEW home, where comfort and scenery meet in perfect harmony. The kitchen has just been re done new cabinets, granite counter tops new flooring, adding a fresh touch to the heart of the home. Inside, you’ll find a desirable split floor plan, a huge living room with plenty of space to relax or entertain, and stunning lake views that can be enjoyed right from the screened-in porch plus wood patio. Tucked away on a dead-end road, this property offers added privacy and a peaceful setting. Move-in ready and waiting for you to call it home.
2007 9TH ST NE, WINTER HAVEN, FL 33881
$1,75055 Days on yellowkey MLS ID: S5148784
REDUCED by $50 (2.8%) on 05/18/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1242 Built: 1967Community: Lake Idyll EstatesSingle Family
Remarks: FREE APPLICATION. NO CREDIT CHECK. Step outside to a generous yard—ideal for outdoor enjoyment, gatherings, or simply unwinding after a long day. Key Features: * Spacious living areas * Ample natural light * Functional kitchen with storage * Private yard space * Convenient location near amenities JULY MOVE IN SPECIALS: FREE APPLICATION & FIRST MONTH HALF OFF
Listing is courtesy of: RODRIGUEZ PROPERTY MANAGEMENT (407-936-4061)
Listing Agent: Francisco Medina (407-931-6738)
1019 MOCKINGBIRD CIR, WINTER HAVEN, FL 33884
$1,65094 Days on yellowkey MLS ID: L4960465
0 Days Off yellowkey (back on 6/19/2026)
REDUCED by $50 (2.9%) on 06/01/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1662 Built: 1977Community: Garden Grove South Ph 1 And 2Single Family
Elementary School: Garden Grove Elem
High School: Winter Haven Senior
Middle School: Denison Middle
Remarks: 3 bedroom 2 bath home with 2 car garage located in SE Winter Haven near Legoland. Modern custom cabinets throughout the home, open island kitchen design with pantry, bedrooms with plenty of closet space. Large master suite with roomy walk-in closet, spacious tiled master bath, and sliding doors to screened porch. Double pane windows throughout. Fenced yard. Located in a family friendly neighborhood right down the street from Garden Grove Elementary School. Convenient to Walmart, CVS, and Walgreen, and just a short drive away from Eagle Ridge Mall.
Listing is courtesy of: REMAX EXPERTS (863-802-5262)
Listing Agent: Donna Williams (863-701-3663)
1743 AVENUE C NE, WINTER HAVEN, FL 33881
$1,59540 Days on yellowkey MLS ID: L4961926
REDUCED by $100 (5.9%) on 06/15/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1016 Built: 1988Community: Elbert AcresSingle Family
Remarks: 3BR/2BA home available now in Winter Haven! This home features all ceramic tile flooring, fresh paint, nice recently renovated kitchen, and a single car garage.
Listing is courtesy of: SUPERIOR PROPERTY MGMT & SALES (863-853-2770)
Listing Agent: Tracey Crews (863-698-1783)
WINTER HAVEN, FL 33880
$1,79971 Days on yellowkey MLS ID: TB8497765
0 Days Off yellowkey (back on 6/1/2026)
REDUCED by $20 (1.1%) on 05/27/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1300 Built: 2010Community: Central PointeSingle Family
Remarks: Take a look at this beautiful home, Clean and Move-In Ready, featuring 4 bedrooms, 2 bathrooms, 2 car garage and approximately 1,300 heated square feet. Enjoy the freedom of a virtually maintenance free lifestyle while residing in a great community. Smart Home Tech - $21.95/mo; Washer/Dryer - $35/mo; High Speed Cable/Internet (if applicable by 3rd Party user) $55/mo; Renters insurance reqrd, Pool service (if applicable) is $150/mo, Septic System (if applicable)- $35/mo; Admin Fee - $150 after lease is generated.
Listing is courtesy of: TAH FLORIDA LLC (844-874-2661)
Listing Agent: Laidy Mataushek (407-298-0779)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.