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- S5150858 - 2029 CARROLL LN., WINTER HAVEN, FL 33880 Just Added on 05/29/2026 12:21PM
$2,500 | Single Family Home 4 bedrooms, 3.0 bathroom, 2 car garage
Welcome to this stunning new-construction home (2024), situated in the highly sought-after community of Sutton Preserve in Winter Haven. This beautifully designed single-story residence features a spacious open floor plan comprising 4 bedrooms and 3 bathrooms—including a spacious primary suite highlighted by a large walk-in closet and private en-suite bath. Enjoy a modern kitchen equipped with quartz countertops, brand-new stainless steel appliances, and generous storage space. The split-bedroom layout ensures both privacy and functionality, with abundant natural light filling every living area. A fully fenced backyard offers ample space and security to meet all your needs. Additional features include large walk-in closets in several bedrooms and a two-car garage. Conveniently located just minutes from LEGOLAND, as well as local shops, restaurants, and the area's major attractions.
This listing is courtesy of: AGENT TRUST REALTY CORPORATION
LARAMORE SUB - O6411725 - 1830 2ND ST NW #B, WINTER HAVEN, FL 33881 Just Added on 05/29/2026 11:08AM
$1,600 | Half Duplex 3 bedrooms, 1.0 bathroom
3 Bedroom, 1 bathroom Duplex Winter Haven! Freshly painted, new flooring on bedrooms. Tile floors throughout living areas. Spacious open kitchen to the living room. Close to shopping and restaurants. Stackable Washer and dryer!
This listing is courtesy of: HAMPTON & HAMPTON MGMT LEASING
LARAMORE SUB - O6411721 - 1830 2ND ST NW #A, WINTER HAVEN, FL 33881 Just Added on 05/28/2026 4:11PM
3 Bedroom, 1 bathroom Duplex Winter Haven! Freshly painted, new flooring on bedrooms. Tile floors throughout living areas. Spacious open kitchen to the living room. Close to shopping and restaurants. Washer and dryer hookups. No pets.
KENSINGTON VIEW - WINTER HAVEN, FL 33880 2 Days on yellowkey
$1,929 | Single Family Home 3 bedrooms, 2.0 bathroom, 2 car garage
Take a look at this beautiful home, Clean and Move-In Ready, featuring 3 bedrooms, 2 bathrooms, 2 car garage and approximately 1,678 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. Applications are First Come First Serve basis. Variable Rent Option – go to “Apply” on website and select Term for monthly rental options. This home is professionally managed and maintained by Owner. You deserve single family rental living at its best!
This listing is courtesy of: TAH FLORIDA LLC
EAGLE POND CONDO - P4938816 - 1005 EAGLE POND DR #1005, WINTER HAVEN, FL 33884 2 Days on yellowkey
$1,550 | Condo 2 bedrooms, 2.0 bathroom
MOVE-IN READY second floor Eagle Pond condominium in the highly desirable gated community of Cypresswood Golf and Country Club. This meticulously-maintained condo features hard floors throughout (no carpet!), newer interior paint, newer kitchen appliances, interior laundry (with newer front load LG washer/dryer provided), 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 hallway, plus an additional outside storage closet offers plenty of room to store all of your extras. The Cypresswood community features an 18-hole championship golf course designed by Ron Garl, junior Olympic-sized community pool, lighted tennis courts, clubhouse, event space, and so much more. The pool and tennis amenities, repairs, pest control, and trash collection are INCLUDED with your lease! Minutes from Highway 27 and the I-4 corridor, Winter Haven's very own Legoland Florida Resort, the Polk Parkway, and in the center of a thriving community with many convenient grocery, restaurant, shopping, and commuting options, this one will surely not last long. Applications are approved based on creditworthiness and monthly income equal to at least 3x monthly rental amount. One pet up to 25 lbs allowed with $100.00 non-refundable pet fee and $25.00/month.
This listing is courtesy of: JOHN WOOD REALTY, INC.
EAGLE CREST - P4938778 - 2429 TWIN LAKE VIEW RD, WINTER HAVEN, FL 33881 2 Days on yellowkey
$2,350 | Single Family Home 4 bedrooms, 2.0 bathroom, 2 car garage
Welcome home to this beautifully maintained 4-bedroom, 2-bath single-family residence in Winter Haven offering 1,860 square feet of thoughtfully designed living space. Featuring rich real wood flooring, this home combines warmth, character, and timeless appeal with the comfort and functionality today’s tenants are looking for. The spacious layout offers generous living areas perfect for both everyday living and entertaining, while the well-designed floorplan provides flexibility for families needing extra bedrooms, a home office, or guest space. Natural light enhances the inviting interior, creating a bright and welcoming atmosphere throughout. Ideally suited for those seeking space, comfort, and a polished residential setting, this home offers the feel of upscale living at an exceptional value. Conveniently located near shopping, dining, schools, and major roadways, residents will enjoy both everyday convenience and the comfort of a well-established Winter Haven location. A rare rental opportunity offering space, style, and classic charm. Schedule your private showing today.
This listing is courtesy of: AMERICAN HOMES REALTY GROUP
BOUNT & WHITLEDGE SUB - S5150683 - 2529 PINE PL, WINTER HAVEN, FL 33881 2 Days on yellowkey
$1,895 | Single Family Home 3 bedrooms, 2.5 bathroom, 2 car garage
One or more photo(s) has been virtually staged. Waterfront Living in Winter Haven – Beautiful 3-Bedroom Home with Stunning Views! Welcome to 2529 Pine Pl, a beautifully maintained 3-bedroom, 2.5-bath home offering the perfect blend of comfort, style, and peaceful waterfront living in Winter Haven, FL. Wake up to serene water views and enjoy relaxing mornings or quiet evenings right from your own backyard. This inviting home features a spacious open-concept layout ideal for both everyday living and entertaining. The modern kitchen offers excellent functionality and style, while the generously sized living spaces create a warm and welcoming atmosphere throughout. The private primary suite serves as a relaxing retreat with plenty of space and comfort, making it the perfect place to unwind after a long day. With thoughtful design and beautiful natural surroundings, this home truly stands out. Conveniently located near shopping, dining, schools, and major roadways, this property offers both tranquility and accessibility. Don’t miss your chance to make this waterfront gem your next home—schedule your private tour today!
This listing is courtesy of: TRANSCEND REALTY
BOUNT & WHITLEDGE SUB - S5150681 - 2607 TANOAK TER, WINTER HAVEN, FL 33881 2 Days on yellowkey
One or more photo(s) has been virtually staged. Modern 3-Bed, 2.5-Bath Townhome in Winter Haven – Style, Space & Convenience! Welcome to 2607 Tanoak Terrace, a beautifully designed 3-bedroom, 2.5-bathroom townhome nestled in a peaceful community in Winter Haven, FL. This spacious and modern home offers the perfect blend of comfort and functionality—ideal for families, professionals, or anyone seeking low-maintenance living in a prime location. Step into an open-concept floor plan filled with natural light, featuring a stylish kitchen with stainless steel appliances, plenty of cabinet space, and a large center island perfect for casual meals or entertaining. The adjoining living and dining areas flow seamlessly, creating a welcoming space to relax and unwind. Upstairs, the primary suite offers a private retreat with a walk-in closet and an en-suite bathroom. Two additional bedrooms and a second full bath provide space for family, guests, or a home office. A convenient half-bath is located downstairs for added functionality. Enjoy outdoor time in your private patio area, and take advantage of the community’s amenities and great location—just minutes from shopping, dining, schools, and major highways.
PEACE CREEK RESERVE 40'S - O6410980 - 2154 CHRIS DR, WINTER HAVEN, FL 33884 3 Days on yellowkey
$2,190 | Single Family Home 4 bedrooms, 2.5 bathroom, 2 car garage
FOR RENT! Beautiful and move-in ready home located in the heart of Winter Haven! This charming property offers a bright and spacious floor plan with comfortable living areas, generously sized bedrooms, and a welcoming atmosphere perfect for everyday living. Enjoy a functional kitchen, plenty of natural light, and a peaceful neighborhood setting. Conveniently located near shopping, restaurants, schools, medical facilities, and major highways for easy commuting. This home is clean, well-maintained, and ready for immediate occupancy. Don’t miss this incredible rental opportunity — homes like this lease quickly!
This listing is courtesy of: NOSSA REALTY LLC
INMAN GRVS PH 2 - S5149718 - 712 GROVE ST, WINTER HAVEN, FL 33881 3 Days on yellowkey
$1,900 | Single Family Home 3 bedrooms, 2.0 bathroom, 2 car garage
Beautiful 3-bedroom, 2-bathroom home built in 2023, located in the desirable Inman Groves community. This modern single-story property features an open-concept floor plan with spacious living and dining areas, a well-appointed kitchen with modern appliances, walk-in closets, and a dedicated laundry room with washer and dryer included. Enjoy energy-efficient living with roof-mounted solar panels, helping reduce utility costs. The home also offers a covered garage, patio, and contemporary finishes throughout. Conveniently located near shopping, dining, schools, and major highways. Available July 1, 2026. Minimum 12-month lease required. Tenant screening required.
This listing is courtesy of: HOMESIDE REALTY CORP.
TRADITIONS VILLAS - TB8511789 - 2872 ATTWATER LOOP, WINTER HAVEN, FL 33884 3 Days on yellowkey
$2,400 | Villa 2 bedrooms, 2.0 bathroom, 1 car garage
Beautifully furnished and move-in ready, this pristine residence in the highly desirable 55+ gated community of Traditions at Lake Ruby offers comfort, style, and an easy Florida lifestyle. Available for occupancy June 1, this home has been thoughtfully maintained and is offered fully furnished, making it ideal for tenants looking for a turnkey rental in one of Winter Haven’s premier active-adult communities. The home features a bright, open layout with comfortable living and dining areas, a well-appointed kitchen, spacious bedrooms, and a relaxing Florida-style setting perfect for everyday living or seasonal enjoyment. The furnishings are tasteful and inviting, creating a warm, move-in-ready atmosphere from the moment you enter. With its clean condition, functional floor plan, and low-maintenance feel, this property is ready to be enjoyed immediately. Residents of Traditions enjoy access to an impressive lakefront clubhouse and resort-style amenities, including a fitness center, outdoor pool, aerobics/dance studio, ballroom, card room, arts and crafts studio, library, billiards, walking and biking trails, tennis, bocce, shuffleboard, basketball, scenic lakes and ponds, outdoor patio areas, gazebo, and boat launch access. The clubhouse is located along beautiful Lake Ruby, offering a peaceful waterfront setting for social gatherings, relaxation, and community events. Located in Winter Haven, this home offers the best of Central Florida living with convenient access to shopping, dining, medical services, golf, lakes, and recreation. Known for its Chain of Lakes lifestyle and relaxed small-city charm, Winter Haven provides a quiet residential feel while still being within reach of Lakeland, Orlando, Tampa, and area attractions. A beautifully furnished, well-kept rental in a sought-after 55+ community — ready for occupancy June 1.
This listing is courtesy of: DOUGLAS ELLIMAN
VILLAGE/CRYSTAL BEACH - WINTER HAVEN, FL 33880 4 Days on yellowkey
$2,500 | Single Family Home 3 bedrooms, 2.0 bathroom, 2 car garage
Beautiful 3-bedroom, 2-bath home available for rent in Winter Haven! This well-maintained property features a spacious open-concept layout with the living and dining areas seamlessly connected to the kitchen, creating the perfect space for everyday living and entertaining. Enjoy a large backyard with plenty of room for outdoor activities, family gatherings, or simply relaxing. Conveniently located near shopping, dining, schools, and major roadways. Rent is $2,500/month unfurnished or $2,800/month furnished. Schedule your private showing today!
This listing is courtesy of: LPT REALTY, LLC
KENSINGTON VIEW - TB8512014 - 509 KENSINGTON VIEW DR, WINTER HAVEN, FL 33880 4 Days on yellowkey
$1,853 | Single Family Home 3 bedrooms, 2.0 bathroom, 2 car garage
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.
This listing is courtesy of: DALTON WADE INC
PEACE CRK RESERVE - O6410479 - 1993 SARAH ST, WINTER HAVEN, FL 33884 6 Days on yellowkey
$1,998 | Single Family Home 4 bedrooms, 2.0 bathroom, 2 car garage
Welcome to this spacious, modern 4-bedroom, 2-bathroom one-story home in the sought-after Peace Creek Reserve community! Perfectly positioned near Hwy 27, this prime location offers quick access to Legoland, Downtown Winter Haven & Lake Wales, shopping, dining, and the stunning Chain of Lakes—ideal for boating, fishing, and outdoor adventures. Step inside and spoil yourself with the upscale Bloom floor plan, designed for effortless living and entertaining. The open-concept layout features a gorgeous kitchen with a center island, solid surface countertops, and brand-new stainless steel appliances, seamlessly flowing into a cozy café space and a bright, airy family room. Host gatherings with ease or unwind in your private owner’s suite, complete with a serene bedroom, a spa-like bathroom, and a roomy walk-in closet. Three additional bedrooms and a sleek second bathroom provide ample space for family or guests. Everything is included – from the oversized tile flooring in wet areas to the low-maintenance finishes that blend style and practicality. Step outside to your huge backyard, a blank canvas for gardening, play, or future upgrades. Peace Creek Reserve has a tranquil, nature-inspired lifestyle with amenities like a resort-style pool, playground, and scenic walking trails along a peaceful creek. Enjoy the charm of a safe, tight-knit community with the convenience of city living. Winter Haven’s bike paths, lakeside parks, and vibrant downtown ensure there’s always something to explore. This home combines modern luxury with small-town warmth. Don’t miss your chance to live in one of Winter Haven’s most desirable neighborhoods.
WINTER HAVEN - P4938796 - 658 AVENUE B NW, WINTER HAVEN, FL 33881 6 Days on yellowkey
$1,095 Reduced | Apartment 1 bedrooms, 1.0 bathroom
Enjoy the charm of historic Winter Haven in this newly renovated ground-floor 1-bedroom, 1-bath apartment located just minutes from Lake Howard and downtown Winter Haven. This cozy unit offers a private fenced yard, giving you your own outdoor space to relax, garden, or enjoy the Florida weather. Inside, the apartment features updated countertops, newer appliances, a renovated bathroom with new vanity and shower, and classic built-in details that add character. The kitchen includes an electric range and refrigerator, and the home is cooled with AC window units. Please note this is a lower-ceiling unit, adding to the cozy cottage-style feel of the space. Water is included in the rent, and residents also enjoy 1 assigned parking space plus onsite coin laundry facilities. Conveniently located near shopping, dining, parks, and downtown attractions. Contact us today to schedule your showing.
This listing is courtesy of: HAINES AND HAVEN RESIDENTIAL
- P4938795 - 669 AVENUE B NW #4, WINTER HAVEN, FL 33881 6 Days on yellowkey
$1,195 Reduced | Apartment 1 bedrooms, 1.0 bathroom
Discover the charm of historic Winter Haven in this newly renovated 1-bedroom, 1-bath apartment located just steps from beautiful Lake Howard and within walking distance to downtown Winter Haven. This updated unit blends classic character with modern touches, featuring built-in details, new countertops, updated appliances, a new vanity, and a newly renovated shower. The kitchen includes an electric range and refrigerator, and the home is cooled with AC window units. Water is included in the rent, and residents also enjoy 1 assigned parking space plus access to onsite coin laundry facilities. Enjoy lakeside living with nearby shopping, dining, parks, and downtown attractions all just minutes away. Contact us today to schedule your private showing!
- P4938794 - 669 AVENUE B NW #10, WINTER HAVEN, FL 33881 6 Days on yellowkey
$1,295 | Apartment 1 bedrooms, 1.0 bathroom
WHISPER LAKE 01 - WINTER HAVEN, FL 33880 7 Days on yellowkey
$1,899 | Single Family Home 3 bedrooms, 2.0 bathroom, 2 car garage
Take a look at this beautiful home, Clean and Move-In Ready, featuring 3 bedrooms, 2 bathrooms, 2 car garage and approximately 1,961 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. Applications are First Come First Serve basis. Variable Rent Option – go to “Apply” on website and select Term for monthly rental options. This home is professionally managed and maintained by Owner. You deserve single family rental living at its best!
CYPRESSWOOD MDWS - WINTER HAVEN, FL 33884 7 Days on yellowkey
$2,119 | Single Family Home 3 bedrooms, 2.0 bathroom, 2 car garage
Take a look at this beautiful home, Clean and Move-In Ready, featuring 3 bedrooms, 2 bathrooms, 2 car garage and approximately 2,136 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. Applications are First Come First Serve basis. Variable Rent Option – go to “Apply” on website and select Term for monthly rental options. This home is professionally managed and maintained by Owner. You deserve single family rental living at its best!
VILLA MANOR - O6410263 - 2014 10TH ST NW, WINTER HAVEN, FL 33881 7 Days on yellowkey
$1,600 | Single Family Home 2 bedrooms, 2.0 bathroom, 1 car garage
Step into this renovated farmhouse charm : 2-bedroom, 2-bathroom home, nestled on a spacious lot in the established Villa Manor neighborhood. NO HOA This move-in-ready residence presents luxury finishes, laminate flooring throughout, a sleek new kitchen with updated cabinets, carrara quarts countertops, and stainless steel appliances, and a freshly tiled bathroom with contemporary finishes. Fresh interior and exterior paint, and upgraded lighting fixtures. Roof 2020 - - Repipe 2025 - The large backyard offers plenty of space for outdoor living or future expansion. Located minutes from local schools, parks, and downtown Winter Haven’s shops and restaurants.
This listing is courtesy of: KELLER WILLIAMS LEGACY REALTY
LAKE SMART POINTE - L4962064 - 295 LAKE SMART CIR, WINTER HAVEN, FL 33881 7 Days on yellowkey
$2,100 | Single Family Home 3 bedrooms, 2.0 bathroom, 2 car garage
295 Lake Smart Circle in Winter Haven offers comfortable Florida living with scenic water views in a peaceful lakeside setting. This well-maintained 3-bedroom, 2-bath home features a spacious open floor plan with plenty of natural light, creating a warm and inviting atmosphere throughout. The kitchen offers ample cabinet and counter space and opens to the main living and dining areas, making it ideal for both everyday living and entertaining. The primary suite includes a private bathroom and generous closet space, while the additional bedrooms provide flexibility for family, guests, or a home office. Enjoy relaxing lake views from the front of the property and take advantage of the home’s convenient location near shopping, dining, schools, parks, and major roadways. Combining comfort, convenience, and beautiful surroundings, this home is a great opportunity to enjoy the best of Central Florida living.
This listing is courtesy of: COLDWELL BANKER REALTY
TRANQUILITY PARK 02 REP - S5149633 - 1539 ROSELAWN ST SW, WINTER HAVEN, FL 33880 7 Days on yellowkey
$1,800 | Single Family Home 3 bedrooms, 2.0 bathroom
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.
This listing is courtesy of: LA ROSA REALTY KISSIMMEE
INMAN GRVS PH 2 - S5150395 - 680 GROVE ST, WINTER HAVEN, FL 33881 7 Days on yellowkey
Welcome to this beautiful newer construction home located in the desirable community of Inman Groves in Winter Haven. Built in 2023, this spacious 3-bedroom, 2-bath residence offers over 2,000 square feet of comfortable living space with a modern open-concept design perfect for everyday living and entertaining. The home features a bright and inviting layout with stylish finishes throughout, a spacious kitchen with modern appliances, built-in features, and a large living area filled with natural light. In addition to the bedrooms, the home also includes a versatile flex space perfect for a home office, playroom, formal dining area, gym, or additional sitting room. The primary suite offers plenty of space and privacy, while the additional bedrooms provide comfort and flexibility for family or guests. Enjoy the convenience of a 2-car garage, indoor laundry room with washer and dryer included, and a pet-friendly policy for small dogs and cats. Conveniently located near shopping, dining, schools, and major roadways with easy access throughout Central Florida. Available June 1st. Schedule your private showing today before it’s gone!
This listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS
WINTER RIDGE CONDO - S5150403 - 245 WINTER RIDGE BLVD, WINTER HAVEN, FL 33881 8 Days on yellowkey
$1,550 | Half Duplex 2 bedrooms, 2.0 bathroom
One or more photo(s) has been virtually staged. Nestled in the peaceful Winter Ridge community, this beautifully renovated 2-bedroom, 2-bath END-UNIT condo villa offers comfort, convenience, and low-maintenance Florida living. Recent upgrades include a NEW ROOF (2024), TILE FLOORING THROUGHOUT. Tucked away toward the back of the community, this home provides added privacy and a serene setting. Inside, you’ll find a bright and open floor plan with spacious living and dining areas filled with natural light. The kitchen features ample cabinetry, generous counter space, and a breakfast bar perfect for casual dining. The primary suite includes a walk-in closet and private en-suite bathroom, while the second bedroom is ideal for guests, a home office, or flex space. Enjoy relaxing mornings and evenings on the private enclosed rear lanai overlooking mature landscaping. Washer and dryer are included for added convenience. Residents of Winter Ridge enjoy access to a community pool, scenic walking paths, and a private dock on Lake Smart, perfect for fishing and boating enthusiasts. Conveniently located near shopping, dining, golf courses, and downtown Winter Haven. Don’t miss this opportunity to enjoy the Florida lifestyle in a quiet lakeside community!
This listing is courtesy of: R&J REALTY AND PROPERTY MANAGEMENT LLC
HARMONY/LK ELOISE PH 2 - O6409720 - 2587 SAGE VALLEY WAY, WINTER HAVEN, FL 33884 9 Days on yellowkey
$2,300 | Single Family Home 3 bedrooms, 2.0 bathroom, 2 car garage
Welcome to your dream home! This beautiful property offers 3 spacious bedrooms, 2 modern bathrooms, and is move-in ready with top-of-the-line finishes. Located in the desirable Winter Haven area, this home features appliances and smart home technology, offering you the convenience of a fully integrated, intelligent home system. Key Features: 3 Bedrooms – Generously sized for comfort. 2 Modern Bathrooms – Tastefully designed with contemporary finishes. Appliances included – energy-efficient models. Smart Home Technology. Don't miss the opportunity to rent this exceptional home! Perfect for those who appreciate modern living with smart features. Contact us today for a private viewing.
This listing is courtesy of: EXP REALTY LLC
BOUNT & WHITLEDGE SUB - S5150332 - 2414 WILLOW WAY, WINTER HAVEN, FL 33881 9 Days on yellowkey
$1,850 | Single Family Home 3 bedrooms, 2.5 bathroom, 2 car garage
One or more photo(s) has been virtually staged. Modern Comfort Meets Style – Beautiful 3-Bed, 2.5-Bath Home in Winter Haven! Welcome to 2414 Willow Way, a stunning and move-in-ready 3-bedroom, 2.5-bathroom home nestled in one of Winter Haven’s most desirable and fast-growing communities! Step into a bright and open floor plan designed for both relaxing and entertaining. The spacious living area flows effortlessly into a modern kitchen featuring sleek countertops, ample cabinet space, and stainless steel appliances—perfect for cooking up your favorite meals. Upstairs, you’ll find three generously sized bedrooms, including a private primary suite with a walk-in closet and en-suite bath. The additional bedrooms are ideal for family, guests, or a home office. With 2.5 baths, there’s plenty of space for everyone. Enjoy Florida living in the private backyard, perfect for weekend barbecues or morning coffee. This home also features an attached garage, indoor laundry, and plenty of storage throughout. Conveniently located near shopping, dining, schools, and major highways—everything you need is just minutes away! Don’t miss this opportunity to live in comfort and style—schedule your showing today!
EAGLE POND CONDO - P4938663 - 508 EAGLE POND DR #508, WINTER HAVEN, FL 33884 9 Days on yellowkey
$1,500 Reduced | Condo 2 bedrooms, 2.0 bathroom
Eagle Pond #508 Located in Cypresswood Golf & Country Club! This Immaculate 2 bed/2 bath condominium, upstairs unit has never been offered for rent before, It is sparkling clean & offers a spacious kitchen that is open to dining and living spaces. Both bedrooms feature walk-in closets. Pretty blinds and ceiling fans throughout, a full size washer & dryer, 10' ceilings, crown molding, ceramic tile and carpet. Outside storage closet for your extras. You will have one assigned parking space, plus access to guest parking. Cypresswood residents enjoy a resort & country club lifestyle! The 18 hole championship golf course & on-site restaurant are open to the public. Featuring Chef prepared meals and live music Thurs, Fri & Sat nights. Your Rent Includes use of the half Olympic size pool and the newly resurfaced tennis & pickleball courts. Located just minutes to trendy downtown Winter Haven, and convenient to Hwy 27 & I-4. Close to Legoland, Bok Tower, shopping, dining, a brand new Publix & health care. ALL applicants must apply and pay for financial & background screening, provide valid ID, proof of employment and verifiable income.
This listing is courtesy of: CHAIN OF LAKES REALTY INC
PEACE CRK RESERVE - O6409324 - 1662 TEAGAN LN, WINTER HAVEN, FL 33884 9 Days on yellowkey
$2,400 | Single Family Home 3 bedrooms, 2.0 bathroom, 1 car garage
Beautiful 3-bedroom, 2-bath home located in the desirable community of Winter Haven. This property features a spacious and bright floor plan with an open living and dining area, perfect for entertaining. The kitchen offers ample cabinet space and modern appliances. The primary suite includes a private bathroom and generous closet space. Enjoy a large backyard ideal for relaxing or outdoor gatherings. Conveniently located near shopping, restaurants, schools, and major highways. A wonderful opportunity to own or rent a charming home in a great location!
This listing is courtesy of: OPTIMAR INTERNATIONAL REALTY
BUCKEYE POINTE - WINTER HAVEN, FL 33884 10 Days on yellowkey
$2,000 | Single Family Home 4 bedrooms, 3.0 bathroom, 2 car garage
Beautiful 4-bedroom, 3-bath home located in a great family-friendly neighborhood! This spacious home features a desirable 3-way split floor plan, vaulted ceilings, and stylish LVP wood-look plank flooring throughout the main living areas. The open kitchen offers granite countertops, ample cabinet space, and overlooks the bright living and dining areas, creating the perfect space for everyday living and entertaining. The large primary suite includes a private ensuite bath with a relaxing soaking tub and separate step-in shower. Additional features include an inside laundry room, 2-car garage, and a covered open lanai overlooking the spacious partially fenced backyard. Conveniently located near shopping, dining, schools, and major roadways, this home offers both comfort and convenience in a welcoming community. Administration Fee: Upon approval tenants will be subject to a $250 one-time administration fee. This property is proud to offer deposit-free living to qualified renters through Obligo! We understand that moving costs can add up, so we want to extend financial flexibility to our residents. Resident Benefit Package (Included in rental amount): -Bi-monthly A/C Filter Delivery -$100,000 Tenant Liability Insurance/ $10,000 Content Coverage -PestShare Service -Identity Protection -Credit building (All Credit Bureaus) -Piñata Tenant Rewards Program -Tenant Portal Access: Online payments & submission of maintenance requests -24 Hour Emergency Maintenance Hotline -One time Late Fee Forgiveness -$500 Rebate after closing if you purchase a home with one of our preferred Realtors
This listing is courtesy of: S & D REAL ESTATE SERVICE LLC
VILLAMAR PHASE 6 AND PHASE 6D - TB8510050 - 3912 GIORGIO DR, WINTER HAVEN, FL 33884 10 Days on yellowkey
Brand new, energy-efficient home available NOW for rent! Retreat to your primary suite located in the back of the home for plenty of privacy and offers a huge walk-in closet. This is a split floor plan allowing everyone their privacy. The square footage is the perfect size so you don't feel crowded, but you won't spend an eternity trying to keep it clean. Enjoy the easy clean up in your spacious kitchen with the easy to clean granite countertops. Residents have access to two resort-style amenity centers featuring a clubhouse, pool, and playground. Winter Haven is known for its beautiful chain of lakes with lakeside restaurants and its award-winning community theater. Nearby attractions include Legoland Florida and Peppa Pig Theme Park.
This listing is courtesy of: KEY PREMIER REALTY
LAMPLIGHTER VILLAGE - L4961998 - 1103 CYPRESS GARDENS BLVD #17, WINTER HAVEN, FL 33884 10 Days on yellowkey
$1,200 | Condo 1 bedrooms, 1.0 bathroom
One or more photo(s) has been virtually staged. Chain of Lakes WATERFRONT living with stunning views of Lake Roy! This beautifully updated 1-bedroom condo offers the perfect blend of peaceful lakeside charm and everyday convenience, located just minutes from shopping, dining, and entertainment. Step inside to find wood-look tile flooring throughout, fresh calming oasis-blue paint, and abundant natural light pouring in through updated windows showcasing picturesque lake views. The spacious living area flows into a versatile window-lined nook, ideal for a home office, reading corner, or expanded seating area. The updated kitchen features modern appliances and an efficient layout designed to maximize space and functionality. The bedroom offers two closets for ample storage along with a convenient stackable washer and dryer nook. The bathroom has been tastefully renovated with a modern subway-tiled tub surround. Just outside your front door, enjoy a large HOA-maintained green space with picnic seating overlooking the water. Beyond that, you’ll have direct access to Lake Roy, perfect for kayaking, paddle boarding, or simply soaking in the serene setting. The community dock provides additional space for fishing, relaxing, and enjoying breathtaking lakefront sunsets. Don’t miss this rare opportunity to lease a charming lakeside retreat on the Chain of Lakes!
This listing is courtesy of: REMAX EXPERTS
SAVANNA POINTE - L4962004 - 219 CLOVERDALE RD, WINTER HAVEN, FL 33884 10 Days on yellowkey
$2,300 | Single Family Home 4 bedrooms, 2.0 bathroom, 2 car garage
~Fully Furnished 4/2 Winter Haven Residence Offered for Lease - Just bring your wardrobe and toothbrush!~ This resort-style home boasts a fully furnished Florida-themed beautiful interior, ceramic tiling throughout, spacious kitchen with breakfast bar and plenty of cabinetry/counter space, sizeable primary bedroom with large walk-in closet and en-suite bath featuring dual vanities and a garden jacuzzi tub. Additional features include sliding door access to a serene, screened in Mediterranean-style patio, inside utility with washer/dryer, and a two car garage. Well positioned, this property is convenient to LegoLand, dining, shopping, educational and medical facilities.
This listing is courtesy of: HOUSE OF GLASS REAL ESTATE PM
HEATHER GLEN PH 02 - P4938759 - 612 HEATHER GLEN LOOP, WINTER HAVEN, FL 33884 10 Days on yellowkey
$2,000 | Single Family Home 3 bedrooms, 2.0 bathroom, 2 car garage
This is the ONLY rental in Winter Haven that has a pool!! This cute 3 bedroom 2 bath home 2 garage screened pool home has a fully PVC fenced in back yard, perfect for kids to play or aminals to run free. Located in a quiet neighborhood. Clean freshly painted interior and ready for a tenant!
This listing is courtesy of: SIGNATURE PROPERTIES OF CENTRAL FLORIDA LLC
TWIN OAKS ADD - S5150205 - 332 AVENUE D SE, WINTER HAVEN, FL 33880 10 Days on yellowkey
$2,000 | Apartment 2 bedrooms, 2.0 bathroom
This 2 bedroom 2 bathroom end unit is fully furnished with a modern flair. Renovated with new roof, energy efficient tankless water heater, paint, appliances & more. Featuring luxury vinyl floors throughout, granite countertops in the kitchen, both bathrooms feature renovated showers & tub, vanities & fixtures. This home is turnkey including all linens, electronics and kitchenware. The living room is spacious while offering a 75" smart TV and sectional couch. Master bedroom features a king size bed, large walk-in closet, 55" smart TV, en suite bathroom with shower/tub combo. The guest bedroom offers a queen size bed and 43" smart TV. The guest bathroom has a walk-in shower. This unit is equipped with a washer & dryer in the laundry closet. There is a private parking area onsite. Located close to hospitals, schools, shopping, restaurants and more.
This listing is courtesy of: THE PROPERTY FIRM
SANDY COVE WINTER HAVEN - O6408764 - 900 AVENUE Z SE #A3, WINTER HAVEN, FL 33880 11 Days on yellowkey
$1,375 | Condo 2 bedrooms, 1.0 bathroom
Welcome to your new home at 900 Avenue Z SE in the heart of Winter Haven! This beautifully updated ground-floor 2-bedroom, 1-bathroom unit offers 840 square feet of comfortable living space with no carpet throughout. Enjoy brand-new vinyl plank flooring in the bedrooms, while the living room features a stylish combination of tile and bamboo flooring for a modern touch. The kitchen is equipped with sleek stainless steel appliances and includes a convenient top and bottom loader washer and dryer. Step outside to your small covered balcony, perfect for relaxing, and take advantage of the front space ideal for chairs and unwinding after a long day. This unit also includes one designated parking spot and access to a community pool for your enjoyment. Rent includes water and trash services for added value. ESA-designated pets are welcome with proper documentation, making this a great place to call home!
COUNTRY LAKE CONDO PH 01 - P4938736 - 702 COUNTRY LN NE #702, WINTER HAVEN, FL 33881 14 Days on yellowkey
$1,700 | Condo 2 bedrooms, 2.0 bathroom , 1 car carport
LAKEFRONT LIVING AT ITS BEST. REFRESHED FIRST FLOOR 2BR-2BA CONDO WITH COVERED PARKING AND BEAUTIFUL VIEWS OF LAKE BUCKEYE. FEATURES INCLUDE FRESH INTERIOR PAINT THROUGHOUT, LUXURY VINYL WOOD PLANK FLOORING, STAINLESS REFRIGERATOR AND MICROWAVE, OPEN GREAT ROOM DESIGN WITH LIVING AND DINING COMBO. RELAX IN THE FLORIDA ROOM OVERLOOKING THE LAKE AND ENJOY STUNNING SUNRISE VIEWS WITH YOUR MORNING COFFEE. COMMUNITY AMENITIES INCLUDE POOL AND TENNIS COURTS. CONVENIENT LOCATION NEAR POLK STATE COLLEGE AND THE LAKE ELBERT WALKING TRAIL AROUND LAKE ELBERT. ONLY MINUTES TO DOWNTOWN WINTER HAVEN WITH SHOPPING AND RESTAURANTS.
This listing is courtesy of: FLORIDA HOME CHOICE REALTY
ELBERT ACRES - L4961926 - 1743 AVENUE C NE, WINTER HAVEN, FL 33881 14 Days on yellowkey
$1,695 | Single Family Home 3 bedrooms, 2.0 bathroom, 1 car garage
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.
This listing is courtesy of: SUPERIOR PROPERTY MGMT & SALES
LE VALLEY SUB - L4961738 - 711 LAKE JESSIE DR, WINTER HAVEN, FL 33881 14 Days on yellowkey
$1,400 | Apartment 2 bedrooms, 2.0 bathroom
Well maintained 2BR 2BA apartment (part of triplex). Vaulted ceilings, granite countertops, Washer/Dryer hookups
This listing is courtesy of: LOCKHART & ASSOCIATES INC
SPIRIT LNDGS - TB8508068 - 257 SPIRIT LANDINGS CIR, WINTER HAVEN, FL 33880 15 Days on yellowkey
$2,250 | Single Family Home 3 bedrooms, 2.0 bathroom, 2 car garage
Spacious 3-bedroom, 2-bathroom rental home featuring an open layout, a versatile bonus room perfect for an office or playroom, and a garage for parking and extra storage. This well-maintained property offers comfort, space, and flexibility for modern living.
VILLAMAR PH 4 - O6408068 - 3927 PALAZZO PL, WINTER HAVEN, FL 33884 15 Days on yellowkey
MOVE-IN READY and available now! Rare opportunity to lease the FINAL Amarylis model in the community—a beautifully maintained 2023-built home offering modern comfort, style, and convenience. Featuring 3 bedrooms, 2 bathrooms, soaring ceilings, a bright open-concept layout, luxury vinyl flooring throughout the main living areas, and an inviting walk-in foyer. The spacious primary suite includes a walk-in closet and en-suite bath with dedicated vanity seating. Enjoy added perks including a full security camera system for tenant use, playground set, charming front porch, and private backyard space perfect for relaxing or entertaining. Residents also enjoy access to resort-style community amenities including a pool, cabana seating, and recreational areas. Conveniently located near shopping, dining, and everyday essentials. Skip the wait—this home is ready for immediate occupancy! THIS HOME IS ALSO AVAILABLE FOR PURCHASE UNDER MLS #O6383833.
This listing is courtesy of: MAINFRAME REAL ESTATE
LAKE FOX SHORES - P4938716 - 5667 STRUTHERS CT, WINTER HAVEN, FL 33884 15 Days on yellowkey
$1,350 | Half Duplex 2 bedrooms, 1.0 bathroom
Clean and cozy 2-bedroom, 1-bathroom duplex in southeast Winter Haven. Featuring wood laminate flooring in living areas and bedrooms, with ceramic tile flooring in the kitchen and bathroom. Kitchen equipped with newerKitchen cabinets and comes with range/oven, refrigerator, and washer/dryer hookups in utility closet. Both bedrooms of ample size with ceiling fans. Recently remodeled bathroom with tile tub/shower. Conveniently located near shopping, Walmart, Publix, Legoland, and quick access to HWY 27 for Orlando/Tampa.
This listing is courtesy of: STAR REALTY OF WINTER HAVEN
INMANS ALLOTMENT - L4961475 - 1705 3RD ST NW #A, WINTER HAVEN, FL 33881 15 Days on yellowkey
$1,650 Reduced | Single Family Home 3 bedrooms, 2.0 bathroom
1/2 DUPLEX - UNIT A Be the next to enjoy this newer construction (2023) 3-bedroom, 2-bathroom duplex unit offering 1,472 sq ft of modern living! Unit A features a bright open-concept floor plan with tile flooring throughout the entire unit, a spacious living room and dining room area, and a well-appointed kitchen with stainless steel appliances, granite countertops, and ample cabinetry. The home includes a beautifully tiled shower, generously sized bedrooms with large closet space, and a dedicated indoor laundry room for added convenience. Neutral finishes throughout create a clean, modern feel. You will find this unit to be conveniently located near downtown Winter Haven where there is plenty of shopping, dining, and near major roadways. Note: This is Unit A. See separate listing for Unit B.
This listing is courtesy of: LA ROSA REALTY PRESTIGE
SUNSET PARK - K4903489 - 710 AVENUE C SW #4A, WINTER HAVEN, FL 33880 15 Days on yellowkey
$1,150 | Apartment 1 bedrooms, 1.0 bathroom
This well maintained first floor 1 BD/1 BA apartment is on a quiet street near Lake Howard. Centrally located, approximately 10 min. walking distance to downtown Winter Haven. The apartment has been freshly painted for the new residence and is ready for immediate move in! The building has a free on site laundry facility and off street parking. Call today to schedule your private tour!
This listing is courtesy of: 1513 REALTY LLC
ROCHELLE GARDENS - L4961819 - 3895 CONINE DR E, WINTER HAVEN, FL 33881 17 Days on yellowkey
Charming 3BR/2BA Lakefront Home with Private Dock & No HOA Enjoy peaceful waterfront living in this beautiful 3-bedroom, 2-bath lakefront home featuring stunning water views and a private dock perfect for fishing, boating, or relaxing by the lake. The home offers a spacious layout with comfortable living areas, abundant natural light, and a screened porch ideal for enjoying morning coffee or evening sunsets. Furniture is included for a convenient move-in-ready experience but can also be removed if preferred. With no HOA, you’ll enjoy added freedom and flexibility in this serene lakefront setting.
- S5149630 - 279 SUNFISH DRIVE DR, WINTER HAVEN, FL 33881 18 Days on yellowkey
$2,200 Reduced | Single Family Home 4 bedrooms, 2.0 bathroom, 2 car garage
4 bedrooms 2 baths for rent in lovely Winter Haven, spacious home with open concept family room, dining and fully equiped kitchen. Home has a laundry room with washer and Dryer. Spacious yard for entertaining family and friends. No neighbors in the back. New tile floors. Bedrooms are carpeted, Community pool.
This listing is courtesy of: LA ROSA REALTY CENTRAL FLORIDA LLC
PEACE CRK RESERVE - S5149706 - 693 REGGIE RD, WINTER HAVEN, FL 33884 18 Days on yellowkey
$2,300 | Single Family Home 4 bedrooms, 2.5 bathroom, 2 car garage
READY TO MOVE !!!! This almost 1900 sq ft beautiful two-story home features four bedrooms, two and a half baths, and a two-car garage. The perfect plan with the perfect color scheme makes this home stand out compare to others that are similar. It provides an open floor plan with great room, dining room, and kitchen with large island. The kitchen features ample counter space, and generous pantry. The casual dining area allows outdoor access to a large backyard via sliding glass doors. The second floor includes an owner's retreat featuring an owner's bath with large walk-in shower, dual vanity, and spacious walk-in closet. Three additional bedrooms, a bathroom, a spacious loft, and laundry room finish off this beautiful home. This home comes fully equipped with Everything Included Features like new appliances, solid surface countertops throughout and oversized tile flooring in the wet areas. Peace Creek Reserve is a masterplan community of new single-family homes with a beautiful natural creek. Winter Haven is the chain of lakes city, with over 26 linked together by canal. There are lots of shops, restaurants, bike paths. Peace Creek Reserve is what you have been looking for. A safe small town feel with convenience, the perfect place to live.
This listing is courtesy of: WF REALTY CORP.
INWOOD - P4938674 - 1407 28TH ST NW, WINTER HAVEN, FL 33881 18 Days on yellowkey
$1,800 | Single Family Home 4 bedrooms, 2.0 bathroom, 2 car garage
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.
FLORIDA HIGHLAND CO - L4961811 - 304 LA SERENA, WINTER HAVEN, FL 33884 18 Days on yellowkey
$1,700 | Single Family Home 2 bedrooms, 2.0 bathroom, 1 car garage
Nestled in the tranquil neighborhood of Winter Haven, 304 La Serena offers a comfortable living experience with its recent upgrades and convenient location. Step inside to discover a freshly painted interior that welcomes you with warmth and brightness. The new flooring adds a touch of modern charm to the living spaces, while providing durability for everyday life. The kitchen has been tastefully renovated, boasting new countertops and appliances that make meal preparation a breeze. With ample cabinet space, organizing your kitchen essentials is effortless. Both bedrooms feature their own updated bathrooms, providing privacy and convenience for residents and guests alike. A new roof ensures peace of mind, while the single-car garage offers practical storage solutions for your vehicles and belongings. Outside, the spacious yard invites you to enjoy the Florida sunshine, whether you're relaxing on the patio or tending to your garden. Lawn care included by the HOA. Administration Fee: Upon approval tenants will be subject to a $250 one-time administration fee. Ask how you can skip your security deposit with Obligo Resident Benefit Package (Included in rental amount): -Bi-monthly A/C Filter Delivery -$100,000 Tenant Liability Insurance/ $10,000 Content Coverage -Identity Protection -Credit building (All Credit Bureaus) -Piñata Tenant Rewards Program -Tenant Portal Access: Online payments
TIMBER WOOD - P4938588 - 267 LAKE THOMAS DR, WINTER HAVEN, FL 33880 18 Days on yellowkey
$1,800 | Single Family Home 2 bedrooms, 2.0 bathroom
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.
FLA HIGHLANDS CO SUB - P4938440 - 3601 CYPRESS GARDENS RD #6, WINTER HAVEN, FL 33884 18 Days on yellowkey
$1,200 | Apartment 2 bedrooms, 2.0 bathroom
Spacious 2-bedroom/2-bathroom apartment in a prime southeast Winter Haven location. New luxury vinyl flooring throughout, minutes from Legoland Florida Resort, tons of convenient restaurant, grocery, shopping, and dining options. Extremely commutable to Highway 27 and the Polk Parkway.