Winter Haven Apartments for Rent - 133 rentals

Remarks: Beautifully renovated home with private pool and separate efficiency, just minutes from LEGOLAND! This stunning property features a fully remodeled main house offering 3 bedrooms and 2 bathrooms, showcasing modern finishes, an updated kitchen, and a bright, open layout perfect for comfortable living. Step outside to enjoy a private pool, ideal for relaxing or entertaining family and guests. The property also includes a separate efficiency with its own private entrance, featuring a newly renovated bathroom and dedicated parking space—perfect for extended family, guests, or added privacy. Conveniently located near shopping, dining, major roadways, and just minutes from LEGOLAND Florida Resort, this unique rental offers flexibility, comfort, and an unbeatable location. Don’t miss this incredible opportunity!

Listing is courtesy of: AGENT TRUST REALTY CORPORATION (407-251-0669)

Listing Agent: Zulmy Serrano (407-252-7205)

Remarks: 3BR/2BA home available now in Winter Haven. Home features all ceramic tile flooring, single car garage, and spacious yard on a corner lot.

Listing is courtesy of: SUPERIOR PROPERTY MGMT & SALES (863-853-2770)

Listing Agent: Tracey Crews (863-698-1783)

Remarks: This charming first-floor 1 bed, 1 bath condo sits just off Cypress Gardens Blvd, tucked in a spot where the lake becomes part of your everyday view. As you pull into the parking lot, the water is the first thing you see — calm, open, and only a short walk from your front door. The unit itself offers easy living with a simple, comfortable layout and an in-unit washer and dryer for added convenience. Being on the ground floor means quick access in and out, and the lakeside path just steps away gives you a peaceful place to unwind, sip your morning coffee, or enjoy the quiet at the end of the day. Reach out to schedule a tour and see the tranquility for yourself.

Listing is courtesy of: PROPERTY MANAGEMENT OF POLK (863-259-4600)

Listing Agent: Christin Davis (863-259-4600)

Remarks: AVAILABLE MAY 1ST!!! Welcome to this wonderful house at the Villa Mar in Winter Haven! With plenty of natural light, this home features 3 comfortable bedrooms, 2 bathrooms, a spacious open concept floor with a living room, a kitchen with an island, breakfast bar, elegant cabinets, all stainless-steel appliances and granite countertops. The Villa Mar Community features amenities such as a playground, swimming pool and Clubhouse. Very well located, it’s just minutes from restaurants, shopping malls, and world-famous theme parks! Don't miss this opportunity and schedule your visit today!

Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)

Listing Agent: Alessandra Barreto (732-762-8180)

Remarks: This is a 2 bedroom/2 bath with one bedroom having an en-suite bath. Open floor plan, all new stainless steel appliances with washer/dryer included. Also, luxury vinyl plank flooring through out the unit for easy cleaning. Come and see if this is for you. Will not be on the market for too long.

Listing is courtesy of: WEICHERT REALTORS HALLMARK PRO (407-585-0500)

Listing Agent: Hitesh Lallu (863-899-6841)

Remarks: 4/2 home in Winter Haven available now! Features ceramic tile and laminate flooring, inside laundry room, nice yard, and 2 car carport. Approval subject to credit, income, and rental verification.

Listing is courtesy of: SUPERIOR PROPERTY MGMT & SALES (863-853-2770)

Listing Agent: Tracey Crews (863-698-1783)

Remarks: Beautiful 3-bedroom, 2-bathroom home located at 235 Hayley St, Winter Haven, FL 33884. This well-maintained property offers a comfortable and functional layout, perfect for families or anyone seeking a peaceful living environment. Enjoy a bright and inviting interior, with spacious living areas and a practical floor plan designed for everyday living. The home provides a great balance of comfort and convenience. Pet-friendly (with breed and size restrictions), making it a great option for tenants with pets. Ideally situated in a desirable area of Winter Haven, this home offers easy access to shopping centers, restaurants, schools, and major roadways. The community is known for its quiet atmosphere, family-friendly environment, and proximity to beautiful lakes and outdoor recreational areas. Don’t miss the opportunity to live in a well-located home that combines comfort, convenience, and lifestyle.

Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)

Listing Agent: Djanira Puyosa (407-717-5231)

Remarks: Modern 2-Bed, 2.5-Bath Townhome in Desirable Casa del Sol... Step into comfort and convenience in this beautifully designed two-story end unit townhome, perfect for professionals seeking a stylish, low-maintenance lifestyle. Downstairs Living: Formal living room ideal for relaxing or entertaining, Convenient guest half bath, Bright kitchen featuring refrigerator, range, microwave, dishwasher, and breakfast bar, Spacious family/dining room combination that opens to a private screened back porch overlooking the community pool. Upstairs Retreat: Primary bedroom with ensuite bath (tub/shower combo), double built-in closets, and a peaceful screened balcony, Second bedroom with its own private ensuite bath (tub/shower combo), Laundry closet with stackable washer and dryer for added convenience, Additional Features: One-car garage with automatic opener, Private gated front patio entry. Rent includes water and trash collection. Community Amenities for Casa del Sol offers a welcoming community atmosphere with great amenities, including: Clubhouse and pool overlooking scenic Lake Idylwild, Additional centrally located community pool. Conveniently located between Winter Haven and Auburndale and just minutes from Winter Haven Regional Airport, this townhome offers both comfort and accessibility. Schedule your showing today and make Casa del Sol your next home.

Listing is courtesy of: FL REALTY (863-967-0096)

Listing Agent: Dorothea Bogert (863-967-0096)

Remarks: One or more photo(s) has been virtually staged. This welcoming 3 bedroom, 2 bathroom home in the Winter Haven Oaks 55+ community blends comfort, convenience, and an upbeat, easygoing lifestyle. The layout offers three flexible bedrooms along with a bright sun room that quickly becomes the heart of the home — an ideal spot for morning coffee, quiet afternoons, or simply enjoying the peaceful surroundings. An attached carport provides effortless covered parking, and there is also a storage shed located under the carport for added convenience. Residents can choose the setup that fits their needs: $1,650 per month unfurnished or $1,750 per month fully furnished for a true move-in-ready experience. Monthly rent includes water, pest control, lot rent, and lawn care, keeping living simple and stress-free. Winter Haven Oaks elevates the experience with two clubhouses, two swimming pools, and a charming teahouse overlooking the lake. The community also features a large hot tub, tennis courts, pickleball courts, billiards and a game room, a fitness room, and shuffleboard. Numerous weekly planned activities create plenty of opportunities to stay social and engaged. As a gated community, it also provides an added sense of safety and peace of mind. With friendly neighbors, well-kept grounds, and amenities designed for an enjoyable 55+ lifestyle, this home offers a warm and inviting place to settle in and feel right at home.

Listing is courtesy of: PROPERTY MANAGEMENT OF POLK (863-259-4600)

Listing Agent: Christin Davis (863-259-4600)

Remarks: Check out this waterfront STUDIO apartment. This home boasts tile floors, freshly painted interior. Screen lanai with great views of Lake Lulu. Community includes lawn care. 1 car carport. Great location of chain of lakes. Close to shopping and grocery store. 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

Listing is courtesy of: S & D REAL ESTATE SERVICE LLC (863-824-7169)

Listing Agent: Richard Eijo (863-397-5707)

Remarks: One or more photo(s) has been virtually staged. Welcome to this brand-new 2025-built home located in the highly desirable Villa Mar community in Winter Haven. Offering 4 bedrooms, 2 full bathrooms, and 1 half bath, this modern residence combines style, functionality, and comfort in one beautifully designed floor plan. Step inside to an open-concept layout filled with natural light, creating the perfect space for both everyday living and entertaining. The spacious kitchen features contemporary finishes, ample cabinetry, and generous counter space, seamlessly connecting to the dining and living areas. The primary suite provides a private retreat with a well-appointed en-suite bath, while three additional bedrooms giving flexibility for family, guests, or a home office. Built in 2025, this home offers the peace of mind and energy efficiency of new construction. The layout is thoughtfully designed to maximize space and flow, making it ideal for growing families or anyone seeking a move-in-ready property in a thriving community. Villa Mar is known for its welcoming, family-friendly atmosphere, featuring sidewalks, green spaces, and convenient access to schools, shopping, dining, and major roadways. Located in one of Central Florida’s fastest-growing areas, this property presents an excellent opportunity for both homeowners and investors. Don’t miss your chance to own a newly built home in a prime Winter Haven location.

Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)

Listing Agent: Rodrigo Araujo Machado (347-776-2005)

Remarks: Move In Ready 4 bedroom 2 bathroom home in the gated community of Terranova. This home has been well maintained and boasts fresh interior paint Ceramic Tile throughout the home. Located close to shopping, restaurants, and Lego Land. The tenants will benefit from the solar panels with the average electric costs for the previous tenants have been less than $100.00 month. Home offers vinyl fenced rear yard, screen room, and open floor plan. This home will not disappoint.

Listing is courtesy of: CRAIG BURKE REAL ESTATE GROUP, LLC (863-899-5010)

Listing Agent: Craig Burke (863-899-5010)

Remarks: Located in an established neighborhood this home offers 2 bedrooms and 2 bathrooms. Galley kitchen overlooking large fenced backyard with mature landscaping and plenty of shade. Inside laundry room and 2 car garage with room for storage. New interior paint throughout. Laminate flooring throughout. Located close to schools, shopping and medical facilities. Central location in between Orlando and Tampa. Minutes to Legoland. Available and ready for immediate occupancy.

Listing is courtesy of: THE HOME COMPANY (863-268-8157)

Listing Agent: Sue Ann Williamon (863-258-3115)

Remarks: Welcome to this beautifully maintained home in the sought-after Villa Mar community in Winter Haven. Designed for comfort and modern living, this home offers a bright, open layout that is both functional and inviting perfect for everyday living and entertaining. Interior Highlights: Open-concept floor plan filled with natural light Spacious living and dining areas with seamless flow Well-appointed kitchen with ample cabinetry and workspace Generously sized bedrooms ideal for families, guests, or a home office Resort-Style Community Amenities: Beautiful resort-style swimming pool Family-friendly playground Exciting future additions including a fitness center and a second pool, enhancing long-term value and lifestyle Prime Location: Situated in a quiet, well-maintained neighborhood Minutes to shopping, dining, and daily conveniences Easy access to major highways for commuting The owner will be responsible for paying the property tax and HOA fees. The tenant is responsible for all utilities, including water, electricity, and internet. The tenant is also responsible for lawn maintenance. No smoking and no pets are allowed.

Listing is courtesy of: AAA GLOBAL VENTURES PA (407-717-5232)

Listing Agent: Asher Chen (407-717-5232)

Remarks: Welcome to this incredible Winter Haven pool home offering the perfect blend of comfort, upgrades, and true Florida lifestyle living. This move-in ready 3-bedroom home sits on a large oversized lot and is ideal for first-time homebuyers, families, or investors looking for a prime Central Florida opportunity. Step inside to find generous living space, a functional layout, and fresh upgrades that make this property stand out in today’s market. Major Upgrades Include: Brand-new roof – big-ticket item already done, New HVAC system + thermostat – energy-efficient comfort year-round, New water heater, New pool pump & chlorinator – easy, low-maintenance swimming, New laundry units included, New front exterior doors, Expansive driveway with ample parking The private in-ground pool creates your own backyard oasis, while the oversized lot gives you room to expand, build an outdoor kitchen, add a firepit, store boats or recreational toys, or design the ultimate entertaining space. With no mention of restrictive HOA, this property offers flexibility buyers are searching for. Located in the heart of Winter Haven, you’re minutes from everything that makes this area one of Central Florida’s hidden gems. Boat lovers and anglers will love being near Gene’s Lakeside Marina with access to the famous Chain of Lakes — featuring over 50 interconnected lakes perfect for boating, fishing, and waterfront dining. Spend weekends exploring local farmers markets, golfing at one of nine nearby courses, or making family memories at LEGOLAND Florida Resort. Winter Haven is known as the Water Ski Capital of the World and offers a thriving, growing community atmosphere with exciting development underway — including a new hospital opening December 2025, further strengthening property values and long-term investment potential. If you’ve been searching for: • Florida pool home • Move-in ready home in Winter Haven • Large lot property • Investment opportunity in Central Florida • No-fuss upgrades already completed • Close to lakes & boating This is the one. Schedule your private showing today — homes with this many upgrades, a pool, and this location do not last.

Listing is courtesy of: THE URBAN GROUP, INC. (954-522-6226)

Listing Agent: Ashlee Morrell (941-740-9134)

Remarks: Newly built home. 4 Bedrooms: 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)

Remarks: The community of Winter Ridge Condos has a lot to offer: Swimming pool, club house and private boat dock on lake Smart. This tranquil community is everybody's dream to enjoy and relax. this bright and inviting condo features 2 large bedrooms and 2 bathrooms. An open layout living/dinning combo and abundant natural light, Conveniently located near shopping, dining, and major roadways, this well-kept unit is perfect for comfortable living.

Listing is courtesy of: AGENT TRUST REALTY CORPORATION (407-251-0669)

Listing Agent: Luz Solano (217-853-2424)

Remarks: Currently offering 1 months free upfront and a 99.00 app/ admin fee which is credited to rental account. Prices, promotions, and availability are subject to change. Multiple floor plans available. Days on market is not specific to this current plan listed. Discover Prose Cypress Pointe and make every day feel like a getaway. Nestled in the heart of Winter Haven and just a short drive from Lakeland, our pet-friendly luxury apartment community offers spacious floor plans, upscale finishes, and resort-style amenities—all thoughtfully crafted with you in mind. Here, you’ll find more than a home, you’ll discover a curated lifestyle. Lounge by the resort style pool and entertainment cabana, stay energized in the 24-hour fitness center, join invigorating on-site fitness classes, or grab complimentary breakfast on your way to work. It’s boutique living designed to elevate your everyday. With convenient access to Tampa, Orlando, and beyond, Prose Cypress Pointe let’s you live chic, live central and completely you.

Listing is courtesy of: THE APARTMENT BROTHERS LLC (704-502-7778)

Listing Agent: Aj Rebhan (704-502-7778)

Remarks: Currently offering 1 months free upfront and a 99.00 app/ admin fee which is credited to rental account. Prices, promotions, and availability are subject to change. Multiple floor plans available. Days on market is not specific to this current plan listed. Discover Prose Cypress Pointe and make every day feel like a getaway. Nestled in the heart of Winter Haven and just a short drive from Lakeland, our pet-friendly luxury apartment community offers spacious floor plans, upscale finishes, and resort-style amenities—all thoughtfully crafted with you in mind. Here, you’ll find more than a home, you’ll discover a curated lifestyle. Lounge by the resort style pool and entertainment cabana, stay energized in the 24-hour fitness center, join invigorating on-site fitness classes, or grab complimentary breakfast on your way to work. It’s boutique living designed to elevate your everyday. With convenient access to Tampa, Orlando, and beyond, Prose Cypress Pointe let’s you live chic, live central and completely you.

Listing is courtesy of: THE APARTMENT BROTHERS LLC (704-502-7778)

Listing Agent: Aj Rebhan (704-502-7778)

Remarks: Welcome to Lake Buckeye Condos, where easy living meets everyday comfort. Enjoy access to the community pool without the hassle of maintenance, just relax and unwind. This move-in ready 2 bedroom, 2 bathroom condo offers a cozy and inviting layout perfect for making yourself at home. Step outside onto the spacious porch, an ideal spot to enjoy your morning coffee in the Florida sunshine or unwind in the evenings after a long day. Conveniently located and ready for its next tenant, this charming unit has everything you need to settle in comfortably. Call today to schedule your private showing.

Listing is courtesy of: STAR REALTY OF WINTER HAVEN (863-299-7827)

Listing Agent: William Beasley (863-299-1256)