Apartments for Rent Near Denison Middle in Winter Haven - 27 rentals

Remarks: Cozy 1 bed / 1 bath + den with built-in closet, perfect for a home office or guest space, located on the ground floor for easy access. Freshly painted and offering a functional layout with great natural light. Enjoy a shared backyard and on-site coin laundry for added convenience. Includes 1 assigned parking space. Situated in a quiet, well-kept neighborhood near a local school, just 5 minutes from downtown and 10–15 minutes from Legoland, with easy access to shopping and dining. No pets allowed. Available now with a minimum 1-year lease.

Listing is courtesy of: MASIS ROYALTY REAL ESTATE (760-620-2065)

Listing Agent: Liljana Masis (760-620-2065)

Remarks: Welcome home to this newly built, stunning 5-bedroom, 3 FULL bath two-story home! From the moment you step through the modern frosted-glass entry, you’re welcomed into an open and airy layout perfect for families, guests, or anyone who loves space and convenience. The first floor features an open-concept design with a stylish kitchen complete with Silestone countertops, a large center island, stainless steel appliances, walk-in pantry, and chic subway tile backsplash all overlooking the living and dining areas. A full bedroom and bathroom on the main floor is the perfect setup for guests or multi-generational living. Upstairs, enjoy a spacious loft ideal for an office. The primary suite includes a generous walk-in closet and private bathroom with double vanities. Three additional bedrooms, a full bathroom, and a conveniently located laundry room complete the second floor along with plenty of extra storage space throughout. This home also includes smart home features, allowing you to control key functions from your mobile device whether you're home or away. Enjoy resort-style living with access to a beautiful community pool year-round. LOCATION PERKS: • 10 minutes from LEGOLAND • 35 minutes from Disney • Near plenty of retail, grocery stores, and dining • Close to major highways for easy commuting • A short drive to the new upscale lakefront hangout spot Port 27 • Pet-friendly! If you’re looking for a spacious, modern home in a prime location, this property has everything you need and more.

Listing is courtesy of: THE KLR GROUP LLC (407-814-3293)

Listing Agent: Vanessa Exil (407-715-1088)

Remarks: A RARE RENT-TO-OWN OPPORTUNITY in the heart of Winter Haven, offering the chance to enjoy lake-view living now while working toward ownership. This beautifully updated 4-bedroom, 3.5-bath home sits just minutes from downtown and the Chain of Lakes, combining location, flexibility, and long-term potential. Inside, the home features a well-designed layout with two primary suites, making it ideal for multi-generational living or those who want additional privacy and space. The main living areas are filled with natural light, highlighted by a warm family room with views of Lake Lulu and French doors that open to a wrap-around screened porch—perfect for relaxing mornings or evening sunsets. The kitchen is equipped with granite countertops, custom maple cabinetry, and stainless steel appliances, while the formal living and dining areas feature original hardwood floors, adding character and charm. Outside, a large paver driveway provides ample parking, and the fenced backyard offers space for entertaining, pets, or family activities. With no HOA, added storage through a two-car garage, and a location close to dining, shopping, and waterfront recreation, this home offers both convenience and lifestyle. This rent-to-own program is ideal for buyers who want to secure a home now while taking the next steps toward mortgage readiness. Homes with lake views, flexible layouts, and ownership pathways like this are rarely available. Serious inquiries only — opportunities like this don’t last.

Listing is courtesy of: LOKATION (954-545-5583)

Listing Agent: Chad Lindsey (863-660-7837)

Remarks: Welcome to this spacious 3/2 near Legoland! Nestled in the heart of Winter Haven, FL, this home boasts three generously sized bedrooms and two full bathrooms. The split bedroom floor plan ensures privacy, while the eat-in kitchen nook provides a cozy space for meals. The master suite is a true retreat, complete with a luxurious garden tub. The entire home is outfitted with ceramic tiled flooring, adding a touch of elegance and ease of maintenance. The property also features a large yard, perfect for outdoor activities, and a two-car garage for your vehicles or extra storage. Plus, lawn service and interior pest control are included, providing you with a worry-free living experience. This home offers the perfect blend of comfort, convenience, and style. Don't miss out on this gem in Winter Haven! *Tenant must provide their own washer and dryer. **RESIDENTS BENEFIT PACKAGE Residents are enrolled in the Resident Benefits Package (RBP). There is an additional $35.00 a month charge for this added to the advertised rent and is considered additional rent. RBP includes HVAC air filter delivery, utility concierge services making utility connection a breeze during your move-in, our best-in-class resident rewards program, and much more! More details upon application. If approved for this home, new tenants must pay a $200.00 lease coordination fee due at the same time as the security deposit payment. **RENTERS INSURANCE REQUIRED $100K min liability coverage. Personal property coverage is not required.

Listing is courtesy of: CT HOMES REALTY CORPORATION (407-578-6545)

Listing Agent: Francisco Nieves-Taranto (321-248-4149)

Remarks: Welcome to this beautiful and spacious rental home located in the heart of Winter Haven, just minutes away from LEGOLAND Florida and top-rated shopping centers. This residence features a bright, open-concept floor plan with modern finishes, perfect for comfortable family living and entertaining. The property boasts a large, private backyard and is situated in a quiet, well-maintained community. Parents will appreciate being zoned for Garden Grove Elementary and having easy access to local parks and lakes. This home offers the perfect blend of suburban peace and city convenience, making it the ideal choice for your next move.

Listing is courtesy of: GLASSTONE GROUP INC (321-988-4663)

Listing Agent: Ashley Porto (407-360-7386)

Remarks: One or more photo(s) has been virtually staged. Check out this 3 bedroom 2bath townhome. Open floor plan, formal dining room, open lanai, Spacious master bedroom with double walk in closets and vaulted ceilings. 2 car carport.Freshly painted, new carpets upstairs. LVP flooring downstairs. Open lanai. Great community. Close to shopping and grocery store. Washer and dryer hook ups. 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 -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 -Pest control

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

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

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: Located in Peace Creek Reserve—one of Winter Haven’s most tranquil and appealing communities—this property offers the ideal balance between peace, comfort, and convenient access to everything a family needs for daily living. Surrounded by charming natural scenery and situated close to lakes, trails, recreational areas, shops, and major roadways, this neighborhood has become an excellent choice for those seeking to enjoy a higher quality of life without straying far from what matters most. Back on the market, this residence represents a special opportunity for those seeking spaciousness, functionality, and a living space that truly feels like home. The property features five bedrooms plus a spacious loft—ideal for use as an office, study area, entertainment room, or a versatile flex space tailored to your family's specific needs. Its open-concept design fosters a harmonious flow between the kitchen, dining area, and living room—all bathed in abundant natural light and featuring direct access to a covered patio, perfect for socializing, relaxing, or entertaining guests. On the second level, the layout prioritizes privacy and comfort, highlighted by a spacious primary suite complete with a walk-in closet and private en-suite bath—a space designed to offer ultimate relaxation and tranquility. With modern finishes, generous living spaces, and a location that seamlessly blends serenity with convenience, this move-in-ready property has everything it takes to become your perfect new home.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Carla Moreno Pineda (561-410-9003)

Remarks: Located in the gated community of Mandolin, this well-maintained, move-in ready home checks all the boxes—a functional layout, comfort and privacy, 10x15 screened in lanai and a fully fenced backyard. The open-concept living space is designed for both everyday living and entertaining, while the kitchen is the heart of the home featuring oak cabinetry, ample counter space, pantry closet, and a seamless flow into the dining area. The spacious primary suite offers a true retreat, complete with dual walk-in closets, a garden tub, tile walk-in shower, and a private water closet. Ideally located in Southeast Winter Haven, just minutes from shopping, dining, Publix, Walmart, and Legoland, with quick access to HWY 27 for an easy commute to Orlando or Tampa.

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

Listing Agent: Carlee Marchetti (863-258-3338)

Remarks: Gorgeous sunset views over Lake Winterset… this is the kind of rental you don’t come across often. Located in the gated Winterset community, this well-maintained 2-bedroom, 2-bath upstairs condo with a private one-car garage offers easy, low-maintenance lakeview living. Inside, you’ll find an open and airy layout with vaulted ceilings, skylights, and large sliding glass doors that bring in tons of natural light while framing peaceful lake views. The spacious great room serves as the main living area, while the kitchen is tucked just off to the side featuring an eat-in area, breakfast bar, closet pantry, and a convenient laundry closet with washer/dryer. The primary suite overlooks the lake and offers private access to the screened-in lanai, along with a large walk-in closet and an updated en-suite bath with a walk-in shower. The split bedroom layout provides privacy, with the guest bedroom offering ample space and easy access to a full second bath with a tub/shower combination. Guest parking is available nearby. Winterset residents enjoy access to a lakeside community pool, clubhouse, tennis courts, and a private boat ramp with direct access to the Chain of Lakes—ideal for boating, fishing, and enjoying lake life. Conveniently located near Publix, Walmart, Legoland, dining, shopping, medical facilities, and easy access to Highway 27. Move-in ready—schedule your showing today.

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

Listing Agent: Carlee Marchetti (863-258-3338)

Remarks: One or more photo(s) has been virtually staged. Experience refined Florida living in this elegant 4 bedroom, 3 bathroom residence, where thoughtful design and upscale comfort come together seamlessly. The home welcomes you with spacious living areas, a well-appointed kitchen, and a layout that offers both openness and privacy. The primary suite provides a serene retreat, while the additional bedrooms and baths offer flexibility for guests, family, or a dedicated workspace. A 2-car garage adds convenience and secure storage. Step outside to your private backyard sanctuary, fully fenced for peace of mind and designed for effortless outdoor enjoyment. The highlight of the home is the stunning in-ground pool, enclosed within an expansive, fully screened structure that creates a resort-style environment perfect for lounging, entertaining, and year-round relaxation. With pool maintenance included in the rent, you can indulge in the luxury without lifting a finger. This home blends sophistication, comfort, and an elevated outdoor lifestyle into one exceptional living experience. Schedule your tour today!

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

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

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: Beautiful 4-bedroom/3.5-bathroom home with additional bonus room ideal for an office, den, gym, or play room in the prestigious Woodpointe community of SE Winter Haven! Elegant custom and designer finishes throughout, screened lanai, walk-in closets, open-concept and split-bedroom floor plan, and so much more. Applications evaluated on creditworthiness and income equal to at least 3x monthly rent and income.

Listing is courtesy of: JOHN WOOD REALTY, INC. (863-324-9663)

Listing Agent: Kayly Malinas, Pa (863-258-1426)

Remarks: MOVE-IN READY upstairs Eagle Pond condominium in the highly desirable gated community of Cypresswood Golf and Country Club. This professionally-managed condominium includes interior laundry, walk-in closets, open concept living space, 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 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. Monthly rent includes maintenance and repairs, pest control, and trash collection. Up to three pets allowed with prior approval; applications approved based on creditworthiness and income equal to at least 3x monthly rent, otherwise additional security deposit may be required.

Listing is courtesy of: JOHN WOOD REALTY, INC. (863-324-9663)

Listing Agent: Kayly Malinas, Pa (863-258-1426)

Remarks: Welcome to the desirable Villamar community in Winter Haven, where comfort, convenience, and modern living come together in one of the area’s fastest-growing neighborhoods. This FULLY FENCED like-new 4-bedroom, 3-bathroom home offers a thoughtfully designed layout that perfectly balances functionality and style, making it ideal for families, entertaining, or simply enjoying everyday life. Designed with both comfort and connection in mind, the open-concept floor plan flows effortlessly through the main living areas. The spacious great room opens to the dining area and kitchen, creating a bright and inviting atmosphere filled with natural light. The kitchen overlooks the living space, allowing you to stay connected with family and guests while preparing meals, making it the true heart of the home. Location truly sets this home apart. Villamar offers a variety of community amenities including a pool, playground, dog park, and scenic walking paths, creating a lifestyle that’s both active and relaxing. Just minutes away, you’ll find everyday conveniences like Publix and Walmart, along with quick access to US-27 for an easy commute. Enjoy weekends full of fun just 5 minutes from LEGOLAND Florida Resort, or take a short 10-minute drive to explore dining, shopping, and entertainment in downtown Winter Haven. Zoned near local elementary and middle schools just minutes away, this home offers convenience for families at every stage. This is more than just a home, it’s a lifestyle opportunity in one of Central Florida’s most convenient and growing communities. Don’t miss your chance to own this beautiful, move-in ready home in Villamar. Schedule your private tour today!

Listing is courtesy of: LIFESTYLE INTERNATIONAL REALTY (305-809-8085)

Listing Agent: Fanny Stollmeyer (704-905-0698)

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: 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: Additional reduction of this 4 bedroom 2.5 Baths is located in Villa Mar in Winter Haven, Florida. Master-planned amenities including a pool with cabana that is walking distance from your home, a playground, and shaded seating area. Highway 27, less than 10 minutes away, has everything you are looking for. Grocery stores, movie theaters, shopping centers, golf courses, restaurants, and so much more. Step in from the 2-car garage and enjoy the good life. Find it in the large family room. Share stories around the island or outside on the lanai. The 1st floor features a study. Upstairs, 4 bedrooms and a 2 full bath provide privacy while a loft adds extra entertaining space. Your deluxe owner’s suite includes double vanities, a seated shower, and 2 walk-in closets. All Ryan Homes now include WIFI-enabled garage opener and Ecobee thermostat.

Listing is courtesy of: CROWN INVESTMENT BROKERS (407-876-8719)

Listing Agent: Sushama Sharma (321-303-3306)

Remarks: This 3 bedroom, 2 bathroom home brings a fun mix of comfort and flexibility, featuring a bonus room that’s ready to become whatever you need next — a home office, gaming room, craft space, or an extra spot to unwind. The interior offers an easy, functional flow with bedrooms that make the most of the home’s footprint, and the primary suite includes its own private bath for added convenience. Step outside and you’ll find one of the property’s biggest highlights: a large fenced-in backyard with room to spread out, garden, host weekend cookouts, or give pets the space they deserve. It’s a manageable home with great energy, solid potential, and a location in Winter Haven that keeps daily errands, dining, and recreation close by. Schedule your tour today!

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

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