Apartments for Rent Near Denison Middle in Winter Haven - 22 rentals

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: Beautiful 3-bedroom/3-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: 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)

Remarks: Immaculate home still feels like brand new construction! 4 bedroom 2 bath home in the Estates of Lake Florence. This home is ideally located in Winter Haven minutes from HWY 17, near I-4 and SR 60, for easy access to the Greater Orlando Area and Lakeland. The living area is bright and open connecting the living room space with the dining area and kitchen. The stylish kitchen showcases a convenient island, a large single bowl sink, white cabinets, granite countertops and Whirlpool stainless steel appliances including a dishwasher, microwave, and range. This home makes great use of space, the primary bedroom is located at the back of the house, featuring a full primary bathroom with dual sinks, a step in shower with private water closet, and large closet space. Bedrooms 2 and 3 are located at the front of the house and share the hall bath. The 4th bedroom sits by itself, perfect for a home office or bonus room. The large laundry room features extra storage space. Small pet may be accepted with owner's approval and non-refundable pet fee.

Listing is courtesy of: REMAX EXPERTS (863-802-5262)

Listing Agent: Jake Bellamy (863-838-7804)

Remarks: Beautiful home for rent in Eagle Crest, Winter Haven, just minutes from Polk State College. This property offers an open floor plan with 3 bedrooms and 2 bathrooms, den for office space, screened lanai, plus a fenced-in yard. HOA approval required. Tenant must provide renters insurance.

Listing is courtesy of: CENTURY 21 WATSON & MYERS REALTY (863-324-1000)

Listing Agent: Marisol Padilla (863-604-7252)

Remarks: FOR RENT - 1 Bedroom/1 Bathroom Executive Condo in beautiful Park Lake. This ground floor unit has access to Lake Lulu, a community pool, a dock, and a clubhouse/recreational facility. The association fees are included in the rent. If you like skiing, Winter Haven is the Ski Capital of World! Downtown Winter Haven has about a dozen restaurants plus activities for the family every month. These activities include arts and crafts/farmer's markets, music, games, and more. The Winter Haven Public Library offers not only books but movies, family activities and a "kiddie corner". Winter Haven has 26 buildings registered with the US National Register of Historic Places. DISNEYWORLD and the Orlando attractions are only 45 minutes away. You just can't beat it...an active community, with parks, lakes, theatres, and restaurants. Just come to Winter Haven...it's the home of LEGOLAND!

Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)

Listing Agent: Linda Andre (863-852-5747)

Remarks: Discover this beautiful 2-bedroom, 2-bath home with an additional flex room, perfect for a home office, den, or guest space, enclosed with a stylish barn door. Located in the desirable lakefront community of Cypress Landing, this home offers a welcoming and open layout with vaulted ceilings and abundant natural light. The kitchen is designed for both function and style, featuring ample cabinetry, generous counter space, and a breakfast bar that flows seamlessly into the dining area. A sliding glass door leads to a cozy 7x15 screened lanai—ideal for relaxing with your morning coffee. The primary suite is a private retreat, complete with an en-suite bathroom including a walk-in shower and 5x5 walk-in closet. The primary bedroom also has elegant French doors giving access to the flex room. Additional highlights include an inside utility room, updated laminate flooring throughout most of the home, and a fenced backyard for added privacy. Residents of Cypress Landing enjoy fantastic community amenities, including a clubhouse with social events, a heated pool, tennis courts, and a private boat ramp with lake access for fishing, boating, and watersports on Lake Dexter. Conveniently located just minutes from Legoland, shopping, and dining, this move-in-ready home offers the perfect balance of comfort and convenience.

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: This cozy and well-maintained home offers a warm and inviting layout, ideal for comfortable and easy living. The property features a functional floor plan with a modern kitchen, bright and spacious bedrooms, and low-maintenance living areas designed for convenience. Centrally located with quick access to US-27, US-17, SR-540, and I-4, this home provides easy commutes to Orlando and Tampa, as well as proximity to major attractions such as Disney and Legoland. Enjoy being just minutes away from lakes, parks, shopping centers, and a variety of dining options. A perfect rental opportunity for those seeking comfort, convenience, and a well-connected location in the growing Winter Haven area.

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

Listing Agent: Jenny Caso (407-694-9682)

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: Available for immediate move-in! Experience the perfect blend of historic charm and modern updates in this beautifully remodeled 1957 home, ideally located in the heart of Winter Haven. Just off First Street and minutes from shopping, public transportation, and major roadways, this home offers both convenience and character. Inside, you'll find a contemporary interior with brand-new flooring and crisp paint that highlights the home's timeless features. With three generously sized bedrooms, a giant Florida room, and easy access to everything Winter Haven has to offer, this home is as practical as it is charming.

Listing is courtesy of: HOMETRUST REALTY GROUP (813-444-5777)

Listing Agent: Sylvain Sara (727-623-5327)

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: Freshly updated and full of charm, this 2-bedroom, 1.5-bath home offers a comfortable layout with stylish modern touches throughout. From the moment you arrive, you’re welcomed by a fully fenced front courtyard — a private entry space that adds both character and functionality, perfect for outdoor seating or a quiet retreat. Inside, the home features a bright and open living space that flows effortlessly into the kitchen and dining area, creating an easy, connected feel for everyday living. The kitchen has been updated with newer appliances and finishes, complementing the clean, refreshed interior. Both bedrooms are generously sized, with the primary bedroom featuring its own private half bath for added convenience. The full bathroom has also been updated, tying in with the home’s overall modern feel. To the rear, a screened-in porch provides an additional space to relax or entertain, overlooking a private backyard. With in-home laundry and a practical layout, this home is designed for both comfort and ease. Located directly across from an elementary school and just a short drive to downtown Winter Haven, you’ll enjoy quick access to shopping, dining, and everyday conveniences. A well-updated home in a convenient location — ready for its next tenant to enjoy.

Listing is courtesy of: HAINES AND HAVEN RESIDENTIAL (863-443-8845)

Listing Agent: Tricia Hohn (863-207-4774)

Remarks: Newly updated 2 Bedroom /1 bathroom with private fenced yard. Welcome to this beautifully renovated 2-bedroom, 1.5-bath home offering comfort, convenience, and modern updates throughout. Thoughtfully refreshed from top to bottom, this property features new appliances, updated finishes, and a bright, open-concept living and kitchen area designed for easy everyday living and entertaining. The spacious layout provides two well-sized bedrooms, including a primary suite with its own private half bath for added convenience. The main living area flows seamlessly into the kitchen, creating an inviting space filled with natural light and functionality. Step outside to enjoy the screened-in porch — perfect for relaxing mornings or unwinding in the evening — overlooking a private, fully fenced backyard that offers both security and space to enjoy the outdoors. Additional features include in-home laundry and convenient off-street access. Ideally located directly across from an elementary school and just minutes from downtown Winter Haven, you’ll have easy access to local restaurants, shops, parks, and community events. This move-in-ready home combines modern updates with an unbeatable location — a perfect place to settle in and enjoy all that Winter Haven presents.

Listing is courtesy of: HAINES AND HAVEN RESIDENTIAL (863-443-8845)

Listing Agent: Tricia Hohn (863-207-4774)

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)