Apartments for Rent Near Denison Middle in Winter Haven - 38 rentals

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: 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.

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

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

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)

Remarks: Welcome to 630 Pavare Ct, a charming 2-bedroom, 2-bath end-unit condo available for rent in the desirable Orchid Springs community. This second-floor residence offers 823 square feet of comfortable living space with an open floor plan, ceramic tile flooring throughout, with carpet in the bedrooms and neutral paint tones. The spacious great room flows into the dining area and kitchen, creating a functional layout for everyday living. The kitchen includes a gas range, microwave, refrigerator, garbage disposal, closet pantry, and a stackable washer and dryer. The primary bedroom features a walk-in closet and private bath with a walk-in shower, while the guest bathroom offers a tub/shower combination. Enjoy relaxing views from the private balcony. An assigned parking space is located near the unit, with additional guest parking available. Conveniently located near shopping, dining, entertainment, medical facilities, and major roadways with easy access to Tampa and Orlando. Call today for your private showing!

Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)

Listing Agent: Amy Reynolds (863-412-2279)

Remarks: 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!

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Nomar Rosa (646-673-3900)

Remarks: One or more photo(s) has been virtually staged. Move in READY! Located in Estates of Lake Florence, this 4-bedroom, 2-bath home with a 2-car garage offers 1,850 sq. ft. of open living, highlighted by a beautiful kitchen and a fully fenced backyard with two gate access points—the true showstoppers of the home, where you’ll create lasting memories whether you’re cooking, enjoying family time, entertaining, or simply unwinding. Step inside to a long hallway that leads past three well-positioned bedrooms and a dedicated indoor laundry room with washer, dryer, and built-in shelving, before opening into the heart of the home. The kitchen flows seamlessly into the dining and living areas, featuring granite countertops, a stylish backsplash, a large island, and a walk-in pantry, all filled with natural light. Bedrooms are carpeted for comfort, with tile in all wet areas for easy upkeep. The primary bedroom and en-suite is tucked just off the living room, offering privacy along with dual sinks, a spacious walk-in closet, a private toilet room, and a walk-in shower. Out back, enjoy a fully fenced yard and covered porch—perfect for relaxing, entertaining, or giving pets room to roam. Located in Winter Haven, you’re approximately 10 minutes to downtown, 10 minutes to Cypress Lanes, 15 minutes to LEGOLAND Florida Resort, about 25 minutes to Lakeside Village, and within 45–60 minutes of Walt Disney World Resort and Universal Orlando Resort. Easy access to US-27, FL-540, and I-4 makes commuting simple. Application requirements: Must make 2x monthly rent, pass background and credit screening. Pets considered with owner approval, photo, and non-refundable deposit. No smoking permitted inside the home. Renters insurance required. Scheule you're showing today. RentSpree link to apply https://apply.link/6rTqkaM

Listing is courtesy of: ORANGE SLICE PROPERTIES (863-632-9765)

Listing Agent: Lisa Siner, Llc (407-486-8605)

Remarks: A comfortable first-floor 2 bed, 2 bath condo in the gated Winterset community, this home offers an easy, open layout with plenty of natural light and convenient ground-level access. Each bedroom has its own full bathroom, giving you a setup that works well for roommates, guests, or anyone who wants a little extra privacy. The condo can be leased furnished for a turnkey move-in or unfurnished if you prefer to bring your own style. Winterset adds to the appeal with lakefront views, a community pool, tennis courts, and beautifully maintained grounds that make everyday living feel calm and inviting. Don't miss your opportunity to live in this luxurious community! Schedule a tour today! ($1,750 with furniture, $1,650 without)

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

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

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: Cozy 1 bedroom, 1 bathroom unit located on the second floor. Situated in a calm, residential neighborhood near a local school, with convenient access to downtown just minutes away. Approximately 10–15 minutes from Legoland, offering an ideal central location. No pets allowed. First month’s rent and security deposit required. A great option for comfortable and convenient living.

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

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

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: A studio apartment with 1 bath for rent off of Lake Roy. Included in the rent is Water, and Lawn service. This property does not have a washer or dryer hook-up. Call soon before this property is gone! Application Fee runs $50 per adult with a onetime $50 Lease Fee. For this home we are asking for First Month's Rent ($800), and Security Deposit ($1000) making total move in cost assuming one adult to be $1900 if you move in on the first of the month.

Listing is courtesy of: AT YOUR SERVICE REALTY, LLC (863-665-5663)

Listing Agent: Daniel Gonzalez (863-226-9614)

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: 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: 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: MOVE-IN READY Eagle Pond condominium in the highly desirable gated community of Cypresswood Golf and Country Club available beginning 12/1/2023. This meticulously-maintained condo features hard floors throughout (no carpet!), new interior paint, NEW kitchen appliances, interior laundry (with brand new 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.

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

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