Apartments for Rent Near Denison Middle in Winter Haven - 34 rentals

Remarks: Welcome to **5850 Cypress Gardens Boulevard, Unit #608**, a move-in ready rental offering comfort, convenience, and exceptional value in the heart of Winter Haven. Priced to rent, this well-maintained residence is the perfect place to call home. Enjoy a bright and inviting interior designed for easy living, along with access to a community swimming pool—ideal for relaxing and enjoying Florida's year-round sunshine. Conveniently located near shopping, dining, medical facilities, and major roadways, this home offers an excellent combination of location and lifestyle. Don't miss this opportunity to lease a move-in ready home at a great price. Schedule your private showing today!

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

Listing Agent: Helen Moreno Porras (786-227-4907)

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: CURRENTLY AVAILABLE!! CORNER UNIT WITH VAULTED CEILINGS, PRIVATE BALCONY AND LAKEFRONT COMMUNITY- Welcome to your new retreat in the highly sought-after chain of lakes community of Park Lake — where comfort, style, and location come together beautifully. Step inside this charming one-bedroom, one-bath home and you’ll immediately notice the open feel created by vaulted ceilings and luxury vinyl flooring throughout the main living areas. The kitchen is a true highlight, featuring quartz countertops, sleek cabinets, stylish backsplash a modern tile floor, and all-new stainless steel appliances — including a five-burner stove, low-profile microwave, and refrigerator with exterior ice-maker. Thoughtful upgrades like new sinks, faucets, a garbage disposal, and modern lighting add both function and sophistication. The bathroom feels spa-like with a sleek tile shower, coordinating tile floor, quartz countertop, new sink, fixtures, and an elegant multi-illuminating with anti fog mirror that provides perfect lighting for any time of day. Two sliding glass doors — one from the living room and another from the bedroom — open to your private screened balcony, filling the home with natural light and offering peaceful outdoor views. The spacious bedroom includes a large closet, providing plenty of storage. Updated blinds, modern ceiling fans, and an inside utility with a washer/dryer combo add even more comfort and convenience. One designated parking space along with additional parking nearby. Just five minutes from vibrant downtown Winter Haven and next door to the state-of-the-art Advent Health Field House — complete with basketball courts and an Olympic-size swimming pool — this home’s location can’t be beat. Park Lake sits on the shores of beautiful Lake Lulu, where residents can fish from the pier or enjoy skiing right on the water. Perfectly centered near shopping, dining, and grocery stores, this prime location truly offers it all — comfort, convenience, and the best of the Florida lifestyle.

Listing is courtesy of: LIONHEART BROKERS (321-214-4640)

Listing Agent: Claudia Centesimo (407-383-8882)

Remarks: Looking for a Country Club lifestyle?? Conveniently Located in Cypresswood Golf & Country Club. This Immaculate 2 bed/2 bath condominium offers an open concept with a spacious kitchen open to great room. 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 from trendy downtown Winter Haven, convenient to Hwy 27 & I-4. Close to Legoland, Bok Tower, shopping, dining, hospital and medical facilities, plus a brand new Publix. ALL applicants must apply and pay for financial & background screening, provide valid ID, proof of employment and verifiable income.

Listing is courtesy of: CHAIN OF LAKES REALTY INC (863-287-4679)

Listing Agent: Laura Barnes (863-287-4679)

Remarks: 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!

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

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

Remarks: Welcome home to this spacious 3-bedroom, 2-bath duplex in the heart of Winter Haven! This well-maintained home offers an oversized living room with plenty of space to relax or entertain, a separate dining room, and generously sized bedrooms throughout. Enjoy the convenience of a one-car garage, in-unit laundry, and ceiling fans in multiple rooms to keep you comfortable year-round. Step outside to a fully fenced backyard—perfect for children, pets, or simply enjoying your own private outdoor space. With no HOA, you'll appreciate the added flexibility and freedom. Conveniently located just minutes from Polk State College, public transportation, shopping, dining, medical facilities, and everything Winter Haven has to offer, this home combines comfort, space, and an unbeatable location. Don't miss this fantastic rental opportunity—schedule your showing today! This version reads professionally while emphasizing the features that tend to attract renters: space, privacy, no HOA, fenced yard, garage, laundry, and proximity to Polk State College and major conveniences.

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

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

Remarks: This charming three-bedroom, two bathroom situated in a golf community. Located in Cypresswood, a gated community with controlled access and security, this home features an open-concept layout and a kitchen equipped with an island, dishwasher, double-oven range, garbage disposal, and microwave. The primary bedroom boasts a spacious walk-in closet. At the rear of the house, there are two spacious porches—one with vinyl windows and another that is screened-in with brick paver flooring—offering an ideal spot to relax and enjoy the sunshine. The property includes a two-car garage with screen doors. Cypress Golf & Country Club amenities include an 18-hole championship golf course, a clubhouse, a restaurant, a swimming pool, and tennis courts. It offers easy access to Highway 27, I-4, and Legoland.

Listing is courtesy of: PROPERTY OUTLET INTERNATIONAL (407-723-7000)

Listing Agent: Migdalia Moreira (407-797-8100)

Remarks: 3 bedroom, 2 full bath house features master suite with spacious walk in closet. The home has an open floor plan with a kitchen island to entertain and enjoy the company of your guests. This neighborhood offers easy access to major employment centers and great schools. Located in Winter Haven, Villamar offers great location and amenities.

Listing is courtesy of: SUNNY 365 REALTY GROUP (407-574-7048)

Listing Agent: Isabel Sirizzotti (407-361-8236)

Remarks: Spacious New 5-Bedroom Residence Available for Lease in Winter Haven Experience the comfort of a never-before-occupied home in one of Winter Haven’s growing residential communities. This newly completed two-story property offers an impressive combination of space, modern design, and everyday convenience, featuring five bedrooms, two full bathrooms, and a guest powder room. The thoughtfully designed layout provides generous living spaces that flow seamlessly from one room to another, creating an inviting environment for both entertaining and daily family life. Abundant natural light fills the interior through oversized windows, enhancing the home's bright and airy feel. At the heart of the home, the contemporary kitchen showcases quality craftsmanship with rich wood cabinetry, sleek stone surfaces, and a full package of stainless-steel appliances. Whether preparing weeknight meals or gathering with friends and family, this space is designed to accommodate both functionality and style. The primary bedroom serves as a relaxing retreat, offering ample space, a large walk-in wardrobe, and a well-planned layout for privacy and comfort. Secondary bedrooms are generously proportioned and feature built-in closet storage, providing flexibility for family members, guests, or home office needs. Additional features include an attached two-car garage, modern fixtures and finishes throughout, and the advantages of energy-efficient construction designed to help reduce utility costs while enhancing year-round comfort. Ideally positioned near shopping centers, restaurants, schools, and major transportation routes, residents will enjoy convenient access to everyday necessities while benefiting from the peaceful atmosphere of a residential neighborhood. This exceptional rental presents a rare opportunity to enjoy the benefits of a brand-new home with abundant living space, contemporary finishes, and a convenient Winter Haven location.

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

Listing Agent: Alexandre Zapparoli Llc (321-444-8701)

Remarks: FIRST MONTH FREE! Beautiful 2 bedroom, 1 bathroom duplex located in a quiet and desirable area off Cypress Gardens Boulevard. This move-in ready home features a brand-new roof, renovated interior, block construction, and a spacious oversized lot with 2 parking spaces. The property includes a bright and comfortable living area, new stove, washer and dryer, and a large deep freezer for additional food storage. Enjoy the relaxing screened-in lanai/balcony, perfect for outdoor seating and extra living space. Conveniently located just minutes from shopping centers, restaurants, schools, and major highways while still offering the privacy and comfort of a peaceful community. Limited-time offer: First month's rent free with an approved application and executed lease. Property Features: • 2 Bedrooms • 1 Bathroom • Newly Renovated • Brand New Roof • Screened-In Lanai / Porch • Washer & Dryer Included • New Stove Included • Large Deep Freezer Included • 2 Parking Spaces • Oversized Lot • Quiet Community • Excellent Location

Listing is courtesy of: D & D PROPERTY MANAGEMENT SOLUTIONS LLC (407-434-1693)

Listing Agent: Teresa Dishington (407-346-5001)

Remarks: Virtually Staged. Wonderful 2 bedroom/2 bath unit with spacious, soaring ceilings, neutral colors, and very ENERGY EFFICIENT: Brand New A/C system, Brand New Gas Hot Water Heater, Brand New Gas Heat Furnace---so low utility bills! Just professionally painted inside, new door hardware, new bathroom light fixtures & sink faucets. Easy-to-maintain ceramic tile floors throughout, STAINLESS appliances and any chef's delight, a gas range. There's a large inside laundry, plenty of storage, and ceiling fans in every room. Primary bedroom has sliders opening to a small private backyard. This is a quiet neighborhood, with 2 parking spots assigned per unit, with easy access to lakes, shopping, Legoland, and Polk State and dining (like Tanners, only minutes away).

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

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

Remarks: Welcome to Lamplighter Village with this one of a kind 2 bedroom/1 bath condo. The property was nicely renovated and features updated vinyl flooring and updated stainless steel kitchen appliances with a gas stove. New solid wood cabinets and granite countertops. The condo was freshly painted and is turn key ready. Property also includes a stand up washer and dryer and new window blinds. The location offers 1 parking space in front and visitor parking directly across from the unit. Enjoy views of beautiful Lake Roy and central location to all of the main restaurants, markets and attractions including (two) Walmarts, LEGOLAND, Panda Express, Starbucks, McDonalds, Chic-fil-A, Publix and so much more just minutes away! If you are looking to be centrally located and surrounded by many opportunities, this is the place to be! . Schedule a showing today.

Listing is courtesy of: MAYOLET REALTY LLC (407-491-4893)

Listing Agent: Mayolet Bornas Moreira (407-491-4893)

Remarks: Welcome home to this inviting upstairs condo located in the peaceful Lake Buckeye Condo community, where tranquil lake views and relaxed living come together. Step inside to find laminate and ceramic tile flooring throughout, offering both durability and easy maintenance. The open living and dining area is light and welcoming, seamlessly extending to a private 3x7 balcony, the perfect place to enjoy your morning coffee or unwind at the end of the day. Just beyond, the well-appointed kitchen comes complete with all appliances, granite countertops, and an adjacent utility room with washer/dryer hookups and extra cabinet storage. The split-bedroom floor plan provides excellent privacy. The primary suite features a walk-in closet and a private en-suite bathroom with a walk-in tile shower, while the second bedroom is conveniently located near the hall bath, ideal for guests or a home office. Residents enjoy access to community amenities, including a sparkling pool overlooking beautiful Lake Buckeye and community docks, perfect for lakeside relaxation and peaceful views. This condo offers a wonderful blend of comfort, convenience, and serene surroundings—an opportunity you won’t want to miss!

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

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

Remarks: Beautiful Corner Lot Home for Rent in Lawson Dunes! Welcome to this stunning 4-bedroom, 2-bathroom home located on a premium corner lot in the highly desirable Lawson Dunes community. The rent is $ 2,100 Unfurnished and $2,300 furnished This beautifully designed home features an open-concept floor plan with abundant natural light, a spacious living area, and a modern kitchen complete with a large center island, stainless steel appliances, and plenty of cabinet space—perfect for everyday living and entertaining. Property Features: 4 Spacious Bedrooms 2 Full Bathrooms 2-Car Garage Premium Corner Lot Fully Fenced Modern Kitchen with Center Island Separate Laundry Room Contemporary Finishes Throughout Community Amenities: Community Swimming Pool Playground Dog Park Scenic Walking Trails Conveniently located just minutes from US-27, shopping centers, restaurants, schools, and major highways, providing easy access to Davenport, Winter Haven, Lakeland, and Orlando. Don’t miss this opportunity to live in a beautiful, family-friendly community!

Listing is courtesy of: A & V FLORIDA REALTY GROUP LLC (786-641-7923)

Listing Agent: Edgar Brito (786-641-7923)

Remarks: Nestled in a sought-after neighborhood just off Cypress Gardens Boulevard, this spacious 1-bedroom, 1-bathroom apartment on the second floor offers a perfect blend of comfort and convenience. The bright, welcoming living area seamlessly connects to a cozy kitchen and combined dining area. A nicely sized bedroom provides a peaceful retreat with sliding glass doors looking out to the screened-in balcony. The balcony is an ideal spot to unwind and enjoy the fresh air in peace while also providing an extra storage closet. Residents also have access to a sparkling community pool, beautifully maintained grounds, and a location that places shopping, dining, and entertainment within easy reach. Experience a comfortable lifestyle in a vibrant setting. Contact us to schedule a viewing today!

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

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

Remarks: Amazing location! In this beautiful house you will find a 3 bedroom 2 full bath and a bonus room (use it as an extra bedroom, office, etc.) This modern house sits on a corner lot, spacious living area, very sunny and inviting, ceramic tiles, stainless steal appliances, quartz counter tops, walking closet and a 2 car garage. Call to schedule a showing and move in to this lovely community.

Listing is courtesy of: LA ROSA REALTY CENTRAL FLORIDA LLC (407-861-8009)

Listing Agent: Britzeida Pichardo (347-549-7568)

Remarks: 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!

Listing is courtesy of: R&J REALTY AND PROPERTY MANAGEMENT LLC (407-729-3280)

Listing Agent: Jose Marrero Cruz (407-729-3280)

Remarks: Discover easy downtown living in this bright and inviting studio apartment located in the heart of Winter Haven. The spacious combined living and bedroom area offers plenty of room to relax and make the space your own. A large sliding glass door fills the apartment with natural light and opens to a large, quiet yard. This studio blends comfort, convenience, and simplicity, all within steps of the energy and amenities of downtown Winter Haven.

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

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

Remarks: Cute and clean downstairs end unit in Winterset, a gated community. Features wood laminate flooring in living area and bedrooms and ceramic tile in the wet areas. Open floor plan, kitchen with breakfast bar overlooking living room with mirror wall and dining area. Master bedroom has sliding glass doors to a private 6x7 screened in patio. Master suite includes walk-in closet, stackable washer & dryer, tile walk-in shower with shelving in the bathroom, plus another lien closet or storage space outside. Guest bath also has a tile walk-in shower. Enjoy the amenities Winterset offers, includes waterfront gated community, tennis courts, clubhouse, community heated pool and hot tub, access to Lake Winterset and Chain-of-Lakes. Great location and easy access to shopping centers, Publix & Walmart, and Legoland.

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

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