Winter Haven Apartments for Rent - 120 rentals

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! ($1,900 with furniture, $1,800 without)

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

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

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: Experience lakefront living at its best in this 2-story townhouse with 3-bedroom 3 bath on Lake Buckeye, located just minutes from Winter Haven Christian School. !Enjoy breathtaking panoramic lake views from the living room, master bedroom balcony, . this spacious home is perfect for anyone. ONLY ONE MONTHS RENT & SECURITY $1950.00 TO MOVE IN. Housing Choice Voucher Programs are always Welcome.

Listing is courtesy of: KURUVILA REALTY ASSOCIATES LLC (954-530-9477)

Listing Agent: Joe Kuruvila (954-822-7900)

Remarks: One or more photo(s) has been virtually staged. Wake up every morning to the most breath taking views imaginable. Almost every room in the home overlooks the spectacular private Lake Ruby & Lake Bess. Upon entering the home you will find yourself captivated with the spacious and luxurious open floor plan and high degree of natural light that envelops you. Besides having the exquisite view, this home also features a screened in pool and spa with lost of room to entertain. Both the pool and jacuzzi were resurfaced just a couple of years ago. The house, which was built in 2000, has many alluring features including a 3 car garage, cathedral ceilings, an extra large master suite, formal living room, and a family room with a fireplace over looking the lake. This property also features the use of you own private doc, boat house with life and a very important boat ramp since there is no public access to the lake. Please note: the rental includes $300 toward electric and $100 toward the water bill each month. An additional overages will be du by the lessee, Nature calls to those who enjoy water as fishing, boating, and skiing are outstanding on clean Ruby Lake, Some of the best views are from this home. Since it is connected to Lake Bess there are also two slalom courses nearby. The Ruby Lake community is gated an is also close to shopping and restaurants. Hwy 27 is only about 2 miles away. It is only 1 mile to Legoland. After enjoying all of the daily activities this property and nearby attractions, the home offers the night time sunsets that are gorgeous and a wonderful way to end the day. Both Tampa International and Orlando International airports are close by

Listing is courtesy of: KLINE REAL ESTATE SERVICES (863-287-0204)

Listing Agent: Scott Kline (863-287-0204)

Remarks: Now available for rent in the Lake Lucerne community—this well-maintained 4-bedroom, 2-bathroom home features a spacious and open floor plan.Newly fenced yard. The kitchen is equipped with granite countertops, stainless steel appliances, and a center island that overlooks the living and dining areas. The primary suite offers a walk-in closet and private bath. Tile flooring is featured in the main living spaces, with carpet in all bedrooms. The home also includes an interior laundry room with washer/dryer hookups, a two-car garage, and a covered patio overlooking the backyard. Lawn care is included in the rent. Conveniently located near US-17, shopping, dining, and local attractions.

Listing is courtesy of: HONEST EXPERTS REAL ESTATE LLC (407-697-6611)

Listing Agent: Leslie Soto (617-461-2522)

Remarks: Beautiful brand-new 4-bedroom, 2-bathroom home located in a great area of Winter Haven. The property features a charming front porch, perfect for relaxing. Inside, the home offers a spacious open-concept living room seamlessly connected to the dining area and kitchen, creating a modern and functional layout. Sliding glass doors provide access to a large outdoor area, ideal for entertaining and everyday enjoyment. The kitchen is fully equipped with appliances, wood cabinets, and a breakfast bar for quick meals. The primary suite includes generous closet space, offering comfort and convenience. The home is located in a planned community with newly built single-family homes and offers excellent amenities such as a community pool, playground, sidewalks, and a beautiful natural creek, providing a peaceful and family-friendly environment. Excellent location, close to: Schools and supermarkets Restaurants and local shopping Quick access to US-27 and main roads Just minutes from LEGOLAND® Florida Resort Easy access to downtown Winter Haven and nearby cities Don’t miss this opportunity to rent a brand-new home with comfort, amenities, and a prime location. Schedule your showing today!

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

Listing Agent: Jessyka Dos Santos (407-364-0170)

Remarks: Brand New Two-Story Home for Rent in Winter Haven Welcome to this stunning brand new two-story home located in the heart of Winter Haven, offering the perfect combination of space, style, and convenience. Designed with modern living in mind, this beautiful property is ideal for families or anyone looking for comfort and quality in a prime location. The home features 5 spacious bedrooms, including a generous primary suite with a walk-in closet, while the additional bedrooms are equipped with built-in closets, providing excellent storage throughout. With 2 full bathrooms and 1 half bathroom, the layout is both functional and comfortable for everyday living. Enjoy an open floor plan that seamlessly connects the expansive living room and dining room, creating a bright and inviting space perfect for relaxing or entertaining. The beautiful kitchen stands out with solid wood cabinets, elegant stone countertops, a pantry, and all appliances included, making it as practical as it is stylish. Additional highlights include a 2-car attached garage and a great location, conveniently close to major roads and highly rated schools, offering easy access to everything Winter Haven has to offer. This is a rare opportunity to rent a brand new home in a desirable area. Schedule your showing today and experience comfort, space, and modern living all in one place.

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

Listing Agent: Jessyka Dos Santos (407-364-0170)

Remarks: Comfortable 1BR Apartment in Desirable 55+ Community, well-maintained one-bedroom, one-bath apartment located in a quiet and welcoming 55+ community. Features a functional floor plan with bright living and dining areas, a spacious bedroom with ample closet space, and a clean, well-appointed kitchen. Enjoy community amenities and a peaceful setting designed for active living. Conveniently located near shopping, dining, medical facilities, and public transportation. Perfect for comfortable, low-maintenance living.

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

Listing Agent: Elsa Gonzalez (407-235-4018)

Remarks: 3 bedroom 2 bath home with 2 car garage located in SE Winter Haven near Legoland. Modern custom cabinets throughout the home, open island kitchen design with pantry, bedrooms with plenty of closet space. Large master suite with roomy walk-in closet, spacious tiled master bath, and sliding doors to screened porch. Double pane windows throughout. Fenced yard. Located in a family friendly neighborhood right down the street from Garden Grove Elementary School. Convenient to Walmart, CVS, and Walgreen, and just a short drive away from Eagle Ridge Mall.

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

Listing Agent: Donna Williams (863-701-3663)

Remarks: Beautiful single-family home located in the desirable Lake Lucerne Community. This property offers an open-concept kitchen with luxury finishes, vinyl flooring in the main living areas, and fully carpeted bedrooms for added comfort.The kitchen comes fully equipped with stainless steel appliances, granite countertops, and ample cabinet space for storage.Enjoy the outdoors in the covered lanai patio, perfect for spending quality time with family and guests. For added privacy, the spacious backyard is fully fenced.Schedule your showing today and experience the comfort of living in this wonderful property! the house has two car garage. Weeks and Months

Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)

Listing Agent: Alfredo Bastidas (689-248-6507)

Remarks: One or more photo(s) has been virtually staged. Welcome to 2521 Pine Pl, where modern elegance meets peaceful lakefront living. This beautifully designed 3-bedroom, 2.5-bath home offers spectacular lake views right from your backyard, creating the perfect backdrop for morning coffee, sunset relaxation, or weekend gatherings. Inside, enjoy a bright open-concept floor plan, a sleek contemporary kitchen, and a luxurious primary suite built for comfort and retreat. Nestled in one of Winter Park’s most desirable communities, you’re just minutes from top-rated schools, upscale dining, shopping, and local attractions. Lake-view homes like this are rare—schedule your private tour today and experience it for yourself! *** SECTION 8 IS NOT ACCEPTED. All Innovation Property Management residents are enrolled in the Resident Benefits Package (RBP) for $45.00/month which includes liability insurance, HVAC air filter delivery (for applicable properties), on-demand pest control, and much more! More details upon application. Price may be reduced depending on tenant’s desire to add pest control and/or provide proof of adequate insurance coverage. HOW TO APPLY: 1. Visit the website of Innovation Property Management, Inc. 2. Click "Rentals" at the top of the page. 3. Find the rental unit you are interested in on the list and click "Apply Now”.

Listing is courtesy of: TRANSCEND REALTY (407-518-7653)

Listing Agent: Jacob Hara (407-933-5478)

Remarks: Welcome home to 165 Osprey Heights Drive! This well-maintained 3-bedroom, 2-bath home offers a desirable split floor plan, providing both privacy and functionality. The home features brand-new vinyl flooring in the main living areas and fresh interior paint, giving it a clean, updated feel throughout. The bedrooms are comfortably carpeted, creating a warm and cozy retreat. The kitchen is both cute and functional with plenty of space to cook and gather. Additional highlights include a two-car attached garage for convenient parking and storage, plus a small shed in the backyard for extra space to keep tools, lawn equipment, or outdoor items organized. This home is move-in ready and waiting for its next Tenant. Schedule your showing today!

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

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

Remarks: Welcome to your next home! This well-maintained 4-bedroom, 2-bathroom home offers 1,701 sq. ft. of comfortable living space with an open-concept layout that creates a bright and inviting atmosphere—perfect for relaxing or entertaining family and friends. Located in a friendly and welcoming community, residents enjoy access to the community pool and playground, providing great options for outdoor enjoyment. The home is ideally situated just minutes from Highway 27, offering convenient access to everyday essentials, shopping, and dining. Posner Park is a short drive away and features a variety of retail stores, restaurants, and entertainment options. Grocery stores such as Publix and Walmart are nearby, along with popular local restaurants including Manny’s Chophouse and other dining options along Highway 27. With its spacious layout and prime Central Florida location, this home offers the perfect blend of comfort, convenience, and community living. Available for move-in May 1st.

Listing is courtesy of: UNITED REALTY GROUP INC (954-450-2000)

Listing Agent: Yashira Arroyo Colon (407-864-4904)

Remarks: Check out this well-kept 2BR 2BA Golf Villa with a spacious bonus room in Cypresswood! The community is perfect for family and friends. You'll love the awesome amenities, including a pool, tennis courts, fitness center, clubhouse with a restaurant, and even exclusive golf discounts. The location is unbeatable—just minutes from major highways, downtown Winter Haven, Legoland, restaurants, shopping, and more. Sorry, no pets or smoking allowed. Call today for your personal showing!

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

Listing Agent: Steve Lockhart (863-289-9801)

Remarks: Check out this move-in ready rental home located in the desirable Hamilton West community in Winter Haven. This well-maintained residence offers 4 generously sized bedrooms, 2 full bathrooms, and a 2-car garage, along with excellent curb appeal. Inside, you’ll find brand-new carpeting throughout, a formal dining room, and a versatile den/office space. The spacious kitchen includes all appliances, a closet pantry, and a cozy dinette area, and opens to an enormous living room with plenty of space for larger furnishings and entertaining. Additional features include an inside utility room equipped with a washer and dryer and a covered back patio overlooking the large backyard. The oversized primary bedroom features private access to the back patio and an en-suite bathroom with a dual sink vanity, garden tub, walk-in shower, and dual walk-in closets. The remaining three bedrooms are well-sized and share a full bathroom with a tub/shower combination. Lawn care is included and maintained by the owner for added convenience. A $40 application fee is required for all applicants over the age of 18. No pets and no smoking permitted. This home is available for immediate occupancy. Schedule your showing today!

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

Listing Agent: David Fridovich (863-430-1700)

Remarks: Welcome to your new home just off Cypress Gardens Blvd — a spacious and inviting first-floor condo with 2 bedrooms and 2 full bathrooms. This unit features high ceilings in the living room that create an open, airy feel, and the master bedroom includes its own private ensuite for added comfort. Located in a quiet, well-kept community, you’ll also enjoy access to a sparkling pool perfect for relaxing or entertaining. With convenient first-floor access and a prime location near shopping, dining, and entertainment, this condo offers the perfect blend of comfort and convenience.

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

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

Remarks: Now available for rent in desirable Planter’s Walk! This beautifully updated 3-bedroom, 2-bath home features ceramic tile flooring throughout, a remodeled kitchen with quartz countertops and new cabinets, vaulted ceilings, and a spacious open layout filled with natural light. Enjoy a large Florida room, screened porch, and a fully fenced backyard with shed—perfect for relaxing or entertaining. Two-car garage, large driveway, and a prime Southeast Winter Haven location just minutes from LEGOLAND, shopping, dining, and major highways. Move-in ready and waiting for you!

Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)

Listing Agent: Manny Quiros (863-221-3036)

Remarks: VACANT, MOVE-IN READY & PET FRIENDLY! Lease for just $1,600/month! Located in the lovely and up-and-coming Winter Haven area, this completely remodeled historic 1930s home has been beautifully restored to its former glory. This charming home offers 2 bedrooms and 1 well-appointed full bathroom, perfect for comfortable living. Situated on an oversized, fully fenced corner lot—perfect for pets—the backyard provides peace of mind and privacy. A wooden picnic bench and table add convenience for enjoying your morning coffee or relaxing outdoors. Inside, enjoy a cozy open floor plan filled with natural light. Recent updates include: new appliances, tankless water heater, roof with decking, plumbing, electrical, wood cabinets, and quartz countertops. All major systems have been updated—this is a true turnkey home! Utilities to be covered by the tenant. Do NOT wait, it will NOT last long! Contact us today to schedule a showing!

Listing is courtesy of: HUT TEAM REALTY (407-559-2929)

Listing Agent: Daniel Hut (863-400-6090)

Remarks: Lovely older home with original hardwood flooring located near downtown Winter Haven. Fenced in yard great for kids or animals. Located half way between Tampa and Orlando.

Listing is courtesy of: BARON HOLDINGS REAL ESTATE LLC (863-651-1783)

Listing Agent: Steven Baron (863-651-1783)

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)