Winter Haven Condos For Rent - 27 condos

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: Remodeled and updated 2nd floor condo with picturesque views of the pool and lush landscaping. This 3 bedroom unit is ready for immediate occupancy. Recent updates include fresh interior paint, new flooring, new kitchen cabinets and solid surface counters. This established 55 and over community is nestled on the shores of Lake Howard on the famous Chain of Lakes and includes a community boat dock/fishing pier. Additional amenities include a heated pool, gazebo with bathrooms, shuffleboard, activities and secure storage. Located close to the heart of downtown Winter Haven, This condo provides an opportunity to enjoy the Lakefront Florida lifestyle at an affordable price. Monthly fees include water, cable, internet, trash, sewer, exterior maintenance and grounds maintenance making this an attractive opportunity for year round residents or snowbirds. Seller is a licensed Realtor in the State of Illinois.

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

Listing Agent: Steven Smith, Pa (863-224-2297)

Remarks: Located in the attractive and quiet Winter Ridge area! This is an excellent single-story home featuring 3 bedrooms and 2 bathrooms, situated right by Smart Lake. The house boasts numerous upgrades, including fresh paint throughout and kitchen appliances, a washer, a dryer, and an electric water heater that are all just one year old. It also features a spacious covered patio and a good-sized yard. If you are looking for peace and tranquility, this is the ideal community and home for you. The community offers a boat dock, swimming pool, clubhouse, and shuffleboard courts, all while enjoying a convenient location near entertainment, shopping, and medical facilities. Available immediately!

Listing is courtesy of: EMPIRE NETWORK REALTY (407-440-3798)

Listing Agent: Rafael Casallas, Pa (407-404-0472)

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: LAKEFRONT LIVING AT ITS BEST. REFRESHED FIRST FLOOR 2BR-2BA CONDO WITH COVERED PARKING AND BEAUTIFUL VIEWS OF LAKE BUCKEYE. FEATURES INCLUDE FRESH INTERIOR PAINT THROUGHOUT, LUXURY VINYL WOOD PLANK FLOORING, STAINLESS REFRIGERATOR AND MICROWAVE, OPEN GREAT ROOM DESIGN WITH LIVING AND DINING COMBO. RELAX IN THE FLORIDA ROOM OVERLOOKING THE LAKE AND ENJOY STUNNING SUNRISE VIEWS WITH YOUR MORNING COFFEE. COMMUNITY AMENITIES INCLUDE POOL AND TENNIS COURTS. CONVENIENT LOCATION NEAR POLK STATE COLLEGE AND THE LAKE ELBERT WALKING TRAIL AROUND LAKE ELBERT. ONLY MINUTES TO DOWNTOWN WINTER HAVEN WITH SHOPPING AND RESTAURANTS.

Listing is courtesy of: FLORIDA HOME CHOICE REALTY (863-412-2727)

Listing Agent: Glenda Pruitt (863-412-2727)

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: 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: Welcome to 333 Lake Howard Dr NW #303A, where everyday living comes with beautiful views of Lake Howard and the convenience of being just minutes from downtown Winter Haven. This 3rd-floor condo offers a peaceful setting overlooking one of Winter Haven’s most loved lakes, creating the perfect backdrop for morning coffee, quiet evenings, or simply enjoying the Florida lifestyle from home. Inside, the unit features 2 bedrooms, 2 full bathrooms, an open floor plan, solid surface counters, and comfortable living space designed for easy day-to-day living. The building includes an elevator, and the unit also offers a covered rear porch and assigned carport parking. The condo building roof was replaced approximately 2 years ago, and damage from the hurricane around that same time has been repaired. Located near downtown Winter Haven, you will love being close to local dining, shopping, coffee shops, parks, medical offices, and the Chain of Lakes lifestyle. If you are looking for a rental with a great view, a central location, and convenient access to everything Winter Haven has to offer, this Lake Howard condo is one you will want to see.

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

Listing Agent: Chris Loschiavo (863-280-2201)

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)

Remarks: FOR RENT - 2 Bedroom/2 Bath Condo at Imperial Harbours. This community is for ages 55+. The unit comes with all of the appliances and faces the garden area. The bedrooms are generously sized, and the porch area is enclosed. The community features a very nice pool with a TIKI Bar area for relaxing and sipping your favorite drinks. In the distance you can watch the sun rise over Lake Howard in the early morning hours of the day. The amenities include an in-ground community pool, pool maintenance, grounds maintenance, one assigned parking space, elevator access, WI-FI, landscaping, sewer, and trash collection. Come visit this lovely unit today!

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

Listing Agent: Linda Andre (863-294-7541)

Remarks: **FLORIDA LAKEFRONT CONDO FOR RENT AT 1,500.00 PER MONTH & INCLUDES UTILITIES.**AGE 55+ HOWEVER, A LOWER AGE MAY BE CONSIDERED. NICELY FURNISHED & 1,190 SQUARE FEET OF LIVING SPACE. THERE IS NO LONGER A PRIVATE 2ND BEDROOM AS IT HAS BEEN INCORPORATED AS MORE LIVING SPACE. THE LANDLORD IS LOOKING FOR A LONG-TERM TENANT & NO SMOKING OR PETS ALLOWED. BOAT SLIP CURRENTLY AVAILABLE FOR YEARLY FEE & APPROVAL. APPLICATION FEE, BACKGROUND CHECK AND MEETING WITH BOARD ARE REQUIRED. CREDIT CHECK FEE PAID BY TENANT. MONTHLY RENT AMOUNT INCLUDES ELECTRICITY, CABLE, INTERNET, WATER, SEWER, TRASH, USE OF RECREATIONAL FACILITIES. This open floor plan has plenty of natural lighting, and beautiful lake views. The updated kitchen with stainless steel appliances has a pass-through to the dining area. The oversized bedroom easily accommodates a king-size bed, has an en-suite bathroom and a walk-in closet. The bonus room and Florida room provide additional living space along with a storage closet. This condo has a washer & Dryer for your convenience. The parking lot is well lit & cameras in use. After 7pm each day the elevator access is by use of the resident's key. Northgate Shopping Center with Publix grocery store is across the adjacent street. One assigned covered parking space is provided. The swimming pool, dock, library, fitness room, and laundry are located on the basement/lake level. The association occasionally offers activities if you wish to participate. Immaculate and well-managed condominium complex that has successfully completed the integrity inspections. The association & landlord must both approve the tenant. The Background check/application fees are non-refundable. Tenant and any visiting guest are required to abide by all association rules and restrictions. A boat slip may be available with approval and a yearly fee.

Listing is courtesy of: JUDY B CLEAVES PROPERTIES INC (863-299-5878)

Listing Agent: Chris Goode (863-287-5454)

Remarks: Winter Haven's premier condominium located directly overlooking the picturesque Lake Spring that is part of the famous 17-lake Winter Haven Chain of Lakes. Be the first to enjoy this beautiful extensively remodeled and upgraded 5th floor deluxe center unit directly off of the elevators. Lots of natural light through the expansive windows looking out to Lake Spring & Lake Mirror and directly down to the pool area. Lots of storage closets and an extra storage locker too. Its turn-key ready to move into and hasn't been occupied since finishing the remodeling. Exquisitely maintained building and has passed the newly required Florida state mandated Milestone Inspection & Reserve Study. Many community amenities including a covered assigned parking space, car washing area, garbage shut drop, designated guest parking, boat slips & fishing pier, paver brick pool area with cornhole & shuffle board, large equipped fitness room, library and community room w/ kitchen & big screen TV. Outdoor grills for your use, & patio furniture on the huge pool deck overlooking Lake Spring. Publix shopping center by walking across the side street is a great convenience. Close to downtown No pets or smoking. Owner will consider different leasing and/or purchase options. Short term seasonal or long term lease. Tenants and/or buyers have to be approved and interviewed by the HOA as this is a 98% owner occupied building. It is a 55+ building, but is under the minimum number of under 55+ required. Nicest condominium building in Polk County with full-time maintenance and management on-site daily.

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

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

Remarks: Welcome to this beautifully maintained 2-bedroom, 2-bath condominium located in the desirable Winter Ridge community in Winter Haven. Offering approximately 1,073 square feet of comfortable living space, this inviting home features a bright and open floor plan designed for both everyday living and entertaining. The spacious living and dining areas flow seamlessly, creating a warm and welcoming atmosphere. The primary suite offers a private retreat with an en-suite bathroom and generous closet space, while the second bedroom and bath provide flexibility for guests, family members, or a home office. Winter Ridge residents enjoy a variety of community amenities, including a community pool, clubhouse, fishing opportunities, private boat ramp, dock access, and direct access to beautiful Lake Smart. The community is golf-cart friendly and offers a relaxed Florida lifestyle with convenient access to shopping, dining, medical facilities, and major roadways. Whether you're looking for a primary residence, seasonal retreat, or investment opportunity, this charming condo offers exceptional value in a sought-after lakefront community. Schedule your private showing today!

Listing is courtesy of: EG ORLANDO LLC (407-453-8679)

Listing Agent: Isamanda Hernandez (786-542-3725)

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: Updated 2 bedroom 2 bath first floor end unit condo located in the Eagle Pond neighborhood at Cypresswood Golf and Country Club. This unit has just undergone a professional interior paint job along with the installation of new laminate flooring. The country club amenities include access to the clubhouse with bar and grill, jr. olympic swimming pool and pickleball/tennis courts. The championship 18 hole golf course is open to the public. As an added bonus, Publix just opened a brand new location just a mile down the road which is sure to attract other popular businesses.

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

Listing Agent: Steven Smith, Pa (863-224-2297)

Remarks: A SPACIOUS GROUND FLOOR END UNIT NEAR FAST FOOD, SHOPPING & BUS LINE. UNIT HAS GAS RANGE & HOT WATER, PLUS GAS HEAT, READY TO MOVE IN NO AGE RESTRICTIONS. CLUB HOUSE & POOL WITH DOCK ON CHAIN OF LAKE.

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

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

Remarks: THIS IS A SUPER CLEAN CONDO. HASSLE-FREE OPEN KITCHEN THAT OPENS UP TO LIVING ROOM WITH EXPANSIVE VIEWS OF LAKE HOWARD AND THE TRAIL. WALKING DISTANCE TO ALL OF DOWNTOWN RESTAURANTS. BEAUTIFUL SUNSETS.

Listing is courtesy of: COLLANY PROPERTIES (863-295-9886)

Listing Agent: Christopher Collany (863-412-2170)