Winter Haven Apartments for Rent - 168 rentals

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: Welcome to 368 Kayden Cove, a beautifully designed home offering a spacious and functional open-concept floor plan perfect for modern living. The layout features a bright living area that flows seamlessly into the kitchen and dining space, ideal for entertaining and everyday comfort. The kitchen is equipped with ample cabinetry, modern appliances, and a central island that adds both style and convenience. The bedrooms are generously sized, with a comfortable primary suite that includes a private bathroom and walk-in closet. Located in a well-maintained community, residents can enjoy amenities such as a resort-style pool, playground, and walking areas that enhance the neighborhood’s appeal. The home is conveniently situated in Winter Haven, providing easy access to shopping, dining, schools, and major roadways for commuting. You’ll also be just a short drive from local attractions and the beautiful chain of lakes the area is known for. The application process is simple and straightforward, making it easy to move forward quickly. Don’t miss the opportunity to make this wonderful home yours!

Listing is courtesy of: GLASSTONE GROUP INC (321-988-4663)

Listing Agent: Ashley Porto (407-360-7386)

Remarks: This is a 2 bedroom/2 bath with one bedroom having an en-suite bath. Open floor plan, all new stainless steel appliances with washer/dryer included. Also, luxury vinyl plank flooring through out the unit for easy cleaning. Come and see if this is for you. Will not be on the market for too long.

Listing is courtesy of: WEICHERT REALTORS HALLMARK PRO (407-585-0500)

Listing Agent: Hitesh Lallu (863-899-6841)

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: The community of Winter Ridge Condos has a lot to offer: Swimming pool, club house and private boat dock on lake Smart. This tranquil community is everybody's dream to enjoy and relax. this bright and inviting condo features 2 large bedrooms and 2 bathrooms. An open layout living/dinning combo and abundant natural light, Conveniently located near shopping, dining, and major roadways, this well-kept unit is perfect for comfortable living.

Listing is courtesy of: AGENT TRUST REALTY CORPORATION (407-251-0669)

Listing Agent: Luz Solano (217-853-2424)

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: Like brand new 4-bedroom, 2-bath home located in the desirable Villa Mar community in Winter Haven for rent. This property offers 1,665 sq ft of living space with an open-concept floor plan that connects the kitchen, dining, and living areas, creating a functional layout for everyday living and entertaining. The kitchen features modern finishes, ample cabinet space, and a center island. The primary suite includes a walk-in closet and private bathroom. Three additional bedrooms provide flexibility for guests, office space, or family needs. The home also includes a 2-car garage, driveway parking, and a landscaped yard. Villa Mar residents enjoy community amenities including a swimming pool, playground, dog park, and walking trails. Conveniently located near major roads, shopping, dining, entertainment and more.

Listing is courtesy of: PROPERTY PARTNERS REALTY INC (407-803-1393)

Listing Agent: Patricia Padron (407-803-1393)

Remarks: One or more photo(s) has been virtually staged. Spacious rental located in the heart of Winter Haven! This updated unit offers comfortable living with generous room sizes and a functional layout. Conveniently located near shopping, dining, schools, and major roadways, making daily commutes a breeze. Public water and sewer, city utilities, and easy access to everything Winter Haven has to offer. Ideal for tenants seeking affordability, convenience, and central location. Available for immediate occupancy!

Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)

Listing Agent: David Small (407-601-8351)

Remarks: 2BR/2BA Ground Floor Condo in the Gated neighborhood of Winterset. Wood laminate flooring (no carpet) throughout. New granite countertops and appliances in kitchen. Updated bathrooms. Primary bedroom has a very large walk in closet. Full size washer and dryer included. Community features a clubhouse with swimming pool overlooking Lake Winterset, tennis courts, boat ramp, and dock for fishing. Great SE location near medical, shopping, restaurants, and Legoland! Sorry NO PETS!

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

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

Remarks: Discover modern living in this stunning newly built 3-bedroom, 2-bath home, where style meets comfort. Bright, spacious bedrooms provides the perfect retreat, while sleek, thoughtfully designed bathrooms add a touch of luxury. The open-concept layout flows effortlessly from the kitchen to the living and dining areas, ideal for entertaining or relaxing. A generous walk-in closet keeps everything organized in style. Step outside to your private, pet-friendly backyard, perfect for play, lounging, or weekend barbecues. With high-end finishes, abundant natural light, and a warm, welcoming vibe, this move-in-ready home is everything you’ve been looking for. Don’t miss the home you've been looking for! Excuse the front facing photo of property. Yard has been maintained and cleaned.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Christopher Gallon, Pa (407-967-9363)

Remarks: This three-bedroom and two-bath home is nearly 1,700 SF. The home is a split floor plan for added privacy of the master suite. The master suite is 15 x 20 and has its own brand-new private bathroom. The living room provides an open concept to entertain guests. The kitchen is bright and airy with a dining area located in the kitchen. The property comes equipped with full sized stackable washer and dryers. The backyard is massive and has plenty of room to store boats, trailers or an RV. The rear yard is also fully fenced for pets. Don't wait and miss out on this opportunity to make this your next home!!

Listing is courtesy of: MAVREALTY (727-314-3942)

Listing Agent: Robert Kirkwood, Iv (321-297-6489)

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: This is a very spacious, beautiful, freshly painted and professionally cleaned 3-bedroom/2-bath/ 2-car garage single family home in the quiet and well-kept Crescent View Community. Property features an open floor plan, beautiful ceramic and laminate flooring, a very spacious kitchen with lots of cabinet space, granite countertops and stainless steel appliances. The primary bedroom is very spacious and features a large walk-in closet. The secondary bedrooms are very spacious with large closets. The backyard is fenced so you have lots of privacy. The patio and backyard are perfect for entertaining family and friends. Close to shopping, dining, schools, and major roadways. Also listed for sale, whichever comes first. This one is just waiting for you to come home to!

Listing is courtesy of: EATON REALTY SERVICES (800-630-1990)

Listing Agent: Arlene Cowan (800-630-1990)

Remarks: Welcome to this brand-new 2025-built home located in the highly desirable Villa Mar community in Winter Haven! Offering 3 bedrooms, 2 full bathrooms, 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 primary suite provides a private retreat with a well-appointed en-suite bath, while two 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. Home is 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.

Listing is courtesy of: CENTURY 21 MCBRIDE REALTY GROUP (386-866-1007)

Listing Agent: Paola Martinez (386-866-1007)

Remarks: Welcome to this brand-new 2025-built home located in the highly desirable Villa Mar community in Winter Haven! Offering 3 bedrooms, 2 full bathrooms, 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 primary suite provides a private retreat with a well-appointed en-suite bath, while two 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. Home is 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.

Listing is courtesy of: CENTURY 21 MCBRIDE REALTY GROUP (386-866-1007)

Listing Agent: Paola Martinez (386-866-1007)

Remarks: Furnished Mini Master Bedroom Suite for rent in beautiful private home. Rent includes all utilities and Wi-Fi. Private fridge available for tenant's use. Owner looking for single professional or travel nurse.

Listing is courtesy of: MAHOGANY REAL ESTATE GROUP (305-971-6161)

Listing Agent: Patricia Townsend (954-732-6322)

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: 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)