Apartments for Rent in Winter Haven 33884 - 48 homes

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: 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: One or more photo(s) has been virtually staged. For Lease: Private In-Law Suite in Winter Haven, FL – $1,500/Month Looking for a clean, private rental in Winter Haven? This 450 sq. ft. in-law suite offers comfortable living in a quiet, well-located neighborhood. Important: This is a separate in-law suite attached to the main home. The main house is owner-occupied. This listing is not for the full home. Property Features: Rent: $1,475 /month Size: Approx. 450 sq. ft. Lease Term: Minimum 12 months Security Deposit: $1,475.00 Move-In Costs: First month’s rent + security deposit Application Fee: $50 (non-refundable) Max Occupancy: 2 Parking: Street parking only Amenities: Access to community pool Access to playground area Additional Details: Pets: No pets allowed Utilities: Included (Electric, Water, Internet) Private entrance for added privacy This rental is ideal for a single tenant or couple looking for an affordable, low-maintenance home near shopping, dining, and major roads in Winter Haven. Great location with easy access to local amenities and highways.

Listing is courtesy of: DALTON WADE INC (888-668-8283)

Listing Agent: Andrea Jastemski (813-516-0865)

Remarks: One or more photo(s) has been virtually staged. Welcome to this brand-new 2025-built home located in the highly desirable Villa Mar community in Winter Haven. Offering 4 bedrooms, 2 full bathrooms, and 1 half bath, 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 spacious kitchen features contemporary finishes, ample cabinetry, and generous counter space, seamlessly connecting to the dining and living areas. The primary suite provides a private retreat with a well-appointed en-suite bath, while three 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. The layout is thoughtfully designed to maximize space and flow, making it 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. Located in one of Central Florida’s fastest-growing areas, this property presents an excellent opportunity for both homeowners and investors. Don’t miss your chance to own a newly built home in a prime Winter Haven location.

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

Listing Agent: Rodrigo Araujo Machado (347-776-2005)

Remarks: WINTER HAVEN NEW BUILD 3 BED/2 BATH HOME FOR RENT! MOVE-IN SPECIAL! Priced Low, Call Now! Very Clean Property, Move-in Ready, 2 Car Garage, Brand New Build—First Tenancy! Huge Master Suite, Eat-In Kitchen, Corian Countertops, Upgraded Kitchen, Brand New Kitchen, Carpeted Bedrooms, Laminate Wood-Look Flooring, COMMUNITY Pool, COMMUNITY Playground, COMMUNITY Multiple Lakes, COMMUNITY Walking & Nature Trails, Convenient to LEGOLAND Florida, Convenient to Lake Eloise Boat Ramp Access, New Appliances, New Window Treatment, Stainless Steel Appliances INCLUDED, Blinds INCLUDED, Washer and Dryer in Unit. The deposit amount is based upon the application results. Pets: OK - 1 Small only (up to 35 lbs.) (Dangerous Pets are not permitted, Pit Bulls, etc.) Priced $1,750.00 for the first 4 months, $1,850.00 for the remaining 8 months (Average: $1,817.00/mo). AVAILABLE: NOW

Listing is courtesy of: ORLANDO REALTY & PROPERTY MGNT (407-641-5782)

Listing Agent: Jay Myers (407-641-5782)

Remarks: Beautiful 3-bedroom/3-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: Located in an established neighborhood this home offers 2 bedrooms and 2 bathrooms. Galley kitchen overlooking large fenced backyard. Inside laundry room and 2 car garage. Available and ready for immediate occupancy.

Listing is courtesy of: THE HOME COMPANY (863-268-8157)

Listing Agent: Sue Ann Williamon (863-258-3115)

Remarks: Enjoy year-round lakeside living in the desirable Mandolin community! This beautifully maintained 4-bedroom, 2-bath single-story home is available for annual rental and offers a spacious, open layout with soaring cathedral ceilings. The bright central kitchen features granite countertops, a pantry, breakfast bar, and newer appliances, seamlessly flowing into the expansive family room with sliding doors leading to a screened lanai and deck overlooking the water—perfect for relaxing or entertaining. The primary suite offers serene lake views, a walk-in closet, dual sinks, a walk-in shower, and a soaking tub. A split floor plan provides three additional bedrooms and a full bath, offering flexibility for guests, a home office, or growing households. Additional highlights include a dedicated laundry room, ceiling fans throughout, irrigation system, and fresh interior and exterior paint. Enjoy a generous yard and peaceful waterfront setting, all conveniently located near shopping, dining, medical facilities, Chain of Lakes Elementary, Legoland, and Bok Tower Gardens. Don’t miss this opportunity for comfortable, long-term Florida living!

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

Listing Agent: Daniel Mcintee (877-366-2213)

Remarks: Additional reduction of this 4 bedroom 2.5 Baths is located in Villa Mar in Winter Haven, Florida. Master-planned amenities including a pool with cabana that is walking distance from your home, a playground, and shaded seating area. Highway 27, less than 10 minutes away, has everything you are looking for. Grocery stores, movie theaters, shopping centers, golf courses, restaurants, and so much more. Step in from the 2-car garage and enjoy the good life. Find it in the large family room. Share stories around the island or outside on the lanai. The 1st floor features a study. Upstairs, 4 bedrooms and a 2 full bath provide privacy while a loft adds extra entertaining space. Your deluxe owner’s suite includes double vanities, a seated shower, and 2 walk-in closets. All Ryan Homes now include WIFI-enabled garage opener and Ecobee thermostat.

Listing is courtesy of: CROWN INVESTMENT BROKERS (407-876-8719)

Listing Agent: Sushama Sharma (321-303-3306)

Remarks: Stunning New Construction Home for Rent in Winter Haven Be the first to live in this beautiful new construction home located in a desirable Winter Haven neighborhood. Designed with comfort and style in mind, this spacious residence offers a modern open floorplan that is perfect for both everyday living and entertaining. The home features 5 generously sized bedrooms, including a luxurious primary suite with a walk-in closet. The additional bedrooms are equipped with built-in closets, providing excellent storage throughout. With 2 full bathrooms and 1 half bathroom, the layout is ideal for families or anyone who appreciates space and functionality. Enjoy bright and open living and dining rooms that flow seamlessly into a stunning kitchen. The kitchen is thoughtfully designed with solid wood cabinets, elegant stone countertops, and included appliances, making it as practical as it is beautiful. Additional highlights include a 2-car attached garage and a prime location close to a main road, offering easy access to shopping, dining, and daily conveniences. The property is also near highly rated schools, making it an excellent choice for families. This is a rare opportunity to rent a brand-new home in a great Winter Haven location. Schedule your showing today and experience modern living at its best.

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

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

Remarks: Immaculate home still feels like brand new construction! 4 bedroom 2 bath home in the Estates of Lake Florence. This home is ideally located in Winter Haven minutes from HWY 17, near I-4 and SR 60, for easy access to the Greater Orlando Area and Lakeland. The living area is bright and open connecting the living room space with the dining area and kitchen. The stylish kitchen showcases a convenient island, a large single bowl sink, white cabinets, granite countertops and Whirlpool stainless steel appliances including a dishwasher, microwave, and range. This home makes great use of space, the primary bedroom is located at the back of the house, featuring a full primary bathroom with dual sinks, a step in shower with private water closet, and large closet space. Bedrooms 2 and 3 are located at the front of the house and share the hall bath. The 4th bedroom sits by itself, perfect for a home office or bonus room. The large laundry room features extra storage space. Small pet may be accepted with owner's approval and non-refundable pet fee.

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

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

Remarks: Discover this beautiful 2-bedroom, 2-bath home with an additional flex room, perfect for a home office, den, or guest space, enclosed with a stylish barn door. Located in the desirable lakefront community of Cypress Landing, this home offers a welcoming and open layout with vaulted ceilings and abundant natural light. The kitchen is designed for both function and style, featuring ample cabinetry, generous counter space, and a breakfast bar that flows seamlessly into the dining area. A sliding glass door leads to a cozy 7x15 screened lanai—ideal for relaxing with your morning coffee. The primary suite is a private retreat, complete with an en-suite bathroom including a walk-in shower and 5x5 walk-in closet. The primary bedroom also has elegant French doors giving access to the flex room. Additional highlights include an inside utility room, updated laminate flooring throughout most of the home, and a fenced backyard for added privacy. Residents of Cypress Landing enjoy fantastic community amenities, including a clubhouse with social events, a heated pool, tennis courts, and a private boat ramp with lake access for fishing, boating, and watersports on Lake Dexter. Conveniently located just minutes from Legoland, shopping, and dining, this move-in-ready home offers the perfect balance of comfort and convenience.

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

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

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: This cozy and well-maintained home offers a warm and inviting layout, ideal for comfortable and easy living. The property features a functional floor plan with a modern kitchen, bright and spacious bedrooms, and low-maintenance living areas designed for convenience. Centrally located with quick access to US-27, US-17, SR-540, and I-4, this home provides easy commutes to Orlando and Tampa, as well as proximity to major attractions such as Disney and Legoland. Enjoy being just minutes away from lakes, parks, shopping centers, and a variety of dining options. A perfect rental opportunity for those seeking comfort, convenience, and a well-connected location in the growing Winter Haven area.

Listing is courtesy of: LIFESTYLE INTERNATIONAL REALTY (305-809-8085)

Listing Agent: Jenny Caso (407-694-9682)

Remarks: Discover modern comfort and thoughtful design in this newly built home at 1116 Tyler Loop in Winter Haven, FL, crafted by Lennar Homes. This residence showcases high-quality construction paired with stylish finishes, including an open-concept layout perfect for both everyday living and entertaining. The home features energy-efficient systems, smart home technology, and a contemporary kitchen equipped with sleek cabinetry, stainless steel appliances, and ample counter space. Spacious bedrooms and well-appointed bathrooms provide a relaxing retreat, while the private outdoor space offers room to unwind or host gatherings. Residents also enjoy access to desirable community amenities, which include a resort-style pool, clubhouse, playground, and beautifully maintained common areas that enhance the neighborhood’s appeal. With Lennar’s signature attention to detail and included upgrades, this home delivers exceptional value, convenience, and a move-in-ready experience.

Listing is courtesy of: JOHN SILVA REALTY & ASSOCIATES (407-420-7908)

Listing Agent: Julien Silva (352-348-9219)

Remarks: Spacious and beautifully laid out home now available for rent! This open floor plan features 2 bedrooms, 2 bathrooms, plus a versatile flex space that can easily function as a third bedroom, office, or additional living area. Inside, you’ll find laminate flooring throughout with tile in the bathrooms, along with fresh interior paint and updated finishes that enhance the home’s overall appeal. The kitchen is designed for both functionality and style, offering a counter-height breakfast bar, movable island, oak cabinetry, two pantries, and ample counter space. The generously sized bedrooms provide comfort and flexibility, while additional features include upgraded ceiling fans, pull-down attic access, a lawn irrigation system, and a fully fenced backyard for added privacy. Conveniently located near Legoland, shopping, dining, and major roadways, this home offers both comfort and accessibility. Don’t miss this opportunity. Schedule your showing today!

Listing is courtesy of: FHG REALTY, LLC (407-505-7600)

Listing Agent: Jeff Inman (407-505-7600)

Remarks: Welcome to Peace Creek Reserve! This like-new Atlanta Plan home offers exceptional space and modern living with 4 bedrooms, 2.5 bathrooms, a loft, and a 2-car garage. The open-concept layout features a spacious great room, dining area, and a beautifully designed kitchen with a large quartz island, stainless steel appliances, ample counter space, and a generous pantry—perfect for everyday living and entertaining. Sliding glass doors lead to a private backyard with serene views, ideal for relaxing and enjoying the peaceful surroundings. Tile flooring runs throughout the main living and wet areas for easy maintenance. Upstairs, you’ll find a versatile loft, a convenient laundry room, and a spacious owner’s retreat with dual vanities, a large walk-in shower, and a walk-in closet. Three additional bedrooms provide plenty of space for family, guests, or a home office. Situated on a peaceful lot with no rear neighbors overlooking a dry pond, this home offers added privacy and tranquil views—a rare find in the community. Located in the master-planned community of Peace Creek Reserve in Winter Haven, known as the Chain of Lakes City with 26 connected lakes, you’ll enjoy nearby shopping, dining, and scenic bike paths while still experiencing a charming small-town atmosphere. Move-in ready! Don’t miss this opportunity to rent a beautiful home in a highly desirable community.

Listing is courtesy of: STAR BAY REALTY CORP. (813-533-6467)

Listing Agent: Shira Bhagavatula (813-533-6467)

Remarks: Affordability meets Comfort. First Floor unit for easy access in a highly desirable gated community of Cypresswood Golf & Country Club. This rental will include access to community pool, 24-hour security, exterior maintenance, common area taxes, trash service, pest control, and private road upkeep. Residents can also enjoy an 18-hole golf course, on-site restaurant, tennis courts, and a fitness center. Conveniently accessible to Hwy 27, I-4, medical facilities, Legoland, shopping, & dining. Applicants must complete the application form for pre-screening, once the landlord review the application & ready to proceed there will be an application fee of $50 for a background screening. All applicants 18 years old and above must complete a background screening. Applicants must provide proof of Verifiable Income & must meet landlord minimum income requirements, Proof of Employment, Valid Proof of Identification, & must honestly disclose the number of occupants residing in the home. Showing schedules are by appointment only.

Listing is courtesy of: MAZELG REALTY (863-399-0226)

Listing Agent: Lienyvette Grimaldo (863-399-0226)

Remarks: Appointment Only, Combination Lockbox, See Remarks, Use ShowingTime Button

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

Listing Agent: Daniela Leal Castro (407-219-2183)