Apartments for Rent in Downtown Winter Haven, Winter Haven, FL

Property Status: Active Charming Furnished Cottages for Rent in the Heart of Winter Haven Welcome to Rose Hill Cottages, a thoughtfully restored collection of furnished cottages nestled in a quiet, established neighborhood just minutes from downtown Winter Haven. These cottages offer the perfect blend of charm, comfort, and convenience — ideal for professionals, relocations, extended stays, or anyone seeking a peaceful retreat with easy access to city amenities. Each cottage is fully furnished and designed with intention, featuring inviting living spaces, comfortable sle

Property Status: Active Discover this beautifully renovated 2-bedroom, 1-bathroom downstairs apartment, available now just steps from the scenic shores of Lake Howard and in the heart of downtown Winter Haven. Thoughtfully designed for comfort and convenience, this home maximizes every inch of space to create a warm, inviting atmosphere. Enjoy a spacious bedroom with a generous walk-in closet and a well-appointed bathroom offering dual access from both the bedroom and the main living area—perfect for hosting guests while maintaining privacy. The bright, airy living space f

Rent with confidence from a licensed Real Estate Brokerage. We have a quick and simple application process. Contact us through this website or call to set up a tour and apply today! WE PROUDLY WELCOME ALL PETS. Welcome to this cute 2-bed, 1-bath home! Our spacious layout is perfect for comfortable living. Enjoy the yard to unwind after a long day, enjoy the fresh air, and gather for fun-filled activities. As you enter the home, you will be greeted with an open floor plan showcasing the living room. This company is committed to supporting the guidelines of the U.S. Fair

NEWLY RENOVATED!!! 2 bedroom, 1.5 bath unit. Featuring brand new carpet in living area, spacious living room with separate flex space that can be used as den or office, 2 large bedrooms and more! Located just a street away from Winter Haven's downtown with food, shopping and more! Schedule your tour today!

Discover this beautifully updated second-floor 2-bedroom, 1-bath apartment, available now in the heart of downtown Winter Haven—just steps from the picturesque shores of Lake Howard. Designed with comfort and functionality in mind, this home makes excellent use of space to create a welcoming and inviting atmosphere. One bedroom features a spacious walk-in closet, while the well-appointed bathroom offers convenient dual access from both the bedroom and the main living area, allowing for privacy when entertaining guests. The bright, open living area is enhanced by large wind

Property Status: Active 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. Office Phone: (863) 259-4600 Copyright © 2026 Stellar MLS. All rights reserved. All information provided by

Rent with confidence from a licensed Real Estate Brokerage. We have a quick and simple application process. Contact us through this website or call to set up a tour and apply today! WE PROUDLY WELCOME ALL PETS Welcome to this cute 2-bed, 1-bath home! Our spacious layout is perfect for comfortable living. Enjoy the yard to unwind after a long day, enjoy the fresh air, and gather for fun-filled activities. Approaching the home, you will find enough space for chairs to enjoy the outdoors. As you enter the home, you will be greeted with an open floor plan showcasing the liv

Property Status: Active Experience the perfect blend of historic charm and modern updates in this beautifully remodeled 1928 home, ideally located in the heart of Winter Haven. This property can be leased as a home or commercially!! Bring your business an update with a new office space! Just off First Street and minutes from shopping, public transportation, and major roadways, this home offers both convenience and character. Inside, you'll find a contemporary interior with brand-new flooring and crisp paint that highlights the home's timeless features. With three generousl

Property Status: Active Discover this beautifully updated second-floor 2-bedroom, 1-bath apartment, available now in the heart of downtown Winter Haven—just steps from the picturesque shores of Lake Howard. Designed with comfort and functionality in mind, this home makes excellent use of space to create a welcoming and inviting atmosphere. One bedroom features a spacious walk-in closet, while the well-appointed bathroom offers convenient dual access from both the bedroom and the main living area, allowing for privacy when entertaining guests. The bright, open living area i

Beautifully renovated office building with a total of 7 offices - 3 offices downstairs, and 4 offices upstairs. There is no elevator. An additional area upstairs, could be used for a reception desk or work station. Also includes a tiled kitchen with granite counters, 2.5 tiled baths, and real wood floors throughout the rest of building. There are at 10 parking spaces plus street parking available. Current land use is R-4. The property is listed as Residential but R-4 has many uses that can be applied with changes made for multiple commercial and office uses. $18.00/ SF NNN

IMMACULATE DOWNSTAIRS END UNIT OVERLOOKING LAKE HOWARD AVAILABLE FOR IMMEDIATE MOVE-IN!!! This unbelievable 2 bed/2 bath condo has been completely redone and has BRAND NEW EVERYTHING. New tile flooring, new granite countertops, new stainless steel appliances, new paint, this place has it all! CABLE/WATER INCLUDED, no carpet, 2 covered parking spaces, oversized closets, tastefully updated bathrooms, a screened-in balcony spanning the entire width of the condo, all with an INCREDIBLE view of Lake Howard! Conveniently located minutes away from Downtown, this is a can't miss o

NEWLY RENOVATED!!! 2 bedroom, 1 bath unit with washer and dryer hookups. Featuring vinyl flooring throughout, spacious living room with separate dining room, 2 large bedrooms and more! Located just a street away from Winter Haven's downtown with food, shopping and more! Schedule your tour today!

Beautiful 2 Bedroom 1 Bathroom apartment in Winter Haven HOA APPROVAL MANDATORY Lessee(s) are required to provide proof of liability insurance in the amount of $100,000, prior to occupancy. Real Property Management Lakeside can provide the required coverage for an additional charge of $12.00 per month or you can purchase coverage from your preferred provider. All residents are enrolled in the Resident Benefits Package (RBP) at a cost of $25/per month, which includes HVAC air filter delivery (for applicable properties), utility concierge service making utility connection

Come take a look at this newly built 3 bedroom 3 bath apartment located near downtown Winter Haven and a stones throw from Lake Howard. The second story unit comes with great views, and open concept living, private bathrooms for each bedroom, washer and dryer hook ups, and so much more. Call today to schedule your showing. All Pro X Property Management The Swain Group. LLC residents are enrolled in the Resident Benefits Package (RBP) for $40/month which includes renters insurance, HVAC air filter delivery (for applicable properties), credit building to help boost your

Property Id: 2325298 Welcome to your new home on 5th Ave NE in Winter Haven, FL! This single-unit property offers modern amenities including an oven, microwave, and refrigerator. Enjoy the convenience of included utilities and on-site laundry. Pets allowed, with a beautiful lawn and security cameras for peace of mind. Water, Sewer, Trash, WiFi & Electric Included. Don't miss out on this perfect rental opportunity for $1400/month. SE HABLA ESPAÑOL!

One or more photo(s) has been virtually staged. Discover modern comfort and privacy in this fully renovated single-family home just moments from downtown Winter Haven. Thoughtfully updated from top to bottom, the home features a new roof, new A/C, and a beautifully redesigned kitchen and bathroom with granite countertops and sleek finishes. Porcelain tile flooring flows throughout the home, complementing the high ceilings and large windows that fill the space with natural light. The open-concept living area centers around a cozy fireplace, creating the perfect spot to unwi

Property Status: Active One or more photo(s) has been virtually staged. Discover modern comfort and privacy in this fully renovated single-family home just moments from downtown Winter Haven. Thoughtfully updated from top to bottom, the home features a new roof, new A/C, and a beautifully redesigned kitchen and bathroom with granite countertops and sleek finishes. Porcelain tile flooring flows throughout the home, complementing the high ceilings and large windows that fill the space with natural light. The open-concept living area centers around a cozy fireplace, creating