$1,400 Per Month
- 2 Beds
- 2 Baths
- 884 Sq Ft
- Apartment for Rent
711 Lake Jessie Dr, Winter Haven, FL 33881
711 Lake Jessie Dr, Winter Haven, FL 33881
230
Winter Haven, FL Homes for Rent under $1,500
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Starting at $1,441
Total Monthly Price
- 1 - 2 Beds
3110 Gowan Dr, Winter Haven, FL 33884
3110 Gowan Dr, Winter Haven, FL 33884Welcome home to Prose Cypress Pointe, a brand-new multifamily community located in Winter Haven, Florida. Our spacious one- and two-bedroom apartment homes feature modern stainless-steel appliances, walk-in closets, dining-sized kitchen islands, premium plank flooring throughout and full-sized washers and dryers in every apartment home. And with convenient, must-have amenities like a fitness
Prose Cypress Pointe
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$1,400 Per Month
- 2 Beds
- 2 Baths
- 930 Sq Ft
- Condo for Rent
8302 Waterview Way, Winter Haven, FL 33884
8302 Waterview Way, Winter Haven, FL 33884 -
Starting at $1,295 Per Month
- 1 - 2 Beds
200 Avenue C SW, Winter Haven, FL 33880
200 Avenue C SW, Winter Haven, FL 33880Discover a living experience that moves with you. At Raindance, we have reimagined the modern residence as a sanctuary of light and fluid design. Each floor plan is a masterclass in spatial harmony, meticulously curated to balance expansive windows with intimate, designer-led interiors. Our commitment to excellence is woven into the very bones of the building, exceeding the highest energy
Raindance
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$1,300 Per Month
- 2 Beds
- 2 Baths
- 1,148 Sq Ft
- Condo for Rent
1550 11th St NE Unit D7, Winter Haven, FL 33881
1550 11th St NE Unit D7, Winter Haven, FL 33881 -
Starting at $1,259 Per Month
- 1 - 2 Beds
5004 Dream Dr, Winter Haven, FL 33880
5004 Dream Dr, Winter Haven, FL 33880Embrace the art of living fully at Dream Winter Haven, where each day is a masterpiece waiting to be painted. Here, life is about more than just a home—it's about thriving in a community designed to enrich your every experience. Discover the charm of brand-new luxury 1, 2, and 3-bedroom apartments, complemented by resort-style amenities that encourage you to live fully. Set in the heart of Winter
Dream Winter Haven
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$1,300 Per Month
- 1 Bed
- 1 Bath
- 2,109 Sq Ft
- House for Rent
1453 Austin St Unit B, Winter Haven, FL 33884
1453 Austin St Unit B, Winter Haven, FL 33884 -
Starting at $1,275 Per Month
- Studio - 2 Beds
265 Ave E SW, Winter Haven, FL 33880
265 Ave E SW, Winter Haven, FL 33880Discover the essence of upscale living at The Breeze, where the vibrant spirit of Winter Haven meets the serenity of a private retreat. Our community was designed for those who demand more from their surroundings. Each residence serves as a masterclass in architectural efficiency, blending high-performance energy standards with "luxury-first" essentials. From gourmet-inspired kitchens to living
The Breeze
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$1,350 Per Month
- 2 Beds
- 1 Bath
- 775 Sq Ft
- Townhouse for Rent
5667 Struthers Ct, Winter Haven, FL 33884
5667 Struthers Ct, Winter Haven, FL 33884 -
Starting at $1,350 Per Month
- 1 - 3 Beds
2850 W Lake Hamilton Dr, Winter Haven, FL 33881
2850 W Lake Hamilton Dr, Winter Haven, FL 33881Welcome Home to Magnolia at Lake Hamilton!
Magnolia at Lake Hamilton
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Starting at $959 Per Month
- Studio - 3 Beds
7676 Carlton Arms Blvd, Winter Haven, FL 33884
7676 Carlton Arms Blvd, Winter Haven, FL 33884Carlton Arms of Winter Haven located on 122 acres of wooded lakefront property, offers country club living at many different rental rates. With its cascading fountains, beautifully landscaped grounds, peaceful woods and 5 freshwater lakes, this resort-style community provides every resident with professional management and maintenance that are trademarks of all Mahaffey planned properties.
Carlton Arms Of Winter Haven
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Starting at $995 Per Month
- Studio - 2 Beds
350 24th St NW, Winter Haven, FL 33880
350 24th St NW, Winter Haven, FL 33880Haven at Lake Deer is the retreat you've been looking for in Winter Haven, FL. Our lakeside community features studio, one and two bedroom homes complete with patios, wood-style flooring, and upgraded kitchens. What's more, as a member of the community you'll also have access to our sparkling swimming pools and a 24-hour gym. At Haven at Lake Deer, you're guaranteed to find a place to live with a
Haven at Lake Deer
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Starting at $1,200 Per Month
- 1 - 2 Beds
1150 3rd St SW, Winter Haven, FL 33880
1150 3rd St SW, Winter Haven, FL 33880The Best Amenities in TownThe Jade offers the most comprehensive amenity package in town, offering an unmatched blend of luxury, comfort, and convenience at one inclusive price—no other apartment complex nearby provides such a diverse range of options under one roof.
The Jade
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Starting at $1,310 Per Month
- 1 - 3 Beds
3005 Willow Glen Cir, Lake Wales, FL 33859
3005 Willow Glen Cir, Lake Wales, FL 33859Set Your Own Pace at Alera at Hunters GlenDiscover a modern vision for upscale apartment living at Alera at Hunters Glen—where style meets simplicity in Lake Wales, FL. Embrace the freedom of a lock-and-leave lifestyle in a sophisticated community designed for those who live life on their own terms. With a seamless blend of contemporary design and refined elegance, Alera is where your
Alera at Hunters Glen
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Starting at $1,165 Per Month
- 1 - 2 Beds
1101 Cambridge Square, Winter Haven, FL 33880
1101 Cambridge Square, Winter Haven, FL 33880Barrington Place at Winter Haven is an intimate and charming community located in Winter Haven, FL. Our exclusive residences offer a serene retreat for residents seeking comfort and convenience. Discover the perfect balance of tranquility and accessibility, with proximity to Cypress Gardens Blvd., top-rated schools, healthcare facilities, and shopping destinations just moments away. Choose from
Barrington Place At Winter Haven
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Starting at $1,301 Per Month
- 1 - 3 Beds
4025 Lake Ned Village Cir, Winter Haven, FL 33884
4025 Lake Ned Village Cir, Winter Haven, FL 33884Flow through the good life at Vista Lake Ned Apartments. The park-like setting, eclectic amenities, and expansive interiors will make you fall in love with our apartments in Winter Haven. Even better, our Cypress Gardens location places you right off Highway 27 and close to Legoland! Add in the top-notch services that have earned us glowing reviews throughout the years, and you know you're in the
Vista Lake Ned
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Starting at $1,160 Per Month
- 1 - 3 Beds
4200 Mahogany Run, Winter Haven, FL 33884
4200 Mahogany Run, Winter Haven, FL 33884Della Vita Apartments offers the best in brand new interior finishes, abundant community amenity offerings and quick and easy access to some of the best shopping, entertainment and dining Winter Haven has to offer. We’ve recently started a multi-million dollar renovation that will enhance your everyday lifestyle. Our 1, 2 & 3 bedroom apartment homes include large bedrooms with walk-in closets,
Della Vita Apartments
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Starting at $1,475 Per Month
- 1 - 3 Beds
1300 Lake Howard Dr SW, Winter Haven, FL 33880
1300 Lake Howard Dr SW, Winter Haven, FL 33880Welcome to luxury living in Winter Haven. Lakeshore Club is located on the Chain of Lakes between Lake Howard and Lake Mary minutes from downtown Winter Haven.
Lakeshore Club
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Starting at $997 Per Month
- 1 - 3 Beds
200 Avenue K SE, Winter Haven, FL 33880
200 Avenue K SE, Winter Haven, FL 33880Welcome to Briarcrest at Winter Haven Apartments, ideally located near downtown Winter Haven, FL where convenience meets comfort in a picturesque setting. Choose from our spacious and versatile one, two, and three-bedroom floor plans, each thoughtfully designed to suit diverse lifestyles. Our community boasts not just one, but two sparking pools for residents to unwind and enjoy Florida's
Briarcrest at Winter Haven
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Starting at $1,310 Per Month
- 1 - 3 Beds
4900 Cypress Gardens Rd, Winter Haven, FL 33884
4900 Cypress Gardens Rd, Winter Haven, FL 33884A variety of spacious and inviting floor plans await you at Arbours at Garden Grove. Choose from one of our three floor plans offering one, two and three bedrooms, designed with your comfort in mind. Enjoy an assortment of amenities such as vaulted ceilings, a wet bar, air conditioning and double vanities to name a few! The Arbours at Garden Grove amenities extend far beyond your doorstep. Take a
The Arbours at Garden Grove
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Starting at $993 Per Month
- 2 - 3 Beds
4225 Vista Del Lago Dr, Winter Haven, FL 33881
4225 Vista Del Lago Dr, Winter Haven, FL 33881You've found your slice of paradise at Villas at Lake Smart in sunny Winter Haven, FL! Our spacious and affordable two and three-bedroom apartment homes offer the perfect sanctuary for you to unwind after a long day. Ensuring you don't have to go far for fun and fitness, our community features a volleyball court, playground, fitness center, clubhouse, pool, and more! Looking for some
Villas at Lake Smart Apartments
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Starting at $1,250 Per Month
- 1 - 2 Beds
101 Parker Ln NE, Winter Haven, FL 33881
101 Parker Ln NE, Winter Haven, FL 33881Call for availability! Our apartment complex is nestled back in a residential housing lakeside community, away from busy traffic. Quiet surroundings for families and single professionals to relax in their home. We provide high tech security cameras throughout the whole complex to assure your safety. Lake Buckeye owners want to provide a drug-free and safe environment for your family to call
Lake Buckeye Apartments
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Starting at $1,000 Per Month
- Studio - 2 Beds
130 Avenue C SE, Winter Haven, FL 33880
130 Avenue C SE, Winter Haven, FL 33880Central Haven Apartments
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Starting at $899 Per Month
- 1 - 2 Beds
102 Landings Way, Winter Haven, FL 33880
102 Landings Way, Winter Haven, FL 33880Welcome to The Landings, a tranquil pet friendly retreat nestled among towering trees and lush greenery in the heart of Winter Haven, Florida. As one of our three Winter Haven locations, The Landings offers upgraded 1 and 2 bedroom apartments designed with spacious layouts that maximize comfort and livability. Each home features modern white cabinets that brighten the space, durable vinyl
The Landings Apartment Homes
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Starting at $950 Per Month
- 1 Bed
745 Avenue A SW, Winter Haven, FL 33880
745 Avenue A SW, Winter Haven, FL 33880Lakeview Tower offers newly remodeled studio and one bedroom apartment homes. It is an exceptional senior living, 62+ and disabled Community. Lakeview Tower sits right on Lake Howard, allowing breath taking views from your window.
Lakeview Tower
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$1,500 Per Month
- 2 Beds
- 2 Baths
- 1,366 Sq Ft
- Condo for Rent
400 El Camino Dr Unit 203, Winter Haven, FL 33884
400 El Camino Dr Unit 203, Winter Haven, FL 33884Property Id: 2712857***55+ Senior Community***Amazing 2 bedroom, 2 bathroom apartment in Winter Haven. Amenities included: balcony, central air, central heat, and dishwasher. No Utilities included. Is pet friendly. Date Available: Jun 27th 2026. $1,500/month rent. $1,500 security deposit required. Please submit the form on this page or contact Oscar at to learn more. This property is
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$1,395 Per Month
- 2 Beds
- 1 Bath
- 1,206 Sq Ft
- House for Rent
850 17th Terrace NE, Winter Haven, FL 33881
850 17th Terrace NE, Winter Haven, FL 33881This home is move-in ready. Schedule your tour now or start your application today.Welcome to this 2-bedroom, 1-bathroom home in Winter Haven, Florida, offering a practical layout and inviting living spaces throughout. An attached carport adds everyday convenience, while the enclosed patio provides additional versatile space to enjoy.Inside, hard surface flooring runs through the
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$1,400 Per Month
- 2 Beds
- 2 Baths
- 1,015 Sq Ft
- Condo for Rent
1935 Ave O SW Unit 201, Winter Haven, FL 33880
1935 Ave O SW Unit 201, Winter Haven, FL 33880Property Id: 2515636MOVE IN SPECIAL-$500 OFF FIRST MONTHHome features: Plank flooring throughout (easy to clean) Wood cabinetry + granite countertops Stainless steel appliances including dishwasher and garbage disposal Ceiling fans in the bedroom and living roomIn-unit washer & dryer Bedroom and living room are cable-readyLocation: Minutes to downtown
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$1,199
Total Monthly Price
- 1 Bed
- 1 Bath
- 675 Sq Ft
- Condo for Rent
399 Ave B Ave SE Unit 399. Ave B, Winter Haven, FL 33880
399 Ave B Ave SE Unit 399. Ave B, Winter Haven, FL 33880Trendy and chic boutique style apartment. If you are looking for something unique, different and trendy look no further. This cute upscale yet affordable apartment has real white marble tile throughout, newly updated shower, kitchen, laundry room with washer and dryer hook ups included, a private fenced in court yard and lots of neat touches you wont find in the "run of the mill" cookie cutter
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$900
Total Monthly Price
- 1 Bed
- 1 Bath
- 450 Sq Ft
- Condo for Rent
1131 5th St SW Unit 4 downstairs, Winter Haven, FL 33880
1131 5th St SW Unit 4 downstairs, Winter Haven, FL 33880Centrally located to restaurants, Aldis, Lowe's and other shopping within walking distance. Small quiet apartments - property has security lights for safety.
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$1,375
Total Monthly Price
- 1 Bed
- 1 Bath
- 600 Sq Ft
- Condo for Rent
448 Avenue A NE Unit Cozy Cottage, Winter Haven, FL 33881
448 Avenue A NE Unit Cozy Cottage, Winter Haven, FL 33881This cozy Cottage is a 1/1 in Winter Haven Fl. Walk to downtowns restaurant and local shops and breweries. Close to Legoland. Short term unit with small kitchenette. Fenced yard with private spa. This home is set up for short term rental and has kitchenette with Convection Microwave, coffee pot, and all dishware. Washer Dryer, queen bed, TVs in the living room and bedroom. This is a duplex
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$1,500
Total Monthly Price
- 2 Beds
- 2 Baths
- 1,073 Sq Ft
- Condo for Rent
357 Winter Ridge Blvd Unit 357, Winter Haven, FL 33881
357 Winter Ridge Blvd Unit 357, Winter Haven, FL 33881 -
$1,397 Per Month
- 2 Beds
- 1 Bath
- 914 Sq Ft
- Townhouse for Rent
3008 Saint Paul Dr Unit 3012, Winter Haven, FL 33880
3008 Saint Paul Dr Unit 3012, Winter Haven, FL 33880Beautiful 2/1 VIEW TODAY!
Adan Ordonez ADAN INVESTMENTS REAL ESTATE GROUP, PLLC
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$1,075 Per Month
- 2 Beds
- 1 Bath
- Condo for Rent
3025 St Paul Dr, Winter Haven, FL 33880
3025 St Paul Dr, Winter Haven, FL 33880Updated paint 2 bedrooms one bath quad. Kitchen with breakfast bar. Large living room/dining room combo. Two large bedrooms. Inside utility room with washer and dryer hook ups. Yard service is included in the rent. Tenants must carry renters' insurance. $1075.00 per month. Call today for your private showing. Pet free/smoke free.
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$1,425 Per Month
- 2 Beds
- 2 Baths
- 1,030 Sq Ft
- Condo for Rent
333 Lake Howard Dr NW Unit 312C, Winter Haven, FL 33880
333 Lake Howard Dr NW Unit 312C, Winter Haven, FL 33880FOR 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
Linda Andre COLDWELL BANKER REALTY
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$1,125 Per Month
- 2 Beds
- 1 Bath
- 864 Sq Ft
- Condo for Rent
3039 St Paul Dr, Jan Phyl Village, FL 33880
3039 St Paul Dr, Jan Phyl Village, FL 33880Beautiful 2-bedroom unit off of Winter Lake Rd in Winter Haven is move-in ready! Enjoy the vaulted ceiling and exposed beams in the living room. Kitchen features include breakfast bar, granite counters, & custom cabinets. Washer/dryer hookups and lawn care for stress-free living. Up to 2 small pets welcome-30 lbs. or less. Schedule your showing today!Applications do not hold the property
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$850 Per Month
- 1 Bed
- 1 Bath
- 288 Sq Ft
- House for Rent
115 Avenue F SW Unit B, Winter Haven, FL 33880
115 Avenue F SW Unit B, Winter Haven, FL 33880This brand-new studio apartment in Winter Haven offers efficient, low-maintenance living with an open layout and vinyl flooring throughout. The space features a bright main living area and a bathroom with a walk-in shower. With its fresh construction and easy-care design, the space maintains a straightforward, functional feel ideal for someone seeking a no-frills place to call home.
Christin Davis PROPERTY MANAGEMENT OF POLK
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$950 Per Month
- 1 Bed
- 1 Bath
- 450 Sq Ft
- Condo for Rent
663 Ave J NW Unit 2, Winter Haven, FL 33881
663 Ave J NW Unit 2, Winter Haven, FL 33881Discover the perfect blend of comfort, privacy, and convenience in this well-maintained Winter Haven residence. Ideally suited for anyone seeking a low-maintenance, independent living space, this cozy 1-bedroom, 1-bathroom apartment delivers a peaceful residential feel with excellent functional perksLease & Move-In Details:Availability: Ready for immediate move-in.Parking:
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$1,150 Per Month
- 2 Beds
- 1 Bath
- 468 Sq Ft
- Apartment for Rent
514 Avenue C NE Unit 4, Winter Haven, FL 33881
514 Avenue C NE Unit 4, Winter Haven, FL 33881Fantastic 2 bedroom/1.0 bathroom apartment totally renovated and ready for its new occupants. Unit is in close proximity of schools, including Jewett School of the Arts, Fred G. Garner Elementary School, and Frank E. Brigham Academy. 2 minute walk to Rotary Park. 7 minute walk to Kiwanis Park. 14 minute walk to Winter Haven Tennis Center. Water is included in the rent.
Angela Chapman CAPITAL REALTY GROUP FLORIDA
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$1,350 Per Month
- 2 Beds
- 2 Baths
- 1,003 Sq Ft
- House for Rent
2366 Lake Dr NW, Winter Haven, FL 33881
2366 Lake Dr NW, Winter Haven, FL 33881Welcome to 2366 Lake Dr in Winter Haven — a freshly updated home offering both style and functionality. Inside, you’ll find spacious bedrooms with modern flooring, ceiling fans, and ample natural light. The bathrooms feature clean tile finishes and practical layouts, while the kitchen is equipped with essential appliances including a range oven, range hood, and dishwasher, making everyday living
Showing Results 1 - 40, Page 1 of 3
Rental Trends in Winter Haven, FL
There are currently 99 homes available for rent in Winter Haven, FL. The median rent is $1,800 per month, with single-family homes renting at $1,895, townhouses at $1,350 and condos at $1,350.
Rental Home Trends
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Number of Homes for Rent
99
|
Median Rent
$1,800
|
|
Median Single Family Home Rent
$1,895
|
Median Townhouse Rent
$1,350
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Median Condo Rent
$1,350
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