Location: Winter Haven
Do Not Show Listings
267 LAKE THOMAS DR, WINTER HAVEN, FL 33880
$1,80027 Days on yellowkey MLS ID: P4938588
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1033 Built: 1984Community: Timber WoodSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: None
High School: None
Tax Year:
Middle School: None
Remarks: Welcome to this beautiful WATERFRONT VIEW home, where comfort and scenery meet in perfect harmony. The kitchen has just been re done new cabinets, granite counter tops new flooring, adding a fresh touch to the heart of the home. Inside, you’ll find a desirable split floor plan, a huge living room with plenty of space to relax or entertain, and stunning lake views that can be enjoyed right from the screened-in porch plus wood patio. Tucked away on a dead-end road, this property offers added privacy and a peaceful setting. Move-in ready and waiting for you to call it home.
Listing is courtesy of: STAR REALTY OF WINTER HAVEN (863-299-7827)
Listing Agent: William Beasley (863-299-1256)
106 SHELTON ST, WINTER HAVEN, FL 33880
$1,45027 Days on yellowkey MLS ID: P4938587
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1140 Built: 1961Community: Wahneta FarmsSingle Family
Elementary School: Wahneta Elem
Remarks: Welcome home to this charming three-bedroom, one-bath residence that is move-in ready and waiting for its next occupants. You’ll likely find yourself spending plenty of time on the generous screened-in porch, the perfect spot for family gatherings, relaxing evenings, or enjoying your morning coffee. Inside, the home offers a comfortable layout designed for everyday living. Ready for immediate occupancy, this property is one you won’t want to miss. Schedule your showing today!
304 LA SERENA, WINTER HAVEN, FL 33884
$1,70027 Days on yellowkey MLS ID: L4961811
0 Days Off yellowkey (back on 5/12/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1079 Built: 1978Community: Florida Highland CoSingle Family
Remarks: Nestled in the tranquil neighborhood of Winter Haven, 304 La Serena offers a comfortable living experience with its recent upgrades and convenient location. Step inside to discover a freshly painted interior that welcomes you with warmth and brightness. The new flooring adds a touch of modern charm to the living spaces, while providing durability for everyday life. The kitchen has been tastefully renovated, boasting new countertops and appliances that make meal preparation a breeze. With ample cabinet space, organizing your kitchen essentials is effortless. Both bedrooms feature their own updated bathrooms, providing privacy and convenience for residents and guests alike. A new roof ensures peace of mind, while the single-car garage offers practical storage solutions for your vehicles and belongings. Outside, the spacious yard invites you to enjoy the Florida sunshine, whether you're relaxing on the patio or tending to your garden. Lawn care included by the HOA. Administration Fee: Upon approval tenants will be subject to a $250 one-time administration fee. Ask how you can skip your security deposit with Obligo Resident Benefit Package (Included in rental amount): -Bi-monthly A/C Filter Delivery -$100,000 Tenant Liability Insurance/ $10,000 Content Coverage -Identity Protection -Credit building (All Credit Bureaus) -Piñata Tenant Rewards Program -Tenant Portal Access: Online payments
Listing is courtesy of: S & D REAL ESTATE SERVICE LLC (863-824-7169)
Listing Agent: Holly Piccola (813-966-5147)
5320 LAUREL OAK DR, WINTER HAVEN, FL 33880
$1,65061 Days on yellowkey MLS ID: P4938371
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1508 Built: 2008Manufactured Home
Elementary School: John Snively Elem
High School: Winter Haven Senior
Middle School: Denison Middle
Remarks: One or more photo(s) has been virtually staged. This welcoming 3 bedroom, 2 bathroom home in the Winter Haven Oaks 55+ community blends comfort, convenience, and an upbeat, easygoing lifestyle. The layout offers three flexible bedrooms along with a bright sun room that quickly becomes the heart of the home — an ideal spot for morning coffee, quiet afternoons, or simply enjoying the peaceful surroundings. An attached carport provides effortless covered parking, and there is also a storage shed located under the carport for added convenience. Residents can choose the setup that fits their needs: $1,650 per month unfurnished or $1,750 per month fully furnished for a true move-in-ready experience. Monthly rent includes water, pest control, lot rent, and lawn care, keeping living simple and stress-free. Winter Haven Oaks elevates the experience with two clubhouses, two swimming pools, and a charming teahouse overlooking the lake. The community also features a large hot tub, tennis courts, pickleball courts, billiards and a game room, a fitness room, and shuffleboard. Numerous weekly planned activities create plenty of opportunities to stay social and engaged. As a gated community, it also provides an added sense of safety and peace of mind. With friendly neighbors, well-kept grounds, and amenities designed for an enjoyable 55+ lifestyle, this home offers a warm and inviting place to settle in and feel right at home.
Listing is courtesy of: PROPERTY MANAGEMENT OF POLK (863-259-4600)
Listing Agent: Christin Davis (863-259-4600)
6472 DOMIZIO DR, WINTER HAVEN, FL 33884
$2,30027 Days on yellowkey MLS ID: O6406688
Bed: 5 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2112 Built: 2026Community: Villamar Ph 7Single Family
Remarks: Brand-New 5-Bedroom Home for Rent in Winter Haven Be the first to live in this stunning new construction two-story home located in the desirable area of Winter Haven. Designed with comfort, style, and functionality in mind, this spacious property offers 5 bedrooms, 2 full bathrooms, and 1 half bathroom, making it the perfect home for families or tenants looking for extra space and modern living. The home features an open-concept floorplan with expansive living and dining areas that create the ideal setting for entertaining, relaxing, and everyday living. Large windows bring in plenty of natural light, enhancing the bright and welcoming atmosphere throughout the home. The beautiful kitchen is designed to impress, featuring solid wood cabinets, elegant stone countertops, and included stainless steel appliances. Whether you enjoy cooking for family or hosting guests, this kitchen offers both style and practicality. The oversized primary suite provides a private retreat with a spacious walk-in closet and a comfortable layout. The additional bedrooms are generously sized and include built-in closets, offering convenience and ample storage space for everyone in the household. Additional highlights include a 2-car attached garage, modern finishes throughout, and energy-efficient new construction features that provide both comfort and peace of mind. Conveniently located near major roads, shopping, dining, and highly rated schools, this home offers easy access to everything Winter Haven has to provide while still providing a quiet and family-friendly environment. This is an exceptional rental opportunity for tenants seeking a brand-new, spacious, and beautifully designed home in a prime Winter Haven location.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Jessyka Dos Santos (407-364-0170)
1407 28TH ST NW, WINTER HAVEN, FL 33881
$1,80027 Days on yellowkey MLS ID: P4938674
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1709 Built: 1955Community: InwoodSingle Family
Remarks: List Agent is Related to Owner. Please call if interested in seeing it. Detached garage and shop building combo has limited access. Please talk to property manager. Home has wood, tile and vinyl flooring; cabinets are only 3 years old with granite counter tops and stainless steel appliances. Large pantry & dining area. Large primary bed room has extra large closet and big Wilkin shower bath. Near elementary schools. Ideal for tenant who needs lots of storage or work shop.
3601 CYPRESS GARDENS RD #6, WINTER HAVEN, FL 33884
$1,20027 Days on yellowkey MLS ID: P4938440
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1200 Built: 1975Community: Fla Highlands Co SubApartment
Elementary School: Garden Grove Elem
Remarks: Spacious 2-bedroom/2-bathroom apartment in a prime southeast Winter Haven location. New luxury vinyl flooring throughout, minutes from Legoland Florida Resort, tons of convenient restaurant, grocery, shopping, and dining options. Extremely commutable to Highway 27 and the Polk Parkway.
Listing is courtesy of: JOHN WOOD REALTY, INC. (863-324-9663)
Listing Agent: Kayly Malinas, Pa (863-258-1426)
810 TERRANOVA RD, WINTER HAVEN, FL 33884
$1,90032 Days on yellowkey MLS ID: S5149408
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2056 Built: 2006Community: Terranova Ph VSingle Family
Remarks: FOR RENT: Spacious 4 bedrooms and 2 bathrooms all tile home ready to move in. Large open kitchen combo family room. Seperate laundry room.
Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)
Listing Agent: Mark Peters (407-552-1499)
5850 CYPRESS GARDENS BLVD #604, WINTER HAVEN, FL 33884
$1,59528 Days on yellowkey MLS ID: S5149588
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 1260 Built: 1975Community: Royal Crescent CondoSpa: NoCondo
Remarks: Welcome to Cypress Gardens Blvd-SE, Winter Haven, charming and completely updated, move-in ready 2-bedroom, 1.5-bath condo for LEASE! nestled right on Cypress Gardens Blvd in Winter Haven — just minutes from shopping, dining, and walking distance from the famous LEGOLAND Florida Resort! Spacious kitchen with an eat-in space. Bedrooms are upstairs with a full bath for privacy. A fenced patio provides outdoor relaxation, 2 designated parking lots, a community pool is just steps away, and a tennis court - call the listing agent for a quick process and see this property
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Markus Khalil (407-929-3450)
320 SPIRIT LANDINGS CIR, WINTER HAVEN, FL 33880
$1,295111 Days on yellowkey MLS ID: S5144017
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 900 Built: 2024Community: Spirit LndgsSingle Family
Remarks: Fully furnished 1-bedroom apartment available for immediate occupancy. Rent includes all utilities electric, water, internet, and trash providing a truly hassle-free living experience. Well-maintained unit featuring comfortable furnishings, a functional layout, and abundant natural light. Ideal for professionals, traveling nurses, or anyone seeking a turnkey rental. Conveniently located near shopping, dining, and major roadways. No setup required—just bring your suitcase.
Listing is courtesy of: RE/MAX HERITAGE PROFESSIONALS (863-256-2188)
Listing Agent: Laura Medina Ruiz (863-207-4784)
236 RUBY LAKE LN, WINTER HAVEN, FL 33884
$4,500103 Days on yellowkey MLS ID: B4902182
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2266 Built: 2000Spa: NoSingle Family
Remarks: One or more photo(s) has been virtually staged. Wake up every morning to the most breath taking views imaginable. Almost every room in the home overlooks the spectacular private Lake Ruby & Lake Bess. Upon entering the home you will find yourself captivated with the spacious and luxurious open floor plan and high degree of natural light that envelops you. Besides having the exquisite view, this home also features a screened in pool and spa with lost of room to entertain. Both the pool and jacuzzi were resurfaced just a couple of years ago. The house, which was built in 2000, has many alluring features including a 3 car garage, cathedral ceilings, an extra large master suite, formal living room, and a family room with a fireplace over looking the lake. This property also features the use of you own private doc, boat house with life and a very important boat ramp since there is no public access to the lake. Please note: the rental includes $300 toward electric and $100 toward the water bill each month. An additional overages will be du by the lessee, Nature calls to those who enjoy water as fishing, boating, and skiing are outstanding on clean Ruby Lake, Some of the best views are from this home. Since it is connected to Lake Bess there are also two slalom courses nearby. The Ruby Lake community is gated an is also close to shopping and restaurants. Hwy 27 is only about 2 miles away. It is only 1 mile to Legoland. After enjoying all of the daily activities this property and nearby attractions, the home offers the night time sunsets that are gorgeous and a wonderful way to end the day. Both Tampa International and Orlando International airports are close by
Listing is courtesy of: KLINE REAL ESTATE SERVICES (863-287-0204)
Listing Agent: Scott Kline (863-287-0204)
3905 GIORGIO DR, WINTER HAVEN, FL 33884
$2,10030 Days on yellowkey MLS ID: O6406247
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1707 Built: 2026Single Family
Remarks: Brand new corner-lot home for rent in the desirable Villamar community! This beautifully designed 3-bedroom + flex room home offers a bright open-concept layout, modern finishes, and a versatile flex space perfect for a home office, playroom, or additional living area. Enjoy added privacy with the premium corner lot location and the convenience of included washer and dryer. The owner is also considering installing a backyard fence for additional outdoor privacy. Located in a resort-style community with pool, clubhouse, playground, and easy access to shopping, dining, and major highways. Move-in ready!
Listing Agent: Carolina Inacio (407-401-6340)
241 MEADOWBROOK BLVD, WINTER HAVEN, FL 33881
$2,00031 Days on yellowkey MLS ID: S5149482
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1725 Built: 2020Community: Lucerne Park ReserveSingle Family
Remarks: Welcome home! This cheerful 3-bedroom, 2-bath beauty is just four years young and sits in the sought-after community of Lucerne Park Reserve. Step inside, and bright open spaces and plenty of space for the whole family will greet you. The island kitchen is ready for real everyday living with stainless steel appliances and a roomy pantry that keeps everything in its place. The primary suite offers a comfortable retreat with a walk-in closet and a comfortable walk-in shower featuring a dual-sink vanity. With its split floor plan, you’ll also enjoy two additional bedrooms, a second full bath, and an indoor laundry room. Out back, the covered porch gives you a relaxing spot to unwind and soak up that famous Florida sunshine. You’ll be less than 10 minutes from Highway 27 and only about 20 minutes from Legoland—making everyday errands and weekend fun easy. Schedule your showing today! SUBMIT YOUR APPLICATION HERE: https://apply.link/nVCV-_o
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Luis Colon, Jr (407-748-2765)
630 PAVARE CT #630, WINTER HAVEN, FL 33884
$1,25031 Days on yellowkey MLS ID: L4961715
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 823 Built: 1982Community: Lake Kit CondoCondo
Elementary School: Elbert Elem
Remarks: Welcome to 630 Pavare Ct, a charming 2-bedroom, 2-bath end-unit condo available for rent in the desirable Orchid Springs community. This second-floor residence offers 823 square feet of comfortable living space with an open floor plan, ceramic tile flooring throughout, with carpet in the bedrooms and neutral paint tones. The spacious great room flows into the dining area and kitchen, creating a functional layout for everyday living. The kitchen includes a gas range, microwave, refrigerator, garbage disposal, closet pantry, and a stackable washer and dryer. The primary bedroom features a walk-in closet and private bath with a walk-in shower, while the guest bathroom offers a tub/shower combination. Enjoy relaxing views from the private balcony. An assigned parking space is located near the unit, with additional guest parking available. Conveniently located near shopping, dining, entertainment, medical facilities, and major roadways with easy access to Tampa and Orlando. Call today for your private showing!
Listing is courtesy of: LOCKHART & ASSOCIATES INC (863-293-1234)
Listing Agent: Amy Reynolds (863-412-2279)
118 OAK CREST DR NW, WINTER HAVEN, FL 33881
$1,100121 Days on yellowkey MLS ID: L4959244
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 600 Built: 1984Community: Us GorvernmentApartment
Remarks: Recently updated apartment available for lease! This bright and comfortable unit features updated cabinets, crown molding, ceiling fans, and modern light fixtures throughout, making it both stylish and easy to maintain. Enjoy private off-street parking. Located on a quiet street with no thru traffic and just minutes from shopping, dining, parks, and everyday conveniences.
Listing is courtesy of: KELLER WILLIAMS REALTY SMART 1 (863-508-3000)
Listing Agent: David Small (407-601-8351)
570 SANCTUARY BLVD, WINTER HAVEN, FL 33881
$2,70054 Days on yellowkey MLS ID: S5147830
0 Days Off yellowkey (back on 5/6/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2884 Built: 2022Community: Sanctuary By The LakeSingle Family
Remarks: Bring the entire family at this majestic home artfully laid out in an airy, open floor plan with plenty of rooms & abundant spaces. Resident(s) are responsible for utilities as well as renter's insurance, & lawn maintenance. All occupants 18 yrs. old above must complete the application. Applicants are encourage to disclose employment & credit information prior to scheduling a showing. Application fee $55.00 is non-refundable for every applicant, and lease administrative fee of $75. Fees are only collected after initial screening to save your money. Tenants will be required to provide proof of Income. First month rent and security deposit are required. Let’s make this your happy home. The huge entry foyer welcomes you to the delightful formal dining room w/ alluring arch-designed interiors, & natural light freely flowing to the grand living areas. The luxurious kitchen encompasses a counter-height island, a wide seated breakfast bar, the raised range cabinets & 42’’ upper cabinets are infusing a classic elegance & functionality. Fall in love of your fabulous owner's suite showcasing a classic tray ceiling, a suitable access to your office room, & the seamless connection of your French door to your screened lanai allows you to embrace sunshine. The splendor of your ensuite master bathroom presents a stylish his & hers walk-in wardrobe closets, a garden tub, the versatility of your dual vanities, a tiled walk-in shower w/ seat, & closeted toilet. A dedicated laundry room is equipped with a utility sink. Offering an oversize side-entry garage w/ an added garage length extension of 6 ft & 8’ ft tall garage-door, & a lengthen driveway for your comfort. Save on energy costs, w/ its energy efficient double paned windows. Enjoy being step away from the community lake access & across the street is the refreshing picturesque of the Chain of Lakes. Nestled in a gated community of Sanctuary By The Lake it has a playground, & direct access to a walking/biking trail that stretches from Lake Echo to Spring Lake. Close proximity to Hwy 17, US-92, & easy access to I-4. Centrally located; Lakeland is only 15.1 miles Orlando is 43.6 miles, Tampa is 53 miles & drive to Clearwater beach in just 1 hr & 30 mins.
Listing is courtesy of: MAZELG REALTY (863-399-0226)
Listing Agent: Lienyvette Grimaldo (863-399-0226)
333 LAKE HOWARD DR NW #312C, WINTER HAVEN, FL 33880
$1,42547 Days on yellowkey MLS ID: L4961272
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1030 Built: 1974Community: Imperial Harboursphases 01 & 02Condo
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)
3412 COSTELLO CIR, WINTER HAVEN, FL 33884
$2,50034 Days on yellowkey MLS ID: O6404736
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2540 Built: 2025Community: Villamar Ph 6 & Ph 6DSingle Family
Remarks: Discover your next rental home! This spectacular two-story property in Winter Haven offers 5 spacious bedrooms, 3 full bathrooms, and a versatile second-floor loft perfect for your lifestyle. With 2,447 square feet, you will enjoy an open-concept layout that seamlessly connects the modern kitchen, dining area, and large living room, creating the ideal space for entertaining. Features include a 2-car garage, walk-in closets, and premium finishes for a life without limits on comfort. Open for section 8. Move-in ready so you can start enjoying all its amenities immediately!
Listing is courtesy of: VENOSA REALTY LLC (407-442-6164)
Listing Agent: Kelita Uzcategui (772-203-9845)
100 EL CAMINO DR #309, WINTER HAVEN, FL 33884
$1,65034 Days on yellowkey MLS ID: P4938609
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1579 Built: 1971Community: Orchid Spgs Vill 100 CondoCondo
Remarks: Welcome to easy, low-maintenance living in this charming 2-bedroom, 2-bath condo located in a peaceful 55+ community tucked away from the main road. This spacious home features an open-concept layout with a large living and dining area, perfect for relaxing or entertaining. Enjoy your morning coffee or unwind in the beautiful Florida room overlooking a serene lagoon. The community offers a refreshing pool, convenient elevator access, and on-site laundry facilities. Even better, your monthly rent includes water, cable, internet, and gas—making this an exceptional value in a quiet, well-kept setting.
Listing is courtesy of: ASSOCIATE REALTY (863-618-4000)
Listing Agent: Chrissi Jasso (863-618-4000)
616 CRYSTALS BLVD, WINTER HAVEN, FL 33884
$1,90066 Days on yellowkey MLS ID: O6395877
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1575 Built: 1993Community: Crystals LandingSingle Family
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)
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