Location: Winter Haven
Keyword(s): Chain O Lakes Elem
Keyword(s) Elementary School: Chain O Lakes Elem
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1313 DIEGO TER #In-Law Suite, WINTER HAVEN, FL 33884
$1,30093 Days on yellowkey MLS ID: O6385566
REDUCED by $100 (7.1%) on 05/27/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 2093 Built: 2024Community: Peace Crk ReserveSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:
Elementary School: Chain O Lakes Elem
High School: Bartow High
Tax Year:
Middle School: Bartow Middle
Remarks: One or more photo(s) has been virtually staged. For Lease: Private In-Law Suite in Winter Haven, FL – $1,300/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: $1,400 /month Size: Approx. 450 sq. ft. Lease Term: Minimum 12 months Security Deposit: $1,300.00 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)
521 REGGIE RD, WINTER HAVEN, FL 33884
$2,60066 Days on yellowkey MLS ID: L4960535
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2093 Built: 2024Community: Peace Crk ReserveSingle Family
High School: Winter Haven Senior
Middle School: McLaughlin Academy Of Excellence
Remarks: Rent a home and have an extra area for your friends or family to live while visiting . This near new !! 4 bedroom 3 bathroom Lennar Next Gen home available for lease in Peace Creek Reserve in Winter Haven. This layout features a private mother in law suite with its own entrance, living area, kitchenette, bedroom, and full bath, ideal for multigenerational living or added privacy. Main home offers an open concept floor plan with a large living area, modern kitchen with island, and separate dining space. Primary suite includes a walk in closet and private bath with dual sinks and walk in shower. Secondary bedrooms are well sized with a shared full bath. Interior features includes tile in main living areas, carpet in bedrooms, and tile in all wet areas. Laundry room included. Attached 2 car garage. Move in ready. Schedule your showing today.
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (863-701-2350)
Listing Agent: Michael Hochadel (863-604-0018)
3110 GOWAN DR #A1, WINTER HAVEN, FL 33884
$1,424352 Days on yellowkey MLS ID: O6317379
REDUCED by $1 (0.1%) on 05/22/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 835 Built: 2024Apartment
High School: Lake Region High
Middle School: Denison Middle
Remarks: Currently offering 1 months free upfront and a 99.00 app/ admin fee which is credited to rental account. Prices, promotions, and availability are subject to change. Multiple floor plans available. Days on market is not specific to this current plan listed. Discover Prose Cypress Pointe and make every day feel like a getaway. Nestled in the heart of Winter Haven and just a short drive from Lakeland, our pet-friendly luxury apartment community offers spacious floor plans, upscale finishes, and resort-style amenities—all thoughtfully crafted with you in mind. Here, you’ll find more than a home, you’ll discover a curated lifestyle. Lounge by the resort style pool and entertainment cabana, stay energized in the 24-hour fitness center, join invigorating on-site fitness classes, or grab complimentary breakfast on your way to work. It’s boutique living designed to elevate your everyday. With convenient access to Tampa, Orlando, and beyond, Prose Cypress Pointe let’s you live chic, live central and completely you.
Listing is courtesy of: THE APARTMENT BROTHERS LLC (704-502-7778)
Listing Agent: Aj Rebhan (704-502-7778)
3110 GOWAN DR #B1, WINTER HAVEN, FL 33884
$1,725352 Days on yellowkey MLS ID: O6317387
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1180 Built: 2024Apartment
1734 CARNOSTIE RD, WINTER HAVEN, FL 33884
$2,05046 Days on yellowkey MLS ID: TB8497301
REDUCED by $50 (2.4%) on 05/07/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1418 Built: 2023Community: Villamar Ph 3Single Family
Remarks: Beautiful Comfortable home awaits your tenant and their family. This 3/2/2 has an open floor concept. The great room plan opens up to vaulted ceiling . The kitchen has is a comfy breakfast nook. The home also features a Gourmet Kitchen The beautiful master bedroom is a split plan. All bedrooms are comfortable sized. Carpet in all bedrooms and tiles in the wet area. This is a must see. Wont last long.
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Hillorie Dias (813-417-9549)
1103 CYPRESS GARDENS BLVD #17, WINTER HAVEN, FL 33884
$1,20010 Days on yellowkey MLS ID: L4961998
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 575 Built: 1980Community: Lamplighter VillageSpa: NoCondo
Remarks: One or more photo(s) has been virtually staged. Chain of Lakes WATERFRONT living with stunning views of Lake Roy! This beautifully updated 1-bedroom condo offers the perfect blend of peaceful lakeside charm and everyday convenience, located just minutes from shopping, dining, and entertainment. Step inside to find wood-look tile flooring throughout, fresh calming oasis-blue paint, and abundant natural light pouring in through updated windows showcasing picturesque lake views. The spacious living area flows into a versatile window-lined nook, ideal for a home office, reading corner, or expanded seating area. The updated kitchen features modern appliances and an efficient layout designed to maximize space and functionality. The bedroom offers two closets for ample storage along with a convenient stackable washer and dryer nook. The bathroom has been tastefully renovated with a modern subway-tiled tub surround. Just outside your front door, enjoy a large HOA-maintained green space with picnic seating overlooking the water. Beyond that, you’ll have direct access to Lake Roy, perfect for kayaking, paddle boarding, or simply soaking in the serene setting. The community dock provides additional space for fishing, relaxing, and enjoying breathtaking lakefront sunsets. Don’t miss this rare opportunity to lease a charming lakeside retreat on the Chain of Lakes!
Listing is courtesy of: REMAX EXPERTS (863-802-5262)
Listing Agent: Jake Bellamy (863-838-7804)
123 TREMONT DR, WINTER HAVEN, FL 33884
$2,35023 Days on yellowkey MLS ID: L4961568
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 1260 Built: 1971Community: Eloise Woods Lake Roy UnSingle Family
Remarks: FOR RENT - 3/2 Single Family Home with a 1/1 Detached Mother-in-Law Suite. Two homes for the price of one! Come see thse two homes that have been completely updated from top to bottom. The homes come with the range and refrigerator. They are located in desirable Southeast Winter Haven and are walking distance from Lake Summit and Lake Roy which have public boat ramps. Only two minutes from LEGOLAND. Come see these homes today!
Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)
Listing Agent: Linda Andre (863-294-7541)
5202 WATERVIEW WAY #5202, WINTER HAVEN, FL 33884
$1,75091 Days on yellowkey MLS ID: P4937984
REDUCED by $50 (2.8%) on 05/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 930 Built: 1992Community: Garden Villas 02 Ph 01Condo
Remarks: A comfortable first-floor 2 bed, 2 bath condo in the gated Winterset community, this home offers an easy, open layout with plenty of natural light and convenient ground-level access. Each bedroom has its own full bathroom, giving you a setup that works well for roommates, guests, or anyone who wants a little extra privacy. The condo can be leased furnished for a turnkey move-in or unfurnished if you prefer to bring your own style. Winterset adds to the appeal with lakefront views, a community pool, tennis courts, and beautifully maintained grounds that make everyday living feel calm and inviting. Don't miss your opportunity to live in this luxurious community! Schedule a tour today! ($1,750 with furniture, $1,650 without)
Listing is courtesy of: PROPERTY MANAGEMENT OF POLK (863-259-4600)
Listing Agent: Christin Davis (863-259-4600)
715 MAGNOLIA PL #715, WINTER HAVEN, FL 33884
$1,65056 Days on yellowkey MLS ID: P4938303
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1078 Built: 1987Community: Winterset 03 A Condo Ph 01Condo
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)
3511 COSTELLO CIR, WINTER HAVEN, FL 33884
$2,10073 Days on yellowkey MLS ID: O6391046
REDUCED by $100 (4.5%) on 04/21/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2234 Built: 2025Community: Villamar Ph 6 & Ph 6DSingle Family
Middle School: Mclaughlin Academy Of Excellence
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)
2014 8TH TER SE, WINTER HAVEN, FL 33880
$3,45042 Days on yellowkey MLS ID: L4961092
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2722 Built: 1959Community: Laha Wa ManorSingle Family
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)
620 REFLECTIONS LOOP, WINTER HAVEN, FL 33884
$1,750240 Days on yellowkey MLS ID: O6348886
0 Days Off yellowkey (back on 4/17/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1489 Built: 1998Community: Reflections East Ph 01Spa: NoSingle Family
Remarks: Welcome to this spacious 3/2 near Legoland! Nestled in the heart of Winter Haven, FL, this home boasts three generously sized bedrooms and two full bathrooms. The split bedroom floor plan ensures privacy, while the eat-in kitchen nook provides a cozy space for meals. The master suite is a true retreat, complete with a luxurious garden tub. The entire home is outfitted with ceramic tiled flooring, adding a touch of elegance and ease of maintenance. The property also features a large yard, perfect for outdoor activities, and a two-car garage for your vehicles or extra storage. Plus, lawn service and interior pest control are included, providing you with a worry-free living experience. This home offers the perfect blend of comfort, convenience, and style. Don't miss out on this gem in Winter Haven! *Tenant must provide their own washer and dryer. **RESIDENTS BENEFIT PACKAGE Residents are enrolled in the Resident Benefits Package (RBP). There is an additional $35.00 a month charge for this added to the advertised rent and is considered additional rent. RBP includes HVAC air filter delivery, utility concierge services making utility connection a breeze during your move-in, our best-in-class resident rewards program, and much more! More details upon application. If approved for this home, new tenants must pay a $200.00 lease coordination fee due at the same time as the security deposit payment. **RENTERS INSURANCE REQUIRED $100K min liability coverage. Personal property coverage is not required.
Listing is courtesy of: CT HOMES REALTY CORPORATION (407-578-6545)
Listing Agent: Francisco Nieves-Taranto (321-248-4149)
2772 SAN MARCO WAY, WINTER HAVEN, FL 33884
$2,20051 Days on yellowkey MLS ID: O6397232
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1988 Built: 2024Community: VillamarSpa: NoSingle Family
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)
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