Winter Haven, FL Homes for Rent

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  $2,605 per month

  • 3 Beds
  • 2 Baths
  • 2,229 Sq Ft
  • House for Rent

  26 The Village Blvd, Winter Haven, FL 33880

  We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home

  26 The Village Blvd, Winter Haven, FL 33880
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  $2,300 per month

  • 3 Beds
  • 2 Baths
  • 1,725 Sq Ft
  • House for Rent

  295 Lake Smart Cir, Winter Haven, FL 33881

  MORE PHOTOS TO COMEWelcome to your beautiful new home located in the lakefront community of Lake Smart Pointe! Perfectly positioned near Highway 27, I-4, and Legoland, this home offers quick access to shopping, dining, and entertainment, while still providing the tranquility of lakeside living. Downtown Winter Haven is just minutes away, offering local restaurants, boutique shops, and

  Grant Powers COLDWELL BANKER REALTY

  295 Lake Smart Cir, Winter Haven, FL 33881
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  $1,900 per month

  • 4 Beds
  • 2.5 Baths
  • House for Rent

  1191 Tyler Lp, Winter Haven, FL 33884

  Property Id: 2243962Discover this beautiful 4-bedroom, 2.5-bath home available for rent in the lovely city of Winter Haven. Offering spacious and bright living areas, this well-maintained property is perfect for families or anyone seeking comfort and convenience. With four generously sized bedrooms, two full bathrooms, and an additional half bath for guests, the layout is both

  1191 Tyler Lp, Winter Haven, FL 33884
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  $1,795 per month

  • 3 Beds
  • 2 Baths
  • 1,317 Sq Ft
  • House for Rent

  1517 Majestic Ln, Winter Haven, FL 33880

  Ready for a new tenant, this beautiful home is conveniently located within close commute to restaurants, shopping, and Legoland theme park. Home features granite tops, stainless appliances, and tile in all main areas. Great starter home for a small family, schedule your showing today!

  Yari Villarrubia LA ROSA REALTY LLC

  1517 Majestic Ln, Winter Haven, FL 33880
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  $2,180 per month

  • 3 Beds
  • 2 Baths
  • 2,053 Sq Ft
  • House for Rent

  529 Vittorio Dr, Winter Haven, FL 33884

  Welcome to this beautifully maintained 2021 single-family home in the sought-after Villamar community. This bright and open 3BR/2BA home with a den features high ceilings, plenty of natural light, French doors, and plank flooring throughout—NO carpet! The modern open floor plan offers spacious living areas and an oversized primary bedroom with ample comfort. Additional perks include a built-in

  529 Vittorio Dr, Winter Haven, FL 33884
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  $1,700 per month

  • 3 Beds
  • 2 Baths
  • 1,537 Sq Ft
  • House for Rent

  57 Saint Kitts Cir, Winter Haven, FL 33884

  Pet-Friendly! (Conditions Apply). 18 month lease. First, last and security with monthly payment option. Beautiful 3-Bedroom, 2-Bath Home with Garage in a Quiet, Secluded Neighborhood. Many restaurants and amenities nearby. Close to Legoland, Bok Tower, and a short trip to Orlando This well-maintained home offers a spacious open floor plan featuring 3 generously sized bedrooms and 2 full

  Sherri Hudson LANDSEARCH LLC

  57 Saint Kitts Cir, Winter Haven, FL 33884
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  $1,800 per month

  • 3 Beds
  • 2 Baths
  • 1,140 Sq Ft
  • House for Rent

  608 Maggie Cir, Winter Haven, FL 33880

  608 Maggie Cir, Winter Haven, FL 33880
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  $2,250 per month

  • 3 Beds
  • 2 Baths
  • 1,709 Sq Ft
  • House for Rent

  3805 Osprey Pointe Cir, Winter Haven, FL 33884

  Modern design with comfort in mind! Available for Lease November 15, 2025! Spacious 3-Bedroom, 2-Bath Home in a Charming Winter Haven Neighborhood Welcome to this beautifully maintained 3-bedroom, 2-bath home offering over 1,700 square feet of living space in a quaint and friendly community. Conveniently located near downtown Winter Haven, with easy access to theme parks, shopping, and dining,

  Oswald Carrerou CARREROU ENTERPRISES, LLC

  3805 Osprey Pointe Cir, Winter Haven, FL 33884
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  $1,150 - $1,225 per month

  • 1 Bed
  • 1 Bath
  • 589 Sq Ft
  • Condo for Rent

  669 Avenue B NW, Winter Haven, FL 33881

  Settled in a quiet neighborhood 1 block from Lake Howard is a spacious 1 bedroom, 1 bath second floor unit. Unit features a claw-foot tub, stove, refrigerator, built-in pantry hardwood floors and large closet. With views of Lake Howard from all windows, this unit makes an excellent home. The property is part of the Pope Historic District which has been undergoing revitalization through

  669 Avenue B NW, Winter Haven, FL 33881
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  $1,850 per month

  • 3 Beds
  • 2 Baths
  • 1,485 Sq Ft
  • House for Rent

  1241 Denali Dr, Winter Haven, FL 33881

  "Charming 3-Bedroom Home with 2 Full Baths in Winter Haven – Spacious 1485 Sq. Ft. Gem on Denali Drive!" Inspired by the tranquil charm of Winter Haven, 1241 Denali Drive offers a harmonious blend of comfort and style. This inviting 3-bedroom, 2-bathroom home is located on a double cul-de-sac and spans 1485 square feet, providing ample space for relaxation and entertainment. Step inside to

  Shannon Cornell PMI ARRICO REALTY AND PRTP MGT

  1241 Denali Dr, Winter Haven, FL 33881
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  $2,150 per month

  • 4 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • House for Rent

  1108 29th St NW, Winter Haven, FL 33881

  4 bed/2 bath home with a large fenced backyard.Fully renovated for your convenience.Contact me to visit this beautiful property you will soon call home!

  1108 29th St NW, Winter Haven, FL 33881
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  $1,995 per month

  • 4 Beds
  • 2.5 Baths
  • 2,526 Sq Ft
  • House for Rent

  5179 Michelle St, Winter Haven, FL 33881

  MOVE In Special for month of December.......December FREE RENT with good rental history and good credit! This beautiful 4 bedroom, 2.5 bath, two story home is very large and has BRAND NEW LVP in bedrooms. It's located in Buckeye Ridge and features carpet in living areas and tile in wet areas and freshly painted walls. Kitchen has an island with sink and room for bar stools, opens to separate

  Ronald Gentile ORLANDO REO PROF I INC

  5179 Michelle St, Winter Haven, FL 33881
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  $900 per month

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • House for Rent

  1845 Orangewood Ave SW, Winter Haven, FL 33880

  1 /1 duplex with screened front porchLaundry room with washer dryer hook upLarge yardWater included!Small pets considered for a pet fee

  1845 Orangewood Ave SW, Winter Haven, FL 33880
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  $2,100 per month

  • 3 Beds
  • 2 Baths
  • 1,674 Sq Ft
  • House for Rent

  3998 Cypress Landing S, Winter Haven, FL 33884

  AMAZING LOCATION! IMMEDIATE MOVE IN! Can be rented FULLY FURNISHED or Unfurnished!! Welcome to this beautifully updated home in theheart of Winter Haven. This 3 bedroom 2 bathroom home has almost 1700sqft of living plus an enclosed lanai adding almost 300 sqft of livingspace which is great for entertaining or could even be used as another bedroom or office space. Enjoy all the natural

  Brooke Curtis PROBITY REALTY

  3998 Cypress Landing S, Winter Haven, FL 33884
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  $2,150 per month

  • 4 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • House for Rent

  2420 Edwin St NE, Winter Haven, FL 33881

  Are you looking for a 4/2 move-in ready? This property has been fully renovated from top to bottom for your peace of mind.With a big lot fully fenced yard, you can already plan a lot of fun family activities!Feel free to reach out to schedule a visit!

  2420 Edwin St NE, Winter Haven, FL 33881
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  $1,900 per month

  • 4 Beds
  • 2 Baths
  • 2,056 Sq Ft
  • House for Rent

  810 Terranova Rd, Winter Haven, FL 33884

  FOR RENT: Spacious 4 bedrooms and 2 bathrooms all tile home ready to move in. Large open kitchen combo family room. Seperate laundry room.

  Mark Peters LA ROSA REALTY LLC

  810 Terranova Rd, Winter Haven, FL 33884
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  $1,699 per month

  • 3 Beds
  • 2 Baths
  • 2,250 Sq Ft
  • House for Rent

  926 30th St NW, Winter Haven, FL 33881

  Large fully remodeled 3/2 house ( could also be converted to a 4 bedroom ) with huge back yard all fenced in and large screened in patio with washer and dryer hook ups.lots of space

  926 30th St NW, Winter Haven, FL 33881
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  $1,850 per month

  • 4 Beds
  • 2 Baths
  • 1,665 Sq Ft
  • House for Rent

  3452 Costello Cir, Winter Haven, FL 33884

  Brand New 4 bedroom/2 bath home in Villamar community in Winter Haven. This home combines modern convenience with timeless elegance, showcasing granite and tile floors throughout. Once inside, you are in the foyer that leads you into the heart of the home. The open-concept layout seamlessly connects the living room, dining area, and kitchen, creating a perfect space for entertaining family and

  Michael Bouchard GLOBAL FLORIDA REALTY

  3452 Costello Cir, Winter Haven, FL 33884
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  $1,600 per month

  • 2 Beds
  • 1 Bath
  • 780 Sq Ft
  • House for Rent

  5626 Struthers Ct, Winter Haven, FL 33884

  This property at 5626 Struthers Ct features a beautifully maintained 2-bedroom, 1-bath residence located in a quiet, established neighborhood. With washer/dryer included, a brand-new central A/C system, and a spacious open yard, this home offers comfort and convenience in one perfect package.Features:* 2 bedrooms / 1 bathroom* Washer & dryer included* New central air* Tile

  5626 Struthers Ct, Winter Haven, FL 33884
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  $2,250 per month

  • 4 Beds
  • 2 Baths
  • 2,836 Sq Ft
  • House for Rent

  5328 Michael Dr, Winter Haven, FL 33884

  Welcome to this beautifully maintained 4-bedroom, 2.5-bathroom home located in the desirable Bentley Place community of Winter Haven! Offering over 2,800 square feet of living space, this spacious two-story residence is ideal for growing families, remote professionals, or anyone seeking comfort, functionality, and style. As you enter, you're greeted by a formal living and dining room combo,

  Silvia Odebrecht ICON REALTY ASSOCIATES INC

  5328 Michael Dr, Winter Haven, FL 33884
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  $1,150 - $1,225 per month

  • 1 Bed
  • 1 Bath
  • 589 Sq Ft
  • Condo for Rent

  669 Avenue B NW, Winter Haven, FL 33881

  Settled in a quiet neighborhood 1 block from Lake Howard is a spacious 1 bedroom, 1 bath second floor unit. Unit features a claw-foot tub, stove, refrigerator, built-in pantry hardwood floors and large closet. With views of Lake Howard from all windows, this unit makes an excellent home. The property is part of the Pope Historic District which has been undergoing revitalization through

  669 Avenue B NW, Winter Haven, FL 33881
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  $1,900 per month

  • 3 Beds
  • 2 Baths
  • 1,553 Sq Ft
  • House for Rent

  2845 Whispering Trails Dr, Winter Haven, FL 33884

  This beautiful 3-bedroom, 2-bathroom home is nestled in the sought-after Whispering Trails neighborhood of Winter Haven. Inside, you’ll find an open floor plan that creates a bright, airy flow from the living area to the kitchen and dining space—perfect for both everyday living and entertaining. The home comes equipped with a washer and dryer, making move-in easy and convenient. Step outside to

  Christin Davis PROPERTY MANAGEMENT OF POLK

  2845 Whispering Trails Dr, Winter Haven, FL 33884
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  $1,750 per month

  • 3 Beds
  • 2 Baths
  • 1,073 Sq Ft
  • Condo for Rent

  112 Winter Ridge Dr Unit 112, Winter Haven, FL 33881

  Tucked away in the waterfront community with direct access to the Chain of Lakes (Lake Smart), Unit 112 is a stunning, updated 3-bedroom, 2-bath condo that combines low-maintenance living with modern luxury and style. Step inside to discover luxury vinyl plank flooring throughout, complemented by the kitchen that includes a complete set stainless steel appliances with a pair of rose gold Samsung

  112 Winter Ridge Dr Unit 112, Winter Haven, FL 33881
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  $2,400 per month

  • 4 Beds
  • 3 Baths
  • 2,109 Sq Ft
  • House for Rent

  352 Kayden Cove, Winter Haven, FL 33884

  Step into this newly built single-family home that perfectly blends modern comfort with versatile living. Featuring 3 spacious bedrooms, 2 beautifully designed bathrooms, and a flexible bonus room ideal for a mother-in-law suite, guests, or a home office, this residence adapts seamlessly to your lifestyle whether you need extra space for work, play, or guests. At the heart of the home, the

  Yasmin Paulino HOME 21 REALTY & MANAGEMENT INC

  352 Kayden Cove, Winter Haven, FL 33884
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  $1,195 per month

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Condo for Rent

  306 Avenue C NE Unit 1, Winter Haven, FL 33881

  Nicely renovated 2BR / 1BA apartment, right next to a park and looking directly onto Lake Martha. Enjoy your morning coffee while taking in the natural beauty just across the street in this quiet, peaceful neighborhood. Walk to downtown Winter Haven in 10 minutes - and Winter Haven hospital is only a 5 minute walk from here. Bright, open kitchen design with new cabinets and countertops

  306 Avenue C NE Unit 1, Winter Haven, FL 33881
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  $2,300 per month

  • 4 Beds
  • 2 Baths
  • House for Rent

  125 Lake Smart Cir, Winter Haven, FL 33881

  Welcome to this spacious and well-maintained 4-bedroom, 2-bathroom home located in the peaceful Lake Smart Estates community. This home offers a perfect blend of comfort and convenience for your family.? Property Features:4 Spacious Bedrooms2 Full Bathrooms Open-Concept Living and Dining Area Modern Kitchen with Plenty of Cabinet Space Washer and Dryer Inside the Unit Private Lanai –

  Marlene Darrican Florida Realty of Miami Corp

  125 Lake Smart Cir, Winter Haven, FL 33881
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  $2,000 per month

  • 4 Beds
  • 2 Baths
  • 1,384 Sq Ft
  • House for Rent

  3202 Timberline Rd, Winter Haven, FL 33880

  This beautiful block house has 4 beds 2 baths (one has a jacuzzi tub). It is in a safe neighborhood. It has stainless double door fridge with ice and water, a stainless dish washer. It has washer and drier hookup inside. It has a new central heat and air system. The back yard is fenced in. It has a screened back porch. It is centrally located right off the highway 540. Many stores within 1/4 mile

  3202 Timberline Rd, Winter Haven, FL 33880
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  $1,900 per month

  • 3 Beds
  • 2 Baths
  • House for Rent

  308 Lake Smart Cir Unit 308, Winter Haven, FL 33881

  Welcome to this charming 3-bedroom, 2-bathroom home located in the peaceful Lake Smart Estates community of Winter Haven. This spacious and modern home offers an open-concept living area, perfect for relaxing or entertaining guests.? Features: Bright and open floor plan with tile and carpet flooring Modern kitchen with stainless steel appliances and breakfast bar Master suite with walk-in

  Marlene Darrican Florida Realty of Miami Corp

  308 Lake Smart Cir Unit 308, Winter Haven, FL 33881
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  $1,695 per month

  • 4 Beds
  • 2 Baths
  • 1,546 Sq Ft
  • House for Rent

  1220 Salisbury Dr, Winter Haven, FL 33881

  3 bedroom 2 bathroom plus separate 11x13 room(great for office, study or play room), large kitchen with center island, granite counter tops, stainless steel appliances, inside utility room with washer and dryer hookups, 12x16 master bedroom with walk-in closet, master bathroom with dual vanities and stand up shower, tile floors throughout with carpet in the bedrooms, 2 car garage with opener,

  1220 Salisbury Dr, Winter Haven, FL 33881
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  $1,795 per month

  • 3 Beds
  • 2.5 Baths
  • 1,625 Sq Ft
  • House for Rent

  2783 Sycamore St, Winter Haven, FL 33881

  One or more photo(s) has been virtually staged. Welcome to this beautiful 3-bedroom, 2.5-bath home perfectly designed for comfort and style! Step inside to an open and airy floor plan featuring a bright living area, a contemporary kitchen with sleek finishes, and a cozy dining space—ideal for family gatherings or entertaining guests. Upstairs, you’ll find spacious bedrooms including a relaxing

  Jacob Hara TRANSCEND REALTY

  2783 Sycamore St, Winter Haven, FL 33881
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  $2,000 per month

  • 3 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Condo for Rent

  2817 Wingfoot Ct, Winter Haven, FL 33884

  24 hour security with gaurd gate. You will receive one remote control for entrance. It’s on golf course, very quiet and dog friendly place.

  2817 Wingfoot Ct, Winter Haven, FL 33884
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  $1,800 per month

  • 2 Beds
  • 2 Baths
  • 1,536 Sq Ft
  • Townhouse for Rent

  2673 Rutledge Ct, Winter Haven, FL 33884

  Great townhome with Reserve behind and beside it, so no neighbors. Community has a nice pool, dock to fish etc. House has been completely repainted and is very clean inside. Huge master bedroom bathroom and closet, also has a den that can be converted to a 3rd bedroom, washer ad dryer hookups inside the house etc. Close to US 27, Legoland, easy access to Orlando, fantastic location Application

  Chace Vaughn TOWN & COUNTRY REAL ESTATE

  2673 Rutledge Ct, Winter Haven, FL 33884
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  $1,900 per month

  • 3 Beds
  • 2 Baths
  • 1,450 Sq Ft
  • House for Rent

  308 Lake Smart Cir, Winter Haven, FL 33881

  This is a beautiful NEW HOME for RENT! 3 bedroom, 2 full bath, 2 car garage, washer and dryer inside the unity, all new appliances throughout, central AC, about 54 minutes from Orlando. Convenient location, close to 5 lakes and Legoland. Annual Lease only. $5,700 to move in (first month/ 2 Security Deposit). Landscaping is NOT included in rent.

  308 Lake Smart Cir, Winter Haven, FL 33881
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  $1,350 per month

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • Apartment for Rent

  1728 Teagan Ln, Winter Haven, FL 33884

  Beautiful studio apartment for a couple or single person, in a new community, with separate entrance, with defined spaces, laundry area, small but very comfortable kitchen, and bedroom with private bathroom. The parking space is shared with the owner. The house comes with its own separate apartment, built directly by the builder, so its spaces are designed with comfort in mind.

  Adriana Sanchez AGENT TRUST REALTY CORPORATION

  1728 Teagan Ln, Winter Haven, FL 33884
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  $1,380 - $2,265 per month

  Alera at Hunters Glen

  1 - 3 Beds

  3005 Willow Glen Cir, Lake Wales, FL 33859

  Set 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

  3005 Willow Glen Cir, Lake Wales, FL 33859
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  $2,200 per month

  • 5 Beds
  • 2.5 Baths
  • 2,215 Sq Ft
  • House for Rent

  640 Grove St, Winter Haven, FL 33884

  This pet-friendly home features modern finishes and a functional layout with ample kitchen storage, spacious living areas, and abundant natural light throughout. The private yard offers space suitable for gardening or outdoor relaxation. Conveniently located near schools, parks, dining, and local amenities. Technology-enabled maintenance services provide added convenience, and self-touring is

  Daniel Reyes MAIN STREET RENEWAL LLC

  640 Grove St, Winter Haven, FL 33884
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  $2,000 per month

  • 4 Beds
  • 2 Baths
  • 1,840 Sq Ft
  • House for Rent

  3102 Laurel Oak Ln, Winter Haven, FL 33884

  Beautiful Energy-efficient home for Long-Term rental! Built on 2023, like new home, The open floor concept is very spacious and great for family gatherings and entertaining! in the growing community of VILLAMAR, with an open floor concept, very spacious with 1,840 Sqft perfect for family gatherings! 4 Bedrooms 2 full Bathrooms, The kitchen features 42" Dusk cabinets, Ashen granite countertops,

  Tatiana Rojas TBO REAL ESTATE PARTNERS INC

  3102 Laurel Oak Ln, Winter Haven, FL 33884
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  $1,000 per month

  • 1 Bed
  • 1 Bath
  • 678 Sq Ft
  • Property for Rent

  114 Venus Ave, Winter Haven, FL 33884

  Discover convenience in this cute 1 bedroom, 1 bathroom home located in a 55+ community with direct access to beautiful Lake Dexter. This home features a bonus room perfect for storage, a hobby space, or an extra guest room. Rent includes water and landscaping. Nestled in the desirable Cypress Gardens area, you’ll love being close to shopping, dining, and all that Winter Haven has.

  Nadia Aguilar EXIT REALTY 4CORNERS

  114 Venus Ave, Winter Haven, FL 33884
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  $1,990 per month

  • 4 Beds
  • 2 Baths
  • 1,828 Sq Ft
  • House for Rent

  2000 Carnostie Rd, Winter Haven, FL 33884

  Beautiful 4 bedroom, 2 bath home with a 2 car garage in the very desirable Villa Mar Subdivision. A large open floor plan with living, dining and kitchen combo. Huge breakfast bar with granite counters separates the 2. Stainless steel appliances and white wooden cabinets adds to the open concept of this home! Home Is Connected smart home technology as well. The house is completely tiled with

  Mary Clevenger WEICHERT REALTORS HALLMARK PRO

  2000 Carnostie Rd, Winter Haven, FL 33884
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  $1,575 per month

  • 3 Beds
  • 2 Baths
  • 1,357 Sq Ft
  • House for Rent

  247 Lake Eloise Pointe Blvd, Winter Haven, FL 33880

  Welcome home to this charming 3-bedroom, 2-bathroom property located in beautiful Winter Haven! Step inside and enjoy the inviting open layout, featuring a spacious family and dining room combo that's perfect for relaxing or entertaining. The living areas include attractive laminate flooring, while cozy carpet adds comfort to the bedrooms.The kitchen offers modern appeal with stainless steel

  Nancy Guadagnino SPECIALIZED PROPERTY MANAGEMENT

  247 Lake Eloise Pointe Blvd, Winter Haven, FL 33880

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