Winter Haven, FL Homes for Rent under $2,500

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  $1,400 Per Month

  • 2 Beds
  • 2 Baths
  • 1,078 Sq Ft
  • Condo for Rent

  2050 San Marcos Dr SE Unit 214, Winter Haven, FL 33880

  Discover a spacious 2-bedroom, 2-bathroom second floor condo nestled in one of the most sought-after complexes in town. This home offers a perfect blend of comfort and convenience, featuring an open floor plan, natural light, and premium finishes throughout. The condo is located right across from the community's office and mailboxes. The two bedrooms provide plenty of space and privacy, with the

  Christin Davis PROPERTY MANAGEMENT OF POLK

  2050 San Marcos Dr SE Unit 214, Winter Haven, FL 33880
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  $1,550 Per Month

  • 2 Beds
  • 2 Baths
  • 932 Sq Ft
  • Condo in Gated Winterset

  7904 Waterview Way, Winter Haven, FL 33884

  Now Available for rent!!! This beautifully maintained 2 bedroom 2 bath condo is located in the Winterset Gated community in Winter Haven. Conveniently located, a short 5 minute drive to shops, restaurants and LegoLand this home does not disappoint. The primary bedroom features an en suite and stackable washer and dryer for your convenience.This property offers tons of natural lighting and

  7904 Waterview Way, Winter Haven, FL 33884
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  /19

  $1,650 Per Month

  • 2 Beds
  • 2 Baths
  • 988 Sq Ft
  • House for Rent

  427 Greenfield Rd, Winter Haven, FL 33884

  This charming two-bedroom, two bathroom situated in a golf community. Located in Cypresswood, a gated community with controlled access and security, this home features an open-concept layout and a kitchen equipped with an island, dishwasher, double-oven range, garbage disposal, and microwave. The primary bedroom boasts a spacious walk-in closet. At the rear of the house, there are two spacious

  Migdalia Moreira PROPERTY OUTLET INTERNATIONAL

  427 Greenfield Rd, Winter Haven, FL 33884
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  $1,300 Per Month

  • 2 Beds
  • 1 Bath
  • 775 Sq Ft
  • Condo for Rent

  5665 Struthers Ct Unit 5667, Winter Haven, FL 33884

  Clean and cozy 2-bedroom, 1-bathroom duplex in southeast Winter Haven. Featuring wood laminate flooring in living areas and bedrooms, with ceramic tile flooring in the kitchen and bathroom. Kitchen equipped with newerKitchen cabinets and comes with range/oven, refrigerator, and washer/dryer hookups in utility closet. Both bedrooms of ample size with ceiling fans. Recently remodeled bathroom with

  5665 Struthers Ct Unit 5667, Winter Haven, FL 33884
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  $2,055 Per Month

  • 3 Beds
  • 2 Baths
  • 1,802 Sq Ft
  • House for Rent

  2066 Katie Ct, Winter Haven, FL 33884

  3/2 in Southeast Winter Haven near Legoland. Big porch, oversized garage. New Roof! Call owner Bob Jessee for showing info.

  Frank Vaughn TOWN & COUNTRY REAL ESTATE

  2066 Katie Ct, Winter Haven, FL 33884
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  /19

  $1,795 Per Month

  • 3 Beds
  • 2 Baths
  • 1,507 Sq Ft
  • House for Rent

  223 Hibiscus St, Winter Haven, FL 33881

  Check out this spacious 3-bedroom, 2-bathroom home featuring a desirable open-concept floor plan! The kitchen offers granite countertops, a center island, stainless steel appliances, and a pantry, providing plenty of space for cooking and entertaining. The home features hardwood flooring throughout the main living areas and brand-new carpet in the bedrooms. Additional features include an inside

  223 Hibiscus St, Winter Haven, FL 33881
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  $2,250 Per Month

  • 4 Beds
  • 2 Baths
  • 1,717 Sq Ft
  • House for Rent

  308 Lake Lucerne Way, Winter Haven, FL 33881

  Experience comfortable living in this spacious and beautifully maintained 4-bedroom, 2-bathroom home with a 2-car garage, ideally located in the heart of Central Florida. Enjoy the convenience of being just minutes from some of the area’s most popular attractions, including LEGOLAND Florida Resort and Peppa Pig Theme Park Florida, making this home perfect for families and professionals seeking

  Leonarda De La Cruz Medina EXP REALTY LLC

  308 Lake Lucerne Way, Winter Haven, FL 33881
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  $1,175 Per Month

  • 1 Bed
  • 1.5 Baths
  • 768 Sq Ft
  • Condo for Rent

  400 El Camino Dr Unit 123, Winter Haven, FL 33884

  1 Bedroom, 1.5 Bath condo located in the 55+ community of San Miguel. Water, Sewer, Trash, and Gas all included in rent. Tenant is responsible for electric. 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

  400 El Camino Dr Unit 123, Winter Haven, FL 33884
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  $1,400 Per Month

  • 2 Beds
  • 2 Baths
  • 1,017 Sq Ft
  • Condo for Rent

  1101 Eagle Pond Dr, Winter Haven, FL 33884

  Affordability meets Comfort. First Floor unit for easy access in a highly desirable gated community of Cypresswood Golf & Country Club. This rental will include access to community pool, 24-hour security, exterior maintenance, common area taxes, trash service, pest control, and private road upkeep. Residents can also enjoy an 18-hole golf course, on-site restaurant, tennis courts, and a fitness

  Lienyvette Grimaldo MAZELG REALTY

  1101 Eagle Pond Dr, Winter Haven, FL 33884
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  $1,850 Per Month

  • 3 Beds
  • 2 Baths
  • 1,429 Sq Ft
  • House for Rent

  332 Cloverdale Rd, Winter Haven, FL 33884

  Welcome home to this inviting 3-bedroom, 2-bathroom residence offering a spacious layout, plenty of natural light, and a large backyard perfect for enjoying the Florida sunshine.Step inside to a bright, open living area featuring vaulted ceilings, tile flooring, and a ceiling fan. The generous floor plan provides plenty of room for both living and dining while sliding glass doors provide

  332 Cloverdale Rd, Winter Haven, FL 33884
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  $1,000 Per Month

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

  301 Avenue B SE Unit 4, Winter Haven, FL 33880

  Cozy 1 bedroom, 1 bathroom unit located on the second floor. Situated in a calm, residential neighborhood near a local school, with convenient access to downtown just minutes away. Approximately 10–15 minutes from Legoland, offering an ideal central location. No pets allowed. First month’s rent and security deposit required. A great option for comfortable and convenient living.

  Lilhana Masis MASIS ROYALTY REAL ESTATE

  301 Avenue B SE Unit 4, Winter Haven, FL 33880
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  $1,950 Per Month

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

  178 Fall Glo Rd, Winter Haven, FL 33880

  Welcome to Squires Grove! This beautiful home features an open-concept layout, ideal for seamless entertaining and family gatherings. The spacious combined family and dining area boasts durable tile and laminate flooring throughout, creating a warm and inviting atmosphere. The kitchen is well-appointed with abundant cabinetry for ample storage, a convenient breakfast bar, and a central

  178 Fall Glo Rd, Winter Haven, FL 33880
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  $1,350 Per Month

  • 2 Beds
  • 1 Bath
  • 826 Sq Ft
  • Condo for Rent

  1100 Martinique Dr Unit 212, Winter Haven, FL 33884

  Beautifully renovated 2/1 in Winter Haven’s Orchid Springs. This community is NOT 55+, although the area is quiet and relaxed. The unit features LVP in the living room, stainless steel appliances, and modern features throughout such as a barn door, black switch plates and black trims in the bedroom area, and black ac vents. The condo is truly a sight to be seen. Water, sewer, trash, and gas ARE

  Alexios McDonald THE K TEAM REAL ESTATE SERVICES LLC

  1100 Martinique Dr Unit 212, Winter Haven, FL 33884
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  $1,600 Per Month

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

  701 Bates Ave SW Unit 204, Winter Haven, FL 33880

  ***BRAND NEW CONSTRUCTION*** Everything is new!! Never lived in 3 bed 1 bath unit. Beautiful kitchen with open eating concept, granite countertops, and stainless steel appliances. The units also come with a stackable washer and dryer included! Great layout with plenty of storage. Your rent also includes your water and trash for convenience and simplicity. Great location near downtown Winter Haven

  701 Bates Ave SW Unit 204, Winter Haven, FL 33880
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  $1,795 Per Month

  • 2 Beds
  • 2.5 Baths
  • 1,425 Sq Ft
  • House for Rent

  2604 Tanoak Terrace, Winter Haven, FL 33881

  Virtually Staged. Stylish & Spacious Townhome Living in Winter Haven | 2 Bed • 2.5 Bath | Modern Comfort ! Welcome home to this beautifully designed 2-bedroom, 2.5-bath townhome located at 2604 Tanoak Ter, Winter Haven, FL 33881—offering the perfect blend of comfort, convenience, and modern living. Step inside to an inviting open-concept layout designed for everyday ease and entertaining. The

  Jacob Hara TRANSCEND REALTY

  2604 Tanoak Terrace, Winter Haven, FL 33881
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  $2,200 Per Month

  • 4 Beds
  • 2.5 Baths
  • 1,874 Sq Ft
  • House for Rent

  1938 Sarah St, Winter Haven, FL 33884

  Be the FIRST to live in this brand new 2025 Lennar-built home, nestled in the growing community of Peace Creek Reserve! This two-story home blends modern finishes with a spacious layout designed for everyday living and comfort. Step into a long foyer that opens to an inviting great room, where the kitchen overlooks the living and dining areas—perfect for gatherings or cozy nights in. Durable

  1938 Sarah St, Winter Haven, FL 33884
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  $2,200 Per Month

  • 3 Beds
  • 3 Baths
  • 1,829 Sq Ft
  • House for Rent

  507 Lake Lulu Dr, Winter Haven, FL 33880

  Welcome home to this spacious 3-bedroom, 3-bath residence in the desirable Lake Lulu area of Winter Haven. With nearly 1,830 square feet of living space, this home offers a versatile layout designed for comfortable everyday living. Inside, you'll find generous living and dining areas filled with natural light, a functional kitchen with ample cabinet space, and spacious bedrooms that provide

  Tiffani Kline HOUSE OF GLASS REAL ESTATE PM

  507 Lake Lulu Dr, Winter Haven, FL 33880
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  $1,300 Per Month

  • 2 Beds
  • 1 Bath
  • 775 Sq Ft
  • Condo for Rent

  5665 Struthers Ct Unit 5667, Winter Haven, FL 33884

  Clean and cozy 2-bedroom, 1-bathroom duplex in southeast Winter Haven. Featuring wood laminate flooring in living areas and bedrooms, with ceramic tile flooring in the kitchen and bathroom. Kitchen equipped with newerKitchen cabinets and comes with range/oven, refrigerator, and washer/dryer hookups in utility closet. Both bedrooms of ample size with ceiling fans. Recently remodeled bathroom with

  5665 Struthers Ct Unit 5667, Winter Haven, FL 33884
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  $1,900 Per Month

  • 3 Beds
  • 2 Baths
  • 1,483 Sq Ft
  • House for Rent

  4973 Kaia Ave, Winter Haven, FL 33884

  Welcome to this brand-new 2025-built home located in the highly desirable Villa Mar community in Winter Haven! Offering 3 bedrooms, 2 full bathrooms, this modern residence combines style, functionality, and comfort in one beautifully designed floor plan. Step inside to an open-concept layout filled with natural light, creating the perfect space for both everyday living and entertaining. The

  Paola Martinez CENTURY 21 MCBRIDE REALTY GROUP

  4973 Kaia Ave, Winter Haven, FL 33884
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  $1,399 Per Month

  • 2 Beds
  • 1 Bath
  • 930 Sq Ft
  • Condo for Rent

  2405 Ave C SW Unit B, Winter Haven, FL 33880

  This adorable duplex is available immediately. This home offers 930 sf with 2BR/1BA with tile and vinyl flooring, no carpet! All stainless steel appliances included in the kitchen, as well as a stacked washer and dryer. Neutral colors throughout and lots of modern finishes.Owner pays for lawn care.

  2405 Ave C SW Unit B, Winter Haven, FL 33880
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  $1,895 Per Month

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

  310 White Ibis Ln, Winter Haven, FL 33884

  Pool & Lawn Care Included!Welcome to this stunning 3-bedroom, 2-bath single-family pool home in the desirable Hart Lake Cove community! Beautifully manicured grounds, plantation shutters, arched doorways, soaring ceilings, and a combination of tile and carpet flooring create a warm and inviting atmosphere.The spacious kitchen features a breakfast bar with ample seating, a pantry,

  Katrina Anarumo RENT A FLORIDA HOME

  310 White Ibis Ln, Winter Haven, FL 33884
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  $1,250 Per Month

  • 2 Beds
  • 2 Baths
  • 942 Sq Ft
  • House for Rent

  345 24th St NW, Winter Haven, FL 33880

  The maintenance free lifestyle can be at your fingertips with this two-bedroom villa. This home is located in a 55 and older community. There are two assigned parking spots, and one is covered! Right out your back door is a beautiful swimming pool. Community approval required.This is a no pet home.Tenants are required to sign up for our Resident Benefits Package that includes

  345 24th St NW, Winter Haven, FL 33880
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  $1,200 Per Month

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

  1804 3rd Ct SE Unit C, Winter Haven, FL 33880

  New renovated 1 bedroom 1 bath corner unit (575sqft). Unit features updated kitchen, bathroom and flooring throughout the space. Washer/Dryer are included. Private driveway. Great location with easy access to near by restaurants, grocery and shopping. Unit will not last long!

  Othner Stfleurose OSF REAL ESTATE SERVICE

  1804 3rd Ct SE Unit C, Winter Haven, FL 33880
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  $1,695 Per Month

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • House for Rent

  98 Surf Dr, Winter Haven, FL 33880

  3 Bedroom 1 Bath, 1,100 sq. ft. with a carportNewly renovatedVinyl planking floorsCustom paintStove, Fridge and dishwasherCeiling fans and blindsWasher Dryer hook upsScreened in patioFenced in backyardThis is a pet friendly home RentSmartUSA• Applications are per adult ($75). Applicant(s) must earn 3x the monthly, have good to average credit,

  98 Surf Dr, Winter Haven, FL 33880
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  $1,575 Per Month

  • 3 Beds
  • 1 Bath
  • 1,075 Sq Ft
  • Townhouse for Rent

  1830 2nd St NW Unit B, Winter Haven, FL 33881

  3 Bedroom, 1 bathroom Duplex Winter Haven! Freshly painted, new flooring on bedrooms. Tile floors throughout living areas. Spacious open kitchen to the living room. Close to shopping and restaurants. Stackable Washer and dryer! Applications will ONLY be processed if you have viewed the inside of the home, submitted all applications and dropped off a holding deposit. We will hold the property for

  Jessica Martinez Cestero HAMPTON & HAMPTON MGMT LEASING

  1830 2nd St NW Unit B, Winter Haven, FL 33881
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  $1,950 Per Month

  • 3 Beds
  • 2 Baths
  • 1,215 Sq Ft
  • House for Rent

  2435 5th St NE, Winter Haven, FL 33881

  Discover comfortable living at 2435 5th St NE, Winter Haven, FL. This spacious 1,215 sq ft single-family home features 3 bedrooms and 2 bathrooms, perfect for families or roommates. Enjoy modern conveniences including air conditioning, dishwasher, disposal, dryer, microwave, linen closet, large closets, pantry, range, refrigerator, vinyl flooring, washer, and window coverings. The property offers

  2435 5th St NE, Winter Haven, FL 33881
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  $1,950 Per Month

  • 4 Beds
  • 3 Baths
  • 2,070 Sq Ft
  • House for Rent

  3035 Buckeye Pointe Dr, Winter Haven, FL 33881

  **OWN THIS POOL HOME WITH A LEASE OPTION!** Move into this spacious 4-bedroom, 3-bath Buckeye Pointe home and enjoy your own private screened-in pool while working toward homeownership!Offering 2,070 sq ft of living space, this home features high ceilings, a spacious and functional layout, fresh modern interior and exterior paint, and plenty of room for the whole family.**LEASE

  Wil Sanders EXP REALTY LLC

  3035 Buckeye Pointe Dr, Winter Haven, FL 33881
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  $1,200 Per Month

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

  750 Ave C SW Unit 101, Winter Haven, FL 33880

  Come take a look at this newly built 1 bedroom 1 bath apartment located near downtown Winter Haven and a stones throw from Lake Howard. This first floor unit comes with great views, and open concept living, washer and dryer included, and so much more. Water and trash included in rental price. Call today to schedule your showing.All Pro X Property Management The Swain Group. LLC

  750 Ave C SW Unit 101, Winter Haven, FL 33880
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  $1,550 Per Month

  • 2 Beds
  • 2 Baths
  • 930 Sq Ft
  • Condo for Rent

  7904 Waterview Way Unit 7904, Winter Haven, FL 33884

  Now Available for rent!!! This beautifully maintained 2 bedroom 2 bath condo is located in the Winterset Gated community in Winter Haven. Conveniently located, a short 5 minute drive to shops, restaurants and LegoLand this home does not disappoint. The primary bedroom features an en suite and stackable washer and dryer for your convenience. This property offers tons of natural lighting and it's

  Shannon Cornell PMI ARRICO REALTY AND PRTP MGT

  7904 Waterview Way Unit 7904, Winter Haven, FL 33884
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  $1,575 Per Month

  • 3 Beds
  • 1 Bath
  • 1,075 Sq Ft
  • House for Rent

  1830 2nd St NW, Winter Haven, FL 33881

  3 Bedroom, 1 bathroom Duplex Winter Haven! Freshly painted, new flooring on bedrooms. Tile floors throughout living areas. Spacious open kitchen to the living room. Close to shopping and restaurants. Stackable Washer and dryer!Applications will ONLY be processed if you have viewed the inside of the home, submitted all applications and dropped off a holding deposit. We will hold the

  1830 2nd St NW, Winter Haven, FL 33881
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  $2,300 Per Month

  • 4 Beds
  • 2.5 Baths
  • 2,123 Sq Ft
  • House for Rent

  2727 San Marco Way, Winter Haven, FL 33884

  This stunning two-story home on San Marco Way delivers the kind of space and style renters fall in love with. The first floor features a private primary suite with an en suite bathroom and a generous walk-in closet, creating a retreat that feels effortlessly upscale. The dedicated downstairs laundry room adds everyday convenience without disrupting the home’s modern flow. Upstairs, a spacious

  Christin Davis PROPERTY MANAGEMENT OF POLK

  2727 San Marco Way, Winter Haven, FL 33884
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  $1,875 Per Month

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

  412 Orange Blossom Dr, Winter Haven, FL 33880

  Welcome to the 2 bed 2.5 bath Lake Front Townhouse, a stunning property located in the heart of Winter Haven, FL. This home boasts two spacious bedrooms and two and a half bathrooms, offering ample space for comfort and relaxation. The property comes with a one-car garage, providing secure parking and additional storage. The townhouse is situated right on the lakefront, offering breathtaking

  412 Orange Blossom Dr, Winter Haven, FL 33880
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  $2,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,965 Sq Ft
  • House for Rent

  232 Lake Lucerne Way, Winter Haven, FL 33881

  Rent this beautiful, pet-friendly home, available September 1st! Enjoy a huge lot directly across from the community pool and mailboxes. The garage features its own mini-split A/C, making it the perfect bonus space, hangout area, home gym, or game room. Plenty of space inside and out to make this home your own!

  Claire Jesso SERHANT

  232 Lake Lucerne Way, Winter Haven, FL 33881
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  $1,950 Per Month

  • 3 Beds
  • 2 Baths
  • 1,900 Sq Ft
  • House for Rent

  1167 Tyler Lp, Winter Haven, FL 33884

  Welcome to your home! This spacious 3-bedroom house, with an additional office space, offers everything you need for comfortable and convenient living.Featuring 2 full bathrooms, ready for professionals working from home, or anyone who values a bit of extra space. The open and inviting layout provides a seamless flow between the living, dining, and kitchen areas, making it perfect for

  1167 Tyler Lp, Winter Haven, FL 33884
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  $1,900 Per Month

  • 3 Beds
  • 2 Baths
  • 1,690 Sq Ft
  • House for Rent

  948 Summer Glen Dr, Winter Haven, FL 33880

  Welcome to this beautifully maintained 3-bedroom, 2-bathroom single-family home in the desirable Coventry Cove community of Winter Haven! Built in 2019, this spacious home offers approximately 1,690 sq. ft. of comfortable living space and features an open-concept floor plan, a modern kitchen with stainless steel appliances, and a covered rear porch—perfect for relaxing or entertaining.

  Ivette Penalver Cancine AXEN REALTY, LLC

  948 Summer Glen Dr, Winter Haven, FL 33880
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  $1,249 Per Month

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

  151 Avenue C SE, Winter Haven, FL 33880

  Move in Special---Discover comfortable living in this charming 2-bedroom, 1-bath apartment spanning 780 sq ft at 151 Avenue C SE, Winter Haven, FL. The unit features modern conveniences including a microwave, range, refrigerator, and washer/dryer hookup, offering both functionality and ease. Enjoy a well-designed layout that maximizes space and natural light, perfect for relaxing or entertaining.

  151 Avenue C SE, Winter Haven, FL 33880
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  $1,845 Per Month

  • 3 Beds
  • 2 Baths
  • 1,464 Sq Ft
  • House for Rent

  4909 Kaia Ave, Winter Haven, FL 33884

  Welcome to this modern 3-bedroom, 2-bath single-family home in the VillaMar community of Winter Haven. This single-story home offers a bright, open-concept floor plan with a spacious living and dining area that flows seamlessly into the kitchen—perfect for everyday living and entertaining. The kitchen features granite countertops, a large center island with seating, ample cabinetry, and

  Michele Saenz NOVA REAL ESTATE SERVICES INC

  4909 Kaia Ave, Winter Haven, FL 33884
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  $1,175 Per Month

  • 1 Bed
  • 1.5 Baths
  • 768 Sq Ft
  • Condo for Rent

  400 El Camino Dr Unit 123, Winter Haven, FL 33884

  1 Bedroom, 1.5 Bath condo located in the 55+ community of San Miguel. Water, Sewer, Trash, and Gas all included in rent. Tenant is responsible for electric. 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

  400 El Camino Dr Unit 123, Winter Haven, FL 33884
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  $2,200 Per Month

  • 5 Beds
  • 2.5 Baths
  • 2,112 Sq Ft
  • House for Rent

  405 Kayden Cove, Winter Haven, FL 33884

  Welcome to 405 Kayden Cove, a beautiful 5-bedroom, 2-bath home located in the desirable Peace Creek Reserve community in Winter Haven! This well-designed single-story floor plan offers a spacious open-concept layout with a comfortable living area, dining space, and a modern kitchen featuring plenty of cabinet storage, a large island, and stainless-steel appliances. The private owner’s suite

  Ashley Porto GLASSTONE GROUP INC

  405 Kayden Cove, Winter Haven, FL 33884
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  $1,550 Per Month

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

  685 Sears Ave NE Unit 4, Winter Haven, FL 33881

  Welcome home to this warm and cozy 3-bedroom, 1-bath half duplex located in a quiet, well-established community. The home has been beautifully remodeled and features an eat-in kitchen with stainless steel appliances, offering both comfort and modern style.Enjoy an ideal location close to great schools, shopping, healthcare, and entertainment, with a 10-minute drive to US Highway 27 for

  685 Sears Ave NE Unit 4, Winter Haven, FL 33881

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