Winter Haven, FL Homes for Rent under $2,800

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  /41

  $1,795 per month

  • 3 Beds
  • 2 Baths
  • 1,269 Sq Ft
  • House for Rent

  3063 Laurel Oak Ln, Winter Haven, FL 33884

  2ND MONTH RENT FREE: Move-In Ready, Pet-Friendly, 2-Car Garage! Available for immediate occupancy! Step into this stunning 2023 Meritage Home in the heart of Winter Haven, Florida—a highly upgraded 3-bedroom, 2-bath single-story home designed to impress. This move-in ready home features neutral tones throughout, a chef-inspired kitchen with stainless steel appliances, quartz countertops, and a

  Katrina Anarumo RENT A FLORIDA HOME

  3063 Laurel Oak Ln, Winter Haven, FL 33884
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  /15

  $2,060 per month

  • 3 Beds
  • 2 Baths
  • 1,821 Sq Ft
  • House for Rent

  5800 Driftwood Dr, Winter Haven, FL 33884

  Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at Coming soon! This home is

  5800 Driftwood Dr, Winter Haven, FL 33884
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  /25

  $1,295 per month

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

  320 Spirit Landings Cir, Winter Haven, FL 33880

  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

  Laura Medina Ruiz RE/MAX HERITAGE PROFESSIONALS

  320 Spirit Landings Cir, Winter Haven, FL 33880
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  /18

  $1,949 per month

  • 3 Beds
  • 2 Baths
  • 1,961 Sq Ft
  • House for Rent

  914 Whisper Lake Dr, Winter Haven, FL 33880

  Coming soon - this home is currently being enjoyed by another resident but will be available soon. This home is professionally managed by Tricon, dedicated to creating exceptional rental experiences. Featuring 3 bedrooms, 2.0 bathrooms, and approximately 1,961 square feet, this well-maintained home offers a high standard of rental living, supported by a team that puts residents first. As a

  914 Whisper Lake Dr, Winter Haven, FL 33880
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  /33

  $2,250 per month

  • 4 Beds
  • 2 Baths
  • 1,811 Sq Ft
  • House for Rent

  5465 San Pietro Dr, Winter Haven, FL 33884

  Be the first to live in this brand new 4 bedroom, 2 bath home located in the highly desirable Villa Mar community in Winter Haven. Featuring 1,811 sq ft of thoughtfully designed living space with an open-concept floor plan, this home is perfect for modern family living or entertaining guests. The spacious kitchen showcases contemporary finishes, ample cabinetry, and an island that flows into the

  Veronica Martinez MY REALTY GROUP, LLC.

  5465 San Pietro Dr, Winter Haven, FL 33884
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  /2

  $1,950 per month

  • 3 Beds
  • 2 Baths
  • 1,672 Sq Ft
  • House for Rent

  175 Grove Branch Rd, Winter Haven, FL 33880

  Property Id: 2402477Welcome Home This gorgeous modern 3 bed 2 bath and 2 car garage is located in beautiful Winter Haven. This is very open and spacious split floor plan. Perfect for entertaining. Kitchen is tastefully designed with espresso brown 42" cabinets and features an island overlooking the family room. Large pantry closet. Master bedroom suite offers a large walk-in closet and an

  175 Grove Branch Rd, Winter Haven, FL 33880
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  /15

  $1,799 per month

  • 3 Beds
  • 2 Baths
  • 1,718 Sq Ft
  • House for Rent

  Unlisted Address

  Take a look at this beautiful home, Clean and Move-In Ready, featuring 3 bedrooms, 2 bathrooms, 2 car garage and approximately 1,718 heated square feet. Enjoy the freedom of a virtually maintenance free lifestyle while residing in a great community. Smart Home Tech - $21.95/mo; Washer/Dryer - $35/mo; High Speed Cable/Internet (if applicable by 3rd Party user) $55/mo; Renters insurance reqrd, Pool

  Cathy Behe TAH FLORIDA LLC

  Unlisted Address
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  /16

  $1,449 per month

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

  3215 Timberline Rd, Winter Haven, FL 33880

  This home is professionally managed by Tricon, dedicated to creating exceptional rental experiences. Featuring 2 bedrooms, 1.0 bathrooms, and approximately 904 square feet, this well-maintained home offers a high standard of rental living, supported by a team that puts residents first. As a Tricon resident, you'll enjoy access to Tricon Vantage — a program designed to support your rental journey.

  3215 Timberline Rd, Winter Haven, FL 33880
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  /26

  $2,390 per month

  • 6 Beds
  • 3 Baths
  • 2,463 Sq Ft
  • House for Rent

  2142 Chris Dr, Winter Haven, FL 33884

  Brand new, never-lived-in house for rent in Winter Haven! Beautiful two-story, brand new, never-lived-in house featuring 6 bedrooms and 3 full bathrooms, ideal for families seeking comfort, space, and modern living. The home offers a modern open-concept layout with spacious, bright interiors. At the entrance, a welcoming porch with a garden adds charm and curb appeal. The main living area

  Jessyka Dos Santos WRA BUSINESS & REAL ESTATE

  2142 Chris Dr, Winter Haven, FL 33884
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  /17

  $1,815 per month

  • 3 Beds
  • 2.5 Baths
  • 1,320 Sq Ft
  • House for Rent

  669 Lake Dexter Cir, Winter Haven, FL 33884

  Beautiful, pet-friendly home coming soon! Apply now, Move-In is available on or after the listed date. Upon approval, $500 reservation deposit to reserve (applied to security deposit and/or refundable). Application fee: $50 per adult. Security Deposit: one month?s rent. Pet fees: $250 + $40/mo per pet. Some homes may include pool ($150/mo), septic ($15/mo), and/or HOA fees; other fees may apply.

  669 Lake Dexter Cir, Winter Haven, FL 33884
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  /11

  $1,100 per month

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

  102 Oak Crest Dr NW Unit 106, Winter Haven, FL 33881

  HALF OFF FIRST MONTHS RENT! 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

  David Small KELLER WILLIAMS REALTY SMART 1

  102 Oak Crest Dr NW Unit 106, Winter Haven, FL 33881
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  /20

  $1,849 per month

  • 3 Beds
  • 2 Baths
  • 1,442 Sq Ft
  • House for Rent

  509 Kensington View Dr, Winter Haven, FL 33880

  Sign in by April 17, Get 4 Weeks Free! Discover spacious homes for rent at Kensington View in Winter Haven, FL. Pet-friendly living with access to Lakeland and Tampa Bay. Professionally managed by ARK Homes.

  509 Kensington View Dr, Winter Haven, FL 33880
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  /16

  $1,100 per month

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

  118 Oak Crest Dr NW, Winter Haven, FL 33881

  HALF OFF FIRST MONTHS RENT! 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

  David Small KELLER WILLIAMS REALTY SMART 1

  118 Oak Crest Dr NW, Winter Haven, FL 33881
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  /7

  $1,800 per month

  • 3 Beds
  • 2 Baths
  • 1,177 Sq Ft
  • House for Rent

  2006 34th St NW, Winter Haven, FL 33881

  Property Id: 2400855This beautifully maintained 3-bedroom, 2-bath home is now available for rent! Originally listed for sale, this property offers exceptional space, accessibility, and flexibility for a variety of living needs.Designed with wheelchair accessibility in mind, the home features wide entryways and a fully accessible bathroom while still maintaining a stylish,

  2006 34th St NW, Winter Haven, FL 33881
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  /22

  $2,030 per month

  • 4 Beds
  • 2 Baths
  • 1,824 Sq Ft
  • House for Rent

  2122 Chris Dr, Winter Haven, FL 33884

  Beautiful brand-new 4-bedroom, 2-bathroom home located in a great area of Winter Haven. The property features a charming front porch, perfect for relaxing. Inside, the home offers a spacious open-concept living room seamlessly connected to the dining area and kitchen, creating a modern and functional layout. Sliding glass doors provide access to a large outdoor area, ideal for entertaining and

  Jessyka Dos Santos WRA BUSINESS & REAL ESTATE

  2122 Chris Dr, Winter Haven, FL 33884
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  /16

  $1,949 per month

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

  1532 Wallace Manor Ave, Winter Haven, FL 33880

  Coming soon - this home is currently being enjoyed by another resident but will be available soon. Pre-lease this home now with Tricon Pre-Lease Guarantee. This home is professionally managed by Tricon, dedicated to creating exceptional rental experiences. Featuring 4 bedrooms, 2.0 bathrooms, and approximately 1,300 square feet, this well-maintained home offers a high standard of rental living,

  1532 Wallace Manor Ave, Winter Haven, FL 33880
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  $2,220 per month

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

  2134 Chris Dr, Winter Haven, FL 33884

  Brand New Two-Story Home for Rent in Winter Haven Welcome to this stunning brand new two-story home located in the heart of Winter Haven, offering the perfect combination of space, style, and convenience. Designed with modern living in mind, this beautiful property is ideal for families or anyone looking for comfort and quality in a prime location. The home features 5 spacious bedrooms, including

  Jessyka Dos Santos WRA BUSINESS & REAL ESTATE

  2134 Chris Dr, Winter Haven, FL 33884
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  /18

  $1,790 per month

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

  637 Sunway Ln, Winter Haven, FL 33880

  Some photos may feature virtual furniture staging, which is intended to help visualize the space and potential designs. The rental home does not come with any furniture shown in the images and these virtual images do not represent actual furnishings. Residents must furnish their own home.Please note that the advertised price may exclude additional fees. These include a $55 application fee per

  637 Sunway Ln, Winter Haven, FL 33880
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  /14

  $1,395 per month

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • Apartment for Rent

  140 Avenue W NW Unit 2, Winter Haven, FL 33881

  One or more photo(s) has been virtually staged. HALF OFF FIRST MONTHS RENT! Spacious rental located in the heart of Winter Haven! This updated unit offers comfortable living with generous room sizes and a functional layout. Conveniently located near shopping, dining, schools, and major roadways, making daily commutes a breeze. Public water and sewer, city utilities, and easy access to everything

  David Small KELLER WILLIAMS REALTY SMART 1

  140 Avenue W NW Unit 2, Winter Haven, FL 33881
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  /19

  $1,935 per month

  • 3 Beds
  • 2 Baths
  • 1,424 Sq Ft
  • House for Rent

  344 Sand Pine Trail, Winter Haven, FL 33880

  Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at This home is priced to rent

  344 Sand Pine Trail, Winter Haven, FL 33880
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  /21

  $2,250 per month

  • 5 Beds
  • 2.5 Baths
  • 2,254 Sq Ft
  • House for Rent

  Unlisted Address

  Located in the Peace Creek Reserve community, this well-maintained home offers modern living with serene pond views. The two-story residence features 5 bedrooms, 2 full bathrooms, and 1 half bath, providing ample space for families or those needing extra room for work or guests. The open-concept main floor includes a spacious living area that flows seamlessly into the dining space and

  Don Tilack EXP REALTY LLC

  Unlisted Address
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  /15

  $2,270 per month

  • 4 Beds
  • 2 Baths
  • 1,938 Sq Ft
  • House for Rent

  159 Southern Breeze Lp, 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

  159 Southern Breeze Lp, Winter Haven, FL 33880
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  /29

  $2,150 per month

  • 4 Beds
  • 3 Baths
  • 2,093 Sq Ft
  • House for Rent

  1192 Normandy Heights Cir, Winter Haven, FL 33880

  Welcome to this beautifully renovated 4-bedroom, 3-bath single-family home located at 1192 Normandy Heights Cir, Winter Haven, FL 33880, just minutes from Lake Shipp. This spacious residence features fresh interior paint, brand-new tile flooring, and thoughtful updates throughout. The open kitchen flows seamlessly into a formal dining area, making it ideal for entertaining. Enjoy ample space with

  Carissa Lawhun FLORIDA REALTY INVESTMENTS

  1192 Normandy Heights Cir, Winter Haven, FL 33880
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  /20

  $2,010 per month

  • 3 Beds
  • 2 Baths
  • 1,723 Sq Ft
  • House for Rent

  104 Lake Daisy Terrace, Winter Haven, FL 33884

  Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at Coming soon! This home is

  104 Lake Daisy Terrace, Winter Haven, FL 33884
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  /27

  $2,150 per month

  • 5 Beds
  • 2.5 Baths
  • 2,326 Sq Ft
  • House for Rent

  1547 Jessica Blvd, Winter Haven, FL 33884

  Stunning New Construction Home for Rent in Winter HavenBe the first to live in this beautiful new construction home located in a desirable Winter Haven neighborhood. Designed with comfort and style in mind, this spacious residence offers a modern open floorplan that is perfect for both everyday living and entertaining.The home features 5 generously sized bedrooms, including a luxurious

  Jessyka Dos Santos WRA BUSINESS & REAL ESTATE

  1547 Jessica Blvd, Winter Haven, FL 33884
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  /17

  $1,770 per month

  • 3 Beds
  • 2 Baths
  • 1,632 Sq Ft
  • House for Rent

  1405 N Lake Shipp Dr SW, Winter Haven, FL 33880

  Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening!Take advantage of the incredible location,

  1405 N Lake Shipp Dr SW, Winter Haven, FL 33880
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  /13

  $1,395 per month

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • Apartment for Rent

  140 Avenue W NW Unit 3, Winter Haven, FL 33881

  One or more photo(s) has been virtually staged. HALF OFF FIRST MONTHS RENT! Spacious rental located in the heart of Winter Haven! This updated unit offers comfortable living with generous room sizes and a functional layout. Conveniently located near shopping, dining, schools, and major roadways, making daily commutes a breeze. Public water and sewer, city utilities, and easy access to everything

  David Small KELLER WILLIAMS REALTY SMART 1

  140 Avenue W NW Unit 3, Winter Haven, FL 33881
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  /17

  $2,400 per month

  • 3 Beds
  • 2 Baths
  • 1,433 Sq Ft
  • House for Rent

  733 Oleander Dr SE, Winter Haven, FL 33880

  Property Id: 2417966Welcome to your own Florida poolside retreat at 733 Oleander Ave in Winter Haven. This beautifully renovated 3-bedroom, 2-bath home is completely turn-key and move-in ready, featuring bright living spaces, modern updates, and a private backyard pool perfect for relaxing or entertaining. Even better, pool and lawn maintenance are included, so you can enjoy the sunshine

  733 Oleander Dr SE, Winter Haven, FL 33880
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  /28

  $2,300 per month

  • 4 Beds
  • 2 Baths
  • 1,696 Sq Ft
  • House for Rent

  263 Sunfish Dr, Winter Haven, FL 33881

  Now available for rent in the Lake Lucerne community—this well-maintained 4-bedroom, 2-bathroom home features a spacious and open floor plan.Newly fenced yard. The kitchen is equipped with granite countertops, stainless steel appliances, and a center island that overlooks the living and dining areas. The primary suite offers a walk-in closet and private bath. Tile flooring is featured in the main

  Leslie Soto HONEST EXPERTS REAL ESTATE LLC

  263 Sunfish Dr, Winter Haven, FL 33881
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  /10

  $1,665 per month

  • 3 Beds
  • 1.5 Baths
  • 1,750 Sq Ft
  • House for Rent

  1333 Stately Oaks Dr NW, Winter Haven, FL 33881

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $1799.95. That covers your base rent, $1665.00 + our required services designed to make your life easier: Internet & Media ($85), Smart Home with

  1333 Stately Oaks Dr NW, Winter Haven, FL 33881
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  /19

  $1,600 per month

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

  1704 Eagle Pond Dr Unit 1704, Winter Haven, FL 33884

  GROUND FLOOR Eagle Pond condominium in the highly desirable gated community of Cypresswood Golf and Country Club. This professionally-managed condominium has just been partially renovated to include luxury vinyl flooring and fresh paint throughout. Key features are interior laundry, walk-in closets, open concept living space, and so much more. The spacious master bedroom features an en suite

  Kayly Malinas JOHN WOOD REALTY, INC.

  1704 Eagle Pond Dr Unit 1704, Winter Haven, FL 33884
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  /18

  $2,015 per month

  • 4 Beds
  • 2.5 Baths
  • 2,203 Sq Ft
  • House for Rent

  2069 Whispering Trails Blvd, Winter Haven, FL 33884

  Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at Coming soon! This home is

  2069 Whispering Trails Blvd, Winter Haven, FL 33884
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  /25

  $1,850 per month

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

  2727 Rutledge Ct, Winter Haven, FL 33884

  For Rent – 2727 Rutledge Court | $1,950/monthMove-in ready and available now! This end-unit townhome offers 2 bedrooms, 2 bathrooms, plus a flexible office/bonus room that can easily serve as a third bedroom, with 1,536 square feet of bright, low-maintenance Florida living.At $1,950 per month, rent includes internet, cable, lawn care, community pool access, a fishing dock, and a beautiful

  Veronica Bard LA ROSA REALTY PRESTIGE

  2727 Rutledge Ct, Winter Haven, FL 33884
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  /16

  $1,925 per month

  • 4 Beds
  • 2 Baths
  • 1,458 Sq Ft
  • House for Rent

  822 Terranova Rd, Winter Haven, FL 33884

  Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at Coming soon! This home is

  822 Terranova Rd, Winter Haven, FL 33884
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  /40

  $1,600 per month

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

  222 7th St NW Unit 2, Winter Haven, FL 33881

  Charming Furnished Cottages for Rent in the Heart of Winter HavenWelcome to Rose Hill Cottages, a thoughtfully restored collection of furnished cottages nestled in a quiet, established neighborhood just minutes from downtown Winter Haven. These cottages offer the perfect blend of charm, comfort, and convenience — ideal for professionals, relocations, extended stays, or anyone seeking a

  Veronica Bard LA ROSA REALTY PRESTIGE

  222 7th St NW Unit 2, Winter Haven, FL 33881
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  /18

  $1,845 per month

  • 3 Beds
  • 2 Baths
  • 1,428 Sq Ft
  • House for Rent

  5711 Lakeside Landings Blvd, Winter Haven, FL 33881

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $1989.90. That covers your base rent, $1845.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  5711 Lakeside Landings Blvd, Winter Haven, FL 33881
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  /16

  $2,495 per month

  • 3 Beds
  • 2 Baths
  • 2,116 Sq Ft
  • House for Rent

  252 Santa Rosa Dr, Winter Haven, FL 33884

  Great location. Perfect place to call home. 3 bedroom 2 bath spa/pool home with garage. Located in gated community-overlook estates. Minutes from lego-land. Home offers a kitchen, dining room and a formal dining room. 3rd bedroom has a Murphy bed and built in desk/office area. Master features french doors leading to the pool &spa. Offers walk in closets throughout home. Mature landscaping. Lots

  Jennifer Geiger PRESTIGE LIFESTYLES REALTY

  252 Santa Rosa Dr, Winter Haven, FL 33884
• 

  

  /15

  $2,600 per month

  • 3 Beds
  • 2 Baths
  • 1,824 Sq Ft
  • House for Rent

  1581 Lemon Ave, Winter Haven, FL 33881

  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

  1581 Lemon Ave, Winter Haven, FL 33881
• 

  

  /12

  $2,000 per month

  • 3 Beds
  • 2 Baths
  • 1,390 Sq Ft
  • House for Rent

  137 Woodland Dr, Winter Haven, FL 33881

  Like-new 3 bedroom, 2 bathroom home with only one previous tenant. No carpet throughout—easy-care flooring in every room. Open and functional layout with modern finishes, well-maintained and move-in ready.

  Mindy Hunley TRIBUTE REALTY LLC

  137 Woodland Dr, Winter Haven, FL 33881
• 

  

  /20

  $2,080 per month

  • 3 Beds
  • 2 Baths
  • 1,871 Sq Ft
  • House for Rent

  819 Reflections Loop E, Winter Haven, FL 33884

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2224.90. That covers your base rent, $2080.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  819 Reflections Loop E, Winter Haven, FL 33884

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