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

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  $1,950 Per Month

  • 2 Beds
  • 2 Baths
  • 1,276 Sq Ft
  • Condo for Rent

  1300 Eastern Pecan Place Unit 207, Winter Garden, FL 34787

  Enjoy resort-style living in this spacious second-floor condominium featuring 2 bedrooms, 2 bathrooms, and 1,276 square feet of living space. Located in the gated Southern Pines community, residents have access to an impressive selection of amenities, including a community pool and heated spa, a fitness center, indoor basketball and racquetball courts, a tennis court, a playground, outdoor

  Lauren Foley JULIAN PROPERTIES, INC.

  1300 Eastern Pecan Place Unit 207, Winter Garden, FL 34787
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  $1,850 Per Month

  • 2 Beds
  • 2 Baths
  • 1,276 Sq Ft
  • House for Rent

  200 Southern Pecan Cir, Winter Garden, FL 34787

  Welcome to this beautifully maintained 2-bedroom, 2-bath condominium offering 1,276 square feet of comfortable living space in a gated, resort-style community. The open-concept floor plan features spacious living areas, granite countertops, abundant natural light, and a versatile den—perfect for a home office, study, reading room, or additional flex space.Enjoy low-maintenance living with

  200 Southern Pecan Cir, Winter Garden, FL 34787
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  /20

  $2,375 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,347 Sq Ft
  • Townhouse for Rent

  13269 Daniels Landing Cir, Winter Garden, FL 34787

  Great location in Winter Garden near Target, Ross, Marshall's/Home Goods plaza! Easy access to 429 and Florida's Turnpike. Two story Townhouse. ALL BEDROOMS ARE UPSTAIRS, with tile flooring on the 1st floor, with NEW LVP flooring on the 2nd floor, screened porch and single car garage. Freshly painted, recent remodel of the master shower, clean & crisp ready for immediate occupancy. Gated

  Linda Jaramillo DON ASHER & ASSOCIATES, INC.

  13269 Daniels Landing Cir, Winter Garden, FL 34787
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  $1,495 Per Month

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

  502 Dunbar Ave, Winter Garden, FL 34787

  SPECIAL $300 OFF THE 1ST MO RENT IF YOU SIGN A LEASE BEFORE 8/31SECTION 8 WELCOME! Remodeled 2 Bed/1 Bath with Modern Touches in Winter Garden! Step into the comfort of this delightful 2-bedroom, 1-bath gem nestled in Winter Garden. This recently remodeled residence now boasts modern elegance and a functional design.As you enter, you are greeted by an inviting separate

  502 Dunbar Ave, Winter Garden, FL 34787
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  $1,600 Per Month

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

  16042 Micelli Dr, Winter Garden, FL 34787

  Beautiful corner-lot property for rent in Winter Garden!The property features a separate 1-bedroom, 1-bath apartment (approximately 561 sq. ft.), AVAILABLE IMMEDIATELY for $1,600/month. The apartment has a private entrance, designated access, a washer and dryer, and electricity, water, and internet are included in the rent.Schedule your private showing today!

  Sheyla Fernandez Cardenas MELIN REALTY LLC

  16042 Micelli Dr, Winter Garden, FL 34787
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  $1,495 Per Month

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

  36 Windtree Ln, Winter Garden, FL 34787

  Great location! 2nd floor condo in Winter Garden offers 918 square feet of living space, split floor plan, tile, and two assigned parking spaces. Rental application is $75 per lease holder that will run a credit check, criminal background, and a rental history. We also do verify income, so between the lease holders combined together will have to make three times the monthly rent

  36 Windtree Ln, Winter Garden, FL 34787
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  /20

  $1,600 Per Month

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

  234 Southern Pecan Cir Unit 202, Winter Garden, FL 34787

  Charming 1-bedroom, 1-bathroom apartment with a private 1-car garage, ideally located just minutes from the heart of Downtown Winter Garden. This inviting home features a functional layout, a private garage for convenient parking and additional storage, and an unbeatable location in one of Central Florida's most desirable communities. Enjoy being just minutes from local restaurants, coffee shops,

  Michele Saenz NOVA REAL ESTATE SERVICES INC

  234 Southern Pecan Cir Unit 202, Winter Garden, FL 34787
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  $2,345 Per Month

  • 3 Beds
  • 3 Baths
  • 1,300 Sq Ft
  • Condo for Rent

  1120 Lincoln Terrace Unit B, Winter Garden, FL 34787

  Welcome to this stunning brand-new 3-bedroom, 3-bathroom home, thoughtfully designed with modern finishes and abundant natural light throughout. Featuring tile flooring throughout the entire home, this property offers both style and easy maintenance.The contemporary kitchen is equipped with elegant quartz countertops, white cabinetry, stainless steel appliances, and a gas stove, creating

  1120 Lincoln Terrace Unit B, Winter Garden, FL 34787
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  $2,250 Per Month

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

  1007 Carol Anderson Dr, Winter Garden, FL 34787

  4-bedroom, 2 full-bath home with an extra shower in the laundry room. Move-in ready, clean, and well-maintained. Quiet neighborhood with a large backyard, perfect for family activities and gatherings. Conveniently located near major highways with easy access to Winter Garden and Orlando. Standard screening applies. Call or text your agent for more information.

  Charles Maligaya LA REALTY SERVICES LLC

  1007 Carol Anderson Dr, Winter Garden, FL 34787
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  $1,650 Per Month

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

  108 Windtree Ln Unit Building N, Winter Garden, FL 34787

  Welcome to our available 2BR/2BA, 918 sqft condo, located on the second floor of the Windtree Gardens community in desirable Winter Garden FL. Upon entry, you'll be greeted by the open living space. The kitchen overlooks the living and dining rooms and contains a full suite of appliances including the refrigerator, range, dishwasher, disposal and plenty of cabinet and countertop space. Off to the

  108 Windtree Ln Unit Building N, Winter Garden, FL 34787
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  $1,850 Per Month

  • 2 Beds
  • 2 Baths
  • 1,276 Sq Ft
  • Condo for Rent

  200 Southern Pecan Cir Unit 206, Winter Garden, FL 34787

  Welcome to this beautifully maintained 2-bedroom, 2-bath condominium offering 1,276 square feet of comfortable living space in a gated, resort-style community. The open-concept floor plan features spacious living areas, granite countertops, abundant natural light, and a versatile den—perfect for a home office, study, reading room, or additional flex space.Enjoy low-maintenance living with

  Nicole Howell FANNIE HILLMAN & ASSOCIATES

  200 Southern Pecan Cir Unit 206, Winter Garden, FL 34787
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  $2,450 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,567 Sq Ft
  • Townhouse for Rent

  16311 Lakelet Aly, Winter Garden, FL 34787

  Like new townhome located in one of the most desirable communities in Winter Garden. This cozy 3-bedroom, 2.5-bathroom townhome offers a well-designed layout with the kitchen and living area on the first floor, and all bedrooms on the second floor, providing comfort and privacy. Enjoy maintenance-free living no need to worry about lawn care or exterior upkeep while still being surrounded by

  16311 Lakelet Aly, Winter Garden, FL 34787
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  $2,200 Per Month

  • 2 Beds
  • 2 Baths
  • 1,264 Sq Ft
  • Condo for Rent

  225 Southern Pecan Cir Unit 205, Winter Garden, FL 34787

  Hurry, this desirable Winter Garden condo will not last.... What a wonderful place to call home. The largest two bedroom with bonus room, two bath end unit with a private entry is a dream come true! This unit comes with a 1 car garage which is rare!! As you look from your second floor out the green space area that is footsteps to the community pool and clubhouse, expect to be impressed. If sand

  Sharon O'malley MBA REALTY GROUP, INC

  225 Southern Pecan Cir Unit 205, Winter Garden, FL 34787
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  $2,399 Per Month

  • 3 Beds
  • 2 Baths
  • 1,260 Sq Ft
  • House for Rent

  1938 Sherbourne St, Winter Garden, FL 34787

  Discover the enchantment of living in this delightful 3-bedroom, 2-bathroom home nestled in the heart of Winter Garden. This residence is a perfect blend of comfort and style, featuring a welcoming family/dining room combo that boasts exquisite wooden flooring throughout, creating a warm and inviting atmosphere for both entertaining and relaxation.The heart of the home, the kitchen, is

  1938 Sherbourne St, Winter Garden, FL 34787
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  $2,500 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,814 Sq Ft
  • Property for Rent

  9825 Clear Cloud Aly, Winter Garden, FL 34787

  Beautiful end unit, located in a gorgeous community of Waterleigh in Winter Garden. This townhome has 3 bedrooms, 2.5 bathrooms, bonus loft area, fully screened-in patio and a one car garage. The community offers walking trails, huge clubhouse with a pool and gym, tennis courts, fishing pier, and numerous playgrounds,

  Suzanne Seenandan PREFERRED RE BROKERS III

  9825 Clear Cloud Aly, Winter Garden, FL 34787
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  $1,830 Per Month

  • 2 Beds
  • 2 Baths
  • 1,276 Sq Ft
  • Condo for Rent

  200 Southern Pecan Cir Unit 203, Winter Garden, FL 34787

  Welcome home to this bright and spacious 2-bedroom, 2-bath condominium in the desirable gated Southern Pines community. This second-floor residence offers approximately 1,276 square feet of comfortable living space with an open-concept floor plan, abundant natural light, and a functional split-bedroom layout that provides added privacy.The well-appointed kitchen features granite

  Hans Tank FLORIDA SCANDI REALTY LLC

  200 Southern Pecan Cir Unit 203, Winter Garden, FL 34787
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  $1,800 Per Month

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

  341 Southern Pecan Cir Unit 201, Winter Garden, FL 34787

  Your lifestyle deserves the right address!! and this one puts you in the heart of WINTER GARDEN. If you're a busy professional looking for a home that combines privacy, convenience, comfort, and location. This inviting one-bedroom apartment offers the kind of low-maintenance lifestyle that makes coming home easy, with the added convenience of your own private garage-a valuable feature for

  Elizabeth Rodriguez Bello La Rosa Realty Llc

  341 Southern Pecan Cir Unit 201, Winter Garden, FL 34787
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  /22

  $2,000 Per Month

  • 3 Beds
  • 1 Bath
  • 814 Sq Ft
  • House for Rent

  1105 Lincoln Terrace, Winter Garden, FL 34787

  Beautifully updated 3-bedroom, 1-bathroom single-family home located in the desirable Winter Garden area. This move-in ready home offers 814 sq. ft. of living space and features a brand-new roof, newer A/C, fresh interior and exterior paint, a fully remodeled kitchen with a new refrigerator, and a beautifully remodeled bathroom. The single-story layout provides comfortable and functional living

  Simone Pinto de Almeida Santos NOVA REAL ESTATE SERVICES INC

  1105 Lincoln Terrace, Winter Garden, FL 34787
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  $2,500 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,624 Sq Ft
  • Townhouse for Rent

  16097 Pebble Bluff Loop, Winter Garden, FL 34787

  3 Bedroom, 2 Baths Town Home For Rent in Winter Garden, Fl. 34787. Range, Refrigerator, D/W, Disposal, Central Heat and A/C.

  Rick Sein REALSOURCE PROPERTY MANGNT LLC

  16097 Pebble Bluff Loop, Winter Garden, FL 34787
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  $1,950 Per Month

  • 2 Beds
  • 2 Baths
  • 1,264 Sq Ft
  • Condo for Rent

  417 Southern Pecan Cir Unit 204, Winter Garden, FL 34787

  Stunning second floor 2B/2B located on the beautiful Southern Pines , This Unit is in move in ready conditions, featuring Laminate Flooring throughout all living area and Tile on wet areas such as Kitchen and Bathrooms, near major shopping areas and major roadways.

  Alejandro Hernandez HP PROPERTY SOLUTIONS, LLC

  417 Southern Pecan Cir Unit 204, Winter Garden, FL 34787
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  $1,500 Per Month

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

  430 Southern Pecan Cir Unit 203, Winter Garden, FL 34787

  Beautiful 1 bedroom 1 bath condo on second floor in gated community of Southern Pines. Features additional office/solarium room. Open floor plan concept with carpeted living areas and tiled wet areas. Kitchen and bathroom both have granite counter tops. Master bedroom with walk in closet. Community features pool, tennis, basketball, fitness room, playground and more. Great location close to

  Nicholas Horton BANNER INT'L REAL ESTATE

  430 Southern Pecan Cir Unit 203, Winter Garden, FL 34787
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  $1,600 Per Month

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

  15347 Gilligan Ct, Winter Garden, FL 34787

  This is an in-law on the top of the garage, ready to move in. The apartment is brand new and Electricity and water. Ready to move in.

  Chanel Munoz MOSAIC PARTNERS GROUP

  15347 Gilligan Ct, Winter Garden, FL 34787
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  $2,500 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,518 Sq Ft
  • Townhouse for Rent

  11019 Bookmark Ln, Winter Garden, FL 34787

  Discover the charm of this elegant townhouse in Storey Grove, located in the prestigious Horizon West area of Winter Garden. This inviting home boasts 3 bedrooms and 2.5 baths. The gourmet kitchen features sleek stainless steel appliances, stunning granite countertops with a spacious island, and an open-concept layout with high ceilings. Enjoy the privacy of your fenced-in patio and the

  Luis Talavera CENTURY 21 CARIOTI

  11019 Bookmark Ln, Winter Garden, FL 34787
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  /20

  $1,900 Per Month

  • 2 Beds
  • 2 Baths
  • 1,216 Sq Ft
  • Condo for Rent

  1432 Broken Oak Dr Unit 31A, Winter Garden, FL 34787

  Will be available to show on 7/19/2026. Located in the City of Winter Garden, this move in ready, maintenance free 2/2 Condo with attached garage is in the sought after Tucker Oaks neighborhood. Location is key, and living in this West Orange County community puts you near the heart of everything! This 2/2 features a split plan, fridge, microwave, oven, washer, and dryer. Master features an

  Dan Thompson OPTIMA ONE REALTY, INC.

  1432 Broken Oak Dr Unit 31A, Winter Garden, FL 34787
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  $1,675 Per Month

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

  502 Varsity St, Winter Garden, FL 34787

  Location, location, location! Hip patio villas situated on a quiet oak lined street featuring tile flooring throughout, granite counter tops. Huge rear yard with open brick patio & two parking pads. All located within close proximity of the picturesque historic downtown Winter Garden. Wonderful cafes, restaurants, theatre and the new Plant Street market and Crooked Can Brewing Company. AMAZING!!

  Angela Chapman CAPITAL REALTY GROUP FLORIDA

  502 Varsity St, Winter Garden, FL 34787
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  $1,650 Per Month

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

  92 Windtree Ln Unit L, Winter Garden, FL 34787

  CONDO FOR RENT IN WINTER GARDEN 2/2 SECOND FLOOR, ASSIGN 2 PARKINGS, ALLOW SMALL PETS,ALL APLIANCES INCLUDED, THE COMMUNITY HAVE A SWIMMING POOL AND BASKETBALL COURT, CLOSE TO MAYORS ROADS, SHOPPING CENTRS, HOSPITALS, RESTAURANTS , SCHOOLS AND MUCH MORE. IS AVAILABLE FOR OCTOBER.

  maria perez ROMAN'S PRO REALTY LLC

  92 Windtree Ln Unit L, Winter Garden, FL 34787
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  $1,595 Per Month

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

  Unlisted Address

  Move-in ready one-bedroom, one bath corner unit with an attached one-car garage in a private setting. Offering 738 sq ft. of comfortable living space. This unique home is situated above the garage, with no shared Living room, bedroom, kitchen, or bathroom walls with neighbors. Features include an in-unit Laundy closet, water, cable, and internet. Available for immediate occupancy once approved by

  Maria Lloret HOMESMART

  Unlisted Address
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  $1,695 Per Month

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

  430 Southern Pecan Cir Unit 106, Winter Garden, FL 34787

  New upgrades at move in:- All carpets to be replaced with LVP. Refer to sample picture that shows how the new floors will look.- All appliances to be upgraded to new Stainless Steel- Bathroom faucet to be replacedAmazing opportunity in the resort-style Southern Pines Condos in Winter Garden! Freshly painted 1-bedroom, 1-bath condo, ready for move-in. All new LVP flooring

  Seyed Azimi AFT PROPERTY LLC

  430 Southern Pecan Cir Unit 106, Winter Garden, FL 34787
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  /15

  $1,895 Per Month

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

  407 Douglas Way Unit 66, Winter Garden, FL 34787

  Welcome home to this beautiful 2-bedroom, 2-bathroom residence in the highly desirable Winter Garden area! This inviting home features a bright and open floor plan, spacious living areas, and comfortable bedrooms designed for easy everyday living. Enjoy a low-maintenance lifestyle with community-maintained exterior and grounds, giving you more time to relax and take advantage of the community

  Justin V LaManna HOMEVEST REALTY

  407 Douglas Way Unit 66, Winter Garden, FL 34787
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  $2,295 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,647 Sq Ft
  • Townhouse for Rent

  218 Winter Nellis Cir, Winter Garden, FL 34787

  AVAILABLE NOW!Beautiful and Spacious Townhouse located between Downtown Winter Garden and Winter Garden Village Mall in gated community of The Orchard.Middle unit, with no rear neighbors, natural wooded view in back with a retention pond. NEW interior paint throughout! Kitchen offers beautiful cherry wood cabinets, Refrigerator, Microwave, Cooktop, Oven, and Dishwasher. Half

  Vicky Ramos ALL COUNTY CFL PROPERTY MGMT

  218 Winter Nellis Cir, Winter Garden, FL 34787
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  $2,200 Per Month

  • 3 Beds
  • 2 Baths
  • 1,453 Sq Ft
  • Condo for Rent

  143 Southern Pecan Cir Unit 201, Winter Garden, FL 34787

  Awesome opportunity to live in a 3 bedroom 2 bath, 2nd floor unit in Southern Pines. Close to the Winter Garden Village and major highways. Condominium has a community pool, tennis court, racquetball court, fitness center, hot tub, computer room, clubhouse, basketball court, volleyball court, bar-b-que area, and playground. Lease period must be for 12 months no exceptions. New A/C and Water

  Francisco Orchilles LAKESIDE REALTY WINDERMERE INC

  143 Southern Pecan Cir Unit 201, Winter Garden, FL 34787

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