14

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

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  • /8

    $1,695 Per Month

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

    203 N Dillard St Unit 5, Winter Garden, FL 34787

    Property Id: 1701747WALK TO DOWNTOWN HISTORIC WINTER GARDEN! STEPS TO THE HEART OF WG 1 Bedroom WITH LIVING ROOM--SPLIT PLAN DESIGN--(YOU CHOOSE, AS THE SPACE IS THERE), As living room could be 2nd bedroom. MAXIMUM 2 OCCUPANTS PLEASEChoose your set-up and YOUR NEED! 2 ROOMS AT OPPOSITE ENDS OF UNIT/KITCHEN AND BATHROOM DIVIDE IN THE MIDDLE. CUTE HISTORICAL UNIT WITH LOTS OF

    (689) 407-7384

    203 N Dillard St Unit 5, Winter Garden, FL 34787
  • /8

    $1,495 Per Month

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

    203 N Dillard St Unit 4, Winter Garden, FL 34787

    Property Id: 1347362Cute apartment with full size kitchen /bath and all within one block of Downtown Winter Garden. (1) Dedicated on-site parking space. Close to Crooked Can Brewery, WG Farmers market, annual Parade route, houses of worship, grocery shopping, laundrette, and 429 expressway. Hardwood floors and tile in wet areas. Like new refrigerator, compact stove--- Heat and water are

    (689) 407-8490

    203 N Dillard St Unit 4, Winter Garden, FL 34787
  • /20

    $2,351 Per Month

    • 2 Beds
    • 2 Baths
    • 1,192 Sq Ft
    • Condo for Rent

    9223 Vintage Hills Way Unit 5208, Winter Garden, FL 34787

    Landing is a top-rated, fully furnished apartment network with thousands of homes across 250+ U.S. cities. With premium amenities, a mobile app to manage your stay, and 24/7 support. Our apartments have everything you need for monthly and longer stays. 6-Month+ Stay base rent: starts at $2346/mo12-Month+ Stay base rent: starts at $2351/moLanding's apartments at Vintage Horizon

    (415) 466-1384

    9223 Vintage Hills Way Unit 5208, Winter Garden, FL 34787
  • /26

    $1,650 Per Month

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

    80 Windtree Ln Unit J203, Winter Garden, FL 34787

    One or more photo(s) has been virtually staged. AMAZING LOCATION - GREAT PRICE - VERY NICELY UPDATED UNIT! SCREENED IN BALCONY PATIO! 2 Bedroom + 2 Bath condo just 3 minutes from Plant Street in Winter Garden. Kitchen has been beautifully updated and unit has stylish flooring throughout (no carpet). Wonderful split floor plan: the 2 bedrooms are separated by open concept kitchen/ living room

    Brian Lemay ROMAN REALTY GROUP, LLC

    80 Windtree Ln Unit J203, Winter Garden, FL 34787
  • /10

    $1,400 Per Month

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

    8907 Frodsham Way Unit B, Winter Garden, FL 34787

    Property Id: 1351911Utilities Included! Garage Apartment in Winter GardenWelcome home to 8907 Frodsham Way - B. Right in the heart of Winter Garden! Self tours are now available. This charming and cozy garage apartment offers the perfect blend of privacy and convenience ideal for a single professional or college student offering a comfortable, low-maintenance lifestyle.The

    8907 Frodsham Way Unit B, Winter Garden, FL 34787
  • /49

    $1,550 Per Month

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

    1301 Eastern Pecan Place Unit 203, Winter Garden, FL 34787

    Within the gated community of Southern Pines you will enjoy the FLORIDA LIFESTYLE everyday! Soak up the sun by the resort-style pool and spa. What's your pleasure? Enjoy the tennis courts, a volleyball court, or indoor racquetball, basketball courts and full fitness center with a kiddie playroom. The clubhouse feature a media room, theatre room, computer terminals with free internet and then

    Claire Schwartz CLAIRE SCHWARTZ & ASSOCIATES

    1301 Eastern Pecan Place Unit 203, Winter Garden, FL 34787
  • /33

    $1,350

    Total Monthly Price

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

    656 English Lake Dr Unit 2, Winter Garden, FL 34787

    We have an attached and furnished in-law apartment made of one bedroom, living room, one bath, kitchen, laundry in the unit, 550 sq foot. . It has a private entrance and a courtyard. Available from June 1/2026. The rent is $1350 plus 20% of the electric bill. Water, sewer and trash is included in the rent. Small trained dogs are allowed but there is a $500 pet deposit in case of damage. If your

    656 English Lake Dr Unit 2, Winter Garden, FL 34787
  • /23

    $1,995 Per Month

    • 2 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • Condo for Rent

    Unlisted Address

    Prime Location & Resort-Style Living! Welcome home to this beautifully appointed first-floor, 2-bedroom, 2-bath condo in the highly sought-after GATED community of Southern Pines. The desirable open, split floor plan offers both space and privacy, enhanced by wood laminate flooring throughout the living, dining, and kitchen, tile in the baths, and plush carpeted bedrooms. The kitchen features

    Marti Purdy MARTI PURDY PROPERTIES INC

    Unlisted Address
  • /35

    $1,450

    Total Monthly Price

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

    16024 Micelli Dr Unit 1, Winter Garden, FL 34787

    Live in this detached apartment home. RIGHT NEXT TO DISNEY WORLD FLAMINGO CROSSING. Located on the 2nd floor. Would not be connected to anyone else it is a detached apartment feeling like its own house. NO ADMIN FEES!

    16024 Micelli Dr Unit 1, Winter Garden, FL 34787
  • /17

    $1,795 Per Month

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

    233 Southern Pecan Cir Unit 101, Winter Garden, FL 34787

    Welcome to an awesome 2-bedroom, 1-bath condo with an attached garage. Just steps away from the car wash in the beautiful gated community of Southern Pines. The community has a fully equipped state-of-the-art gym, indoor basketball and racquetball courts. BBQ Pavilion for entertaining friends and family with three grills. Pool table and computer room for residents. A theatre with surround sound

    Maria Lloret HOMESMART

    233 Southern Pecan Cir Unit 101, Winter Garden, FL 34787
  • /33

    $1,650 Per Month

    • 2 Beds
    • 2 Baths
    • 1,205 Sq Ft
    • Condo for Rent

    14200 Avalon Rd Unit 431, Winter Garden, FL 34787

    Spacious two-bedroom two full bath condo for rent. Master Bedroom includes private covered patio, walk in closet, stand up shower, and separate bathtub. Large second bedroom with private bathroom and closet. Extended patio with access to the patio from the living room and 2nd bedroom. Washer and dryer in unit. The building features a pool with spa, covered garage, gym, and theater room. The lobby

    14200 Avalon Rd Unit 431, Winter Garden, FL 34787
  • /15

    $2,045 Per Month

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

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

    Beautiful 2-bedroom, 2-bath condo in the desirable Southern Pines community of Winter Garden. This second-floor unit features a bright open floor plan with a spacious living area that flows into a light-filled solarium—ideal for a home office, reading nook, or additional sitting area. The kitchen is centrally located with ample cabinet and counter space, adjacent to a dedicated dining area. The

    Seyed Azimi AFT PROPERTY LLC

    417 Southern Pecan Cir Unit 205, Winter Garden, FL 34787
  • /23

    $2,400 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 recently renovated, bottom floor unit in Southern Pines. Granite counter tops, brand new carpeting, new ceiling fans in bedrooms, brand new appliances in the kitchen. 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,

    Francisco Orchilles LAKESIDE REALTY WINDERMERE INC

    143 Southern Pecan Cir Unit 201, Winter Garden, FL 34787
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    $1,750 Per Month

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

    165 Windtree Ln Unit U, Winter Garden, FL 34787

    Wonderful renovated unit in Windtree Gardens. 2 brm 2 bath, 1st floor unit with screen enclosed front porch. No carpet in unit. Unit has 2 assigned parking spots. 1 small pet OK. Requirements are 600+ credit score and income 2.5 times rent with no evictions on record.

    Cheryl Good ZEAL REALTY

    165 Windtree Ln Unit U, Winter Garden, FL 34787

Rental Home Trends in Winter Garden, FL

Rental Home Trends

Number of Condos for Rent
14
Median Condo Rent
$1,900
Median 1 Bedroom Condo Rent
$1,525
Median 2 Bedroom Condo Rent
$1,882
Median 3 Bedroom Condo Rent
$2,215
How to Rent a Home