340

Winter Garden, FL Homes for Rent under $2,000

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  • /101

    Starting at $1,699 Per Month

    • 1 - 3 Beds

    1223 E Plant St, Winter Garden, FL 34787

    Welcome to Vida Winter Garden, where modern living meets timeless charm. Nestled in the vibrant Gateway District of Winter Garden, our community offers a unique blend of luxury, convenience, and small-town warmth. With thoughtfully designed apartments, resort-style amenities, and easy access to local attractions, Vida Winter Garden is more than just a place to live—it's a place to thrive. Whether

    Vida Winter Garden

    1223 E Plant St, Winter Garden, FL 34787
  • /55

    Starting at $1,499 Per Month

    • 1 - 3 Beds

    17825 Avalon Grove Loop, Winter Garden, FL 34787

    Experience the pinnacle of modern living at Integra Avalon, where every apartment blends sophistication and elegance. Nestled in the serene Four Corners Winter Garden, Florida, Integra Avalon embodies a refined lifestyle enhanced by premium amenities, state-of-the-art facilities, and a vibrant community atmosphere. Indulge in an unparalleled living experience where comfort and luxury seamlessly

    Integra Avalon

    17825 Avalon Grove Loop, Winter Garden, FL 34787
  • /24

    Starting at $1,646

    Total Monthly Price

    • 1 - 2 Beds

    16810 Easthampstead Rd, Winter Garden, FL 34787

    Welcome home to Prose Horizons Village, a brand-new multifamily community located in Winter Garden, FL. Our spacious one and two-bedroom apartment homes feature modern stainless steel appliances, walk-in closets, dining-sized kitchen islands, premium plank flooring throughout, and full-sized washers and dryers in every apartment home. With convenient, must-have amenities like a fitness center,

    Prose Horizons Village

    16810 Easthampstead Rd, Winter Garden, FL 34787
  • /52

    Starting at $1,535

    Total Monthly Price

    • Studio - 2 Beds

    7000 Kiran Patel Dr, Winter Garden, FL 34787

    Apollo boast four stunning buildings that usher in a variety of iving spaces, including spacious studios, stylish one-bedroom, and comfortable two-bedroom apartments. Discover elegant kitchen islands, oversized windows that fill your space with natural light, and modern fixtures that add a touch of sophistication to every room.

    Apollo Apartments

    7000 Kiran Patel Dr, Winter Garden, FL 34787
  • /45

    Starting at $1,557 Per Month

    • 1 - 3 Beds

    10091 Tuller Loop, Winter Garden, FL 34787

    Step into a world of luxury at Halston Waterleigh, an upscale community in Winter Garden, Florida. Experience exquisite design, abundant natural light, advanced technology, and endless comfort in your new home. Enjoy a vacation-like atmosphere daily with our heated saltwater pool, expansive fitness center, and a variety of additional top-tier amenities. Schedule your personal tour today and

    Halston Waterleigh

    10091 Tuller Loop, Winter Garden, FL 34787
  • /13

    Starting at $1,563

    Total Monthly Price

    • 1 - 2 Beds

    14505 Tristan Cir, Winter Garden, FL 34787

    Welcome home to Prose Avalon Pointe, Orlando's newest multifamily community. Our spacious one- and two-bedroom apartments for rent in Winter Garden, FL, feature modern stainless steel appliances, walk-in closets, dining-sized kitchen islands, hardwood flooring throughout and full-sized washer and dryers in every apartment home. And with convenient, must have amenities like a fitness center,

    Prose Avalon Pointe

    14505 Tristan Cir, Winter Garden, FL 34787
  • /50

    Starting at $1,569 Per Month

    • 1 - 3 Beds

    14520 Avalon Rd, Winter Garden, FL 34787

    Welcome home to Registry on Grass Lake, our brand-new apartment community that prioritizes a connection to comfort & convenience through designer touches and thorough consideration of your needs. Enjoy your own space with our studio, one-, two-, and three-bedroom floor plans all thoughtfully curated to bring you the best of apartment living. Within Registry on Grass Lake, you'll find amenities

    Registry on Grass Lake

    14520 Avalon Rd, Winter Garden, FL 34787
  • /25

    Starting at $1,625

    Total Monthly Price

    • 1 - 3 Beds

    14619 Casita Ridge, Winter Garden, FL 34787

    IMT Sonoma Hills’ stunning one, two and three-bedroom apartments will take your breath away with a new level of luxury for West Orlando. Inside each home are five-star features and amenities, including spacious walk-in closets, gourmet kitchens with granite countertops, soaring ten-foot ceilings and sophisticated designer finishes. Start a tour of IMT Sonoma Hills and it won’t take long to

    IMT Sonoma Hills

    14619 Casita Ridge, Winter Garden, FL 34787
  • /30

    Starting at $1,638 Per Month

    • 1 - 3 Beds

    9405 Ascend Falls Dr, Winter Garden, FL 34787

    Welcome to Birchstone Waterleigh, where luxury meets tranquility in the heart of Winter Garden, FL. Designed for those who seek the extraordinary, our community offers an elevated living experience with refined interiors, resort-inspired amenities, and thoughtfully curated experiences. From impeccably crafted apartments to exclusive social spaces, every detail embodies sophistication and

    Birchstone Waterleigh

    9405 Ascend Falls Dr, Winter Garden, FL 34787
  • /96

    Starting at $1,605 Per Month

    • 1 - 3 Beds

    16200 Ascend Village Ln, Winter Garden, FL 34787

    Retreat to a life of ultimate luxury at Ascend Waterleigh Village, a brand-new community offering one, two, and three bedroom apartments in a beautiful lakeside neighborhood. Our open floor plans offer the perfect mix of form and function, with features ranging from modern kitchens with stainless steel appliances and prep islands to spacious bedrooms with oversized walk-in closets. As a resident,

    Ascend Waterleigh Village

    16200 Ascend Village Ln, Winter Garden, FL 34787
  • /23

    Starting at $1,805

    Total Monthly Price

    • 1 - 3 Beds

    15000 Stratus Loop, Winter Garden, FL 34787

    Take the next step in life at Corban Horizon West. A place that draws inspiration from the warmth of the neighborhood and the endless possibilities that surround it, our homes offer a refreshing experience guaranteed to exceed your expectations for modern living. Timeless yet contemporary. Comfortable yet connected. Our residences are a wonderful blend of tasteful design, thoughtful amenities and

    Corban Horizon West

    15000 Stratus Loop, Winter Garden, FL 34787
  • /40

    Starting at $1,579 Per Month

    • 1 - 3 Beds

    9005 Solay Rd, Winter Garden, FL 34787

    Enjoy UP TO 2 MONTHS FREE on Select Homes! Live like you're on vacation every day at our brand new community, offering spacious apartments and the largest amenity offering in the area. With a dedicated onsite team, we are committed to providing exceptional customer service. Call or come by today!

    Solay Horizon West

    9005 Solay Rd, Winter Garden, FL 34787
  • /47

    Starting at $1,838

    Total Monthly Price

    • 1 - 3 Beds

    15100 Free Range Run, Winter Garden, FL 34787

    There’s no place like Home(stead). Inspired by nature’s bounty, our thoughtfully designed one, two, and three-bedroom apartment residences blend perfect neutral tones and ample natural light to create spaces that help you discover the joy of simply being.

    Homestead at Hamlin

    15100 Free Range Run, Winter Garden, FL 34787
  • /75

    Starting at $1,675

    Total Monthly Price

    • 1 - 3 Beds

    8200 Jayme Dr, Winter Garden, FL 34787

    So close yet a world away. Windermere Cay, the premier luxury and 100% Smoke-Free community is NOW OPEN! We are conveniently located on Reams Road, adjacent to Walt Disney World, just minutes from Orlando International airport, area theme parks, Winter Garden Village, Millenia Mall, and much more. Our four-story buildings offer elevators, high-end details, finishes, and an exclusive resident

    Windermere Cay

    8200 Jayme Dr, Winter Garden, FL 34787
  • /35

    Starting at $1,499

    Total Monthly Price

    • 2 Beds

    521 S Park Ave, Winter Garden, FL 34787

    Garden City Apartments is nestled in the heart of Downtown Winter Garden, Florida. Within walking distance or a quick golf cart ride to Historic Plant Street, life is full of excitement with local arts and entertainment, trails and restaurants galore you will surely feel at home and safe living in our newly renovated industrial designed family-friendly apartments. We have a mix between

    Garden City Apartments

    521 S Park Ave, Winter Garden, FL 34787
  • /50

    Starting at $1,830 Per Month

    • 1 - 3 Beds

    14012 Shoreside Way, Winter Garden, FL 34787

    Warm lake breezes and sunshine define the luxe lakeside lifestyle of the Lakewalk apartment residences that will wrap the shoreline of Lake Hancock next to the Town Center’s shopping, dining and entertainment. We offer 1 bedroom, 2 bedroom, and 3 bedroom apartment homes with the most up-to-date luxurious furnishings. If you are looking for relaxing, luxury living, look no further than Lakewalk at

    Lakewalk at Hamlin

    14012 Shoreside Way, Winter Garden, FL 34787
  • /50

    Starting at $1,711

    Total Monthly Price

    • 1 - 3 Beds

    6151 Lake Lodge Dr, Winter Garden, FL 34787

    It’s human nature to want everything at your fingertips. It’s rare to find it. Tucked between the water, sunshine, and cypress trees, discover The Lodge at Hamlin. With nature surrounding you at home and a lakefront village at your doorstep, your hunt for the perfect lifestyle begins and ends here.

    The Lodge at Hamlin

    6151 Lake Lodge Dr, Winter Garden, FL 34787
  • /23

    Starting at $1,460 Per Month

    • 1 - 3 Beds

    1301 Inland Seas Blvd, Winter Garden, FL 34787

    Inland Seas Apartments

    1301 Inland Seas Blvd, Winter Garden, FL 34787
  • /21

    Starting at $1,514

    Total Monthly Price

    • 1 - 3 Beds

    15122 W Colonial Dr, Winter Garden, FL 34787

    Learn more about our current specials! Stylish design at a price that's right! Country Gardens Apartment Homes is located in Winter Garden, Florida, with easy access to Florida's Turnpike and SR-50/Colonial Drive. You'll experience a top selection of amenities and features at this community, like a resort-style pool with sundeck,

    Country Gardens

    15122 W Colonial Dr, Winter Garden, FL 34787
  • /24

    Starting at $1,539 Per Month

    • Studio - 3 Beds

    14680 Westerly Dr, Winter Garden, FL 34787

    Luxury apartment living has never been easier than in your dream apartment home at The Westerly Apartments in Horizon West. Offering pet-friendly homes with modern interiors, abundant amenity spaces and an unparalleled location near Orlando's theme parks.With exceptional craftsmanship and attention to detail, our rentals offer a variety of studio, one, two, and three-bedroom layout to meet your

    The Westerly

    14680 Westerly Dr, Winter Garden, FL 34787
  • /5

    $1,295 Per Month

    • 1 Bed
    • 1 Bath
    • House for Rent

    203 N Dillard St, Winter Garden, FL 34787

    Property Id: 1041843Cute STUDIO apartment with full size kitchen and full size 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. Shower-no tub. Like new

    203 N Dillard St, Winter Garden, FL 34787
  • /6

    $1,690 Per Month

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

    14978 Lebeau Loop, Winter Garden, FL 34787

    Apartment for rent: one bedroom, one bathroom, with all utilities included. The apartment is above the property’s garage, fully furnished, and has a separate entrance. Only 6 minutes from Disney

    christian dellolio AGENT TRUST REALTY CORPORATION

    14978 Lebeau Loop, Winter Garden, FL 34787
  • /6

    $1,480 Per Month

    • 1 Bed
    • 1 Bath
    • 1 bedroom 1 bathroom condo w/DEN

    405 Southern Pecan Cir, Winter Garden, FL 34787

    1 Bed 1 Bath Condo located in Southern Pines gated community in Winter Garden. All appliances included access to GYM, community pool and amenities

    405 Southern Pecan Cir, Winter Garden, FL 34787
  • /20

    $1,850 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,144 Sq Ft
    • Townhouse for Rent

    1257 Winter Green Way, Winter Garden, FL 34787

    Welcome to this extremely spacious 2-bedroom, 1 full-bathroom and 1 half-bath townhome, offering modern updates and a peaceful retreat in a quiet community. Step inside to find a bright and open floor plan with stylish finishes throughout. The fully updated kitchen features new cabinetry, sleek countertops, and stainless-steel appliances, making it a dream for cooking and entertaining. Enjoy the

    Prentice Williams KELLER WILLIAMS ADVANTAGE REALTY

    1257 Winter Green Way, Winter Garden, FL 34787
  • /6

    $2,000 Per Month

    • 2 Beds
    • 2 Baths
    • 2 bedroom 2 bathroom condo ONE CAR GARAGE

    130 Southern Pecan Cir, Winter Garden, FL 34787

    Great 2 bedroom 2 bathroom condo with new flooring and a 1 car garage. Gated community Southern Pines, access to GYM and community pool.

    130 Southern Pecan Cir, Winter Garden, FL 34787
  • /19

    $1,750 Per Month

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

    417 Southern Pecan Cir Unit 207, Winter Garden, FL 34787

    Ready to move-in One-bedroom, one Jack-n-Jill bath. Fully renovated with fresh paint from top to bottom. Luxury Vinyl floors from stairs thru out the unit. the Bathroom has ceramic tile. The unit features a study/den perfect if you have a home office or need a craft room.

    Maria Lloret HOMESMART

    417 Southern Pecan Cir Unit 207, Winter Garden, FL 34787
  • /21

    $1,750 Per Month

    • 2 Beds
    • 2 Baths
    • 1,203 Sq Ft
    • Condo for Rent

    302 Avalon Rd Unit 302, Winter Garden, FL 34787

    This generously sized condo offers a perfect blend of comfort, convenience, and resort-style amenities. Featuring two large bedrooms and two full bathrooms, this unit is ideal for those seeking space, privacy, and modern living.The primary suite includes its own private, covered patio, perfect for enjoying quiet mornings or relaxing evenings. Inside, you'll find a walk-in closet, a

    302 Avalon Rd Unit 302, Winter Garden, FL 34787
  • /7

    $675 Per Month

    • 1 Bed
    • 1 Bath
    • 1,000 Sq Ft
    • House for Rent

    15267 Honeybell Dr, Winter Garden, FL 34787

    Welcome to this One Bedroom in a great location with access to everything Winter Garden has. Near theme parks, shopping centers, banks, hospitals, and a lot of entertainment. Rent includes Water, Electricity and Internet, and kitchen access. Schedule your appointment today!

    Maykol Romo VESTI LLC

    15267 Honeybell Dr, Winter Garden, FL 34787
  • /18

    $1,700 Per Month

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

    165 Windtree Ln, Winter Garden, FL 34787

    Wonderful Windtree Gardens! Renovated 2 brm 2 bath 1st floor unit with screen enclosed balcony. No carpet in unit. Unit has 2 assigned parking spots, washer /dryer. Close to bus lines, shopping & restaurants. Requirements are 600+ credit score and income 2.5 times rent with no evictions on record. Application fee $75 per adult and security deposit = to 1 months rent. Applications can be made

    165 Windtree Ln, Winter Garden, FL 34787
  • /22

    $1,890 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 countertops,

    Hans Tank FLORIDA SCANDI REALTY LLC

    200 Southern Pecan Cir Unit 203, Winter Garden, FL 34787
  • /16

    $1,520 Per Month

    • 2 Beds
    • 2 Baths
    • 918 Sq Ft
    • Great location! 2nd floor condo in Winter Garden

    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
  • /18

    $2,000 Per Month

    • 3 Beds
    • 2 Baths
    • 984 Sq Ft
    • Townhouse for Rent

    1000 Dolphin Dr, Winter Garden, FL 34787

    Enjoy living in this beautiful 3-bedroom, 2-bath home featuring a spacious fenced backyard and situated on a desirable corner lot. The modern kitchen offers elegant quartz countertops, perfect for cooking and entertaining. Conveniently located just 5 minutes from Downtown Winter Garden, you’ll love being close to great schools, restaurants, shopping, farmers markets, and plenty of activities

    Gian Balsamo LA ROSA REALTY KISSIMMEE

    1000 Dolphin Dr, Winter Garden, FL 34787
  • /12

    $1,900 Per Month

    • 2 Beds
    • 2 Baths
    • 1,276 Sq Ft
    • Southern Pines 2 bedroom 2 bath

    330 Southern Pecan Cir, Winter Garden, FL 34787

    LARGEST 2 BEDROOM CONDO WITH A SOLARIUM IN SOUTHERN PINES!!UPGRADED WITH GRANITE COUNTER TOPS, 9' CEILINGS, CROWN MOLDING & DECORATOR PAINT IN NEUTRAL COLOR. Amenities galore include pool/spa, tennis, volleyball, picnic area, car wash area, indoor racquetball, basketball, fitness & play area for the kids plus a clubhouse with a theater room, billiards and computer. Rent includes water/sewer and

    330 Southern Pecan Cir, Winter Garden, FL 34787
  • /13

    $2,000 Per Month

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

    304 Southern Pecan Cir Unit 208, Winter Garden, FL 34787

    For rent: Spacious 2-bedroom, 2-bath, fully renovated corner unit 1264 sq.ft. Featuring fresh paint, modern vinyl flooring, and a peaceful wooded view. Located in a resort-style subdivision with top-notch amenities: indoor basketball and racquet ball courts, a full gym, and a barbecue pavilion. Available now for a quick move-in.

    Maria Lloret HOMESMART

    304 Southern Pecan Cir Unit 208, Winter Garden, FL 34787
  • /51

    $1,995 Per Month

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

    1300 Eastern Pecan Place, Winter Garden, FL 34787

    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

    1300 Eastern Pecan Place, 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
  • /16

    $1,450 Per Month

    • 2 Beds
    • 2 Baths
    • 918 Sq Ft
    • Great location! 2nd floor condo in Winter Garden

    88 Windtree Ln, Winter Garden, FL 34787

    Great location! 2nd floor condo in Winter Garden offers 918 square feet of living space, split floor plan, screened in patio, and two assigned parking spaces.Lessee(s) are required to provide proof of liability insurance in the amount of $100,000, prior to occupancy. Real Property Management South Orlando can provide the required coverage for an additional charge of $13.00 per month or

    88 Windtree Ln, Winter Garden, FL 34787
  • /11

    $1,600 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
  • /25

    $1,600 Per Month

    • 1 Bed
    • 1 Bath
    • 1,000 Sq Ft
    • House for Rent

    17102 Heartwood Loop, Winter Garden, FL 34787

    First floor 1 bedroom suite. Clean and spacious 1 bedroom, 1 bathroom, with seperate entrance, laundry shared. Unfurnished or can be furnished. Long or short term rental, This house sits on a huge lot with beautiful sunrise and sunset views. . parking spot on driveway.This apt is on the first floor, parking available

    Bibi Khan CHARLES RUTENBERG REALTY ORLANDO

    17102 Heartwood Loop, 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

Showing Results 1 - 40, Page 1 of 2

Rental Home Trends

Number of Homes for Rent
46
Median Rent
$2,800
Median Single Family Home Rent
$3,000
Median Townhouse Rent
$2,700
Median Condo Rent
$1,995
How to Rent a Home