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Apartments for Rent in Winter Garden, FL

1-20 of 25 rentals

Apartment for rent at 203 N Dillard St #4, Winter Garden, FL 34787

1 / 8

Managed by Jason

$1,495

Apartment1 Bed1 Bath

203 N Dillard St #4

Winter Garden, FL 34787

Welcome to your bright and happy 1 bed, 1 bath apartment in Winter Garden, FL. This unit features a fully equipped kitchen with an oven and refrigerator, hardwood flooring and a designated parking space. Rent includes the convenience of water, garbage and sewage. One block from the restaurants, Park Ave and West Orange Trail. Unit is wired for internet, perfect for a single professional or couple. Don't miss out on this gem - schedule a tour today. Water, Garbage, Sewage, Carpet, Hardwood, Forced Air, Wall, Range Oven, Refrigerator, Cable Ready, Near Parks, Wired For Internet & Designated Space. Deposit: $1,495.

1 / 10

Updated - today

Managed by Atrium Management Company

$2,195 - $3,205

Apartment1-2 Beds1-2 Baths783-1,113 ft²

11 E Smith St

Winter Garden, FL 34787

Discover Smith & Main, a stunning addition to the sought-after Downtown Winter Garden district. Built in 2023, this exclusive community features striking Mediterranean-style architecture that blends historic charm with contemporary comfort. Modern Interiors. Step inside to premium luxury finishes. Each residence boasts open layouts anchored by sleek granite countertops and stainless steel appliances. Durable, stylish Lvp flooring runs throughout. Select units feature private balconies or terraces for your personal oasis. Amenities & Convenience. Smith & Main offers a lifestyle of ease: Elevator Access: Effortless access to all floors. Resident Grill Area: Perfect for outdoor BBQs with friends.

1 / 5

Provided by Leasing Agent

$1,700

Apartment2 Beds2 Baths918 ft²

165 Windtree Lane #1

Winter Garden, FL 34787

Renovated 2 brm 2 bath 1st floor unit with screen enclosed balcony. No carpet in unit. Unit has 2 assigned parking spots. Requirements are 600+ credit score and income 2.5 times rent with no evictions on record.

1 / 5

Managed by Jason

$1,295

Apartment1 Bed1 Bath305 ft²

203 N Dillard St #6

Winter Garden, FL 34787

Cute Studio apartment with full size kitchen /private 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 refrigerator, comCute Studio apartment with full size kitchen /private bath and all within one block of Downtown Winter Garden.

1 / 10

Featured

Managed by Atrium Management Company

$1,995

Apartment1 Bed1 Bath830 ft²

109 S Boyd St

Winter Garden, FL 34787

Welcome to Tremaine Boyd Apts New, presented by Atrium Management Company. We have several units available for lease. For more information and to schedule a showing, please contact us. Pet Friendly.

1 / 10

New - yesterday

Managed by Northpoint

$2,900

Apartment4 Beds3.5 Baths1,914 ft²

7670 Bowery Dr

Winter Garden, FL 34787

Welcome to 7670 - Bowery - Drive, presented by Northpoint. We have several units available for lease. For more information and to schedule a showing, please contact us. Washer/Dryer In Unit, Dishwasher, Air Conditioning, Disposal, Balcony, Pool, Pets Allowed, Patio, Stove, Refrigerator, Microwave, Community Pool, 2 Car Garage, Lawn, Washer & Electric Dryer. Pet Friendly.

1 / 10

Featured

Managed by Real Property Management South Orlando

$1,500

Condo2 Beds2 Baths918 ft²

88 Windtree Lane Bldg K

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 per month or you can purchase coverage from your preferred provider.

1 / 10

Managed by Vintage Horizon West

$1,540 - $2,065

Apartment1-2 Beds1-2 Baths

Vintage Horizon West

9223 Vintage Hills Way, Winter Garden, FL 34787

Comfortable, sleek and modern, Vintage Horizon West is your piece of paradise. Our spacious one, two & three-bedroom apartment homes provide comfort you'll love and the luxury you deserve. Enjoy a uniquely convenient neighborhood and a prime location offering access to Orlando's theme parks, shopping, dining and entertainment. Each well-appointed floor plan boasts modern features and finishes including quartz countertops, stainless-steel appliances, tile backsplashes, over-sized tubs, hardwood inspired plan flooring, upgraded lighting and hardware packages, full-size washers and dryers and Vino package in select units. Dwell well in unparalleled style at Vintage Horizon West.

Apartment for rent at 15532 Sweet Orange Ave, Winter Garden, FL 34787

1 / 10

New - yesterday

Provided by Leasing Agent

$3,950

Apartment3 Beds3 Baths2,571 ft²

15532 Sweet Orange Ave

Winter Garden, FL 34787

Come view this recently renovated, modern 3 bedroom home in the beautiful Horizon West area. This fully furnished home not only has conservation lake views, but also includes lawncare. Upon entering the foyer, you will immediately notice the high ceilings, custom furnishings, open floorplan, two living rooms and the spacious kitchen. The chef's kitchen features double ovens, a natural gas cooktop with a chrome vented hood, side by side fridge and wine rack. The dry bar is encased with quartz countertops and the large island provides a great backdrop to the custom artwork displayed throughout the home.

1 / 2

Featured

Managed by IRM Investments

$1,750

Condo2 Beds2 Baths1,152 ft²

1300 Eastern Pecan Place #203

Winter Garden, FL 34787

2 Bed 2 Bath Condo in Winter Garden, den, washer and dryer included. Gated community with access to Gym and Pool. HOA approval required, Dna test for dogs and dogs breed restriction and weight by HOA (fee). Pets allowed. Available now. Unit: 2 master bedrooms, dining in living / great room, oven / range, refrigerator, built in dishwasher, sink disposal, washer, electric dryer, refrigeration (air conditioning), library / den, fire sprinklers, unfurnished & mini-blinds. Community: gated community, clubhouse, playground, exercise room, unassigned parking & community pool.

1 / 10

Provided by Leasing Agent

$1,795

Condo2 Beds1 Bath966 ft²

233 Southern Pecan Circle #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, inside 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 and vibrating recliners.

1 / 10

New - yesterday

Managed by CANI Property Management

$1,995

Condo2 Beds2 Baths1,152 ft²

430 Southern Pecan Circle #101

Winter Garden, FL 34787

Welcome to this beautifully renovated 2-bedroom, 2-bath condo in the sought-after Southern Pines community of Winter Garden, where modern upgrades and comfortable living come together effortlessly. Thoughtfully updated with stylish finishes and a bright open floor plan, this home offers an inviting atmosphere perfect for both relaxing evenings and entertaining guests. Natural light fills the spacious living and dining areas, while ceiling fans throughout add comfort and energy efficiency year-round. The upgraded interior features a flexible seating area ideal for a home office, reading nook or cozy lounge space.

1 / 2

New - today

Managed by Real Property Management South Orlando

$1,595

Condo2 Beds2 Baths918 ft²

36 Windtree Lane

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 gross. Lessee(s) are required to provide proof of liability insurance in the amount of $100,000, prior to occupancy.

1 / 10

Managed by Falcon Square at Independence

$1,469 - $2,179

Apartment1-2 Beds1-2 Baths

Falcon Square at Independence

14600 Avenue of The Groves, Winter Garden, FL 34787

Schedule your Self-Guided Tour today. Live it. Love it. at Falcon Square at Independence. Situated in the heart of the desirable Independence neighborhood, Falcon Square at Independence offers one-, two- and three-bedroom apartments in Winter Garden. We are a Golden Key Awards Winner for Luxury Community of the Year 6 years running. Take a tour of the community and you will quickly see why. Among other things, our residents love the gourmet kitchens, full-size washers and dryers, large garden tubs and screened-in patios.

Apartment for rent at 13349 Harbor Shore Lane #1, Winter Garden, FL 34787

1 / 10

Featured

Managed by Central Florida Property Management

$2,159

Apartment2 Beds2.5 Baths1,236 ft²

13349 Harbor Shore Lane #1

Winter Garden, FL 34787

Welcome to this charming 2-bedroom, 2.5-bath townhome in the gated Daniels Landing community of Winter Garden. Both bedrooms feature private en-suite bathrooms and walk-in closets. Enjoy a private courtyard, attached two car garage and all major appliances included. Community amenities include a pool, clubhouse, playground and walking trails. Basic internet and cable are included in the rent. Located minutes from Historic Downtown Winter Garden, Highway 50, SR-429 and the Florida Turnpike, with easy access to top-rated Orange County schools. Shopping, dining and entertainment are all right at your doorstep. This one will not last - schedule your showing today.

1 / 2

Managed by Alta Winter Garden

$1,442 - $2,530

Apartment1-3 Beds1-2 Baths

Alta Winter Garden

1223 E Plant St, Winter Garden, FL 34787

Alta Winter Garden features spacious floor plans, best-in-class amenities and service and top-of-the line finishes, including stainless-steel appliances, oversized side-by-side refrigerators, vinyl wood flooring and quartz countertops. All the amenities you'd find in a modern downtown apartment - tucked away in the laid-back community you prefer to call home. Accessible, Pool, Gym, Pet friendly, Clubhouse, Dog grooming area, Dog park, Game room, Smoke-free community & Yoga.

Apartment for rent at 12572 Westhaven Oak Dr, Winter Garden, FL 34787

1 / 10

Featured

Provided by Leasing Agent

$3,000

Apartment4 Beds3 Baths2,148 ft²

12572 Westhaven Oak Dr

Winter Garden, FL 34787

Welcome to your brand-new single-family home in the highly sought-after community of Osprey Ranch. Located in the heart of charming Winter Garden, this beautiful 4-bedroom, 3-bath residence with a 2-car garage offers the perfect blend of comfort, convenience and community an ideal place to raise a family. Enjoy living just minutes from world-class theme parks, top-rated local schools, major roadways, dining, shopping, parks and vibrant farmers' markets. Families will appreciate the excellent educational opportunities nearby, making this location truly special.

1 / 6

Managed by Heather Fraga

$1,695

Condo2 Beds2 Baths958 ft²

119 Windtree Ln, Building O

Winter Garden, FL 34787

Ground Level Condo available in bustling Winter Garden FL. This ground unit condo is a 2 bedroom 2 bathroom. 958 sqft of living space plus a designated porch and storage closet on site. No pets. Washer and Dryer in unit. Windtree Condominiums also offer pool access, a tennis and basketball court plus club house rental for on-site tenants. Easy access to HWY 50 and only minutes from the 429 and Turnpike.

1 / 10

Featured

Provided by Leasing Agent

$3,750

Apartment4 Beds4 Baths2,489 ft²

15663 Pelican Cay Dr

Winter Garden, FL 34787

Welcome to this beautifully maintained two-story home located in the heart of Winter Garden, Fl, within one of the area's most sought-after communities. This spacious residence features 4 bedrooms, including a convenient in-law suite and 3.5 bathrooms, providing a flexible and functional layout. The open-concept kitchen includes stainless steel appliances and granite countertops, flowing seamlessly into generous living and dining areas designed for comfortable everyday living and entertaining. As one of the community's most popular floor plans, the home features bright, well-proportioned spaces throughout. Enjoy outdoor living with a private balcony overlooking the neighborhood.

1 / 10

Managed by Overture Hamlin Age 55 Apartment Homes

$1,515 - $2,605

Apartment1-2 Beds1-2 Baths

Overture Hamlin Age 55 Apartment Homes

5795 Citrus Village Blvd, Winter Garden, FL 34787

We are offering in-person tours via scheduled appointments and virtual touring at this time. Please schedule yours today. Our touring schedules and operating hours may vary as we continue to follow guidelines from local health officials. Contact us or call us to schedule your tour and learn more about our engaging active adult lifestyle. We are Now Open. Experience a maintenance-free, worry-free life where you can truly focus on yourself. Welcome to Overture Hamlin. Our vibrant community offers spacious living, an engaging lifestyle and meaningful mind-body-social amenities. There is no other community that is so well thought out and inviting.

Viewing 1-20 of 25 rentals in Winter Garden

What to Know About

Life in Winter Garden & Beyond

Winter Garden shares many of the great qualities that make Florida a desirable place to live.

Florida is a sunshine-filled state known for its beautiful beaches, warm weather, and world-famous theme parks like Walt Disney World, Universal Studios, and Sea World. From its iconic beaches to vibrant cities, you have a unique blend of outdoor adventure and urban excitement. Explore the state's past by visiting attractions like the Kennedy Space Center, the Museum of Florida History, or the Perez Art Museum Miami. In addition, Florida is home to renowned universities such as the University of Florida and Florida State University, University of Miami.

With hundreds of miles of sandy beaches, crystal-clear springs, and lush everglades, Florida is a paradise for visitors and residents alike. The state is also home to several professional sports teams, including the Miami Dolphins (NFL), Tampa Bay Buccaneers (NFL), Florida Panthers (NHL), Tampa Lighting (NHL), Miami Marlins (MLB), Orlando Magic (NBA), and Miami Heat (NBA). Experience all that Florida has to offer, from its stunning beaches and vibrant atmosphere to its rich traditions and thriving economy.

Discover the magic of living in Florida, where the sun shines bright, the economy thrives, and the quality of life is unparalleled, making it the perfect place to call home.

Rental Market Trends

Winter Garden, FL

As of June 2026, Winter Garden's rental market is competitive, with strong renter demand causing quick leasing times for well-priced units. Winter Garden's average rent is 19.2% ($404) higher than the Florida average of $2,100 and 39.3% ($707) higher than the U.S. average of $1,797.

Average Rent

$2,504

Monthly ChangeMonth Over Month Change

0.4% ($10)

Yearly ChangeYear Over Year Change

17.9% ($381)

Avg. Days on MarketAverage Days on Market

Unit Type	Average Rent	Monthly ChangeMonth Over Month Change	Yearly ChangeYear Over Year Change
1 Bed	$1,527	17.4% ($226)	8.8% ($147)
2 Beds	$1,886	1.2% ($22)	7.5% ($153)
3 Beds	$2,689	0.2% ($6)	0.9% ($23)

Nearby Cities	Average Rent	Avg. Rent vs. Winter GardenAverage Rent vs. Winter Garden	Avg. Days on MarketAverage Days on Market
Ocoee	$1,825	27.1% ($679)	28 days
Windermere	$2,620	4.6% ($116)	30 days
Clermont	$2,211	11.7% ($293)	28 days
Apopka	$2,056	17.9% ($448)	27 days
Maitland	$1,737	30.6% ($767)	30 days

Rental market trends are calculated using listing data from RentalSource.

Frequently Asked Questions

Winter Garden Rental Market FAQs

Explore rental prices, market trends, and availability in Winter Garden, FL.

What is the average rent in Winter Garden, FL?

The average rent in Winter Garden, FL is $2,504 per month.

What is the rental price range for apartments in Winter Garden, FL?

Apartments in Winter Garden typically rent for between $1,069 and $3,496 per month, with an average of $2,504 per month.

What is the average rent for different bedroom sizes in Winter Garden, FL?

In Winter Garden, the average rent for a 1-bedroom apartment is $1,527 per month, for a 2-bedroom apartment, $1,886 per month, and a 3-bedroom apartment is $2,689 per month.

How do rent prices in Winter Garden, FL compare with the national average?

The average rent in Winter Garden is 39.3% ($707) higher than the national average of $1,797 per month.

How have rent prices in Winter Garden, FL changed recently?

The average rent in Winter Garden has increased by 0.4% ($10) in the last month and increased by 17.9% ($381) over the past year.

How competitive is the rental market in Winter Garden, FL?

The rental market in Winter Garden, FL, is currently competitive, with strong renter demand causing quick leasing times for well-priced units.

How long do rentals stay on the market in Winter Garden, FL?

In Winter Garden, FL, the average rental stays on the market for approximately 35 days. While most properties are rented within this timeframe, factors like seasonality, demand, and property type can affect how quickly a rental leases.

How many rental properties are available in Winter Garden, FL?

There are currently 65 rental properties available in Winter Garden, FL.

Can I afford to rent an apartment in Winter Garden, FL?

Based on the current averages, a household would need an annual income of $75,440 to comfortably afford a 2-bedroom apartment in Winter Garden.