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Homes & Apartments for Rent in Winter Garden, FL

41-60 of 80 rentals

Townhouse for rent at 5875 Cypress Hill Rd, Winter Garden, FL 34787

1/10

Price cut $55

Managed by Number 1 Broker

$2,595

Townhouse2 Beds2.5 Baths1,800 ft²

5875 Cypress Hill Rd

Winter Garden, FL 34787

Two Bedroom Townhouse With Big Loft And Private Balcony on Orchard Hills, Winter Garden. The Auburndale Plan is a two-story townhome with two bedrooms, two and a half baths, and a two-car garage. This end unit home offers an open floor plan with numerous offering lots of natural light in the kitchen, living room, and dining area. The first floor of this home is completed with a powder room.

1/10

Managed by State Property Management - Area 1

$2,795

House4 Beds3 Baths2,382 ft²

1512 Lindzlu St

Winter Garden, FL 34787

Spacious 4 bedroom, 3 bathroom home featuring separate living and dining rooms plus a kitchen and family room combination. The large primary suite includes a garden tub, separate shower, double vanities, and walk-in closet. Enjoy a spacious rear yard with a privacy wall along the back. Conveniently located in Winter Garden near shopping, dining, schools, and major roadways. Amenities: Range.

1/10

Featured

Managed by WPM Southwest Orlando 308

$2,900

House4 Beds2 Baths2,218 ft²

15055 Driftwater Dr

Winter Garden, FL 34787

Move In Special $100 off First Month's Rent. Discover this beautiful 4-bedroom, 2-bathroom single-family home located in the highly desirable Signature Lakes community in Horizons West, Winter Garden. Offering a spacious layout, modern finishes, and a convenient location, this home is designed for comfortable everyday living. The open-concept kitchen features stainless steel appliances, granite countertops, a breakfast bar/island, and ample cabinet space, creating a functional space for cooking, entertaining, and gathering. The adjacent dining area provides a welcoming setting for family meals and special occasions.

1/10

Price cut $45

Managed by Elite Management & Leasing

$2,750

House3 Beds2.5 Baths2,014 ft²

16366 Brisk Breeze Alley

Winter Garden, FL 34787

Welcome to this charming 3-bedroom, 2.5-bathroom home located in the Waterleigh community of Winter Garden. Primary bedroom is on the lower level. Open living room, kitchen combination. Large built in desk and cabinets off of the living room and just outside primary bedroom. Loft area upstairs offers a great work space or extra living space. Covered porch is a great entertaining space. This house offers a resort-style community pool, community fitness center, scenic walking trails, community clubhouse, and grounds care. Enjoy the convenience of living in a vibrant community with plenty of amenities to keep you entertained and active.

1/10

Featured

Managed by Marcus B.

$4,500

House5 Beds3.5 Baths3,500 ft²

7531 Mandarin Grove Way

Winter Garden, FL 34787

Perfect 5 bedroom, 3.5 bathroom house in Winter Garden with no rear neighbors for extra privacy. Lease Term Negotiable. The main floor houses 4 bedrooms and 2.5 bathrooms while the 2nd floor can be used as 5th bedroom or media/game room. This home is the epitome of modern luxury and the ideal choice for those seeking a high-end rental experience. Located in the desirable Sanctuary at Hamlin Neighborhood. Conveniently located one mile from Publix, Walmart and Orlando Health Horizon West. Spacious open floor plan with 3D textured wood tile and Extra padded brand new memory foam carpet.

1/5

Listed by a leasing agent

$3,950

House4 Beds5 Baths2,817 ft²

4753 Terrace Bluff St

Winter Garden, FL 34787

Stunning Home in The Enclave at Hamlin. This beautiful Amelia floor plan offers 4 spacious bedrooms, 4.5 bathrooms, a private study/office, and over 2,800 sq. ft. of elegant living space. The gourmet kitchen seamlessly flows into the large gathering and dining areas-perfect for entertaining. Additional features include: 3-car tandem garage Tray ceilings and 8' doors throughout Modern gourmet kitchen with premium finishes Located in the sought-after Enclave at Hamlin, residents enjoy access to a sparkling community pool and a playground, making it an ideal home for both adults and children.

1/10

Managed by KIM

$2,185

Townhouse3 Beds2 Baths1,352 ft²

1007 Butterfly Blvd

Winter Garden, FL 34787

Amazing 3 bedroom, 2 bathroom townhouse in Winter Garden. Amenities included: central air, central heat, dishwasher, hardwood floors, pool, stainless steel appliance, updated bathroom, washer dryer, yard, and parking. No Utilities included. Is not pet friendly. Date Available: Aug 17th 2026. $2,185/month rent. $2,185 security deposit required along with first and last month rent. This property is managed by a responsible landlord using Avail landlord software.

1/10

Featured

Managed by Ziprent

$2,000

Townhouse2 Beds1.5 Baths1,144 ft²

1229 Winter Green Way

Winter Garden, FL 34787

This property is available. Please inquire on this site to schedule a showing. Welcome to 1229 Winter Green Way, a charming townhouse nestled in the highly sought-after community of Winter Garden, FL 34787. This inviting residence greets you with its distinctive green tile roof and an attractive facade, offering convenient off-street parking right at your doorstep. Step inside to discover an open-concept living area featuring soaring vaulted ceilings and abundant natural light streaming through a large front window, creating an airy and bright atmosphere.

1/20

Featured

Managed by Manager Prop

$3,650

Apartment3 Beds2.5 Baths

6393 Wild Persimmon Way #A

Winter Garden, FL 34787

Welcome to 6393 Wild Persimmon Way, Unit A-a brand-new home in Winter Garden offering modern comfort and a functional layout. Built in 2026, this beautiful residence features 3 bedrooms, 2.5 bathrooms, bright living spaces, modern finishes, and plenty of room for everyday living and entertaining. The thoughtfully designed floor plan provides comfortable bedrooms, inviting common areas, and the fresh, clean feel of a newly built home. The property is vacant, rent-ready, and available for immediate occupancy. Conveniently located in the desirable Winter Garden area, this is a wonderful opportunity to enjoy a modern home in a growing community.

1/20

Featured

Managed by Jackie Shi

$2,500

Townhouse3 Beds2.5 Baths1,568 ft²

10083 Salt Point Dr

Winter Garden, FL 34787

Experience refined living in this stunning two-story luxury townhome, perfectly situated in the prestigious Waterleigh Community of Winter Garden. This beautifully designed residence offers 3 spacious bedrooms and 2.5 baths, blending comfort, sophistication. Step inside to an inviting open-concept layout featuring a gourmet kitchen with generous prep space, and a seamless flow into the expansive family room-ideal for elegant entertaining or relaxed everyday living. For added convenience, the home includes a washer, dryer, and refrigerator. All bedrooms are located at the second floor and 2 full bathrooms.

1/20

Managed by Primax Management

$8,000

House4 Beds4 Baths3,388 ft²

7573 Green Mountain Way

Winter Garden, FL 34787

Step into this extraordinary Lakefront haven, nestled on a sprawling 1.26-acre expanse along the pristine shores of Lake Hancock, renowned as one of Central Florida's most coveted ski lakes dazzling Disney Fireworks, painting the night sky with their radiant colors. You'll find yourself captivated by the breathtaking water view that envelop this home. Meandering through the spacious 3,400 square feet of living space, an open floor plan unfolds. The formal living and dining rooms exude an air of sophistication, while the cozy family room beckons with warmth and comfort. This residence boasts 4 bedrooms and 3.

1/20

Price cut $50

Managed by Merly Leon

$2,600

Townhouse3 Beds2.5 Baths1,567 ft²

16509 Barbours Creek Way

Winter Garden, FL 34787

Brand-new, never-lived-in townhome in the Waterleigh community of Winter Garden, ready for you today. With SR 429 close by, Disney, shopping and dining are all within easy reach. Inside. OPEN-CONCEPT Main Floor: kitchen with bar seating, quartz countertops and stainless steel appliances, flowing into the dining area and living room. Powder Room downstairs and a patio just off the living area. Primary Suite with walk-in closet, double vanity and a spacious shower. Two Additional Bedrooms, a full bath and an Upstairs Laundry Room. Smart Home Package: control your home from your phone, even when you are away. 1-CAR Garage. Your Weekends, Covered.

Managed by Realsource Property Management

$1,800

Townhouse3 Beds2 Baths1,400 ft²

433 Sand Lime Rd

Winter Garden, FL 34787

3 Bedroom 2 Bath Townhome For Rent at 433 Sand Lime Road Winter Garden, FL 34787. This Home has a Range, Refrigerator, Central Heat and A/C. At the time of application. Incomplete applications without application fee payment or proof of income will be deleted. All adults 18 years of age and older are required to submit an individual application. Driving Directions: Take FL Turnpike North toward Ocala, Take the FL-50 exit, EXIT 267B, toward Ocoee, Merge onto W Colonial Dr/FL-50 W via the ramp on the left toward Winter Garden, Turn left onto S Park Ave, Turn right onto Sand Lime Rd.

1/10

Managed by Shri Sharma

$3,300

House5 Beds3 Baths2,918 ft²

1642 Chandelle Lane

Winter Garden, FL 34787

A beautiful property in a quite neighborhood, close to Publix Super market, school, Shopping Mall, Golf Course etc. If this advertisement is still up, the property is still available. Amenities: Freezer, Range/Oven & Near Parks. Heating: forced air. Flooring: concrete.

1/10

Listed by a leasing agent

$3,300

House3 Beds3 Baths2,027 ft²

11834 Shine View Lane

Winter Garden, FL 34787

Discover this beautifully designed 3-bedroom, 2.5-bath single-family home offering modern living in a highly desirable community. Built with all-concrete block construction, this floorplan features an open-concept layout with a seamless flow between the kitchen, dining, and family room areas-perfect for entertaining. The kitchen includes quartz countertops, stainless steel appliances, a spacious walk-in pantry, and a large island with bar seating. The primary bedroom is conveniently located on the first floor and offers privacy along with a well-appointed ensuite bath including dual vanities, a walk-in shower/tub space, and a generous walk-in closet.

1/10

Featured

Managed by Rent A Florida Home

$2,395

Townhouse3 Beds2.5 Baths1,568 ft²

13495 Sagestone Dr

Winter Garden, FL 34787

Lawn Care Included. Pest Control Included. Pet Friendly. Built in 2023 and located in the desirable Waterleigh community of Winter Garden, this beautiful 3-bedroom, 2.5-bath townhome offers a spacious layout, modern finishes, and convenient community amenities. The first-floor features ceramic tile flooring throughout the main living areas and an open-concept kitchen and living space. The kitchen is equipped with granite countertops, stainless-steel appliances, a breakfast bar, and a large walk-in pantry. The kitchen opens to the living room and patio, creating a comfortable space for everyday living and entertaining. A half bathroom and convenient mudroom complete the first floor.

1/10

Listed by a leasing agent

$2,850

Townhouse3 Beds3 Baths1,755 ft²

15609 Water Spring Blvd

Winter Garden, FL 34787

Welcome to your dream home in the highly sought-after, master-planned community of Storey Grove, perfectly located just minutes from Downtown Winter Garden. This beautifully maintained 3-bedroom, 2.5-bath townhome with a 2-car garage offers the ideal blend of comfort, convenience, and resort-style living. Enjoy being close to world-class theme parks, top-rated dining, boutique shopping, local parks, and vibrant farmer's markets, all just a short drive away. Whether you're exploring the outdoors or enjoying the charm of nearby historic Winter Garden, your home here truly puts you at the center of it all. Inside, the open-concept layout is perfect for entertaining.

1/10

Managed by Real Property Management South Orlando

$1,425

Condo2 Beds2 Baths918 ft²

36 Windtree Lane #202

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

New 6 days ago

Managed by Orlando Property Management

$3,100

House4 Beds3.5 Baths2,492 ft²

1392 Viscaya Cove Blvd

Winter Garden, FL 34787

This single-family home is one of the most charming homes in its neighborhood with its spacious bedrooms, luxurious bathrooms, and walk-in closets It is designed to meet a family's evolving needs featuring a well-equipped kitchen, a large, Bar seating Island, lots of storage space, a designed family room ready for home movie nights. Secluded at the front of the first floor, find the first owner's suite including a walk-in closet, and a private spa-like bathroom that showcases quartz-topped dual sinks and a walk-in shower. on the first floor as well, there is a conveniently tucked laundry room with ventilated shelving.

1/10

Managed by Intop Property Management

$2,900

House4 Beds3.5 Baths2,486 ft²

15204 Chapter Way

Winter Garden, FL 34787

Introducing a truly remarkable home with the best floor plan in the community. This house boasts an exceptional layout, featuring two master bathrooms-one conveniently located on the first floor, and another on the second floor. This unique design provides flexibility and convenience for residents.

Viewing 41-60 of 80 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

View full report

As of November 2026, Winter Garden's rental market is balanced, with rentals spending about 33 days on the market, slower than in Florida (30), and rents up 1.6% over the past year. Winter Garden's average rent is 4.4% ($114) higher than the Florida average of $2,584 and 32.5% ($662) higher than the U.S. average of $2,036.

Average Rent

$2,698

Monthly ChangeMonth Over Month Change

0.16% ($4)

Yearly ChangeYear Over Year Change

1.6% ($42)

Days on Market

Unit Type	Average Rent	Monthly ChangeMonth Over Month Change	Yearly ChangeYear Over Year Change
1 Bed	$1,611	0.20% ($3)	0.3% ($5)
2 Beds	$1,916	0.20% ($4)	0.4% ($7)
3 Beds	$2,750	0.10% ($3)	2.4% ($65)

Nearby Cities	Average Rent	Avg. Rent vs. Winter GardenAverage Rent vs. Winter Garden	Days on Market
Ocoee	$2,296	14.9% ($402)	35 days
Windermere	$2,684	0.5% ($14)	36 days
Montverde	$2,545	5.7% ($153)	35 days
Clermont	$2,395	11.2% ($303)	31 days
Apopka	$2,042	24.3% ($656)	37 days

Based on rentals advertised on RentalSource in and around Winter Garden.

Frequently Asked Questions

Winter Garden Rental Market FAQs

Explore rental prices, market conditions, and affordability in Winter Garden, FL.

What is the average rent in Winter Garden, FL?

The average rent in Winter Garden, FL is $2,698 per month.

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

In Winter Garden, the average rent is $1,611 per month for a 1-bedroom home, $1,916 for a 2-bedroom home and $2,750 for a 3-bedroom home.

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

The average rent in Winter Garden is 32.5% ($662) higher than the national average of $2,036 per month.

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

The rental market in Winter Garden, FL is currently balanced, with rentals spending about 33 days on the market, slower than in Florida (30), and rents up 1.6% over the past year.

Can I afford to rent a home in Winter Garden, FL?

Based on the current averages, a household would need an annual income of $76,600 to comfortably afford a 2-bedroom home in Winter Garden.

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