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Apartments for Rent in Courtlea Oaks, Winter Garden, FL

Average rent

$2,019

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Social life
Eco-living
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216 Jean St - Photo 1 of 1
3D tour

1d ago

Courtlea Oaks house for rent in Winter Garden

Residential, Other - Winter Garden, FL

216 Jean St, Winter Garden, FL 34787

In-unit laundry | Garage parking | Ceiling fan

3 beds

2.5 baths

$2,300

House for rent

203 N Dillard St #4 - Photo 1 of 1

5d+ ago

Apartment for rent in Winter Garden

Downtown Winter Garden Apartment one block from the shops

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

Assigned parking | Hardwood floor | Carpet

1 bed

1 bath

$1,495

Apartment for rent

Available May 1

Description

Property Id: 1347362 Cute 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 Cute remodeled corner unit, all you pay is electric and internet---Close to Downtown Winter Garden, allowing you to walk and enjoy all the restaurants and local brewery. Unit is quiet

182 Roper Dr #NA - Photo 1 of 1

5d+ ago

House for rent in Winter Garden

$3,500 - 4 Bedroom 3 Bathroom House In Winter Garden With Great Amenities

182 Roper Dr #NA, Winter Garden, FL 34787

Air conditioning | Garage parking | Assigned parking

4 beds

3 baths

$3,500

House for rent

Available May 1

Description

Amazing 4 bedroom, 3 bathroom house in Winter Garden. Amenities included: central air, central heat, dishwasher, hardwood floors, stainless steel appliance, updated kitchen, updated bathroom, and yard. No Utilities included. Is not pet friendly. Date Available: May 1st 2026. $3,500/month rent. $3,500 security deposit required. Please submit the form on this page or contact Ashlyn Hembrooke at 407-913-9638 to learn more. This property is managed by a responsible landlord using Avail landlord software.

456 Silverdale Ave - Photo 1 of 1

5d+ ago

House for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

456 Silverdale Ave, Winter Garden, FL 34787

Garage parking | Walk-in closets | Ceiling fan

4 beds

2 baths

$3,100

House for rent

Description

Property Status: Pending FOR RENT!!!!! Located in the GOLF CART DISTRICT of HISTORIC Downtown Winter Garden, in COVINGTON CHASE. NO CARPET! All carpet was replaced with light wood laminate flooring. This beautiful 4-bedroom, 2 bath home offers a split floor plan and easy accessibility onto the WEST ORANGE TRAIL. Enjoy the breathtaking nightly sunset views from the screened porch overlooking the pond. Spacious kitchen/family room combo with a wood burning fireplace. Kitchen features island, dark wood cabinets and stainless-steel appliances. Oversized Primary Suite include

Tremaine Boyd Apts NEW - Photo 1 of 1

3d ago

8.1

Very good

Tremaine Boyd Apts NEW

109 S Boyd St, Winter Garden, FL 34787

1 bed

1 bath

$2,045

Apartment for rent

Description

Located at 109 S. Boyd Street, Tremaine Boyd is one block south of Plant Street, the West Orange Trail, and everything Downtown Winter Garden has to offer. The one bedroom has stainless steel energy efficient appliances, washer and dryer, luxury vinyl plank flooring and spacious living area. The unit overlooks Boyd Street with large windows. These new finely-crafted apartments embrace the best of both worlds - spacious living quarters and urban-style amenities with the quaint, small town charm of historic downtown Winter Garden just outside of Orlando, Florida. Convenient

Experience Modern Luxury at Smith & Main: Premier Living in Downtown Winter Garden - Photo 1 of 1

2d ago

8.1

Very good

1–2 beds

1–2 baths

$2,215–$3,205

Apartment for rent

Description

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 lif

Find rentals with popular amenities

Dishwasher

Outdoor Space

Garage Parking

In-Unit Laundry

988 Glenview Cir - Photo 1 of 1

14h ago

Our team has verified this company

Verified

988 Glenview Cir, Winter Garden, FL 34787

On-site laundry | Balcony | Swimming pool

4 beds

3 baths

$3,370

House for rent

Available Jun 23

Description

Apply now or schedule your self-tour today and take the first step toward getting more than just a place to live. Rent with FirstKey Homes for a home that's right for you, plus professional service and maintenance, innovative resident programs, and more… that's the power of purple! This 4-bedroom, 3-bathroom rental home in Winter Garden, FL, might be the perfect fit for your lifestyle. Relax and unwind on the private patio/balcony. Large closets mean more space to store your stuff. See the pictures to learn more. And apply soon – homes can go fast! This home is availabl

525 Garden Heights Dr - Photo 1 of 1

5d+ ago

House for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

525 Garden Heights Dr, Winter Garden, FL 34787

In-unit laundry | Garage parking | Walk-in closets

3 beds

2 baths

$2,550

House for rent

Description

Property Status: Active Charming 3 bedroom, 2 bath home with spacious backyard, screened in patio, and no rear neighbors. Upon entering you are greeted by a formal dining, large living with fireplace, French doors opening to the peaceful patio. Master bedroom features a walk-in closet, ensuite bath, and access to the patio. Split floorplan with two additional bedrooms and full bath. Minutes from Downtown Winter Garden, farmers market, shopping, local dining, West Orange Trail, local parks, and much more! Don't miss your opportunity to call it home, schedule a private showi

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203 S Main St - Photo 1 of 1

5d+ ago

House for rent in Winter Garden

203 S Main St, Winter Garden, FL 34787

On-site management | Package service | Business center

2 beds

2 baths

$2,699

House for rent

Available Jul 15

Description

Available: July 15, 2026 Pets: Ok, Small- Under 24lbs (Dangerous Pets are not permitted, Pit Bulls, etc.) ***EASY To View At A Convenient TIME*** https www rentengine io listings 60909 ***EASY To Apply*** Once All Adults have Viewed this property, go here: https orlandorealestatepropertymanagement findigs com apply unitid=2fff4e60-da70-429b-89fc-010406dcbdf2 SAVE Money On The Application Fees: We recommend that you not fill out an application if any of the following apply to you: Evictions, Unpaid balances due to landlords, a Credit score below 500, insufficient inco

427 Tierra Verde Ln - Photo 1 of 1

5d+ ago

House for rent in Winter Garden

427 Tierra Verde Ln, Winter Garden, FL 34787

Furnished | Carpet | Outdoor space

4 beds

2 baths

$3,300

House for rent

Description

A Beautiful FULLY FURNISHED (can also be made available unfurnished) Home in the Gated Community of Lake Cove Pointe, within the Winter Garden Golf Cart District. Just a stone's throw away from the charming Historic Downtown Winter Garden with its cozy atmosphere and various amenities. This home boasts numerous features that might make you want to stay in. Upon arrival, you'll be greeted by the lush, well-maintained oak trees lining the paver drive and walkway leading to the inviting front porch. Inside, the spacious layout of this nearly 2,400 square feet home with 4 bedr

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Nearby rental good for social life

Nearby rental good for wfh

805 Bainbridge Loop - Photo 1 of 1

5d+ ago

House for rent in Winter Garden

805 Bainbridge Loop, Winter Garden, FL 34787

Swimming pool | Dishwasher | Oven

4 beds

4 baths

$3,995

House for rent

Description

Deposit $3995. Monthly Rent $3995. Available June 10th! Contact Leasing Manager Brock by call or text at 321-507-7604 or **** to schedule a showing of the home! Beautiful home with an ideal floorplan that has the master bedroom, 2 guest bedrooms, and a separate office on the first floor. One bedroom, bath, and loft area on the second floor. Home features granite counters, black appliances, and tile flooring. Gorgeous lot with oversized fully fenced in backyard and long driveway with 3 car garage. Great location in North Winter Garden, walking distance to W. Orange Trail,

502 Dunbar Ave - Photo 1 of 1

5d+ ago

House for rent in Winter Garden

502 Dunbar Ave, Winter Garden, FL 34787

In-unit laundry | On-site laundry | Storage

2 beds

1 bath

$1,495

House for rent

Available May 4

Description

SPECIAL $300 OFF THE 1ST MO RENT IF YOU SIGN A LEASE BEFORE 5/30! SECTION 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 family room that seamlessly transitions into a dining area, both adorned with stylish laminate flooring perfect for entertaining guests or enjoying peaceful evenings. The heart of the home, the kitche

Listings within 5 miles
1136 Dunbrooke St - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

1136 Dunbrooke St Winter Garden, FL 34787

1136 Dunbrooke St, Winter Garden, FL 34787

Garage parking | Walk-in closets | Outdoor space

3 beds

2 baths

$2,880

House for rent

Available May 19

Description

Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $3024.90. That covers your base rent, $2880.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet & Media ($85), Smart Home with video doorbell ($40), and Utility Billing Service Fee ($9.95). Base rent varies based on selected lease term. Taking time for yourself will be even

1021 Temple Grove Pl - Photo 1 of 1

5d+ ago

House for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

1021 Temple Grove Pl, Winter Garden, FL 34787

In-unit laundry | Furnished | Garage parking

4 beds

4.5 baths

$8,500

House for rent

Description

Property Status: Active Lakefront Luxury Lease – Minutes to Historic Downtown Winter Garden Enjoy refined waterfront living on the shores of Lake Apopka in this beautifully updated 4-bedroom, 4.5-bath residence, ideally located just five minutes from the charm, dining, and boutiques of downtown Winter Garden and the vibrant scene along Plant Street. Positioned within the sought-after golf cart district, this property offers both privacy and prime accessibility. Inside, the home showcases rich hardwood flooring throughout and a warm, inviting living area anchored by an elec

508 Varsity St - Photo 1 of 1

5d+ ago

Apartment for rent in Winter Garden

Half Duplex - WINTER GARDEN, FL

508 Varsity St, Winter Garden, FL 34787

Fitness center | Outdoor space

2 beds

1 bath

$1,695

Apartment for rent

Description

Property Status: Active Primo location. Hip patio villas situated on a quiet oak lined street featuring polished concrete flooring throughout, updated kitchen, 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!! For your fitness needs pick up West Orange Trail from downtown, walk, skate, jog or bike the best Florida has to offer. Walk downtown to the

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These rentals are 10%-30% cheaper than the local average price for similar rentals.

224 W Cypress St #NA - Photo 1 of 1

5d+ ago

House for rent in Winter Garden

$2,000 - 3 Bedroom 2 Bathroom House In Near Down Town Winter Garden

224 W Cypress St #NA, Winter Garden, FL 34787

In-unit laundry | Air conditioning | Assigned parking

3 beds

2 baths

$2,000

House for rent

Available May 24

Description

Amazing 3 bedroom, 2 bathroom house in Winter Garden. Amenities included: central air, central heat, deck, hardwood floors, and washer dryer. The 3rd room is smaller than other 2 rooms. It's perfect for home office or studio. No Utilities included. Is not pet friendly. Date Available: now. $2,000/month rent. $2,000security deposit required. Applicant must have at least 650 credit score and no eviction record. Please submit the form on this page or contact KMC Investments at 321-217-5359 to learn more. This property is managed by a responsible landlord using Avail landlord

Arya at Windermere 55+ - Photo 1 of 1
Age restricted
Rent special

2d ago

9.7

Excellent

Our team has verified this company

Verified

Arya at Windermere 55+

1231 Arya Way, Ocoee, FL 34761

On-site laundry | Balcony | Swimming pool

1–2 beds

1–2 baths

$1,945–$2,895

Apartment for rent

Description

B3 Slate 2 BD, 2 BA

Call

1409 Center St - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

1409 Center St, Ocoee, FL 34761

Garage parking | On-site laundry | Walk-in closets

3 beds

2 baths

$2,480

House for rent

Available May 1

Description

Please note, our homes are available on a first-come, first-serve basis and are not reserved until the lease is signed by all applicants and security deposits are collected. Interested in this home? You clearly have exceptional taste. This charming 3.0-bedroom, 2.0-bathroom home is not only pet-friendly, but also equipped with smart home features to make everyday life more convenient and connected. Homes like this don’t stay on the market for long—don’t miss your chance to make it yours. Apply today! The Homeowners Association (HOA) for this home may have a separate appl

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326 Daniels Pointe Dr - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

326 Daniels Pointe Dr, Winter Garden, FL 34787

Garage parking | Walk-in closets | Ceiling fan

3 beds

2 baths

$2,395

$2,230

Price drop

House for rent

Available Mar 24

Description

Please note, our homes are available on a first-come, first-serve basis and are not reserved until the lease is signed by all applicants and security deposits are collected. Rent this home by May 31, 2026 and receive $500 Interested in this home? You clearly have exceptional taste. This charming 3-bedroom, 2.0-bathroom home is not only pet-friendly, but also equipped with smart home features to make everyday life more convenient and connected. Homes like this don’t stay on the market for long—don’t miss your chance to make it yours. Apply today! The Homeowners Associati

266 Regal Downs Cir - Photo 1 of 1

10h ago

Our team has verified this company

Verified

266 Regal Downs Cir, Winter Garden, FL 34787

Garage parking | On-site laundry | Walk-in closets

4 beds

2 baths

$2,725

House for rent

Available Jul 16

Description

Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant. Coming soon! This home is currently being enjoyed by another resident but will be available soon. Please respect their privacy and do not disturb. You can complete the application process and reserve this home for a $500 non-refundable holding fee until it's ready for move-in. This fee must be paid within 24 hours of being pre-qualified and will be applied to your first month’s rent if

114 Parker Cove Ct - Photo 1 of 1
3D tour

5d+ ago

Our team has verified this company

Verified

114 Parker Cove Ct, Ocoee, FL 34761

In-unit laundry | Garage parking | On-site laundry

3 beds

2 baths

$2,350

House for rent

Available May 4

Description

This property is available. Please inquire on this site to schedule a showing. Welcome to 114 Parker Cove Ct, Ocoee, FL 34761, a charming residence nestled in a peaceful neighborhood. This inviting home features a spacious open floor plan with a bright living area, accentuated by large windows that allow natural light to fill the space. The kitchen is well-equipped with modern appliances, ample counter space, and a stylish backsplash, perfect for culinary enthusiasts. Adjacent to the kitchen, the dining area provides an ideal setting for entertaining guests or enjoying fa

308 Forrest Crest Ct - Photo 1 of 1

14h ago

Our team has verified this company

Verified

308 Forrest Crest Ct, Ocoee, FL 34761

On-site laundry | Swimming pool | On-site management

5 beds

3 baths

$3,590

$3,095

Price drop

House for rent

Available May 27

Description

Apply now or schedule your self-tour today and take the first step toward getting more than just a place to live. Rent with FirstKey Homes for a home that's right for you, plus professional service and maintenance, innovative resident programs, and more… that's the power of purple! This 5-bedroom, 3-bathroom rental home in Ocoee, FL, has a lot to offer; does it check all your boxes? See the pictures to learn more. And apply soon – homes can go fast! This home is available to pre-lease! Reserve it by paying a refundable Hold Fee. (Exceptions apply in Colorado.) Find out

314 Daniels Pointe Dr - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

314 Daniels Pointe Dr Winter Garden, FL 34787

314 Daniels Pointe Dr, Winter Garden, FL 34787

Garage parking | Walk-in closets

3 beds

2 baths

$2,265

House for rent

Available May 8

Description

Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2409.90. That covers your base rent, $2265.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet & Media ($85), Smart Home with video doorbell ($40), and Utility Billing Service Fee ($9.95). Base rent varies based on selected lease term. You deserve a quality home that you ca

611 N Lakewood Ave - Photo 1 of 1

5d+ ago

House for rent in Ocoee

Single Family Residence - OCOEE, FL

611 N Lakewood Ave, Ocoee, FL 34761

2 beds

1 bath

$800

House for rent

Description

Property Status: Active Rent with confidence from a licensed leasing agent. Our application process is quick and straightforward — reach out through this website or give us a call to schedule a tour (when the property is available) and apply. Welcome to this charming 2-bed, 1-bath home! The spacious layout offers a comfortable setting for everyday living. As you step inside, you'll be welcomed by a floor plan that highlights the living room and kitchen. To the side of the home, you'll find the bedrooms and the bathroom. We proudly welcome all pets. We fully comply with

Advenir at The Oaks - Photo 1 of 1
Highly rated
3D tour

2d ago

8.8

Very good

Advenir at The Oaks

3100 Old Winter Garden Rd, Ocoee, FL 34761

In-unit laundry | Air conditioning | Balcony

1–3 beds

1–2 baths

$1,330–$2,099

Apartment for rent

Available Apr 25

Description

Dogwood Renovated

Showing 1 - 25 of 25 results
Home > Apartments in Winter Garden > Courtlea Oaks Apartments For Rent
Updated: May 22, 2026

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Learn more about renting in Courtlea Oaks, Winter Garden, FL

Methodology: How we got this data

Zumper’s proprietary rental data fuels our analysis. Rent and market trends, availability, neighborhood popularity, and lifestyle scores are all calculated using real-time and 2024 rental inventory and prices.

Our Lifestyle Categories ("great for eco-living," "great for social life," "great for pet owners," etc.) are determined by set criteria, against which we score each listing and its available features. At the neighborhood level, we calculate the listing count for each category to determine which lifestyles best fit each area.

Zumper, founded in 2012, is North America’s largest privately-owned rental platform, offering over 1 million listings across the U.S. and Canada. Stay informed on the latest trends and shifts in the rental market with our monthly National Rent Report, your go-to resource for key insights into the evolving rental landscape.

Courtlea Oaks Apartments for rent FAQ

What is the average size of an apartment in Courtlea Oaks, FL?

The average size of a 3 bedroom apartment rental in Courtlea Oaks is 1582 square feet.

Can I afford an apartment for rent in Courtlea Oaks, FL?

To help you better understand how much rent you can afford, check out Zumper's rent calculator. Our rent calculator can help you learn more about Courtlea Oaks average rent prices.

What type of apartment rental is most common in Courtlea Oaks, Winter Garden, FL?

3 bedroom apartments are the most common type of rentals in Courtlea Oaks, Winter Garden, FL right now.

What type of apartment rental is least common in Courtlea Oaks, Winter Garden, FL?

3 bedroom apartments are the least common type of rentals in Courtlea Oaks, Winter Garden, FL right now.

Looking for an apartment in Courtlea Oaks, Winter Garden, FL?

🔑Available apartment rentals25
💰Best rent deal502 Dunbar Ave
Popular amenities, ,
🍽With dishwasher
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