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Houses for Rent in Tucker Oaks, Winter Garden, FL

Average rent

$2,772

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1535 Broken Oak Dr #37B - Photo 1 of 1

5d+ ago

Tucker Oaks townhouse for rent in Winter Garden

Tucker Oaks

1535 Broken Oak Dr #37B, Winter Garden, FL 34787

In-unit laundry | Garage parking | Air conditioning

3 beds

3 baths

$2,195

$2,095

Price drop

House for rent

Available Jun 20

1066 Dolphin Dr - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Garden

Townhouse - WINTER GARDEN, FL

1066 Dolphin Dr, Winter Garden, FL 34787

In-unit laundry | Outdoor space | Carpet

3 beds

2 baths

$1,700

House for rent

Description

Property Status: Pending Westside Townhomes 3BR 2BA over 1400 sq/ft. One bedroom and full bath downstairs. Spacious kitchen with ample counter space, combination living room/dining room. Upstairs are 2 bedrooms, a full bath and laundry room. Walk-n closet in upstairs front bedroom!! Washer and Dryer included "as-is" and to be maintained by tenant at tenant's expense. Screened in covered patio in back and FENCED YARD. Owner will consider one small pet, with increase in security deposit (no aggressive breeds). HOA maintains front yard and tenant maintains the back yard. Loca

273 Avalon Rd - Photo 1 of 1

5d+ ago

House for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

273 Avalon Rd, Winter Garden, FL 34787

In-unit laundry | Outdoor space | Storage

4 beds

2 baths

$2,995

House for rent

Description

Property Status: Active Welcome home to 273 Avalon Road, a stunningly beautiful 4 Bedroom, 2 Bath home with 2,459 sqft of living space on almost a 1/2 acre lot !!! Just minutes from Down Town Winter Garden, this is a one of a kind property that was remodeled giving a modern flair to a farmhouse style property. The kitchen has a large center Island, with granite counter tops, stainless steel appliances, custom cabinets, with plenty of bar stool seating. The kitchen flows into a dining/living room space, with lots of windows to let in natural light, a further step down leads

1309 Cardinal Ln - Photo 1 of 1

5d+ ago

House for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

1309 Cardinal Ln, Winter Garden, FL 34787

In-unit laundry | Outdoor space | Ceiling fan

3 beds

2 baths

$1,800

House for rent

Description

Property Status: Pending One story unit 3 bedroom 2 full bath in West side Townhomes. Fenced in backyard area. READY JUNE 1ST. Close to downtown Winter Garden within minutes to shopping, hospital, YMCA, and Winter Garden Village. Office Phone: (407) 408-6662 Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

1000 Dolphin Dr - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Garden

Townhouse - WINTER GARDEN, FL

1000 Dolphin Dr, Winter Garden, FL 34787

In-unit laundry | Outdoor space | Dishwasher

3 beds

2 baths

$2,100

House for rent

Description

Property Status: Active 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 around town. If you haven’t experienced Downtown Winter Garden yet, you definitely should! Office Phone: (407) 930-3530 Copyright © 2026 Stellar MLS. All rights

Nearby rental good for eco-living

Nearby rental good for pet owners

Listings within 5 miles
266 Regal Downs Cir - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

266 Regal Downs Cir, Winter Garden, FL 34787

On-site laundry | Deck | Garage parking

4 beds

2 baths

$2,730

$2,560

Price drop

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

221 Timbercreek Pines Cir - Photo 1 of 1

2d ago

Our team has verified this company

Verified

221 Timbercreek Pines Cir, Winter Garden, FL 34787

Garage parking | High ceilings | Walk-in closets

4 beds

2.5 baths

$2,840

$2,700

Price drop

House for rent

Available Aug 10

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

934 Home Grove Dr - Photo 1 of 1

23h ago

Our team has verified this company

Verified

934 Home Grove Dr Winter Garden, FL 34787

934 Home Grove Dr, Winter Garden, FL 34787

Outdoor space | Garage parking

4 beds

3 baths

$3,445

House for rent

Available Jun 25

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 $3589.90. That covers your base rent, $3445.00 + 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. Loving where you live is easy when you

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1030 Maxey Dr - Photo 1 of 1

4d ago

Our team has verified this company

Verified

1030 Maxey Dr, Winter Garden, FL 34787

On-site laundry | Swimming pool | Balcony

4 beds

1.5 baths

$2,405

House for rent

Available Aug 4

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, 1.5-bathroom rental home in Winter Garden, FL, has a lot to offer; does it check all your boxes? Enjoy outdoor living on the private patio/balcony. 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 r

13841 Daniels Landing Cir - Photo 1 of 1

11h ago

Townhouse for rent in Winter Garden

Townhouse - WINTER GARDEN, FL

13841 Daniels Landing Cir, Winter Garden, FL 34787

In-unit laundry | Outdoor space | Garage parking

3 beds

2.5 baths

$2,250

House for rent

Description

Property Status: Active Nicely maintained, 3 bedroom 2.5 bathroom upgraded townhome in the excellent location of Daniels Landing in Winter Garden. This Community is beautiful, pool, fitness center, playground, clubhouse and gated. Located within a minutes walk or car ride to Fowlers Grove shopping, Hospital, Dr's offices and Downtown Winter Garden with its famous Farmers Market, West Orange Trail, Cafe's, Resturant's and Boutiques. Spacious living area with all three bedrooms having en-suite bathroom access. Grainte and hardwood cabinets, Laminite flooring downstairs and a

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13800 Golden Russet Dr - Photo 1 of 1

1d ago

Townhouse for rent in Winter Garden

13800 Golden Russet Dr, Winter Garden, FL 34787

Outdoor space | Storage | Garage parking

4 beds

2.5 baths

$2,450

House for rent

Available Jul 31

Description

Welcome home to this beautifully upgraded 4-bedroom, 2.5-bath townhome nestled in the exclusive gated community of The Orchard—where comfort, style, and convenience come together in perfect harmony. Available for move-in July 1st!!! This rare rental opportunity won’t last long! Step inside and be wowed by the spacious open-concept layout, perfect for hosting guests or enjoying cozy family nights. The sunlit living and dining areas flow effortlessly, creating a warm and welcoming atmosphere from the moment you walk in. Upstairs, you’ll find generously sized bedrooms, abun

705 Largovista Dr - Photo 1 of 1

2d ago

House for rent in Oakland

705 Largovista Dr, Oakland, FL 34787

In-unit laundry | Outdoor space | Storage

4 beds

4 baths

$6,000

House for rent

Available Jun 20

Description

Come view this newly built 4 bed/4 bath two-story home in the gated community of John's Landing! Inside, you'll find a bright and airy open layout featuring an impressive vaulted ceiling, large windows, and elegant flooring throughout. The stunning kitchen includes custom built-in Thermador appliances and solid wood cabinetry. The primary suite features vaulted ceilings, a spa-style bath with a free-standing tub, a frameless glass shower, his-and-hers vanities with backlit mirrors, and a large walk-in closet. The main level also includes a bedroom with an en-suite bath and

2501 Sky Stone Ct - Photo 1 of 1

5d+ ago

House for rent in Oakland

Single Family Residence - OAKLAND, FL

2501 Sky Stone Ct, Oakland, FL 34787

In-unit laundry | Outdoor space | Garage parking

4 beds

2.5 baths

$3,900

House for rent

Description

Property Status: Active Beautifully maintained home in the desirable Oakland Trails community, ideally located on a quiet dead-end street with peaceful preserve views and no rear neighbors. The open layout features natural light, a spacious living area, a modern kitchen, and large, comfortable bedrooms. Enjoy community amenities, including a pool, playground, and walking paths, with direct access to the West Orange Trail. Just minutes from Downtown Wintergarden, Clermont, and major highways, including the Turnpike, 408, 429, and I-4. Move-in ready and easy to show Office P

5d+ ago

House for rent in Winter Garden

On-site management

3 beds

2 baths

$2,099

House for rent

Available Jun 1

Description

Fresh out of rehab and ready to be your home!! For applications or to schedule a viewing, please visit our website: www keystone-brokers com By submitting your information on this page you consent to being contacted by the Property Manager and RentEngine via SMS, phone, or email.

205 S Woodland St - Photo 1 of 1

5d+ ago

House for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

205 S Woodland St, Winter Garden, FL 34787

In-unit laundry | Outdoor space | Storage

3 beds

2 baths

$3,750

House for rent

Description

Property Status: Pending One or more photo(s) has been virtually staged. Available June 1st. One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 3-bedroom, 2-bathroom, 2500 sq ft ranch-style home, ideally located within a 5-minute walk to historic downtown Winter Garden in the heart of the Golf Cart District. Situated on a spacious corner lot, this home blends classic charm, thoughtful upgrades, and everyday functionality—perfect for families, snowbirds, or anyone seeking a relaxed yet connected lifestyle. Step inside to an open and airy

13349 Harbor Shore Ln #1 - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Garden

13349 Harbor Shore Ln #1, Winter Garden, FL 34787

In-unit laundry | Outdoor space | Garage parking

2 beds

2.5 baths

$1,999

House for rent

Available May 8

Description

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 entert

203 S Main St - Photo 1 of 1

5d+ ago

House for rent in Winter Garden

203 S Main St, Winter Garden, FL 34787

Outdoor space | On-site management | Package service

2 beds

2 baths

$2,650

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 income

13527 Daniels Landing Cir - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Garden

13527 Daniels Landing Cir, Winter Garden, FL 34787

In-unit laundry | Outdoor space | Garage parking

3 beds

2.5 baths

$2,300

House for rent

Description

Property Status: Active Opportunity Awaits in Highly Sought-After Daniels Landing! Welcome to this charming 3-bedroom, 2.5-bath townhome offering comfort, convenience, and an unbeatable location. Perfect for homeowners or investors, this property is nestled in a well-maintained, gated community designed for easy living. Residents of Daniels Landing enjoy resort-style amenities, including a sparkling community pool, clubhouse with fitness center, recreation facility, scenic walking trails, and a playground. Ideally located just minutes from Winter Garden Village, AdventH

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455 Winter Grove Blvd - Photo 1 of 1
New construction

5d+ ago

House for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

455 Winter Grove Blvd, Winter Garden, FL 34787

In-unit laundry | Garage parking | Dishwasher

5 beds

3.5 baths

$5,000

House for rent

Description

Property Status: Active Welcome to this stunning new construction home (2026) located in the desirable city of Winter Garden. This beautifully designed residence offers 5 bedrooms, 3 full bathrooms, and 1 half bath, providing ample space for comfortable living and entertaining. The home features a spacious open floor plan, modern finishes, and abundant natural light throughout. The kitchen flows seamlessly into the living and dining areas, creating the perfect setting for gatherings. Situated within a gated community, residents enjoy added privacy and a peaceful environmen

13613 Larsen Ln - Photo 1 of 1

5d+ ago

House for rent in Winter Garden

13613 Larsen Ln, Winter Garden, FL 34787

Outdoor space | Walk-in closets

4 beds

4 baths

$3,500

House for rent

Description

Welcome to the luxury living! Conveniently located in gated Glynwood II/Stone Crest you will find this charming home. Featuring 4 bedrooms, 4 baths, formal living and dining rooms, office/den, upstairs bedroom and second floor bonus/theatre room. This exquisite residence offers an expansive and open floor plan that effortlessly blends comfort and sophistication. The gourmet kitchen, adorned with solid surface countertops, stainless steel appliances, and a dedicated breakfast nook is the heart of this home. The spacious family room sets the stage for relaxation and gatherin

1331 Daniels Cove Dr #NA - Photo 1 of 1

5d+ ago

House for rent in Winter Garden

$2,525 - 4 Bedroom 2 Bathroom House In Winter Garden With Great Amenities

1331 Daniels Cove Dr #NA, Winter Garden, FL 34787

Outdoor space | Garage parking | Air conditioning

4 beds

2 baths

$2,500

House for rent

Available Jul 1

Description

Amazing and spacious 4 bedroom, 2 bathroom house in family friendly Winter Garden. Right down the street from Winter Garden Village. Amenities included: central air, central heat, dishwasher, and yard. No pets please. Date Available: 1st day of the month. $2,500/month rent. $2,500 security deposit required. $55 application fee/adult, no admin fee due at move-in. Tenants are responsible for utilities and renter's insurance. Please contact Catherine Barrington at four zero seven two two seven zero two three nine (call or text) or email cathybarr30 at gmail. com to learn more

165 Windtree Ln #165WL - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Garden

165 Windtree Lane - 165WL

165 Windtree Ln #165WL, Winter Garden, FL 34787

In-unit laundry | Outdoor space | Air conditioning

2 beds

2 baths

$1,700

House for rent

Available Apr 1

Description

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 online at my zealproperty com rentalapplication HOA does not allow pets over 15 lbs.

314 S Boyd St - Photo 1 of 1

5d+ ago

House for rent in Winter Garden

314 S Boyd St, Winter Garden, FL 34787

In-unit laundry | Outdoor space | Storage

2 beds

2 baths

$2,050

House for rent

Available Jun 15

Description

Discover this charming 2-bedroom home ideally situated in the heart of Winter Garden. Bright, airy, and spacious, this residence is perfect for families seeking comfort and convenience. The open-concept living and dining areas provide a welcoming space for entertaining and everyday living. Both bedrooms are generously sized, featuring ample closet space to meet your storage needs. The kitchen boasts abundant cabinets and counter space, making meal preparation a breeze. Additional highlights include an in-unit washer and dryer for added convenience and a large backyard, per

1725 Portcastle Cir - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

1725 Portcastle Cir, Winter Garden, FL 34787

Deck | Garage parking | Ceiling fan

3 beds

2.5 baths

$3,730

$2,725

Price drop

House for rent

Available Jul 6

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. This home is priced to rent and won't be around for long. Apply now, while we make this home ready for you, or call to arrange a meeting with your local Progress Residential leasing specialist today. Interested in this home? You clearly have exceptional taste. This charming 3-bedroom, 2.5-bathroom home is not only pet-friendly, but also equipped with smart home features to make everyda

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Home > House Rentals in Winter Garden > Tucker Oaks Houses For Rent
Updated: June 23, 2026

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🌇Available house rentals24 houses
💰Best rent deal1066 Dolphin Dr
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