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Apartments for Rent in Winter Garden, FL

Average rent

$2,800
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Ascend Waterleigh Village - Photo 1 of 1
Rent special
New construction

6h ago

9.6

Excellent

Our team has verified this company

Verified

Ascend Waterleigh Village

16200 Ascend Village Ln, Winter Garden, FL 34787

In-unit laundry | Air conditioning | Garage parking

1–3 beds

1–2 baths

$1,605–$2,715

Price drop

Apartment for rent

Lakeside Luxury Living with Resort-Style Amenities

Residents of Ascend Waterleigh Village enjoy a luxurious lifestyle with stunning lakeside views. Spacious one, two, and three-bedroom apartments feature modern kitchens, oversized walk-in closets, and luxury vinyl plank flooring. The community boasts an inviting saltwater pool, a well-equipped fitness center, and an entertainment club room, all in a pet-friendly environment. Conveniently located near shops and restaurants, this is the perfect retreat for relaxation and fun!

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The Westerly - Photo 1 of 1

5d+ ago

9.6

Excellent

Our team has verified this company

Verified

The Westerly

14680 Westerly Drive, Winter Garden, FL 34787

In-unit laundry | Swimming pool | Fitness center

2–3 beds

2 baths

$2,199–$3,121

Apartment for rent

Elegant Apartments with Poolside Luxury

Nestled in Winter Garden, The Westerly Apartments blend contemporary charm with luxury living. Enjoy stylish interiors, a private pool with sun-shelf, and a pet-friendly ambience. Features include quartz countertops, spacious closets, and hardwood-style flooring. Connect with neighbors in the clubhouse or unwind in the sauna. Embrace a lifestyle of comfort and sophistication.

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Corban Horizon West - Photo 1 of 1
Rent special

2d ago

9.6

Excellent

Our team has verified this company

Verified

Corban Horizon West

15000 Stratus Loop, Winter Garden, FL 34787

In-unit laundry | Air conditioning | Garage parking

1–3 beds

1–2 baths

$1,725–$3,086

Price drop

Apartment for rent

Embrace Modern Comfort & Community Living

Corban Horizon West offers a refreshing approach to modern living in Winter Garden. This pet-friendly community blends tasteful design with thoughtful amenities, featuring spacious homes equipped with stainless steel appliances and oversized balconies. Enjoy a fitness center, game room, and a swimming pool, along with outdoor spaces perfect for relaxation. Explore the endless possibilities that await at Corban Horizon West—where comfort meets connection!

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266 Regal Downs Cir - Photo 1 of 1

28m ago

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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

Modern Smart Home with Spacious Yard & 4 Bedrooms

This charming 4-bedroom, 2-bathroom pet-friendly home offers modern living with smart features. Spanning 1,692 sq. ft., it boasts high ceilings, quartz countertops, and a walk-in shower. Enjoy the convenience of an attached garage and outdoor deck. Ideal for families seeking comfort and technology, this home won't last long! Residents will appreciate the nearby retail and neighborhood amenities.

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

Modern Smart Home with Pet-Friendly Charm

This charming 3-bedroom, 2-bathroom residence features cutting-edge smart home technology for a convenient lifestyle. With 1,139 square feet of cozy living space, enjoy the comfort of central air, vinyl plank flooring, and spacious walk-in closets. The pet-friendly home also includes a lovely patio and deck, perfect for outdoor relaxation. Located near walking and biking trails, this home balances modern amenities with the joy of nature.

988 Glenview Cir - Photo 1 of 1

4h ago

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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

Spacious 4-Bedroom Home with Outdoor Enjoyment

This pet-friendly rental features a generous 2,022 sq. ft. layout with 4 bedrooms and 3 bathrooms. Enjoy large closets for ample storage and a lovely patio for outdoor relaxation. Pre-leasing made easy to secure your future home in a great location. Perfect for families or those needing extra space!

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11073 Folklore St - Photo 1 of 1

4h ago

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Verified

11073 Folklore St, Winter Garden, FL 34787

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

4 beds

3 baths

$3,175

$2,870

Price drop

House for rent

Available May 26

Spacious Family Home with Pool, Perfect for Relaxation

This inviting 4-bedroom, 3-bathroom rental home offers 2,475 sq ft of comfortable living space. Enjoy outdoor gatherings by the swimming pool, or relax in the ample indoor areas. Onsite management ensures peace of mind, making this a superb choice for families. With professional service and innovative resident programs, this property promises an enjoyable living experience.

1958 Pantheon Dr - Photo 1 of 1

4h ago

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Verified

1958 Pantheon Dr, Winter Garden, FL 34787

On-site laundry | Balcony | Swimming pool

3 beds

2 baths

$3,125

$2,970

Price drop

House for rent

Available Jun 22

Bright & Spacious 3-Bed Home with Pool Retreat

This pet-friendly 3-bedroom, 2-bath home boasts 1,971 sq ft of comfortable living space. Enjoy relaxing moments on the patio or balcony, and take advantage of generous storage options. Convenient washer/dryer hookups make everyday living a breeze. With an outdoor pool and storage space, this rental home is perfect for enjoying the Florida sunshine and a relaxed lifestyle. Act fast, as properties in this location rent quickly!

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6460 Tabebuia Pkwy - Photo 1 of 1

2d ago

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Verified

6460 Tabebuia Parkway Lot 454 Winter Garden, FL 34787

6460 Tabebuia Pkwy, Winter Garden, FL 34787

Garage parking

3 beds

2.5 baths

$2,699

House for rent

Available May 22

Smart Home Bliss in a Modern Community

Experience modern living in this charming 3-bedroom, 2.5-bath home boasting Smart Home technology and stylish granite countertops. Enjoy an open floor plan with ample natural light, attached garage, and pet-friendly yard. Residents benefit from quality amenities and professional property management, all nestled in the vibrant Silverleaf Oaks community. Enjoy convenient access to nearby retailers and scenic trails in this thoughtfully designed Winter Garden home, perfect for comfortable living.

16390 Grey Pine Dr - Photo 1 of 1

3d ago

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Verified

16390 Grey Pine Dr Winter Garden, FL 34787

16390 Grey Pine Dr, Winter Garden, FL 34787

Garage parking

3 beds

2.5 baths

$2,599

House for rent

Available Mar 19

Modern Smart Home in a Picturesque Community

This pet-friendly 3-bedroom, 2.5-bathroom home offers 1,628 sq ft of stylish living with Smart Home technology. Enjoy an open floor plan featuring a charming kitchen island and recessed lighting. Conveniently located in Silverleaf Oaks, residents benefit from professional property management, community amenities, and easy access to scenic trails and retailers. Ideal for those seeking modern comfort paired with vibrant community living.

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Find rentals with popular amenities

Outdoor Space

In-Unit Laundry

Swimming Pool

Garage Parking

6138 Whispering Glen - Photo 1 of 1

4d ago

Our team has verified this company

Verified

6138 Whispering Glen Winter Garden, FL 34787

6138 Whispering Glen, Winter Garden, FL 34787

Garage parking

3 beds

2.5 baths

$2,699

House for rent

Available May 8

Modern Smart Home with Resort-Style Amenities

This stunning 3-bedroom, 2.5-bath residence combines modern convenience with smart home technology in a vibrant community. Enjoy an open floor plan and a stylish kitchen with granite countertops. Located near scenic trails and public lagoons, residents can unwind in a pet-friendly environment. Additional features include a 2-car garage, air conditioning, and professional property management for a hassle-free lifestyle. Perfect blend of comfort and contemporary living!

9223 Vintage Hills Way - Photo 1 of 1

5d+ ago

9.2

Excellent

Our team has verified this company

Verified

9223 Vintage Hills Way

9223 Vintage Hills Way, Winter Garden, FL 34787

Furnished

2 beds

2 baths

$2,737–$2,746

Apartment for rent

Flexible, Furnished Living with Landing

Nestled in Winter Garden, Landing offers fully-furnished apartments with flexible leases and no deposits. Enjoy deluxe stainless steel appliances, reliable internet, and custom-designed furnishings, all with hassle-free living and 24/7 support from a dedicated team. Experience modern essentials and convenience at your fingertips.

6533 Tabebuia Pkwy - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

6533 Tabebuia Pkwy Winter Garden, FL 34787

6533 Tabebuia Pkwy, Winter Garden, FL 34787

Garage parking

4 beds

2.5 baths

$3,049

House for rent

Available May 18

Modern Home with Smart Features & Community Perks

Enjoy modern living in this newly built 4-bedroom, 2.5-bath home featuring an open floorplan and stylish design. Located in Silverleaf Oaks, it offers Smart Home technology, granite countertops, and a spacious garage. With professional property management and a pet-friendly environment, residents can relish convenience and comfort, along with easy access to nearby amenities and scenic trails in Winter Garden. Available for lease soon!

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

Modern Home with Smart Features & Spacious Yard

This inviting 3-bed, 2-bath home offers 2,146 sq. ft. of stylish living space, featuring premium tile floors and a functional kitchen with stainless steel appliances. Enjoy a large backyard perfect for pets, and access to neighborhood amenities like a park, basketball court, and tennis courts. Smart Home technology and professional property management elevate the leasing experience, making this the perfect space to create lasting memories with family and friends.

6219 Sunny Time Ave - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

6219 Sunny Time Ave Winter Garden, FL 34787

6219 Sunny Time Ave, Winter Garden, FL 34787

Garage parking

5 beds

3 baths

$3,265

House for rent

Available Mar 25

Modern 5-Bedroom Home with Smart Tech Features

This spacious 5-bedroom, 3-bath residence offers 2,231 sq. ft. of stylish living in the Silverleaf Oaks community. Enjoy an open floorplan complete with upgraded granite countertops and smart home technology. The community boasts convenient access to shopping, scenic trails, and public lagoons. A pet-friendly environment and professional property management make this home a fantastic choice for comfortable, modern living just outside Orlando.

6249 Sunny Time Ave - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

6249 Sunny Time Avenue Winter Garden, FL 34787

6249 Sunny Time Ave, Winter Garden, FL 34787

Garage parking

3 beds

2.5 baths

$2,699

House for rent

Available May 13

Modern Home with Smart Features & Easy Living

This pet-friendly 3-bedroom, 2.5-bath residence covers 1,628 sq ft and is perfect for a hassle-free lifestyle. Enjoy the convenience of Smart Home technology, granite countertops, and a spacious layout designed for modern living. Located in the thoughtfully planned Silverleaf Oaks community, it combines comfort with access to nearby retailers and scenic trails, making it an ideal choice for families seeking both style and convenience.

6114 Whispering Glen Dr - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

6114 Whispering Glen Winter Garden, FL 34787

6114 Whispering Glen Dr, Winter Garden, FL 34787

Garage parking

5 beds

3 baths

$3,399

House for rent

Available May 11

Modern Home with Smart Features & Community Perks

This spacious 5-bedroom, 3-bathroom home offers 2,231 sq ft of modern living in the desirable Silverleaf Oaks community. Highlights include a stylish open floor plan, Smart Home technology, and an attached 2-car garage. Enjoy high-end amenities such as granite countertops, luxury vinyl plank flooring, and convenient services like air filter delivery and utility management. Perfect for families or anyone seeking a comfortable, pet-friendly lifestyle with easy access to local attractions.

6243 Sunny Time Ave - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

6243 Sunny Time Ave Winter Garden, FL 34787

6243 Sunny Time Ave, Winter Garden, FL 34787

Garage parking

4 beds

2.5 baths

$2,949

House for rent

Available Apr 16

Modern Home with Smart Features & Pet-Friendly Space

This stylish 4-bedroom, 2.5-bath home spans 1,913 sq. ft., boasting an open floorplan and modern amenities. Enjoy contemporary comfort with Smart Home technology, a kitchen island, and a private patio. Experience hassle-free living with professional management and pet-friendly policies in a thoughtfully planned community, perfect for anyone seeking a blend of modern convenience and a vibrant lifestyle.

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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

Renovated Home with Smart Tech & Community Pool

Enjoy modern living in this beautifully renovated 3-bedroom, 2-bath home featuring luxury vinyl plank flooring and a convenient open floorplan. With smart home technology and a relaxing community pool nearby, this pet-friendly property offers a great blend of comfort and convenience. A spacious primary bedroom with a walk-in closet adds to the appeal, while the attached garage enhances practicality. Embrace a worry-free leasing lifestyle with professional management and essential services included.

6126 Whispering Glen - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

6126 Whispering Glen Winter Garden, FL 34787

6126 Whispering Glen, Winter Garden, FL 34787

Garage parking

4 beds

2.5 baths

$2,949

House for rent

Available May 5

Modern Smart Home with Pet-Friendly Perks

Experience contemporary living in this inviting 4-bedroom, 2.5-bathroom home featuring an open floor plan and stylish kitchen island. Enjoy the convenience of Smart Home technology, air conditioning, and garage parking. Located in Silverleaf Oaks, residents benefit from easy access to scenic trails and local amenities, all while enjoying a pet-friendly environment. Perfect for those seeking comfort and community without the commitment of ownership.

Solay Horizon West - Photo 1 of 1
Rent special

7h ago

8.5

Very good

Solay Horizon West

9005 Solay Rd, Winter Garden, FL 34787

In-unit laundry | Air conditioning | Garage parking

1–3 beds

1–2 baths

$1,604–$2,964

Apartment for rent

Vacation Vibes with Unmatched Amenities Await

Enjoy everyday luxury at this brand new community featuring spacious apartments and a stunning array of amenities. Residents benefit from a dedicated onsite team focused on exceptional service and convenience. Take advantage of up to 8 weeks free on select homes! Live a resort-style life and experience the ultimate blend of comfort and community in your new home.

Halston Waterleigh - Photo 1 of 1
Rent special
3D tour

13h ago

8.8

Very good

Halston Waterleigh

10091 Tuller Loop, Winter Garden, FL 34787

In-unit laundry | Garage parking | Balcony

1–3 beds

1–2 baths

$1,462–$3,977

Price drop

Apartment for rent

Available May 22

Luxury Living with Resort-Style Amenities

Step into a world of luxury at Halston Waterleigh in Winter Garden. This pet-friendly community boasts exquisite design and abundant natural light. Residents enjoy a heated saltwater pool, an expansive fitness center, and a variety of top-tier amenities. Embrace a vacation-like atmosphere with features like a community clubhouse and sand volleyball court, all designed for comfort and convenience. Discover unmatched elegance in your new home!

Brass Ring Apartments - Photo 1 of 1

1d ago

8

Very good

Brass Ring Apartments

722 S Woodland St, Winter Garden, FL 34787

Outdoor space | Oven

1 bed

1 bath

$950

Apartment for rent

Affordable Elegance in Cozy Winter Garden Studio

Brass Ring Apartments offers a charming 1-bedroom studio in Winter Garden, blending style with affordability. Enjoy stylish interiors and an efficient kitchen designed for lasting comfort. The well-lit bedroom is a peaceful retreat, while convenient parking makes life easier. Located near local amenities and parks, this renovated space ensures a vibrant lifestyle without breaking the bank—perfect for anyone seeking cozy living!

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

Charming Downtown Apartment with Dedicated Parking

This cute 1-bedroom, 1-bath apartment features a full kitchen and bath, just a block from vibrant Downtown Winter Garden. Enjoy hardwood floors, a dedicated on-site parking spot, and the convenience of nearby breweries and markets. With heat and water included, only electric and internet are your responsibility, making this quiet corner unit perfect for relaxation and easy living in a lively community. Close proximity to parks adds to the appeal.

15927 Pantuso Aly - Photo 1 of 1

5d+ ago

House for rent in Winter Garden

15927 Pantuso Aly, Winter Garden, FL 34787

Garage parking | On-site laundry | Swimming pool

4 beds

3.5 baths

$3,200

House for rent

Spacious Winter Garden Home with Dual Master Suites

Gorgeous 3,694 sq. ft. home in Horizon West features 4 bedrooms, 3.5 bathrooms, and dual master suites. The open floor plan boasts a sleek kitchen with a large quartz island. Enjoy the first-floor master with a luxurious bath or relax in the upstairs loft. Outdoor entertainment is easy with a paver patio and attached 2-car garage. Community perks include a clubhouse, pool, and playground. Top-rated schools nearby!

8325 Topsail Pl - Photo 1 of 1

5h ago

House for rent in Winter Garden

8325 Topsail Pl, Winter Garden, FL 34787

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

3 beds

2 baths

$4,000

House for rent

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17822 Adrift Rd - Photo 1 of 1
New construction

5h ago

House for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

17822 Adrift Rd, Winter Garden, FL 34787

In-unit laundry | Garage parking | Swimming pool

5 beds

4 baths

$5,200

$4,900

Price drop

House for rent

Modern 5-Bed Home with Resort-Style Amenities

Experience spacious living in this beautifully maintained 5-bedroom, 4-bath home within the desirable Waterleigh community. The bright open-concept interior features ceramic tile flooring and elegant cabinetry. Enjoy resort-style amenities like a pool, fitness center, and trails, perfect for an active lifestyle. Conveniently located near shopping and attractions, this home blends comfort and community living seamlessly in a vibrant environment.

14034 Frasier St - Photo 1 of 1

20h ago

House for rent in Winter Garden

Luxurious & Pet Friendly 4 Bed/2.5 Bath home, designed for Families who love to entertain!

14034 Frasier St, Winter Garden, FL 34787

In-unit laundry | Garage parking | Swimming pool

4 beds

2.5 baths

$3,000

House for rent

Available Jun 30

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

Charming Oasis with Spacious Backyard & Modern Touches

This updated 3-bedroom, 2.5-bathroom home features an open floorplan and a stylish kitchen equipped with modern appliances. Set on a generous 0.34-acre lot with no HOA, the expansive backyard is perfect for gatherings and pet play. Enjoy the convenience of a 1-car garage and proximity to top-rated schools, local parks, and the vibrant charm of Historic Downtown Winter Garden. The ideal blend of comfort, space, and a dynamic location awaits!

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

1d ago

8.1

Very good

1–2 beds

1–2 baths

$2,215–$3,205

Apartment for rent

Chic Mediterranean Living Steps from Local Culture

Premier Living in Downtown Winter Garden offers stunning residences with Mediterranean architecture and modern interiors. Sleek granite countertops and stainless steel appliances elevate the style, while select units feature private balconies. Enjoy effortless living with elevator access, an outdoor grill area, and on-site dining just steps from Plant Street Market, breweries, and the scenic West Orange Trail.

Windermere Cay - Photo 1 of 1
Rent special

2d ago

8.8

Very good

Windermere Cay

8200 Jayme Dr, Winter Garden, FL 34787

In-unit laundry | Swimming pool | Fitness center

1–3 beds

1–2 baths

$1,580–$3,369

Apartment for rent

Luxury Living Near Orlando's Best Attractions

Residents of Windermere Cay enjoy a pet-friendly, smoke-free community minutes from Orlando's attractions. Featuring high-end finishes, elevators, a fitness center, and an exclusive amenity package. Experience style with faux wood flooring, granite countertops, and walk-in closets in spacious layouts.

Summary of resident reviews

Residents of Windermere Cay appreciate the welcoming and attentive office and maintenance staff, with frequent praise for Christy Duryee, Jennifer, Eddie, and Fred. The location is convenient, especially for Disney employees, and the amenities, including pools, gym, and community events, are highly rated. Some mention pricy rent, but overall, residents express satisfaction with their community.

16031 Silver Brook Way - Photo 1 of 1

2d ago

House for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

16031 Silver Brook Way, Winter Garden, FL 34787

In-unit laundry | Garage parking | Swimming pool

5 beds

4.5 baths

$6,500

House for rent

Elegant Home with Pool & Spacious Backyard

This stunning newly built residence features 5 bedrooms and 5 bathrooms, offering bright open spaces and a warm atmosphere. The large backyard is perfect for entertaining, and the private pool adds a touch of luxury. An oversized 2-car garage ensures ample storage, while access to a community clubhouse and pool enhances the lifestyle. Located near excellent schools, this home combines modern living with convenience in a desirable area.

10264 Love Story St - Photo 1 of 1

2d ago

House for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

10264 Love Story St, Winter Garden, FL 34787

In-unit laundry | Garage parking | Swimming pool

5 beds

3 baths

$6,000

House for rent

Expansive Home with Pool and Nature Views

Embrace Florida living in this spacious 5-bedroom, 3-bath home featuring a stunning saltwater pool and a large screened lanai. Enjoy breathtaking sunsets and Disney fireworks from your fenced backyard. With a private office, bonus room, and a guest room with en-suite bath, this home is perfect for families or multi-generational living. Nestled on a conservation lot with no rear neighbors, residents have access to resort-style amenities, top schools, and easy routes to Disney and local attractions.

14899 Apollo Bond Dr - Photo 1 of 1

2d ago

Townhouse for rent in Winter Garden

3 beds

2.5 baths

$2,500

House for rent

Resort-Style Townhouse Near Disney Magic

Enjoy luxury in this 3-bedroom, 2.5-bath townhouse boasting an open floor plan with all tile flooring downstairs. Bedrooms are upstairs, with the master featuring an en-suite bathroom with dual sinks. The community offers a resort-style pool, children's play area, and basketball court. Conveniently close to Disney and Winter Garden Village, this pet-friendly home ensures comfort with a laundry area, washer, and dryer included.

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15350 Oak Apple Ct ##17b - Photo 1 of 1

2d ago

Tucker Oaks townhouse for rent in Winter Garden

15350 Oak Apple Ct ##17b, Winter Garden, FL 34787

In-unit laundry | Swimming pool | Dishwasher

3 beds

2.5 baths

$2,250

House for rent

Bright & Spacious Townhouse in Gated Community

This charming 3-bedroom, 2.5-bath townhouse features an open layout with ample living and dining space. Enjoy the well-appointed kitchen and a private screened patio for outdoor relaxation. The primary suite includes an en suite bath, while the large 2-car garage offers additional storage. Located in the desirable Tucker Oaks community, residents can benefit from a pool and easy access to shopping and dining, all just minutes from downtown Winter Garden.

Tremaine Boyd Apts NEW - Photo 1 of 1

2d 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

Downtown Winter Garden Living by the Trail

Tremaine Boyd Apts NEW offers urban-style one-bedrooms just a block from Plant Street and the West Orange Trail. Residents enjoy stainless steel appliances, full-size washers and dryers, luxury vinyl plank flooring, 10 ft ceilings, farmhouse sinks, granite finishes, crown molding, 42” shaker cabinets, and in-unit bicycle hanging stations—all steps from shops, restaurants, and local culture.

15250 Sunrise Grove Ct - Photo 1 of 1

3d ago

Townhouse for rent in Winter Garden

Townhouse - WINTER GARDEN, FL

15250 Sunrise Grove Ct, Winter Garden, FL 34787

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

3 beds

2.5 baths

$2,700

House for rent

Modern Townhome with Private Backyard Oasis

Experience comfort and style in this stunning 3-bedroom, 2.5-bath townhouse boasting an open-concept design filled with natural light. The beautifully appointed kitchen features modern cabinetry and stainless steel appliances, seamlessly flowing into the living and dining areas. The primary suite offers a walk-in closet and elegant in-suite bath with dual sinks. Enjoy outdoor relaxation in the private backyard, all within a vibrant community near top-rated schools, shopping, and Orlando attractions.

13370 Daniels Landing Cir - Photo 1 of 1

3d ago

Townhouse for rent in Winter Garden

Townhouse - WINTER GARDEN, FL

13370 Daniels Landing Cir, Winter Garden, FL 34787

In-unit laundry | Garage parking | Swimming pool

2 beds

2.5 baths

$2,275

House for rent

Stylish Townhome with Enclosed Patio Retreat

Move-in ready, this spacious 2-bedroom, 2.5-bath townhome features a 1-car garage in the gated Daniels Landing community. Enjoy the open layout with upgraded kitchen cabinets, granite countertops, and brand-new Whirlpool appliances. Relax on the charming enclosed patio with pavers, or unwind in one of the two master suites, each with walk-in closets. Residents can take advantage of the community clubhouse, pool, fitness center, and convenient access to dining and highways.

216 Deepcove Rd - Photo 1 of 1

3d ago

Townhouse for rent in Winter Garden

Townhouse - WINTER GARDEN, FL

216 Deepcove Rd, Winter Garden, FL 34787

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

2 beds

2.5 baths

$2,200

$2,100

Price drop

House for rent

Modern Townhome with Resort-Style Amenities

This beautifully maintained 2-bedroom, 2.5-bath townhome features an open-concept living area and private en-suite bathrooms for both bedrooms. Enjoy a fenced-in patio and easy access to a resort-style pool, fitness center, and playground. Additional conveniences include a laundry room upstairs and inclusive utilities like cable and high-speed internet. Located just minutes from Historic Downtown Winter Garden, this rental offers a blend of comfort and convenience in a prime location.

88 Windtree Ln Bldg K - Photo 1 of 1

3d ago

Condo for rent in Winter Garden

88 Windtree Ln Bldg K, Winter Garden, FL 34787

Air conditioning | Assigned parking | Swimming pool

2 beds

2 baths

$1,650

$1,500

Price drop

Condo for rent

Charming 2nd Floor Condo with Screened Patio

This inviting 2-bedroom, 2-bathroom condo offers 918 square feet of comfortable living space with a desirable split floor plan. Enjoy outdoor relaxation on the screened patio while having two assigned parking spaces for convenience. The amenities enhance the experience, featuring a community pool and basketball courts, perfect for leisure and social activities. A great location makes this condo a cozy retreat in Winter Garden.

16548 Wingspread Loop #NA - Photo 1 of 1

3d ago

House for rent in Winter Garden

$2,850 - 3 Bedroom 2.5 Bathroom House In Horizon West With Great Amenities

16548 Wingspread Loop #NA, Winter Garden, FL 34787

Garage parking | Assigned parking | Swimming pool

3 beds

2.5 baths

$2,850

House for rent

Available Jun 1

Modern 3-Bedroom Home with Community Amenities

This stunning 3-bedroom, 2.5-bathroom home spans 2,027 sq ft in Horizon West. It features a well-equipped kitchen with a fridge and dishwasher. Enjoy access to a community clubhouse, gym, and pool for leisure and fitness. Perfect for those seeking a vibrant lifestyle in a family-friendly environment.

1535 Broken Oak Dr - Photo 1 of 1

3d ago

Tucker Oaks townhouse for rent in Winter Garden

Tucker Oaks

1535 Broken Oak Dr, Winter Garden, FL 34787

In-unit laundry | Air conditioning | Garage parking

3 beds

3 baths

$1,995

House for rent

Available May 25

Modern Townhome in Gated Community Oasis

This exquisite 3-bedroom, 3-bath townhouse offers modern living within the secure confines of the Tucker Oaks gated community. Spanning 1,544 square feet, smart design features include a stylish patio and attached garage. Enjoy the convenience of in-unit laundry, with practical amenities enhancing everyday comfort. Ideal for those seeking a vibrant lifestyle in a serene setting, this home is ready for you to make it your own.

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9451 Komika Ln #NA - Photo 1 of 1

3d ago

House for rent in Winter Garden

9451 Komika Ln - N/A

9451 Komika Ln #NA, Winter Garden, FL 34787

Air conditioning | Garage parking | Swimming pool

3 beds

2 baths

$2,850

$2,750

Price drop

House for rent

Available Apr 30

Delightful Home with Resort-Style Community Perks

This charming 3-bedroom, 2-bath home features a bright, open-concept layout with granite countertops and stainless steel appliances. Enjoy resort-style living in the Waterleigh community, offering pools, fitness centers, and more. The master suite includes a spacious walk-in closet, complemented by a two-car garage and convenient laundry area. Located just minutes from downtown Winter Garden, Disney, and local dining and shopping, this home blends comfort and convenience perfectly!

8119 Laughing Gull St - Photo 1 of 1

3d ago

House for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

8119 Laughing Gull St, Winter Garden, FL 34787

In-unit laundry | Garage parking | Swimming pool

3 beds

2 baths

$3,400

House for rent

Inviting Home with Gourmet Kitchen & Florida Room

This spacious 4-bedroom, 2-bath home spans 2,043 sq. ft. and features beautiful wood-style ceramic tiling throughout. The gourmet kitchen boasts stainless steel appliances, a new Whirlpool refrigerator, and a stunning porcelain tile backsplash. A serene Florida room invites relaxation and entertainment, while plantation shutters offer style and privacy. Enjoy a practical split floor plan and every room equipped with ceiling fans for year-round comfort.

9354 Lake Hickory Nut Dr - Photo 1 of 1

3d ago

House for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

9354 Lake Hickory Nut Dr, Winter Garden, FL 34787

In-unit laundry | Air conditioning | Garage parking

3 beds

3.5 baths

$4,750

House for rent

Stunning Lakefront Home with Disney Firework Views

Experience lakefront living in this beautifully renovated 3-bedroom, 3.5-bathroom home on Lake Hickory Nut. Enjoy breathtaking sunrise views and Disney firework displays from your oversized private balcony. This 2,278 sq. ft. residence features abundant natural light, a cozy wood-burning fireplace, and a dock for relaxing or fishing. An upgraded kitchen and spacious living areas make it perfect for entertaining. Don’t miss the chance to own a piece of paradise on this desirable skiable lake!

15250 Groveside Rd - Photo 1 of 1
New construction

4d ago

Townhouse for rent in Winter Garden

Townhouse - WINTER GARDEN, FL

15250 Groveside Rd, Winter Garden, FL 34787

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

3 beds

2.5 baths

$2,950

House for rent

Stunning New Luxury Townhouse in Hamlin

Experience modern living in this stunning 3-bedroom, 2.5-bathroom luxury townhouse featuring a popular three-story layout and 1,846 sq. ft. of stylish space. The open-concept design is enhanced by luxury vinyl plank flooring and a contemporary kitchen with quartz countertops and an oversized island. The spacious primary suite boasts a walk-in closet and dual vanities. Enjoy the convenience of Hamlin's vibrant lifestyle, close to shopping, dining, and top-rated schools.

16324 Silver Grove Blvd #1 - Photo 1 of 1

5d+ ago

House for rent in Winter Garden

16324 Silver Grove Boulevard - 1

16324 Silver Grove Blvd #1, Winter Garden, FL 34787

Swimming pool | Outdoor space

5 beds

4.5 baths

$5,000

House for rent

Available Jan 1

Modern Two-Story Home in Vibrant Community

This stunning 5-bedroom, 4.5-bath home, built in 2023, offers approximately 3,743 sq. ft. of light-filled living space and a versatile layout ideal for a home office or media lounge. Located in the resort-style Silverleaf Reserve at Hamlin, residents benefit from scenic walking trails, shops, and dining just minutes away from downtown Winter Garden and the Orlando area. An excellent choice for families with schools nearby. Available for rent starting January 1st!

7254 Duxbury Ln - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Garden

Townhouse - WINTER GARDEN, FL

7254 Duxbury Ln, Winter Garden, FL 34787

In-unit laundry | Garage parking | Swimming pool

2 beds

2.5 baths

$2,600

House for rent

Modern Townhouse with Private Patio & Community Pool

This stunning 2-bedroom, 2.5-bath townhouse offers a bright, open floor plan with tile flooring throughout the main level. The contemporary kitchen features granite countertops and stainless steel appliances. Upstairs, the spacious master suite boasts a walk-in closet and en-suite bath with dual vanities. Enjoy outdoor living on the fenced brick patio, and take advantage of community amenities including a pool and playground. Includes a convenient 2-car garage and quick move-in availability.

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

Charming Home with Spacious Backyard Oasis

This delightful 3-bedroom, 2-bath home features a spacious backyard with a screened-in patio and no rear neighbors, ensuring tranquility. The split floorplan includes a formal dining area, a large living room with a fireplace, and French doors leading outside. The master suite boasts a walk-in closet and an ensuite bath with patio access. Conveniently located just minutes from Downtown Winter Garden and local amenities, this charming property is perfect for enjoying Florida living.

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 | Air conditioning | On-site laundry

2 beds

2 baths

$1,700

House for rent

Available Apr 1

Renovated 2-Bedroom First Floor Townhouse Retreat

Experience vibrant living in this renovated 2-bedroom, 2-bathroom townhouse featuring a screened-in balcony and no carpet. Enjoy modern conveniences with assigned parking, in-unit laundry, and easy access to shopping and dining options. The community offers a pool and basketball courts, ensuring a dynamic lifestyle. This pet-friendly unit is perfect for those seeking comfort and quality in a charming setting.

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Updated: May 22, 2026

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Learn more about renting in Winter Garden, FL

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Local insights: What it's like to live in Winter Garden, FL

Residents of Winter Garden, FL appreciate the vibrant downtown area, which is filled with shops and restaurants, making it easy to enjoy a night out. Many enjoy the year-round warm weather and outdoor spaces, like parks and trails, ideal for walking or biking. However, some mention that traffic can be an issue, particularly during peak hours. Overall, the mix of suburban and urban vibes, along with community events, contributes to a lively local atmosphere.

How much is the average rent in Winter Garden, FL for 1-bedroom and 2-bedroom apartments?

Winter Garden's 2025 rental market shows 1-bedroom apartments averaging around $1,800 per month, while 2-bedroom units average around $2,300 monthly. Both bedroom types experienced increases from the previous year, with 2-bedrooms seeing stronger growth at 5.3% compared to 1-bedrooms at 1.4%.

Are rents going up or down in Winter-Garden, FL?

Rents in Winter Garden, FL have experienced a relatively stable trend with a modest 0.19% year-over-year increase. Specifically, 1-bedroom rents have decreased by 1.68%, while 2-bedroom rents have increased by 1.12%.

When is the best time to look for an apartment in Winter Garden, FL?

October offers the lowest rental prices in Winter Garden, while December sees the highest rent with approximately a 3% difference between peak and off-peak pricing. August and November show less competition with reduced demand compared to supply, while March and April are the most competitive months for apartment hunting.

What are the best neighborhoods to rent an apartment in Winter Garden, FL?

Tucker Oaks and Stoneybrook West represent Winter Garden's most in-demand rental areas, generating higher consumer interest despite comprising just 3% of the total rental market. Courtlea Oaks, Tucker Oaks, and Stoneybrook West offer strong community connections with high walk scores and well-developed street infrastructure that encourage neighborhood interaction.

Are there pet-friendly apartments in Winter Garden, FL?

Winter Garden's rental market centers on pet-friendly living, with Tucker Oaks particularly accommodating for pet owners. The neighborhood offers comprehensive pet amenities including pet waste stations, dedicated pet spaces, and pet events that build community among animal lovers, while maintaining no breed restrictions.

Are utilities usually included in rent in Winter Garden, FL?

Utilities are rarely included in Winter Garden rental properties, appearing in less than 1% of total listings across all apartment types. One-bedroom apartments have the highest rate of utility inclusion at 0.14% of listings, while studios, two-bedrooms, and three-bedrooms each include utilities in fewer than 0.02% of available properties.

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.

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