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Apartments for Rent in Highlands, Winter Springs, FL

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475 Macgregor Rd #NA - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

$2,500 - 3 Bedroom 2 Bathroom House In Winter Springs With Great Amenities

475 Macgregor Rd #NA, Winter Springs, FL 32708

In-unit laundry | Air conditioning | Garage parking

3 beds

2 baths

$2,500

House for rent

Available Jul 1

Description

Amazing 3 bedroom, 2 bathroom house in Winter Springs. Amenities included: central air, central heat, dishwasher, appliance, storage, washer dryer hook-ups, yard, and community pool. No Utilities included. Is not pet friendly. Date Available: Jul 1st 2026. $2,500/month rent. $5,000 security deposit required. Please submit the form on this page or contact Vikas at 321-304-1732 to learn more. This property is managed by a responsible landlord using Avail landlord software.

210 Moree Loop #4 - Photo 1 of 1

5d+ ago

Highlands condo for rent in Winter Springs

210 Moree Loop #4, Winter Springs, FL 32708

In-unit laundry | Swimming pool | Dishwasher

1 bed

1 bath

$1,350

Condo for rent

Description

Available Now! Rent includes trash service, lawn care, washer & dryer! Welcome home to this beautiful 2nd-floor corner unit tucked away in the highly desirable Highlands community of Winter Springs. Ideally located just off SR-434 with quick access to SR-417 and I-4, you'll enjoy the perfect blend of convenience and tranquility. Surrounded by mature oak trees, scenic walking trails, and lush landscaping, this established community offers a peaceful retreat while remaining close to shopping, dining, and everyday conveniences. Offering 710 square feet of thoughtfully desig

130 Rhoden Ln - Photo 1 of 1

3d ago

North Orlando townhouse for rent in Winter Springs

TOWNHOME - WINTER SPRINGS, FL

130 Rhoden Ln, Winter Springs, FL 32708

In-unit laundry | On-site laundry | Ceiling fan

2 beds

1.5 baths

$1,625

House for rent

Description

Property Status: Active This 2/1.5 corner-unit townhome features carpet in both bedrooms and bamboo flooring in the living room and common areas. The home has a fireplace in the living room. The screened-in patio has a laundry closet. Torasco Park is just across the street from SPLASH PARK, which includes a basketball court, a soccer field, a playground, and an exercise trail. Keller Williams residents are enrolled in the Resident Benefits Package (RBP), which includes HVAC air filter delivery, credit building to help boost your credit score with timely rent payments, $1M

313 San Gabriel St - Photo 1 of 1

5d+ ago

House for rent in Winter Springs

313 San Gabriel St, Winter Springs, FL 32708

Swimming pool | Ceiling fan | Storage

2 beds

2 baths

$1,650

House for rent

Available Jul 31

Description

Discover Deersong Single Family 2 Bed 2 Bath in Winter Springs, Fl — available now! This two-bedroom, two-bath home features tile floors, fresh interior paint, and new kitchen cabinets with granite countertops. The kitchen includes a pantry closet and there is additional storage with a linen closet and a separate storage closet. The large master bedroom offers a walk-in closet, and ceiling fans are installed throughout. Outside, enjoy a fenced backyard and access to the community pool. Washer/dryer hook-up is included for added convenience. This property offers an option

105 Cory Ln - Photo 1 of 1

5d+ ago

Apartment for rent in Winter Springs

APARTMENT - WINTER SPRINGS, FL

105 Cory Ln, Winter Springs, FL 32708

In-unit laundry | Assigned parking | Ceiling fan

2 beds

2 baths

$1,350

Apartment for rent

Description

Property Status: Active Make your new home in this spacious second-floor apartment in Winter Springs, directly across from beautiful Torcaso Park with easy access to walking trails, green space, and recreation just outside the door. This two-bedroom, two-bathroom apartment features a practical layout with a galley kitchen open to a combined living and dining space that leads to a screen-enclosed covered patio, perfect for relaxing or entertaining. The kitchen is fully-equipped with an electric range, refrigerator, and a dishwasher. The two spacious bedrooms are separated b

1250 N Brassie Dr #NA - Photo 1 of 1

5d+ ago

House for rent in Winter Springs

$1,800 - 2 Bedroom 1 Bathroom House In Winter Springs

1250 N Brassie Dr #NA, Winter Springs, FL 32708

In-unit laundry | Air conditioning | Assigned parking

2 beds

1 bath

$1,800

House for rent

Available Jun 20

Description

Updated 2 bedroom, 1 bathroom house in Winter Springs. Amenities included: central air, central heat, dishwasher, stainless steel appliance, updated kitchen, updated bathroom, and washer dryer. Utilities included: water and landscaping. Is not pet friendly. Date Available: Jun 20th 2026. $1,800/month rent. $1000 security deposit required along with first and last months rent. Please submit the form on this page or contact Natasha at 321-274-2017 to learn more. This property is managed by a responsible landlord using Avail landlord software.

Find rentals with popular amenities

Swimming Pool

In-Unit Laundry

Dishwasher

Outdoor Space

44 S Edgemon Ave - Photo 1 of 1

5d+ ago

North Orlando house for rent in Winter Springs

SINGLE_FAMILY - WINTER SPRINGS, FL

44 S Edgemon Ave, Winter Springs, FL 32708

Ceiling fan | Dishwasher | Outdoor space

4 beds

2 baths

$2,200

House for rent

Description

Property Status: Active 4 bedroom, 2 bathroom, large back patio. All tile floors throughout, large back yard. Desirable community , community park with lots of walking sidewalks. Near the Oviedo Market Place and lots of food and shopping areas, easy access to 417, close to Red Bug Lake Recreational Center. Office Phone: (407) 947-9533 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.

44 S Cortez Ave - Photo 1 of 1

5d+ ago

North Orlando house for rent in Winter Springs

44 S Cortez Ave, Winter Springs, FL 32708

Ceiling fan | Storage | On-site management

3 beds

2 baths

$2,295

House for rent

Available Jun 10

Description

Beautiful 3/2 Home in Winter Springs! This recently refreshed single-family home offers three bedrooms and two bathrooms with brand new flooring and fresh interior paint throughout. Both bathrooms feature new cabinets and brand new tile work, and the property includes a brand new air conditioner for added comfort. Ceiling fans are installed for improved circulation, and washer/dryer hook-ups are available for laundry convenience. Outside, a fenced backyard and an on-site shed provide extra storage. Located in Winter Springs, this home combines modern updates with practical

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112 Cory Ln - Photo 1 of 1

5d+ ago

Apartment for rent in Winter Springs

112 Cory Ln, Winter Springs, FL 32708

In-unit laundry | Dishwasher | Outdoor space

2 beds

2 baths

$1,395

Apartment for rent

Description

Welcome to 112 Cory Lane, a bright and spacious 2-bedroom, 2-bathroom apartment that perfectly balances comfort and convenience. Step inside to find an open-concept living and dining area, designed for seamless entertaining and a relaxed Florida lifestyle. Both bedrooms are generously sized with ample closet space, providing a quiet retreat at the end of the day. Property Highlights: Prime Location: Just a 7-minute walk to the Winter Springs Town Center, featuring Publix, local dining favorites like Huey Magoo's, and various boutiques. Outdoor Recreation: Minutes from

315 San Miguel St - Photo 1 of 1

5d+ ago

House for rent in Winter Springs

House for rent

Description

This 2-bedroom 2 bath villa is equipped with all stainless-steel appliances in the kitchen, all tile flooring, new blinds and W/D hook-ups! Home features a privacy fenced patio with access through slider doors in living room and master bedroom. Great for entertaining! Upgraded kitchen and bathrooms offering new vanities, fixtures and tiled shower/tub areas. Great location close to shopping and restaurants. Small Pets accepted. LB JS All Flarent, Inc new residents are enrolled in the Resident Benefits Package (RBP) which includes liability insurance, credit building to hel

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502 San Gabriel Ct - Photo 1 of 1
3D tour

5d+ ago

House for rent in Winter Springs

502 San Gabriel Ct, Winter Springs, FL 32708

In-unit laundry | On-site laundry | Walk-in closets

3 beds

2 baths

$2,099

House for rent

Available Jul 21

Description

Discover comfortable living in this expansive 3-bedroom, 2-bathroom home nestled in the serene community of Winter Springs. Step inside to a generously sized family room that seamlessly flows into a designated dining area, perfect for entertaining guests or enjoying family meals. The interior boasts a harmonious blend of elegant tile and warm laminate flooring that extends throughout the residence. The heart of the home, the kitchen, comes fully equipped with sleek stainless steel appliances, ample storage space, and a convenient pantry to accommodate all your culinary nee

The Avenues at Winter Springs - Photo 1 of 1

5d+ ago

8.4

Very good

The Avenues at Winter Springs

1 Laurel Oaks Dr, Winter Springs, FL 32708

Carpet

1–2 beds

1–2 baths

$1,264–$1,823

Apartment for rent

Description

Our pet-friendly community offers spacious 1, 2, and 3-bedroom apartment homes with modern finishes and everyday conveniences. Enjoy amenities like a resort-style pool with sundeck, 24-hour fitness and wellness center, tennis court, playground, and leash-free pet park. Stay connected with 400 Mbps internet, and take advantage of on-site management, garages, and short-term lease options. Select homes feature upgraded white cabinetry, stainless steel appliances, granite countertops, hardwood-inspired flooring, private patios/balconies, and wood-burning fireplaces.

Listings within 5 miles
340 Micanopy Ct - Photo 1 of 1

2d ago

Our team has verified this company

Verified

340 Micanopy Ct Casselberry, FL 32707

340 Micanopy Ct, Casselberry, FL 32707

Walk-in closets | Outdoor space

3 beds

2 baths

$2,195

House for rent

Available Aug 7

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 $2339.90. That covers your base rent, $2195.00 + 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. Welcome to this inviting three-bedroom

213 S Moss Rd - Photo 1 of 1

5d+ ago

House for rent in Winter Springs

House for rent

Description

Sweet Home

5d+ ago

Townhouse for rent in Winter Springs

TOWNHOME - WINTER SPRINGS, FL

207 S Moss Rd, Winter Springs, FL 32708

Ceiling fan | Dishwasher | Outdoor space

2 beds

1.5 baths

$1,495

House for rent

Description

Property Status: Pending 2BD/1.5BA home for rent in Winter Springs on S Moss Rd. Features a bright, functional layout, spacious living area, kitchen with ample cabinet space, and well-sized bedrooms. Large yard for outdoor use. Conveniently located near parks, shopping, dining, SR-434, I-4, and Seminole County schools. Office Phone: (407) 829-2418 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.

Find sweet deals near Highlands

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

228 Bitterwood St - Photo 1 of 1

2d ago

North Orlando house for rent in Winter Springs

3 Bedroom Pet-Friendly Home in Winter Springs, FL with Main Street Renewal

228 Bitterwood St, Winter Springs, FL 32708

Swimming pool | Storage | Outdoor space

3 beds

2 baths

$2,255

$2,100

Price drop

House for rent

Description

Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening! Take advantage of the incredible location, nestled in a great neighborhood with access to schools, parks, dining and more. Don't miss a chance to make this house your next home! Beyond the home, experience the ease of our technolog

116 S Moss Rd - Photo 1 of 1

1d ago

North Orlando house for rent in Winter Springs

4 Bedroom Pet-Friendly Home in WINTER SPRINGS, FL with Main Street Renewal

116 S Moss Rd, Winter Springs, FL 32708

Swimming pool | Storage | Outdoor space

4 beds

2 baths

$2,590

House for rent

Description

Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening! Take advantage of the incredible location, nestled in a great neighborhood with access to schools, parks, dining and more. Don't miss a chance to make this house your next home! Beyond the home, experience the ease of our technolog

Reserve at Lake Irene - Photo 1 of 1

8m ago

8.8

Very good

Reserve at Lake Irene

1450 Sunshadow Dr, Casselberry, FL 32707

In-unit laundry | Swimming pool | Fitness center

1–2 beds

1–2 baths

$1,193–$1,536

Price drop

Apartment for rent

Description

The Reserve at Lake Irene is Casselberry's premier destination where modern luxury meets comfort and charm. Choose from our spacious one- and two-bedroom apartment homes and step into a community designed to elevate your everyday, featuring a vibrant, state-of-the-art fitness center, two sparkling resort-style swimming pools, and a welcoming, pet-friendly atmosphere. Stop dreaming about the perfect Florida lifestyle and start living it. Situated in a prime location, you'll discover stylish interiors, lush outdoor spaces, and a dedicated team committed to making your exper

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608 Pheasant Ave - Photo 1 of 1

19h ago

Our team has verified this company

Verified

608 Pheasant Ave, Longwood, FL 32750

Garage parking | Walk-in closets | Ceiling fan

3 beds

2 baths

$2,320

House for rent

Available Oct 12

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

424 Lancers Dr - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

424 Lancers Dr, Winter Springs, FL 32708

Garage parking | Walk-in closets | Ceiling fan

3 beds

2 baths

$2,450

House for rent

Available Sep 21

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

472 Amethyst Way - Photo 1 of 1

12h ago

Our team has verified this company

Verified

472 Amethyst Way, Lake Mary, FL 32746

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

3 beds

2 baths

$2,540

House for rent

Available Jul 23

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

813 Shell Ln - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

813 Shell Ln, Longwood, FL 32750

Garage parking | On-site laundry | Hardwood floor

3 beds

2 baths

$3,310

$2,405

Price drop

House for rent

Available Aug 28

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 3.0-bedroom, 2.0-bathroom home is not only pet-friendly, but also equipped with smart home features to make every

312 Riunite Cir - Photo 1 of 1

4d ago

Our team has verified this company

Verified

312 Riunite Cir, Winter Springs, FL 32708

Garage parking | Walk-in closets | Ceiling fan

3 beds

2 baths

$2,255

House for rent

Available Aug 21

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, 2.0-bathroom home is not only pet-friendly, but also equipped with smart home features to make everyda

395 Cidermill Pl - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

395 Cidermill Pl, Lake Mary, FL 32746

Garage parking | Ceiling fan | Fireplace

3 beds

2 baths

$2,645

House for rent

Available Oct 2

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

534 S Sundance Dr - Photo 1 of 1

8h ago

Our team has verified this company

Verified

534 S Sundance Dr, Lake Mary, FL 32746

Garage parking | On-site laundry | Swimming pool

4 beds

2 baths

$2,905

$2,705

Price drop

House for rent

Available Jul 17

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 4-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 applic

Average rent

The average rent in Highlands, Winter Springs, as of August 2026, is down 16.15% compared to last month and down 1% year-over-year.
$1,830
decreased by1%

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Showing 1 - 25 of 25 results
Home > Apartments in Winter Springs > Highlands Apartments For Rent
Updated: August 11, 2026

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Try our tenant screening, or post rental listings to Zumper, Craigslist Winter Springs, and more.

Learn more about renting in Highlands, Winter Springs, FL

What is the average rent for a 1-bedroom apartment Highlands, Winter Springs, FL?

Based on Zumper's July 2026 data, one-bedroom apartments in Highlands, Winter Springs, FL average around $1,340/month, remaining relatively stable year over year.

What is the average rent for a 2-bedroom apartment Highlands, Winter Springs, FL?

Based on Zumper's July 2026 data, two-bedroom apartments in Highlands, Winter Springs, FL average approximately $1,610/month, down 3.8% year over year.

What is the average rent for a 3-bedroom apartment Highlands, Winter Springs, FL?

Based on Zumper's July 2026 data, three-bedroom apartments in Highlands, Winter Springs, FL average around $2,210/month, up 14.3% year over year.

How much does it cost to rent an apartment in Highlands, Winter Springs, FL?

Based on Zumper's July 2026 data, Highlands apartments in Winter Springs, FL average about $2,030/month across all property types, up 9.5% year over year. August sees the highest rents, running roughly 17% higher than April.

What is the average apartment size in Highlands, Winter Springs, FL?

Based on our current listings, apartments in Highlands, Winter Springs, FL average around 1,340 sqft across all unit types, with three-bedrooms running larger at approximately 1,460 sqft.

What type of apartment is most common in Highlands, Winter Springs, FL?

Based on Zumper's current listings, three-bedroom apartments are the most common rental type in Highlands, Winter Springs, FL, with about 9 listings available monthly.

Why Highlands, Winter Springs is a great place to live

Highlands in Winter Springs is a neighborhood that perfectly complements an active social lifestyle. Our analysis of local data reveals that the area's population density, frequent transit options, well-maintained street infrastructure, high walk score, and emphasis on safety create an ideal environment for those who value community interaction and social connections. With these amenities, residents can easily get around, meet new people, and engage in local activities, making Highlands an excellent choice for those seeking a vibrant social life. If you're looking for a neighborhood that fosters connections and community, Highlands is definitely worth considering.

What type of apartment is least common inHighlands, Winter Springs, FL?

Based on our current listings, one-bedroom apartments and studios have averaged about 0 listings per month in Highlands, Winter Springs, FL, while two-bedrooms see approximately 3 listings monthly.

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 2026 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.

Looking for apartments in Highlands, Winter Springs, FL near you?

🔑Available apartment rentals25
💰Best rent deal1 Laurel Oaks Dr
Popular amenities, ,
🍽With dishwasher
🏠With photos