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Apartments for Rent in Highlands, Winter Springs, FL

Average rent

$1,886
decreased by9%

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Great for

Social life
Pet owners
Wellness

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429 Sheoah Blvd #9 - Photo 1 of 1

15h ago

Our team has verified this company

Verified

BAYTREE VILLAGE

429 Sheoah Blvd #9, Winter Springs, FL 32708

In-unit laundry | On-site laundry | Hardwood floor

3 beds

2 baths

$2,499

House for rent

Available Jan 1

Description

This property is available. Please inquire on this site to schedule a showing. Welcome to your new home at 429 Sheoah Boulevard, Winter Springs, FL 32708. This charming property offers a blend of comfort and style, nestled in a serene neighborhood. The exterior features well-maintained landscaping that enhances the curb appeal. Inside, you'll find a spacious living area with beautiful hardwood flooring and ample natural light streaming through the large sliding glass doors, which lead to a private screened-in patio, perfect for enjoying the peaceful surroundings. The kit

419 Harbor Winds Ct - Photo 1 of 1

2d ago

Highlands townhouse for rent in Winter Springs

Townhouse - WINTER SPRINGS, FL

419 Harbor Winds Ct, Winter Springs, FL 32708

In-unit laundry | Air conditioning | Garage parking

3 beds

2 baths

$2,850

$2,700

Price drop

House for rent

427 Sheoah Blvd #33 - Photo 1 of 1

5d+ ago

Highlands condo for rent in Winter Springs

2 beds

1 bath

$1,900

$1,800

Price drop

Condo for rent

429 Sheoah Blvd #11 - Photo 1 of 1

5d+ ago

Highlands condo for rent in Winter Springs

Condominium - WINTER SPRINGS, FL

429 Sheoah Blvd #11, Winter Springs, FL 32708

In-unit laundry | Balcony | Assigned parking

3 beds

2 baths

$1,650

Condo for rent

624 Huntly Ln - Photo 1 of 1

5d+ ago

Highlands townhouse for rent in Winter Springs

Townhouse - WINTER SPRINGS, FL

624 Huntly Ln, Winter Springs, FL 32708

Garage parking

2 beds

2 baths

$1,680

House for rent

640 Macduff Ln #A - Photo 1 of 1

5d+ ago

Highlands apartment for rent in Winter Springs

640 Macduff Ln #A, Winter Springs, FL 32708

In-unit laundry | Garage parking | High ceilings

3 beds

2 baths

$2,300

Apartment for rent

Find rentals with popular amenities

Dishwasher

Garage Parking

In-Unit Laundry

Outdoor Space

640 Macduff Ln #B - Photo 1 of 1

5d+ ago

Highlands apartment for rent in Winter Springs

640 Macduff Ln #B, Winter Springs, FL 32708

In-unit laundry | Garage parking | High ceilings

3 beds

2 baths

$2,400

Apartment for rent

10 Sheoah Blvd #8 - Photo 1 of 1

5d+ ago

Highlands condo for rent in Winter Springs

Condominium - Other City - In The State Of Florida, FL

10 Sheoah Blvd #8, Winter Springs, FL 32708

2 beds

2 baths

$1,700

Condo for rent

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424 Club Dr - Photo 1 of 1

5d+ ago

Highlands townhouse for rent in Winter Springs

Townhouse - WINTER SPRINGS, FL

424 Club Dr, Winter Springs, FL 32708

In-unit laundry | Swimming pool | Ceiling fan

3 beds

2 baths

$2,000

House for rent

314 San Rafael St - Photo 1 of 1
No deposit

5d+ ago

Condo for rent in Winter Springs

314 San Rafael St, Winter Springs, FL 32708

In-unit laundry | Swimming pool | Ceiling fan

1 bed

1 bath

$1,300

Condo for rent

Description

AVAILABLE NOW! Adorable 1 bedroom, 1 bath villa with fenced area, open patio, shed, all tile flooring, washer and dryer included. Living room/dining area combined, all appliances except microwave. Enjoy the pool and tennis courts too! EQUAL HOUSING OPPORTUNITY FEATURES: All Kitchen Appliances EXCEPT microwave Family Room Tile Flooring Inside Utility with Washer and Dryer Ceiling Fans Open Patio Open Parking Fenced Shed Tenants are REQUIRED to have renters insurance with 100k of liability insurance or landlord’s liability policy ONLY apply via CFRP. com not any other sit

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Nearby rental good for social life

Nearby rental good for wellness

The Avenues at Winter Springs - Photo 1 of 1

15h ago

8.6

Very good

The Avenues at Winter Springs

1 Laurel Oaks Dr, Winter Springs, FL 32708

1–3 beds

1–2 baths

$1,091–$1,797

Price drop

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.

1662 Orrington Payne Place #1662 - Photo 1 of 1

5d+ ago

Townhouse for rent in Casselberry

3 BR, 3 BA in Casselberry

1662 Orrington Payne Place #1662, Casselberry, FL 32707

Hardwood floor | Walk-in closets

3 beds

3 baths

$2,250

House for rent

Available Dec 11

Description

Welcome to your dream townhome in the heart of Casselberry, FL. This stunning 3-bedroom, 2.5-bathroom property offers a perfect blend of comfort and style. The two-story layout features beautiful wood floors throughout, adding a touch of elegance to the spacious living areas. The fully equipped kitchen boasts modern stainless-steel appliances, ready to inspire your inner chef. The primary suite is a true retreat, complete with a walk-in closet and a primary bathroom featuring double sinks and a walk-in shower. The townhome also includes a one-car garage with a paved brick

227 San Gabriel St #227 - Photo 1 of 1

5d+ ago

Apartment for rent in Winter Springs

3 BR, 2 BA in North Orlando

227 San Gabriel St #227, Winter Springs, FL 32708

In-unit laundry | Hardwood floor

3 beds

2 baths

$1,995

Apartment for rent

Available Oct 23

Description

This charming 3-bedroom, 2-bathroom home located in the heart of Winter Springs, FL. The interior features a modern kitchen with stainless steel appliances, granite countertops, and ample cabinet space. The home offers tile and laminate wood flooring throughout, washer and dryer hookups inside the home, and a neutral color palette that complements any décor.

1142 Landmark Ln #1142 - Photo 1 of 1

5d+ ago

Apartment for rent in Casselberry

2 BR, 1 BA in Casselberry

1142 Landmark Ln #1142, Casselberry, FL 32707

In-unit laundry | On-site laundry

2 beds

1 bath

$1,350

Apartment for rent

Available Dec 1

Description

This property located at 1142 Landmark Ln features 2 bedrooms and 1 bathroom within a total of 864 square feet. The bathroom is equipped with a tub/shower combination. 2 Bedrooms, each bedroom provides sufficient room for furnishings and personal storage. The property includes washer/dryer hookups for laundry convenience.

326 San Rafael St #326 - Photo 1 of 1
No deposit

5d+ ago

Apartment for rent in Winter Springs

1 BR, 1 BA in North Orlando

326 San Rafael St #326, Winter Springs, FL 32708

In-unit laundry | Carpet

1 bed

1 bath

$1,350

Apartment for rent

Available Nov 11

Description

1 Bed/1 Bath Villa in Indian Ridge AVAILABLE NOVEMBER 11th! Super cute, 1 bed/1 bath villa with an enclosed porch to enjoy year round. Laminate and tile flooring in living areas and carpet in the bedroom. Washer and dryer included, small fenced area and a shed. Conveniently located. ONLY apply via CFRP site not any other site EQUAL HOUSING OPPORTUNITY C F R P Realty is proud to offer no deposit move-ins to qualified renters through Obligo! We understand that moving costs can add up, so we want to extend financial flexibility to our residents. When you move in with us, yo

1142 Landmark Ln - Photo 1 of 1

5d+ ago

House for rent in Casselberry

Single Family Residence - CASSELBERRY, FL

1142 Landmark Ln, Casselberry, FL 32707

In-unit laundry | On-site laundry | Storage

2 beds

1 bath

$1,350

House for rent

Description

Property Status: Active This property located at 1142 Landmark Ln features 2 bedrooms and 1 bathroom within a total of 864 square feet. The bathroom is equipped with a tub/shower combination. 2 Bedrooms, each bedroom provides sufficient room for furnishings and personal storage. The property includes washer/dryer hookups for laundry convenience. Office Phone: (407) 960-6145 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.

1662 Orrington Payne Place - Photo 1 of 1

5d+ ago

Townhouse for rent in Casselberry

1662 Orrington Payne Place, Casselberry, FL 32707

In-unit laundry | Garage parking | Swimming pool

3 beds

2 baths

$2,250

House for rent

Description

Welcome to your dream townhome in the heart of Casselberry, FL. This stunning 3-bedroom, 2.5-bathroom property offers a perfect blend of comfort and style. The two-story layout features beautiful wood floors throughout, adding a touch of elegance to the spacious living areas. The fully equipped kitchen boasts modern stainless-steel appliances, ready to inspire your inner chef. The primary suite is a true retreat, complete with a walk-in closet and a primary bathroom featuring double sinks and a walk-in shower. The townhome also includes a one-car garage with a paved brick

300 3rd St - Photo 1 of 1

5d+ ago

North Orlando house for rent in Winter Springs

Single Family Residence - WINTER SPRINGS, FL

300 3rd St, Winter Springs, FL 32708

In-unit laundry | Walk-in closets | Ceiling fan

4 beds

2 baths

$2,000

House for rent

Description

Property Status: Pending One or more photo(s) has been virtually staged. Discover the perfect combination of comfort and convenience in this beautifully upgraded 4-bedroom, 2-bathroom home, offering over 1,500 sq. ft. of inviting living space in the heart of Winter Springs. Step inside to find a stylish, modern kitchen featuring granite countertops, sleek cabinetry, and ample room for both cooking and entertaining. The master bath has been tastefully remodeled with a contemporary shower, creating a refreshing, spa-like retreat. Each of the four bedrooms offers generous

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733 Woodhaven Dr - Photo 1 of 1

15h ago

House for rent in Winter Springs

House for rent

Description

Nestled in a serene neighborhood, this exquisite single-family home presents a remarkable blend of modern luxury and comfort, making it a true gem in the market. Recently undergoing a complete remodel, this property showcases an impeccable design with attention to detail in every corner. Featuring three spacious bedrooms and two elegantly remodeled bathrooms, the home caters to both family life and entertaining. The heart of the home, the kitchen, is a masterpiece of modern design, boasting solid surface countertops that complement the sleek, new appliances and cabinetry,

44 N Fairfax Ave - Photo 1 of 1

16h ago

North Orlando house for rent in Winter Springs

44 N Fairfax Ave

44 N Fairfax Ave, Winter Springs, FL 32708

Air conditioning

2 beds

1 bath

$1,500

House for rent

Description

Discover a charming gem nestled in the heart of Winter Springs, FL! This delightful 1981-built home offers the perfect blend of vintage character and modern convenience. With 2 spacious bedrooms and 1.5 bathrooms, this residence provides ample space for relaxation and functionality. The inviting layout features a cozy living area, ideal for unwinding after a long day, and a well-appointed kitchen ready for your culinary adventures. he property is conveniently located near local parks, shopping centers, and dining options, making it easy to enjoy all that Winter Springs ha

40 N Fairfax Ave - Photo 1 of 1

16h ago

North Orlando house for rent in Winter Springs

40 N Fairfax Ave

40 N Fairfax Ave, Winter Springs, FL 32708

In-unit laundry | Air conditioning

2 beds

1 bath

$1,500

House for rent

Description

Welcome to this clean and inviting 2-bedroom, 1.5-bath home in the heart of Winter Springs. Enjoy a comfortable layout and a convenient location close to shopping, dining, and beautiful local parks. With easy access to major highways, commuting to Orlando is a breeze. Perfect for anyone looking for a relaxed lifestyle with everything nearby!

Listings within 5 miles
300 Colony Dr #3 - Photo 1 of 1

5d+ ago

House for rent in Casselberry

Room for rent in a quiet home in Casselberry

300 Colony Dr #3, Casselberry, FL 32707

In-unit laundry | Furnished | On-site laundry

1 bed

1 bath

$750

House for rent

Available Jan 17

Description

Property Id: 2271550 Spacious, fully furnished room located in a quiet neighborhood in Casselberry. House is updated and all utilities are included. Free indoor laundry. Conveniently located near SR 434, shopping and bus service. This is a shared house with three other roommates. We do require background checks.

207 S Moss Rd - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Springs

Townhouse - WINTER SPRINGS, FL

207 S Moss Rd, Winter Springs, FL 32708

In-unit laundry | Ceiling fan | Dishwasher

2 beds

1 bath

$1,495

House for rent

Description

Property Status: Active 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.

Reserve at Lake Irene - Photo 1 of 1

16h 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

$1,199–$1,780

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

402 E Springtree Way - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

402 E Springtree Way, Lake Mary, FL 32746

Garage parking | Hardwood floor | Ceiling fan

3 beds

2 baths

$2,520

$2,420

Price drop

House for rent

Available Feb 18

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

Showing 1 - 25 of 25 results
Home > Apartments in Winter Springs > Highlands Apartments For Rent
Updated: January 30, 2026

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Learn more about renting in Highlands, Winter Springs, FL

Highlands, Winter Springs apartment availability

Highlands in Winter Springs offers a good selection of rental listings, with an average of about 9 rentals available each month. The majority of rentals in Highlands are 3-bedroom apartments, making it a great option for families or those looking for more space. Many apartments in Highlands offer desirable amenities, including a dishwasher, in-unit laundry, and outdoor space, which are available in over half of the apartments. With its range of amenities and spacious apartments, Highlands is a great choice for renters looking for a comfortable and convenient living experience.

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.

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.

Highlands Apartments for rent FAQ

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

The average size of a 2 bedroom apartment rental in Highlands is 1082 square feet. The average size of a 3 bedroom apartment rental in Highlands is 1570 square feet.

Can I afford an apartment for rent in Highlands, 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 Highlands average rent prices.

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

3 bedroom apartments are the most common type of rentals in Highlands, Winter Springs, FL right now.

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

2 bedroom apartments are the least common type of rentals in Highlands, Winter Springs, FL right now.

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

🔑Available apartment rentals25
💰Best rent deal1 Laurel Oaks Dr
Popular amenities, ,
🧦In-unit laundry
🍽With dishwasher
🏠With photos