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Apartments for Rent in Highlands, Winter Springs, FL

Average rent

$1,785
decreased by2%

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Great for

Pet owners
Social life
Wellness

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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

3d 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

47 Macgregor Rd - Photo 1 of 1

5d+ ago

Highlands house for rent in Winter Springs

MacGregor Road, Winter Springs, FL

47 Macgregor Rd, Winter Springs, FL 32708

In-unit laundry | Air conditioning | Garage parking

3 beds

2 baths

$2,500

House for rent

Available Jul 1

Description

Property Id: 2705198 A beautiful 3 bedrooms, 2 bath single-family-home in a family-oriented neighborhood in Winter Springs. Excellent neighborhood for a family with school going kids. The house is ideal for a family with young kids and/or responsible students. The house is in very good shape. Relatively newly painted interior and exterior. The schools are the best in Central Florida A-rated Highlands Elementary, Sanford Middle, Seminole Science Charter School (2-3 mi) and Winter Springs High (IB) schools. There is a lake in the backyard. The neighbors are great, very quie

80 Moree Loop #9 - Photo 1 of 1

5d+ ago

Highlands condo for rent in Winter Springs

Condominium - WINTER SPRINGS, FL

80 Moree Loop #9, Winter Springs, FL 32708

In-unit laundry | Assigned parking | Swimming pool

3 beds

2 baths

$1,700

Condo for rent

404 San Gabriel St #1 - Photo 1 of 1

4d ago

House for rent in Winter Springs

404 San Gabriel Street - 1

404 San Gabriel St #1, Winter Springs, FL 32708

3 beds

2 baths

$1,900

House for rent

Available Jul 15

Description

Very nice home just freshly painted with new floors ready to move in. Spacious and private courtyard with storage for your convenience. Come apply with no credit check or initial cost.

1250 N Brassie Dr #NA - Photo 1 of 1

2d 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

Dishwasher

Outdoor Space

Swimming Pool

In-Unit Laundry

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

$2,395

$2,295

Price drop

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

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. Availability Note: Current residents vacate June 30th. The property will be fully turned, refreshed, and available for move-in on July 10th! (Note: Photos and layout are of a neighboring mirror unit. Finishes are

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The Avenues at Winter Springs - Photo 1 of 1

3d ago

8.6

Very good

The Avenues at Winter Springs

1 Laurel Oaks Dr, Winter Springs, FL 32708

Carpet

1–3 beds

1–2 baths

$1,119–$1,900

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.

Nearby rental good for wellness

Nearby rental good for social life

Listings within 5 miles
409 S Hawthorn Cir - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

409 S Hawthorn Cir Winter Springs, FL 32708

409 S Hawthorn Cir, Winter Springs, FL 32708

Garage parking | Outdoor space

3 beds

2 baths

$2,045

House for rent

Available Jul 20

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 $2189.90. That covers your base rent, $2045.00 + 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. Who said the perfect house doesn't exi

213 S Moss Rd - Photo 1 of 1

5d+ ago

House for rent in Winter Springs

House for rent

Description

Sweet Home

137 Garden Dr - Photo 1 of 1

5d+ ago

North Orlando townhouse for rent in Winter Springs

2 beds

2 baths

$1,515

House for rent

Description

MOVE IN SPECIAL: $500 OFF FIRST MONTH'S RENT. This renovated 2 bedroom and 1.5 bath Winter Springs townhome, features a large living area upon entry. There is a half bath downstairs for guests. The newly updated kitchen provides plenty of room for cooking, while the bedrooms offer peaceful retreats with ample natural light. Step outside to enjoy a private screen enclosed patio space, perfect for relaxing or unwinding after a busy day. Conveniently located near parks, shopping, dining, and top‑rated Seminole County schools, this home blends comfort, convenience, and communi

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133 Garden Dr - Photo 1 of 1

5d+ ago

North Orlando apartment for rent in Winter Springs

2BR/1.5BA

133 Garden Dr, Winter Springs, FL 32708

Microwave

2 beds

1.5 baths

$1,495

Apartment for rent

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

1.5 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

5d+ 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

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

212 S Cortez Ave #NA - Photo 1 of 1

5d+ ago

North Orlando house for rent in Winter Springs

Winter Springs Pool Home

212 S Cortez Ave #NA, Winter Springs, FL 32708

In-unit laundry | Furnished | Air conditioning

4 beds

3 baths

$2,400

House for rent

Available Jun 15

Description

Amazing 4 bedroom, 3 bathroom Furnished house in Winter Springs. Huge fenced in backyard in a safe neighborhood and large screend in patio perfect for summer in Central Florida! This house is NOT Fully furnished, bed frames and some outdoor furniture available. Amenities provided: central air, central heat, dishwasher, hardwood floors, pool, stainless steel appliance, updated kitchen, washer dryer, and yard. Tenant pays electric, water and Wifi. (water bill can be high due to pool -so budget for around $3k/mo total expenses -but landlord pays for lawn care, pest control an

116 S Moss Rd - Photo 1 of 1

5d+ 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

4 beds

2 baths

$2,590

House for rent

Description

Beautiful, pet-friendly home coming soon! Apply now, Move-In is available on or after the listed date. Upon approval, $500 reservation deposit to reserve (applied to security deposit and/or refundable). Application fee: $55 per adult. Security Deposit: one month?s rent. Pet fees: $250 + $40/mo per pet. Some homes may include pool ($150/mo), septic ($15/mo), and/or HOA fees; other fees may apply. We do not advertise on or ask for payments via check, cash, wire transfer, or cash apps. Contact us to schedule a showing.

Reserve at Lake Irene - Photo 1 of 1

5d+ ago

8.3

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

$1,299–$1,693

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

544 Tall Oaks Ter - Photo 1 of 1

5d+ ago

House for rent in Longwood

3 beds

2 baths

$2,295

House for rent

Description

3/2, 2 Car Garage, Single Family Home, Living Room and Dining Room Combo, Family Room, Eat-In Kitchen, Kitchen Appliances Included: Stove, Refrigerator, Disposal and Dishwasher, Kitchen Laundry with Washer and Dryer Included, Laminate Wood and Carpet Throughout Home, Master Bathroom has Dual Sinks and separate Garden Tub and Shower, Vaulted Ceilings, Walk-In Closets, Sprinkler System, Open Patio, Partially Fenced Backyard, Community Tennis and Playground, Pest Control Included by Owner, Dogs Ok - NO CATS, NO SMOKING, Year Built: 1995/ 1601 Sqft. Directions: I-4 WEST: Take

534 Lake Wildmere Cv - Photo 1 of 1

3d ago

Townhouse for rent in Longwood

534 Lake Wildmere Cv, Longwood, FL 32750

Swimming pool | Controlled access

4 beds

3.5 baths

$2,995

House for rent

Description

4/3.5 Two Story Townhouse- End Unit, 2 Car Garage, Living Room, Dining Room, Large Kitchen With Island & Breakfast Bar. Stainless Steel Kitchen Appliances Included: Refrigerator, Stove/Oven, Microwave, DIshwasher & Disposal. First Floor All Tile, Carpet Upstairs, Loft & Office Nook Upstairs, Double Master Upstairs with On Suite Bathrooms, Bedroom 3 Has Balcony Off Bedroom, Inside Utility With Washer & Dryer Included, Covered Porch In Front & Covered Patio In Back, Gated Community, Community Clubhouse & Pool, Community Dock Overlooking Lake, Small Pets Okay Upon Owners App

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424 Lancers Dr - Photo 1 of 1

1d 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

$2,470

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

5d+ 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

$3,630

$2,590

Price drop

House for rent

Available Jul 30

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

1412 Oberlin Ter - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

1412 Oberlin Ter, Lake Mary, FL 32746

Garage parking | Walk-in closets | Ceiling fan

3 beds

2.5 baths

$2,375

House for rent

Available Jun 25

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-bedroom, 2.5-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

439 E Springtree Way - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

439 E Springtree Way, Lake Mary, FL 32746

Garage parking | On-site laundry | Hardwood floor

3 beds

2 baths

$2,440

House for rent

Available Aug 24

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

20h ago

Our team has verified this company

Verified

534 S Sundance Dr, Lake Mary, FL 32746

Garage parking | Swimming pool | Walk-in closets

4 beds

2 baths

$2,905

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

Showing 1 - 25 of 25 results
Home > Apartments in Winter Springs > Highlands Apartments For Rent
Updated: July 20, 2026

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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, ,
🧦In-unit laundry
🍽With dishwasher
🏠With photos