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Luxury Apartments for Rent in Highlands, Winter Springs, FL

25 rentals

10 Sheoah Blvd #8 - Photo 1 of 1

5d+ ago

Luxury Highlands condo for rent in Winter Springs

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

10 Sheoah Blvd #8, Winter Springs, FL 32708

Luxury

2 beds

2 baths

$1,700

Condo for rent

647 Redwood Dr - Photo 1 of 1

22h ago

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Verified

647 Redwood Dr, Winter Springs, FL 32708

Luxury | Garage parking | Ceiling fan

3 beds

2 baths

$1,895

$1,780

Price drop

House for rent

Available Nov 14

543 Willow Way - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

543 Willow Way Winter Springs, FL 32708

543 Willow Way, Winter Springs, FL 32708

Luxury | Garage parking | Outdoor space

4 beds

2 baths

$2,265

House for rent

Available Nov 26

130 Edgemon Avenue - Photo 1 of 1

4d ago

Our team has verified this company

Verified

130 N Edgemon Ave Winter Springs, FL 32708

130 Edgemon Avenue, Winter Springs, FL 32708

Luxury | Outdoor space

4 beds

3 baths

$2,249

$2,080

Price drop

House for rent

Available Nov 26

314 San Rafael Court - Photo 1 of 1
No deposit

5d+ ago

Luxury condo for rent in Winter Springs

314 San Rafael Court, Winter Springs, FL 32708

Luxury | Swimming pool | In-unit laundry

1 bed

1 bath

$1,350

Condo for rent

Top amenities
Ceiling Fan
In-Unit Laundry
Swimming Pool
122 Lori Anne Ln - Photo 1 of 1

5d+ ago

Luxury North Orlando house for rent in Winter Springs

House for rent

Nearby rental good for eco-living

$1,125

North Orlando

Nearby rental good for pet owners

$2,300

North Orlando

20 20 North 2nd Street - Photo 1 of 1

5d+ ago

Luxury North Orlando house for rent in Winter Springs

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

20 20 North 2nd Street, Winter Springs, FL 32708

Luxury | Swimming pool | Storage

4 beds

2 baths

$2,125

House for rent

1662 Orrington Payne Place #1662 - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Casselberry

3 BR, 3 BA in Casselberry

1662 Orrington Payne Place #1662, Casselberry, FL 32707

Luxury | Walk-in closets | Hardwood floor

3 beds

3 baths

$2,250

House for rent

Available Dec 11

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615 Anhinga Road #NA - Photo 1 of 1

5d+ ago

Luxury Highlands house for rent in Winter Springs

$2,700 - 3 Bedroom 2 Bathroom House In Winter Springs With Great Amenities

615 Anhinga Road #NA, Winter Springs, FL 32708

Luxury | Air conditioning | Garage parking

3 beds

2 baths

$2,700

House for rent

Available Jan 1

Top amenities
Assigned Parking
Dishwasher
227 San Gabriel Street #227 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Springs

3 BR, 2 BA in North Orlando

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

Luxury | In-unit laundry | Hardwood floor

3 beds

2 baths

$1,995

Apartment for rent

Available Oct 23

Top amenities
In-Unit Laundry
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Find sweet deals near Highlands

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

$1,780

Winter Springs

$2,265

Winter Springs

$1,995

Winter Springs

$1,350

Casselberry

624 Huntly Lane - Photo 1 of 1

5d+ ago

Luxury Highlands townhouse for rent in Winter Springs

Townhouse - WINTER SPRINGS, FL

624 Huntly Lane, Winter Springs, FL 32708

Luxury | Garage parking

2 beds

2 baths

$1,680

House for rent

1142 Landmark Lane #1142 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Casselberry

2 BR, 1 BA in Casselberry

1142 Landmark Lane #1142, Casselberry, FL 32707

Luxury | In-unit laundry | On-site laundry

2 beds

1 bath

$1,350

Apartment for rent

Available Dec 1

Top amenities
In-Unit Laundry
On-Site Laundry
300 North 3rd Street #300 - Photo 1 of 1

5d+ ago

Luxury North Orlando apartment for rent in Winter Springs

4 BR, 2 BA in North Orlando

300 North 3rd Street #300, Winter Springs, FL 32708

Luxury | Walk-in closets

4 beds

2 baths

$2,300

Apartment for rent

Available Oct 29

1142 Landmark Lane - Photo 1 of 1

5d+ ago

Luxury house for rent in Casselberry

Single Family Residence - CASSELBERRY, FL

1142 Landmark Lane, Casselberry, FL 32707

Luxury | In-unit laundry | On-site laundry

2 beds

1 bath

$1,350

House for rent

Top amenities
In-Unit Laundry
On-Site Laundry
732 Willow Drive - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Springs

732 Willow Drive, Winter Springs, FL 32708

Luxury | Air conditioning | Garage parking

2 beds

2 baths

$1,600

House for rent

Available Nov 22

1662 Orrington Payne Place - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Casselberry

1662 Orrington Payne Place, Casselberry, FL 32707

Luxury | Swimming pool | Fitness center

3 beds

2 baths

$2,250

House for rent

Top amenities
Fitness Center
Hardwood Floor
In-Unit Laundry
Swimming Pool
300 3rd St - Photo 1 of 1

5d+ ago

Luxury North Orlando house for rent in Winter Springs

Single Family Residence - WINTER SPRINGS, FL

300 3rd St, Winter Springs, FL 32708

Luxury | Walk-in closets | In-unit laundry

4 beds

2 baths

$2,300

House for rent

Top amenities
Dishwasher
In-Unit Laundry
Package Service
640 Macduff Ln #A - Photo 1 of 1

5d+ ago

Luxury Highlands apartment for rent in Winter Springs

640 Macduff Ln #A, Winter Springs, FL 32708

Luxury | In-unit laundry | Garage parking

3 beds

2 baths

$2,300

Apartment for rent

Top amenities
High Ceilings
In-Unit Laundry
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640 Macduff Ln #B - Photo 1 of 1

5d+ ago

Luxury Highlands apartment for rent in Winter Springs

640 Macduff Ln #B, Winter Springs, FL 32708

Luxury | In-unit laundry | Garage parking

3 beds

2 baths

$2,400

Apartment for rent

Top amenities
High Ceilings
In-Unit Laundry
429 Sheoah Blvd #12 - Photo 1 of 1

5d+ ago

Luxury Highlands condo for rent in Winter Springs

Condo for rent

Listings within 5 miles
1968 Downs Ct - Photo 1 of 1

2d ago

Our team has verified this company

Verified

1968 Downs Ct, Lake Mary, FL 32746

Luxury | Walk-in closets | Garage parking

4 beds

2 baths

$3,205

$2,775

Price drop

House for rent

Available Nov 25

Top amenities
Ceiling Fan
High Ceilings
On-Site Laundry
503 Evergreen Avenue - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

503 Evergreen Ave Winter Springs, FL 32708

503 Evergreen Avenue, Winter Springs, FL 32708

Luxury | Outdoor space

4 beds

2 baths

$2,070

House for rent

Available Nov 19

312 Moss Road - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

312 S Moss Rd Winter Springs, FL 32708

312 Moss Road, Winter Springs, FL 32708

Luxury | Walk-in closets | Garage parking

3 beds

2 baths

$2,140

House for rent

Available Nov 20

300 Colony Drive #3 - Photo 1 of 1

4d ago

Luxury house for rent in Casselberry

Quiet home in Casselberry

300 Colony Drive #3, Casselberry, FL 32707

Luxury | In-unit laundry | Furnished

1 bed

1 bath

$800

House for rent

Available Dec 13

Top amenities
In-Unit Laundry
Microwave
On-Site Laundry
Showing 1 - 25 of 25 results
Home > Apartments in Winter Springs > Highlands > Highlands Luxury Apartments For Rent
Updated: December 20, 2025

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

🔑Available apartment rentals25
💰Best rent deal122 Lori Anne Ln
✨Popular amenities, ,
🧦In-unit laundry
🍽With dishwasher
🏠With photos

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