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Luxury Apartments for Rent in Highlands, Winter Springs, FL

25 rentals

320 Macgregor Rd - Photo 1 of 1

1d ago

Our team has verified this company

Verified

320 Macgregor Rd, Winter Springs, FL 32708

Luxury | Walk-in closets | Garage parking

3 beds

2 baths

$2,545

House for rent

Available Mar 10

Top amenities
Ceiling Fan
High Ceilings
429 Sheoah Blvd #9 - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

BAYTREE VILLAGE

429 Sheoah Blvd #9, Winter Springs, FL 32708

Luxury | In-unit laundry | On-site laundry

3 beds

2 baths

$2,499

House for rent

Available Jan 1

Top amenities
In-Unit Laundry
On-Site Laundry
227 San Gabriel St #227 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Springs

3 BR, 2 BA in North Orlando

227 San Gabriel St #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
The Avenues at Winter Springs - Photo 1 of 1

12h ago

8.6

Very good

The Avenues at Winter Springs

1 Laurel Oaks Dr, Winter Springs, FL 32708

Luxury | Carpet

1–3 beds

1–2 baths

$1,140–$1,797

Price drop

Apartment for rent

451 Club Dr - Photo 1 of 1

13h ago

Luxury Highlands house for rent in Winter Springs

Luxury | Swimming pool | In-unit laundry

3 beds

2 baths

$2,400

House for rent

Top amenities
In-Unit Laundry
46 N Fairfax Ave - Photo 1 of 1

5d+ ago

Luxury North Orlando house for rent in Winter Springs

46 N Fairfax Ave

46 N Fairfax Ave, Winter Springs, FL 32708

Luxury | Air conditioning | Outdoor space

2 beds

1 bath

$1,500

House for rent

Nearby rental good for eco-living

$1,525

Longwood

Nearby rental good for pet owners

44 N Fairfax Ave - Photo 1 of 1

5d+ ago

Luxury North Orlando house for rent in Winter Springs

44 N Fairfax Ave

44 N Fairfax Ave, Winter Springs, FL 32708

Luxury | Air conditioning

2 beds

1 bath

$1,500

House for rent

427 Sheoah Blvd #33 - Photo 1 of 1

5d+ ago

Luxury Highlands condo for rent in Winter Springs

427 Sheoah Blvd #33, Winter Springs, FL 32708

Luxury | Swimming pool

2 beds

1 bath

$1,900

$1,800

Price drop

Condo for rent

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1662 Orrington Payne Pl #1662 - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Casselberry

3 BR, 3 BA in Casselberry

1662 Orrington Payne Pl #1662, Casselberry, FL 32707

Luxury | Walk-in closets | Hardwood floor

3 beds

3 baths

$2,250

House for rent

Available Dec 11

624 Huntly Ln - Photo 1 of 1

5d+ ago

Luxury Highlands townhouse for rent in Winter Springs

Townhouse - WINTER SPRINGS, FL

624 Huntly Ln, Winter Springs, FL 32708

Luxury | Garage parking

2 beds

2 baths

$1,680

House for rent

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Find sweet deals near Highlands

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

$1,140–$1,785

Winter Springs

$1,495

Winter Springs

$1,350

Casselberry

$1,350

Casselberry

419 Harbor Winds Ct - Photo 1 of 1

5d+ ago

Luxury Highlands townhouse for rent in Winter Springs

Townhouse - WINTER SPRINGS, FL

419 Harbor Winds Ct, Winter Springs, FL 32708

Luxury | Walk-in closets | Swimming pool

3 beds

2 baths

$2,850

$2,700

Price drop

House for rent

Top amenities
Garage Parking
Hardwood Floor
In-Unit Laundry
Swimming Pool
1142 Landmark Ln #1142 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Casselberry

2 BR, 1 BA in Casselberry

1142 Landmark Ln #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
326 San Rafael St #326 - Photo 1 of 1
No deposit

5d+ ago

Luxury apartment for rent in Winter Springs

1 BR, 1 BA in North Orlando

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

Luxury | In-unit laundry | Carpet

1 bed

1 bath

$1,350

Apartment for rent

Available Nov 11

Top amenities
In-Unit Laundry
1142 Landmark Ln - Photo 1 of 1

5d+ ago

Luxury house for rent in Casselberry

Single Family Residence - CASSELBERRY, FL

1142 Landmark Ln, 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
314 San Rafael St #314 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Springs

1 BR, 1 BA in North Orlando

314 San Rafael St #314, Winter Springs, FL 32708

Luxury | In-unit laundry

1 bed

1 bath

$1,350

Apartment for rent

Available Nov 19

Top amenities
In-Unit Laundry
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
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
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
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10 Sheoah Blvd #8 - Photo 1 of 1

1d 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

$1,600

Condo for rent

40 N Fairfax Ave - Photo 1 of 1

5d+ ago

Luxury North Orlando house for rent in Winter Springs

40 N Fairfax Ave

40 N Fairfax Ave, Winter Springs, FL 32708

Luxury | In-unit laundry | Air conditioning

2 beds

1 bath

$1,500

House for rent

Top amenities
In-Unit Laundry
326 San Rafael St - Photo 1 of 1
No deposit

5d+ ago

Luxury house for rent in Winter Springs

326 San Rafael St, Winter Springs, FL 32708

Luxury | Swimming pool | In-unit laundry

1 bed

1 bath

$1,300

House for rent

Top amenities
Dishwasher
In-Unit Laundry
424 Club Dr - Photo 1 of 1

5d+ ago

Luxury Highlands townhouse for rent in Winter Springs

Townhouse - WINTER SPRINGS, FL

424 Club Dr, Winter Springs, FL 32708

Luxury | Swimming pool | In-unit laundry

3 beds

2 baths

$2,000

House for rent

Top amenities
Dishwasher
In-Unit Laundry
733 Woodhaven Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Springs

House for rent

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

5d+ ago

Luxury house for rent in Casselberry

Room for rent in a quiet home in Casselberry

300 Colony Dr #3, Casselberry, FL 32707

Luxury | In-unit laundry | Furnished

1 bed

1 bath

$750

House for rent

Available Jan 17

Top amenities
In-Unit Laundry
Microwave
On-Site Laundry
207 S Moss Rd - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Springs

Townhouse - WINTER SPRINGS, FL

207 S Moss Rd, Winter Springs, FL 32708

Luxury | In-unit laundry | Ceiling fan

2 beds

1 bath

$1,495

House for rent

Top amenities
In-Unit Laundry
Showing 1 - 25 of 25 results
Home > Apartments in Winter Springs > Highlands > Highlands Luxury Apartments For Rent
Updated: February 5, 2026

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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

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