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Luxury Apartments for Rent in Winter Park, FL

27 rentals

651 Trinidad Ct #S - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Park

Condominium - WINTER PARK, FL

651 Trinidad Ct #S, Winter Park, FL 32792

Luxury | Walk-in closets | In-unit laundry

1 bed

1 bath

$1,450

Condo for rent

Top amenities
Ceiling Fan
Dishwasher
High Ceilings
In-Unit Laundry
1850 Whitehall Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

1850 Whitehall Dr, Winter Park, FL 32789

Luxury | Swimming pool | Furnished

3 beds

2 baths

$3,550

House for rent

3075 Aaron Burr Ave #C - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Park

1BR/1.0BA

3075 Aaron Burr Ave #C, Winter Park, FL 32792

Luxury | On-site laundry | Dishwasher

1 bed

1 bath

$1,400

Condo for rent

Top amenities
On-Site Laundry
130 N Center St #2 - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Park

Luxury | In-unit laundry | On-site laundry

1 bed

1 bath

$1,500

Condo for rent

Available Sep 10

Top amenities
In-Unit Laundry
On-Site Laundry
On-Site Management
782 S Pennsylvania Ave #1 - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Park

Condominium - WINTER PARK, FL

782 S Pennsylvania Ave #1, Winter Park, FL 32789

Luxury | In-unit laundry | Garage parking

3 beds

2 baths

$6,000

$5,770

Price drop

Condo for rent

Top amenities
Dishwasher
In-Unit Laundry
428 W Swoope Ave #NA - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Park

$5,800 Walk to Park Ave!! 4 Bedroom 4 Bathroom Townhouse In Winter Park With Great Amenities

428 W Swoope Ave #NA, Winter Park, FL 32789

Luxury | In-unit laundry | Air conditioning

4 beds

4 baths

$5,800

House for rent

Available Feb 15

Top amenities
Air Conditioning
Central Heat
Dishwasher
Garage Parking
In-Unit Laundry
Storage

Nearby rental good for eco-living

Nearby rental good for pet owners

421 W Fairbanks Ave - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Park

Apartment - WINTER PARK, FL

421 W Fairbanks Ave, Winter Park, FL 32789

Luxury | In-unit laundry | Hardwood floor

3 beds

3 baths

$3,750

Apartment for rent

Top amenities
Ceiling Fan
Dishwasher
High Ceilings
In-Unit Laundry
520 N Orlando Ave #119 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Park

Luxury | Fitness center | In-unit laundry

1 bed

1 bath

$1,825

Apartment for rent

Available Apr 10

Top amenities
Elevator
Fitness Center
In-Unit Laundry
On-Site Management
Residents Lounge
Storage
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520 N Orlando Ave #121 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Park

Luxury | Fitness center | In-unit laundry

1 bed

1 bath

$1,675

Apartment for rent

Available Mar 4

Top amenities
Elevator
High Ceilings
In-Unit Laundry
On-Site Management
Residents Lounge
Storage
520 N Orlando Ave #151 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Park

Luxury | Fitness center | In-unit laundry

1 bed

1 bath

$1,685

Apartment for rent

Available Mar 24

Top amenities
High Ceilings
In-Unit Laundry
On-Site Management
Residents Lounge
Advertisement

Find sweet deals in Winter Park

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

$1,200

3002 Antique Oaks Cir #99

$1,258–$2,860

3935 Sutton Place Blvd

$1,410–$1,912

375 Palm Springs Dr

$2,188–$3,884

4460 Lower Park Rd

520 N Orlando Ave #138 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Park

Luxury | Balcony | Fitness center

1 bed

1 bath

$1,995

Apartment for rent

Available Feb 19

Top amenities
Elevator
Fitness Center
In-Unit Laundry
On-Site Management
Residents Lounge
1350 Lyndale Blvd - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

House for rent

1329 Medinah Ct - Photo 1 of 1

5d+ ago

Luxury Golfside house for rent in Winter Park

House for rent

503 W Canton Ave - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Park

Townhouse - WINTER PARK, FL

503 W Canton Ave, Winter Park, FL 32789

Luxury | In-unit laundry | Garage parking

3 beds

3 baths

$6,000

House for rent

Top amenities
Garage Parking
In-Unit Laundry
Storage
Leeward Way #C110 - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Park

Condominium - WINTER PARK, FL

Leeward Way #C110, Winter Park, FL 32792

Luxury | Walk-in closets | In-unit laundry

1 bed

1 bath

$1,400

Condo for rent

Top amenities
Dishwasher
In-Unit Laundry
300 Killarney Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

300 Killarney Dr, Winter Park, FL 32789

Luxury | Walk-in closets | Fitness center

4 beds

3 baths

$7,900

House for rent

Top amenities
Fireplace
Fitness Center
High Ceilings
In-Unit Laundry
2500 Lee Rd #244 - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Park

Condominium - WINTER PARK, FL

2500 Lee Rd #244, Winter Park, FL 32789

Luxury | Swimming pool | In-unit laundry

1 bed

1 bath

$1,465

Condo for rent

Top amenities
Assigned Parking
Dishwasher
In-Unit Laundry
1525 Palmer Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

1525 Palmer Ave, Winter Park, FL 32789

Luxury | Walk-in closets | In-unit laundry

4 beds

3 baths

$4,695

House for rent

Available Nov 11

Top amenities
Ceiling Fan
Concierge Service
In-Unit Laundry
On-Site Laundry
On-Site Management
Package Service
Advertisement
220 Overlook Rd #220 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Park

2 BR, 2 BA in Winter Park

220 Overlook Rd #220, Winter Park, FL 32789

Luxury | Walk-in closets | In-unit laundry

2 beds

2 baths

$3,600

Apartment for rent

Available Sep 22

Top amenities
In-Unit Laundry
1221 Richmond Rd - Photo 1 of 1
New construction

5d+ ago

Luxury Virginia Heights house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1221 Richmond Rd, Winter Park, FL 32789

Luxury | Walk-in closets | Swimming pool

5 beds

5 baths

$19,000

House for rent

Top amenities
Ceiling Fan
High Ceilings
In-Unit Laundry
Swimming Pool
1275 Michigan Ave #1275 - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Park

3 BR, 3 BA in Winter Park

1275 Michigan Ave #1275, Winter Park, FL 32789

Luxury | Walk-in closets | On-site laundry

3 beds

3 baths

$3,950

House for rent

Top amenities
On-Site Laundry
519 Park North Ct - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

519 Park North Ct, Winter Park, FL 32789

Luxury | Walk-in closets | Swimming pool

4 beds

3 baths

$7,000

House for rent

Top amenities
Ceiling Fan
Dishwasher
Hardwood Floor
High Ceilings
In-Unit Laundry
Swimming Pool
1580 Oakhurst Ave #1580 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Park

4 BR, 3 BA in Winter Park

1580 Oakhurst Ave #1580, Winter Park, FL 32789

Luxury | On-site laundry | Hardwood floor

4 beds

3 baths

$4,950

Apartment for rent

Available Nov 19

Top amenities
On-Site Laundry
1580 Oakhurst Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1580 Oakhurst Ave, Winter Park, FL 32789

Luxury | Walk-in closets | In-unit laundry

4 beds

2 baths

$4,895

$4,700

Price drop

House for rent

Top amenities
Dishwasher
Fireplace
Hardwood Floor
In-Unit Laundry
On-Site Laundry
3212 Netherwood Dr - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Park

Apartment - WINTER PARK, FL

3212 Netherwood Dr, Winter Park, FL 32792

Luxury | In-unit laundry | On-site laundry

1 bed

1 bath

$1,400

$1,300

Price drop

Apartment for rent

Top amenities
In-Unit Laundry
On-Site Laundry
296 Lewfield Cir #296 - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Park

$1350 - 1 Bedroom 1 Bathroom Condo In Winter Park With Great Amenities

296 Lewfield Cir #296, Winter Park, FL 32792

Luxury | Balcony | Swimming pool

1 bed

1 bath

$1,350

Condo for rent

Available Feb 10

Top amenities
Air Conditioning
Central Heat
Dishwasher
In-Unit Laundry
On-Site Laundry
Storage
Advertisement
3002 Antique Oaks Cir #99 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Park

3002 Antique Oaks Cir #99, Winter Park, FL 32792

Luxury | Walk-in closets | Swimming pool

1 bed

1 bath

$1,200

Apartment for rent

Available Nov 25

Top amenities
In-Unit Laundry
Showing 1 - 27 of 27 results
Home > Apartments in Winter Park > Winter Park Luxury Apartments For Rent
Updated: March 6, 2026

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Looking for luxury apartments in Winter Park, FL near you?

🔑Available apartment rentals27
💰Best rent deal3002 Antique Oaks Cir #99
✨Popular amenities, ,
🧦In-unit laundry
🏠With photos

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