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Luxury Apartments for Rent in Winter Park, FL

34 rentals

520 N Orlando Ave #147 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Park

Luxury | Balcony | Fitness center

1 bed

1 bath

$1,645

Apartment for rent

Available Oct 14

Top amenities
Assigned Parking
Elevator
Storage
640 N Park Ave #26 - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Park

Condominium - WINTER PARK, FL

640 N Park Ave #26, Winter Park, FL 32789

Luxury | Swimming pool | Garage parking

2 beds

2 baths

$2,600

Condo for rent

3032 Antique Oaks Cir #149 - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Park

3032 Antique Oaks Cir #149, Winter Park, FL 32792

Luxury | Swimming pool | In-unit laundry

1 bed

1 bath

$1,525

Condo for rent

Top amenities
In-Unit Laundry
3014 Antique Oaks Cir - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Park

3014 Antique Oaks Cir, Winter Park, FL 32792

Luxury | Swimming pool | In-unit laundry

1 bed

1 bath

$1,550

Condo for rent

Top amenities
Air Conditioning
Dishwasher
In-Unit Laundry
Microwave
1166 Palmer Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1166 Palmer Ave, Winter Park, FL 32789

Luxury | Walk-in closets | In-unit laundry

3 beds

3 baths

$4,695

House for rent

Top amenities
Carpet
Fireplace
Garage Parking
In-Unit Laundry
Storage
147 S Interlachen Ave #250 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Park

Coming soon Walk to Park Ave. 3 Bedroom 5 Bathroom 3320 s.f. -Single level condo.

147 S Interlachen Ave #250, Winter Park, FL 32789

Luxury | Balcony | Swimming pool

3 beds

5 baths

$10,500

Apartment for rent

Available Oct 8

Top amenities
Assigned Parking
Elevator
In-Unit Laundry
Storage
Swimming Pool
Wheelchair Accessible

Nearby rental good for eco-living

Nearby rental good for pet owners

520 N Orlando Ave #152 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Park

Luxury | Fitness center | Assigned parking

1 bed

1 bath

$1,750

Apartment for rent

Available Oct 11

Top amenities
Fitness Center
High Ceilings
Residents Lounge
520 N Orlando Ave #115 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Park

Luxury | Balcony | Fitness center

1 bed

1 bath

$1,695

Apartment for rent

Available Oct 11

Top amenities
Assigned Parking
Fitness Center
Residents Lounge
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520 N Orlando Ave #116 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Park

Luxury | Assigned parking | Elevator

1 bed

1 bath

$1,675

Apartment for rent

Available Oct 11

Top amenities
Storage
520 N Orlando Ave #157 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Park

Luxury | Fitness center | Assigned parking

1 bed

1 bath

$1,550

Apartment for rent

Available Oct 11

Top amenities
Elevator
Fitness Center
Residents Lounge
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Find sweet deals in Winter Park

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

$1,597–$2,248

1701 Lee Rd

$1,325

2905 Antique Oaks Cir #6

2031 Temple Dr - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Park

2031 Temple Dr, Winter Park, FL 32789

Luxury | Swimming pool | Concierge service

3 beds

2 baths

$5,150

$4,995

Price drop

Apartment for rent

Available Oct 10

Top amenities
On-Site Management
Package Service
2952 De Brocy Way - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Park

2952 De Brocy Way, Winter Park, FL 32792

Luxury | Balcony | Swimming pool

4 beds

2 baths

$4,900

Apartment for rent

Available Oct 10

Top amenities
Concierge Service
In-Unit Laundry
On-Site Management
Package Service
Swimming Pool
1710 Oakhurst Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

House for rent

640 N Park Ave - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Park

640 N Park Ave, Winter Park, FL 32789

Luxury | Swimming pool | Cable

2 beds

1 bath

$3,700

Condo for rent

2712 Goldenrod Dr #NA - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

2712 Goldenrod Dr #NA, Winter Park, FL 32792

Luxury | In-unit laundry | Air conditioning

3 beds

2 baths

$4,450

House for rent

Available Oct 15

Top amenities
Air Conditioning
Assigned Parking
Fireplace
Garage Parking
In-Unit Laundry
645 Huntington Ave #7 - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Park

645 Huntington Ave #7, Winter Park, FL 32789

Luxury | In-unit laundry | Concierge service

2 beds

2 baths

$2,295

House for rent

Available Oct 10

Top amenities
Concierge Service
In-Unit Laundry
On-Site Management
Residents Lounge
1681 Walnut Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1681 Walnut Ave, Winter Park, FL 32789

Luxury | In-unit laundry | Furnished

3 beds

2 baths

$3,799

House for rent

Top amenities
Fireplace
In-Unit Laundry
544 N Knowles Ave #302 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Park

Apartment - WINTER PARK, FL

544 N Knowles Ave #302, Winter Park, FL 32789

Luxury | Balcony | In-unit laundry

1 bed

1 bath

$2,400

Apartment for rent

Top amenities
Ceiling Fan
Dishwasher
Hardwood Floor
In-Unit Laundry
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263 Blossom Ln - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

263 Blossom Ln, Winter Park, FL 32789

Luxury | In-unit laundry | Ceiling fan

2 beds

1 bath

$2,300

House for rent

Top amenities
Ceiling Fan
In-Unit Laundry
1860 Via Contessa #NA - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Newly Renovated - 8 Bedroom 6 Bathroom House In Winter Park

1860 Via Contessa #NA, Winter Park, FL 32789

Luxury | Balcony | Walk-in closets

8 beds

6 baths

$17,550

House for rent

Available Sep 1

Top amenities
Air Conditioning
Fitness Center
Hardwood Floor
In-Unit Laundry
On-Site Laundry
Swimming Pool
123 Scottsdale Sq - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Park

Luxury | In-unit laundry | Air conditioning

1 bed

1 bath

$1,200

Apartment for rent

Top amenities
In-Unit Laundry
1205 Mayfield Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1205 Mayfield Ave, Winter Park, FL 32789

Luxury | Balcony | Swimming pool

4 beds

5 baths

$6,495

$6,245

Price drop

House for rent

Top amenities
Concierge Service
Dishwasher
Garage Parking
Hardwood Floor
In-Unit Laundry
On-Site Management
1181 Woodmere Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1181 Woodmere Dr, Winter Park, FL 32789

Luxury | Swimming pool | In-unit laundry

5 beds

4 baths

$6,995

House for rent

Top amenities
Ceiling Fan
Concierge Service
Dishwasher
Hardwood Floor
In-Unit Laundry
Package Service
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

$1,500

Condo for rent

Top amenities
Assigned Parking
Dishwasher
In-Unit Laundry
632 Gaines Way - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Park

632 Gaines Way, Winter Park, FL 32789

Luxury | In-unit laundry | Furnished

1 bed

1 bath

$2,295

$2,100

Price drop

Apartment for rent

Top amenities
High Ceilings
In-Unit Laundry
939 Aragon Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Luxury | In-unit laundry | Dishwasher

2 beds

2 baths

$2,725

House for rent

Top amenities
In-Unit Laundry
Advertisement
1661 Hillcrest Ave - Photo 1 of 1

5d+ ago

Luxury Virginia Heights house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1661 Hillcrest Ave, Winter Park, FL 32789

Luxury | Balcony | Walk-in closets

4 beds

3 baths

$10,000

House for rent

Top amenities
Ceiling Fan
Garage Parking
High Ceilings
In-Unit Laundry
On-Site Laundry
Storage
700 Melrose Ave #K32 - Photo 1 of 1
Age restricted

5d+ ago

Luxury condo for rent in Winter Park

Condominium - WINTER PARK, FL

700 Melrose Ave #K32, Winter Park, FL 32789

Luxury | Swimming pool | In-unit laundry

1 bed

1 bath

$1,300

Condo for rent

Top amenities
Ceiling Fan
Elevator
In-Unit Laundry
Package Service
Swimming Pool
690 Osceola Ave #407 - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Park

Condominium - WINTER PARK, FL

690 Osceola Ave #407, Winter Park, FL 32789

Luxury | Balcony | Swimming pool

1 bed

1 bath

$2,250

Condo for rent

Top amenities
Dishwasher
Fitness Center
Garage Parking
In-Unit Laundry
2020 Venetian Way - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

2020 Venetian Way, Winter Park, FL 32789

Luxury | Walk-in closets | In-unit laundry

4 beds

3 baths

$8,990

House for rent

Top amenities
Carpet
Fireplace
Garage Parking
In-Unit Laundry
On-Site Laundry
Storage
151 N Orlando Ave #131 - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Park

Condominium - WINTER PARK, FL

151 N Orlando Ave #131, Winter Park, FL 32789

Luxury | Swimming pool | Fitness center

2 beds

1 bath

$3,000

Condo for rent

Top amenities
Ceiling Fan
Fitness Center
Garage Parking
Hardwood Floor
In-Unit Laundry
On-Site Laundry
987 Cherokee Ave - Photo 1 of 1
New construction

5d+ ago

Luxury house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

987 Cherokee Ave, Winter Park, FL 32789

Luxury

Studio

0 baths

$1,500

House for rent

1000 S Semoran Blvd - Photo 1 of 1

5d+ ago

Luxury Golfside condo for rent in Winter Park

Luxury

1 bed

1 bath

$1,300

$1,299

Price drop

Condo for rent

7m ago

Luxury house for rent in Winter Park

216 Rippling Ln #NA, Winter Park, FL 32789

Luxury | In-unit laundry | On-site laundry

3 beds

2 baths

$3,500

House for rent

Available Nov 10

Top amenities
Assigned Parking
Central Heat
In-Unit Laundry
On-Site Laundry
Wi-Fi
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Showing 1 - 34 of 34 results
Home > Apartments in Winter Park > Winter Park Luxury Apartments For Rent
Updated: October 20, 2025

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

🔑Available apartment rentals34
💰Best rent deal123 Scottsdale Sq
✨Popular amenities, ,
🧦In-unit laundry
🏠With photos

For more in depth rent prices, check out our Winter Park, FL rent data, which covers average and median rents in Winter Park, FL.

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