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Luxury Apartments for Rent in Winter Park, FL

29 rentals

104 Interlachen Avenue - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Park

2 BR, 2 BA in Winter Park

104 Interlachen Avenue, Winter Park, FL 32789

Luxury | In-unit laundry | Ceiling fan

2 beds

2 baths

$4,850

Condo for rent

Available Oct 1

Top amenities
In-Unit Laundry
1580 Oakhurst Avenue #1580 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Park

4 BR, 3 BA in Winter Park

1580 Oakhurst Avenue #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
690 Osceola Avenue - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Park

2 BR, 2 BA in Winter Park

690 Osceola Avenue, Winter Park, FL 32789

Luxury | Hardwood floor

2 beds

2 baths

$3,400

Condo for rent

Available Nov 15

3002 Antique Oaks Circle #99 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Park

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

Luxury | Walk-in closets | Swimming pool

1 bed

1 bath

$1,300

Apartment for rent

Available Nov 25

Top amenities
In-Unit Laundry
1309 Bridgeport Drive - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1309 Bridgeport Drive, Winter Park, FL 32789

Luxury | Walk-in closets | Swimming pool

4 beds

3 baths

$5,400

House for rent

Top amenities
Dishwasher
Garage Parking
Hardwood Floor
High Ceilings
In-Unit Laundry
On-Site Laundry
520 Orlando Avenue #133 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Park

520 Orlando Avenue #133, Winter Park, FL 32789

Luxury | Balcony | Fitness center

1 bed

1 bath

$1,655

Apartment for rent

Available Nov 18

Top amenities
Fitness Center
High Ceilings
In-Unit Laundry
On-Site Management
Storage

Nearby rental good for eco-living

Nearby rental good for pet owners

520 Orlando Avenue #128 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Park

520 Orlando Avenue #128, Winter Park, FL 32789

Luxury | Balcony | Fitness center

1 bed

1 bath

$2,145

Apartment for rent

Available Nov 18

Top amenities
Elevator
Fitness Center
High Ceilings
In-Unit Laundry
On-Site Management
Package Service
3044 Antique Oaks Circle #178 - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Park

3044 Antique Oaks Circle #178, Winter Park, FL 32792

Luxury | On-site management

1 bed

1 bath

$1,300

Condo for rent

Available Nov 4

Top amenities
On-Site Management
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1308 Pennsylvania Avenue - Photo 1 of 1

5d+ ago

Luxury Virginia Heights house for rent in Winter Park

Charming 1/1 condo near Lake Virginia

1308 Pennsylvania Avenue, Winter Park, FL 32789

Luxury | Walk-in closets | Assigned parking

1 bed

1 bath

$2,040

House for rent

Top amenities
Concierge Service
Storage
147 Interlachen Avenue #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 Interlachen Avenue #250, Winter Park, FL 32789

Luxury | Balcony | Swimming pool

3 beds

5 baths

$9,500

Apartment for rent

Available Dec 1

Top amenities
Assigned Parking
Elevator
In-Unit Laundry
Storage
Swimming Pool
Wheelchair Accessible
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Find sweet deals in Winter Park

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

$1,350

200 Saint Andrews Blvd

$925

7309 Daniel Webster Dr #A

$1,325

2905 Antique Oaks Circle #6

$1,300

3002 Antique Oaks Circle #99

520 Orlando Avenue #136 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Park

520 Orlando Avenue #136, Winter Park, FL 32789

Luxury | Balcony | Fitness center

1 bed

1 bath

$1,740

Apartment for rent

Available Nov 19

Top amenities
Elevator
Fitness Center
Residents Lounge
Storage
1580 Oakhurst Avenue - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1580 Oakhurst Avenue, Winter Park, FL 32789

Luxury | Walk-in closets | In-unit laundry

4 beds

2 baths

$4,950

House for rent

Top amenities
Dishwasher
Fireplace
Hardwood Floor
In-Unit Laundry
On-Site Laundry
300 Killarney Drive - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

300 Killarney Drive, Winter Park, FL 32789

Luxury | Walk-in closets | Fitness center

4 beds

3 baths

$8,500

House for rent

Top amenities
Fireplace
Garage Parking
High Ceilings
In-Unit Laundry
1525 Palmer Avenue - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

1525 Palmer Avenue, Winter Park, FL 32789

Luxury | Walk-in closets | In-unit laundry

4 beds

3 baths

$4,995

House for rent

Available Nov 11

Top amenities
Ceiling Fan
Garage Parking
In-Unit Laundry
On-Site Laundry
On-Site Management
Package Service
3014 Antique Oaks Circle - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Park

3014 Antique Oaks Circle, Winter Park, FL 32792

Luxury | Swimming pool | In-unit laundry

1 bed

1 bath

$1,345

Condo for rent

Top amenities
Air Conditioning
Dishwasher
In-Unit Laundry
Microwave
520 Orlando Avenue #126 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Park

520 Orlando Avenue #126, Winter Park, FL 32789

Luxury | Balcony | Fitness center

1 bed

1 bath

$1,755

Apartment for rent

Available Nov 17

Top amenities
Fitness Center
High Ceilings
In-Unit Laundry
On-Site Management
Package Service
Residents Lounge
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

$2,450

House for rent

Top amenities
In-Unit Laundry
520 Orlando Avenue #120 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Park

520 Orlando Avenue #120, Winter Park, FL 32789

Luxury | Balcony | Fitness center

1 bed

1 bath

$1,815

Apartment for rent

Available Oct 30

Top amenities
High Ceilings
On-Site Management
Residents Lounge
Storage
Advertisement
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

$1,450

Condo for rent

Top amenities
In-Unit Laundry
520 Orlando Avenue #110 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Park

520 Orlando Avenue #110, Winter Park, FL 32789

Luxury | Balcony | Fitness center

1 bed

1 bath

$1,730

Apartment for rent

Available Oct 9

Top amenities
Fitness Center
High Ceilings
In-Unit Laundry
On-Site Management
Package Service
Residents Lounge
1701 Palmer Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1701 Palmer Ave, Winter Park, FL 32789

Luxury | Walk-in closets | Swimming pool

4 beds

3 baths

$5,400

House for rent

Top amenities
Carpet
Dishwasher
Fireplace
In-Unit Laundry
Swimming Pool
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
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

520 Orlando Avenue #147 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Park

520 Orlando Avenue #147, Winter Park, FL 32789

Luxury | Fitness center | In-unit laundry

1 bed

1 bath

$1,615

Apartment for rent

Available Oct 9

Top amenities
Elevator
In-Unit Laundry
On-Site Management
Residents Lounge
Storage
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

$3,750

House for rent

Top amenities
Fireplace
In-Unit Laundry
200 Saint Andrews Boulevard #606 - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Park

Condominium - WINTER PARK, FL

200 Saint Andrews Boulevard #606, Winter Park, FL 32792

Luxury | In-unit laundry | Hardwood floor

1 bed

1 bath

$1,350

Condo for rent

Top amenities
In-Unit Laundry
Advertisement
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

$1,475

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

Apartment - WINTER PARK, FL

632 Gaines Way, Winter Park, FL 32789

Luxury | In-unit laundry | Furnished

1 bed

1 bath

$2,100

Apartment for rent

Top amenities
High Ceilings
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
Showing 1 - 29 of 29 results
Home > Apartments in Winter Park > Winter Park Luxury Apartments For Rent
Updated: December 5, 2025

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

🔑Available apartment rentals29
💰Best rent deal3044 Antique Oaks Circle #178
✨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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