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Luxury Apartments for Rent in Winter Park, FL

25 rentals

520 N Orlando Ave #103 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Park

Luxury | Balcony | Fitness center

1 bed

1 bath

$1,675

Apartment for rent

Available Jan 11

Top amenities
High Ceilings
In-Unit Laundry
On-Site Management
Storage
520 N Orlando Ave #124 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Park

Luxury | Fitness center | In-unit laundry

1 bed

1 bath

$1,615

Apartment for rent

Available Jan 16

Top amenities
Fitness Center
High Ceilings
In-Unit Laundry
On-Site Management
1350 Lyndale Blvd - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

House for rent

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
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

$16,550

House for rent

Available Sep 1

Top amenities
Air Conditioning
Fitness Center
Garage Parking
Hardwood Floor
In-Unit Laundry
On-Site Laundry
101 S Interlachen Ave #104 - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Park

Condominium - WINTER PARK, FL

101 S Interlachen Ave #104, Winter Park, FL 32789

Luxury | In-unit laundry | Assigned parking

2 beds

2 baths

$3,800

Condo for rent

Top amenities
Dishwasher
In-Unit Laundry

Nearby rental good for eco-living

Nearby rental good for pet owners

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
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

$1,300

Condo for rent

Top amenities
Air Conditioning
Dishwasher
In-Unit Laundry
Microwave
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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
Garage Parking
High Ceilings
In-Unit Laundry
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
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Find sweet deals near Winter Park

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

$1,200

Winter Park

$1,300

Winter Park

$1,300

Winter Park

$1,300

Winter Park

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
3060 George Mason Avenue #N10C - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Park

3060 George Mason Avenue #N10C, Winter Park, FL 32792

Luxury | Balcony | In-unit laundry

1 bed

1 bath

$1,300

Condo for rent

Top amenities
In-Unit Laundry
On-Site Laundry
1275 Michigan Ave - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Park

Townhouse - WINTER PARK, FL

1275 Michigan Ave, Winter Park, FL 32789

Luxury | Walk-in closets | In-unit laundry

3 beds

2 baths

$3,950

House for rent

Top amenities
Ceiling Fan
High Ceilings
In-Unit Laundry
On-Site Laundry
2905 Antique Oaks Circle #6 - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Park

2905 Antique Oaks Circle #6, Winter Park, FL 32792

Luxury | Swimming pool | In-unit laundry

1 bed

1 bath

$1,325

Condo for rent

Top amenities
In-Unit Laundry
1400 S Pennsylvania Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1400 S Pennsylvania Ave, Winter Park, FL 32789

Luxury | Walk-in closets | In-unit laundry

4 beds

3 baths

$7,000

House for rent

Top amenities
Ceiling Fan
Garage Parking
High Ceilings
In-Unit Laundry
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 Ave - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Park

2 BR, 2 BA in Winter Park

690 Osceola Ave, Winter Park, FL 32789

Luxury | Hardwood floor

2 beds

2 baths

$3,400

Condo for rent

Available Nov 15

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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
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
Garage Parking
In-Unit Laundry
Storage
Swimming Pool
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

$4,950

House for rent

Top amenities
Dishwasher
Fireplace
Hardwood Floor
In-Unit Laundry
On-Site 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

$8,500

House for rent

Top amenities
Fireplace
Fitness Center
High Ceilings
In-Unit Laundry
520 N Orlando Ave #136 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Park

Luxury | Balcony | Fitness center

1 bed

1 bath

$1,740

Apartment for rent

Available Nov 18

Top amenities
Elevator
Fitness Center
High Ceilings
In-Unit Laundry
On-Site Management
Residents Lounge
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
Oak Haven Villas - Photo 1 of 1

3d ago

8.3

Very good

Our team has verified this company

Verified

Oak Haven Villas

200 SW St #39, Eatonville, FL 32751

Luxury

1–2 beds

1 bath

$1,195–$1,295

Apartment for rent

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Showing 1 - 25 of 25 results
Home > Apartments in Winter Park > Winter Park Luxury Apartments For Rent
Updated: January 20, 2026

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

🔑Available apartment rentals25
💰Best rent deal200 SW St #39
✨Popular amenities, ,
🧦In-unit laundry
🏠With photos

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