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Luxury Apartments for Rent in Winter Park, FL

25 rentals

2942 Antique Oaks Cir #82 - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Park

Parkview Condominiums

2942 Antique Oaks Cir #82, Winter Park, FL 32792

Luxury | Swimming pool | In-unit laundry

1 bed

1 bath

$1,380

Condo for rent

Available Mar 1

Top amenities
In-Unit Laundry
3032 Antique Oaks Cir #145 - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Park

Condominium - WINTER PARK, FL

3032 Antique Oaks Cir #145, Winter Park, FL 32792

Luxury | Swimming pool | In-unit laundry

1 bed

1 bath

$1,400

Condo for rent

Top amenities
In-Unit Laundry
1814 Barker Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1814 Barker Dr, Winter Park, FL 32789

Luxury | Swimming pool | Fitness center

5 beds

4 baths

$11,000

House for rent

Top amenities
Fitness Center
Garage Parking
High Ceilings
In-Unit Laundry
On-Site Laundry
Swimming Pool
1441 Oneco Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

1441 Oneco Ave, Winter Park, FL 32789

Luxury | Swimming pool | In-unit laundry

4 beds

3.5 baths

$6,000

House for rent

Top amenities
Ceiling Fan
Dishwasher
In-Unit Laundry
Storage
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

$1,200

Condo for rent

Top amenities
On-Site Laundry
1130 Washington Ave #11C - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Park

Condominium - WINTER PARK, FL

1130 Washington Ave #11C, Winter Park, FL 32789

Luxury | Balcony | In-unit laundry

3 beds

2.5 baths

$5,495

Condo for rent

Top amenities
Garage Parking
Hardwood Floor
High Ceilings
In-Unit Laundry
On-Site Laundry
Storage

Nearby rental good for eco-living

Nearby rental good for pet owners

1667 Mizell Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

1667 Mizell Ave, Winter Park, FL 32789

Luxury | Dishwasher | Outdoor space

3 beds

3 baths

$3,995

House for rent

110 Killarney Bay Ct #1 - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Park

Condominium - WINTER PARK, FL

110 Killarney Bay Ct #1, Winter Park, FL 32789

Luxury | Walk-in closets | In-unit laundry

2 beds

2 baths

$2,550

Condo for rent

Top amenities
Ceiling Fan
In-Unit Laundry
Storage
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110 Killarney Bay Ct - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Park

Condo for rent

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

$3,475

House for rent

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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

2.5 baths

$5,490

Condo for rent

Top amenities
Dishwasher
In-Unit Laundry
520 N Orlando Ave #125 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Park

Luxury | Fitness center | In-unit laundry

1 bed

1 bath

$1,710

Apartment for rent

Available May 7

Top amenities
In-Unit Laundry
On-Site Management
520 N Orlando Ave #105 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Park

Luxury | Fitness center | In-unit laundry

1 bed

1 bath

$1,695

Apartment for rent

Available Mar 12

Top amenities
Fitness Center
In-Unit Laundry
On-Site Management
1860 Via Contessa - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1860 Via Contessa, Winter Park, FL 32789

Luxury | Walk-in closets | Swimming pool

8 beds

6 baths

$13,500

House for rent

Top amenities
Garage Parking
Hardwood Floor
High Ceilings
In-Unit Laundry
On-Site Laundry
Swimming Pool
1235 Via Estrella - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1235 Via Estrella, Winter Park, FL 32789

Luxury | Swimming pool | In-unit laundry

4 beds

3 baths

$5,895

House for rent

Top amenities
Ceiling Fan
Dishwasher
Hardwood Floor
In-Unit Laundry
Storage
Swimming Pool
1302 Michigan Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1302 Michigan Ave, Winter Park, FL 32789

Luxury | Walk-in closets | In-unit laundry

3 beds

2.5 baths

$3,850

House for rent

Top amenities
Ceiling Fan
Dishwasher
Garage Parking
In-Unit Laundry
On-Site Laundry
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

$9,500

Apartment for rent

Available Feb 1

Top amenities
Assigned Parking
Elevator
In-Unit Laundry
Storage
Swimming Pool
Wheelchair Accessible
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
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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 Mar 30

Top amenities
Elevator
Fitness Center
In-Unit Laundry
On-Site Management
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
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
Garage Parking
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
1221 Richmond Rd - Photo 1 of 1
New construction

5d+ ago

Luxury Virginia Heights house for rent in Winter Park

House (Detached) - Winter Park, FL

1221 Richmond Rd, Winter Park, FL 32789

Luxury | Walk-in closets | Swimming pool

5 beds

5.5 baths

$19,000

House for rent

Top amenities
Carpet
In-Unit Laundry
Swimming Pool
3075 Aaron Burr Ave #Q8B - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Park

One bedroom apt 7 or 12 months furnish or unfurnished. Apartamento disponible amueblado o sin muebles 7 o 12 meses de renta disponible

3075 Aaron Burr Ave #Q8B, Winter Park, FL 32792

Luxury | Balcony | Swimming pool

1 bed

1 bath

$1,200

Condo for rent

Top amenities
Furnished
On-Site Laundry
Swimming Pool
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 bed

1 bath

$1,075

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: April 21, 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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