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Luxury Houses for Rent in Winter Park, FL

25 rentals

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
1350 Lyndale Blvd - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

1350 Lyndale Blvd, Winter Park, FL 32789

Luxury

4 beds

5 baths

$8,500

$6,995

Price drop

House for rent

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

$15,550

House for rent

Available Jan 27

Top amenities
Fitness Center
Garage Parking
Hardwood Floor
In-Unit Laundry
On-Site Laundry
Swimming Pool
428 W Swoope Ave #NA - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Park

$5,500 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 | Storage

4 beds

4 baths

$6,200

$5,500

Price drop

House for rent

Available Feb 15

Top amenities
Air Conditioning
Central Heat
Dishwasher
Garage Parking
In-Unit Laundry
Storage
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
1315 Westchester Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1315 Westchester Ave, Winter Park, FL 32789

Luxury | Walk-in closets | In-unit laundry

2 beds

2 baths

$2,900

$2,800

Price drop

House for rent

Top amenities
Carpet
Ceiling Fan
Hardwood Floor
In-Unit Laundry
On-Site Laundry
Storage

Nearby rental good for eco-living

$2,505

Winter Park

Nearby rental good for pet owners

$2,435

College Park

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 | In-unit laundry | Garage parking

3 beds

2 baths

$3,950

House for rent

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

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

$2,300

Winter Park

$2,435

College Park

$1,920

Orlando

$2,020

Orlando

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
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
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
2441 Fifeshire Dr - Photo 1 of 1

21h ago

Luxury house for rent in Winter Park

2441 Fifeshire Dr, Winter Park, FL 32792

Luxury | In-unit laundry | Outdoor space

3 beds

2 baths

$2,300

House for rent

Top amenities
Dishwasher
Garage Parking
In-Unit Laundry
Microwave
Oven
525 Conway Rd - Photo 1 of 1

5d+ ago

Luxury Dover Shores East house for rent in Orlando

525 Conway Rd, Orlando, FL 32807

Luxury | Swimming pool | Fitness center

1 bed

1 bath

$1,350

House for rent

Top amenities
Fitness Center
On-Site Laundry
637 Hillcrest St #635 - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

Unit 635 – Move-In Ready 3BR 3BA Duplex Near Lake Eola | Garage | Balcony | 1,481 Sq. Ft. | $3,000/mo

637 Hillcrest St #635, Orlando, FL 32803

Luxury | Balcony | Walk-in closets

3 beds

3 baths

$3,000

House for rent

Available Jan 28

Top amenities
Air Conditioning
Assigned Parking
Business Center
Garage Parking
High Ceilings
In-Unit Laundry
637 Hillcrest St #637 - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

Unit 637 – Move-In Ready 3BR 2.5BA + Office Duplex Near Lake Eola | Garage | Front Porch | 1,854 Sq. Ft. | $3,200/mo

637 Hillcrest St #637, Orlando, FL 32803

Luxury | Walk-in closets | In-unit laundry

3 beds

2 baths

$3,200

House for rent

Available Jan 28

Top amenities
Air Conditioning
Business Center
Dishwasher
High Ceilings
In-Unit Laundry
Microwave
1260 Seminola Blvd #NA - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

RARE RENT-TO-OWN OPPORTUNITY WITH SPECIAL OFFICE/RESIDENTIAL ZONING! (Grandfathered-In)

1260 Seminola Blvd #NA, Casselberry, FL 32707

Luxury | Swimming pool | In-unit laundry

3 beds

2 baths

$2,400

House for rent

Available Sep 12

Top amenities
Air Conditioning
Assigned Parking
Business Center
Hardwood Floor
In-Unit Laundry
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670 Hibiscus Rd - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

670 Hibiscus Rd, Casselberry, FL 32707

Luxury | On-site laundry | Outdoor space

3 beds

1 bath

$3,600

$2,200

Price drop

House for rent

Available Feb 23

Top amenities
On-Site Laundry
1608 Gattis Dr - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

1608 Gattis Dr, Orlando, FL 32825

Luxury | Walk-in closets | Deck

3 beds

2 baths

$1,920

House for rent

Available Feb 20

Top amenities
Hardwood Floor
3363 Hamlet Loop - Photo 1 of 1

1d ago

Our team has verified this company

Verified

3363 Hamlet Loop, Winter Park, FL 32792

Luxury | Walk-in closets | Outdoor space

3 beds

2 baths

$3,440

$2,505

Price drop

House for rent

Available Mar 23

Top amenities
Ceiling Fan
Listings within 10 miles
1320 W Smith St #NA - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

Just Reduced!! Hurry! $2535 - Super Cute old Florida Style Cottage 3 Bedroom 2 Bathroom House In Beautiful College Park!

1320 W Smith St #NA, Orlando, FL 32804

Luxury | In-unit laundry | On-site laundry

3 beds

2 baths

$2,435

House for rent

Available Jan 5

Top amenities
Air Conditioning
Assigned Parking
Central Heat
Dishwasher
In-Unit Laundry
On-Site Laundry
4511 Wyndcliff Cir - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

4511 Wyndcliff Cir, Orlando, FL 32817

Luxury | Walk-in closets | Deck

3 beds

2 baths

$2,370

$2,275

Price drop

House for rent

Available Mar 9

Top amenities
Ceiling Fan
10945 Tangora St - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

10945 Tangora St, Union Park, FL 32825

Luxury | Outdoor space | Garage parking

4 beds

2 baths

$2,165

House for rent

Available Mar 23

9474 Chandon Dr - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

9474 Chandon Dr, Orlando, FL 32825

Luxury | Walk-in closets | Outdoor space

3 beds

2 baths

$2,205

House for rent

Available Jan 21

Top amenities
Garage Parking
Showing 1 - 25 of 25 results
Home > House Rentals in Winter Park > Winter Park Luxury Houses For Rent
Updated: February 4, 2026

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Discover luxury Winter Park, FL houses for rent

🌇Available luxury house rentals25 houses
⭐Popular amenities, ,
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