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Luxury Houses for Rent in Winter Park, FL

25 rentals

1860 Via Contessa #NA - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

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
Assigned Parking
Dishwasher
Fireplace
On-Site Laundry
Swimming Pool
438 W Swoope Ave - Photo 1 of 1

3d ago

Luxury townhouse for rent in Winter Park

438 W Swoope Ave, Winter Park, FL 32789

Luxury | Walk-in closets | Swimming pool

4 beds

3 baths

$4,995

House for rent

Available Dec 17

Top amenities
Garage Parking
In-Unit Laundry
On-Site Laundry
On-Site Management
Package Service
Storage
1221 Richmond Road - 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 Road, 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 Avenue #1275 - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Park

3 BR, 3 BA in Winter Park

1275 Michigan Avenue #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 Court - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

519 Park North Court, Winter Park, FL 32789

Luxury | Walk-in closets | Swimming pool

4 beds

3 baths

$7,000

House for rent

Top amenities
Ceiling Fan
Dishwasher
Garage Parking
Hardwood Floor
High Ceilings
In-Unit Laundry
1275 Michigan Avenue - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Park

Townhouse - WINTER PARK, FL

1275 Michigan Avenue, 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

Nearby rental good for eco-living

$2,399

Winter Park

Nearby rental good for pet owners

$2,500

College Park

1400 Pennsylvania Avenue - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

1400 Pennsylvania Avenue, 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
1817 Loch Berry Road #NA - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

$3,400 - 3 Bedroom 2 Bathroom Updated House In Winter Park With Great Amenities

1817 Loch Berry Road #NA, Winter Park, FL 32789

Luxury | In-unit laundry | Outdoor space

3 beds

2 baths

$3,400

House for rent

Available Dec 13

Top amenities
Air Conditioning
Ceiling Fan
Dishwasher
In-Unit Laundry
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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
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
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Find sweet deals near Winter Park

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

$2,500

College Park

$2,355

Winter Park

$1,960

Orlando

$2,310

Orlando

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
1807 N Park Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

House for rent

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
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 | Outdoor space

3 beds

2 baths

$3,750

House for rent

Top amenities
Fireplace
In-Unit Laundry
2128 Sycamore Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

2128 Sycamore Dr, Winter Park, FL 32789

Luxury | Walk-in closets | In-unit laundry

3 beds

2 baths

$3,300

House for rent

Top amenities
Dishwasher
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
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1835 Edwin Boulevard - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

1835 Edwin Boulevard, Winter Park, FL 32789

Luxury | In-unit laundry | On-site laundry

3 beds

2 baths

$3,225

House for rent

Top amenities
Dishwasher
Garage Parking
Hardwood Floor
In-Unit Laundry
On-Site Laundry
3531 Norwich Ct - Photo 1 of 1

2d ago

Our team has verified this company

Verified

3531 Norwich Ct, Casselberry, FL 32707

Luxury | Walk-in closets | On-site laundry

4 beds

2 baths

$2,730

$2,620

Price drop

House for rent

Available Dec 29

Top amenities
Ceiling Fan
On-Site Laundry
141 Seville Pointe Ave - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

141 Seville Pointe Ave, Azalea Park, FL 32807

Luxury | Walk-in closets | On-site laundry

3 beds

2 baths

$2,435

$2,200

Price drop

House for rent

Available Nov 25

Top amenities
Garage Parking
On-Site Laundry
Listings within 10 miles
2146 Kimberwicke Cir - Photo 1 of 1

5d+ ago

Luxury house for rent in Oviedo

House for rent

126 Alder Ave - Photo 1 of 1

4d ago

Our team has verified this company

Verified

Luxury | On-site laundry | Deck

4 beds

1 bath

$1,955

$1,715

Price drop

House for rent

Available Nov 11

Top amenities
High Ceilings
On-Site Laundry
1320 Smith Street #NA - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

$2,500 - Super Cute old Florida Style Cottage 3 Bedroom 2 Bathroom House In College Park!

1320 Smith Street #NA, Orlando, FL 32804

Luxury | In-unit laundry | On-site laundry

3 beds

2 baths

$2,500

House for rent

Available Jan 15

Top amenities
Air Conditioning
Assigned Parking
Central Heat
Dishwasher
In-Unit Laundry
On-Site Laundry
1936 Durrand Avenue - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

1936 Durrand Avenue, Maitland, FL 32751

Luxury | Walk-in closets | On-site laundry

3 beds

2 baths

$3,075

House for rent

Available Jan 19

Top amenities
Ceiling Fan
Hardwood Floor
On-Site Laundry
Showing 1 - 25 of 25 results
Home > House Rentals in Winter Park > Winter Park Luxury Houses For Rent
Updated: December 21, 2025

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Discover luxury Winter Park, FL houses for rent

🌇Available luxury house rentals25 houses
⭐Popular amenities, ,
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