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Luxury Houses for Rent in Winter Park, FL

25 rentals available

3065 George Mason Ave #E2B - Photo 1 of 1

8h ago

Luxury house for rent in Winter Park

3065 George Mason Ave #E2B, Winter Park, FL 32792

Luxury | Walk-in closets | Swimming pool

1 bed

1 bath

$1,200

House for rent

Available Jul 17

Top amenities
Concierge Service
On-Site Laundry
Package Service
151 N Orlando Ave #238 - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Luxury

2 beds

1 bath

$2,750

House for rent

418R Gilbert Rd - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Single Family Residence - WINTER PARK, FL

418R Gilbert Rd, Winter Park, FL 32792

Luxury | Walk-in closets | Swimming pool

3 beds

3 baths

$4,000

House for rent

Top amenities
Ceiling Fan
Dishwasher
Garage Parking
In-Unit Laundry
Swimming Pool
2500 Lee Rd #145 - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Great complex on Lake Killarney

2500 Lee Rd #145, Winter Park, FL 32789

Luxury | On-site laundry

1 bed

1 bath

$1,399

House for rent

Available Jun 10

Top amenities
On-Site 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

$10,000

House for rent

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

5d+ ago

Luxury house for rent in Winter Park

House for rent

Nearby rental good for eco-living

$2,635

Casselberry

Nearby rental good for pet owners

$2,830

Goldenrod

1667 Mizell Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

1667 Mizell Ave, Winter Park, FL 32789

Luxury | Outdoor space | Dishwasher

3 beds

3 baths

$3,995

House for rent

5563 Pats Pt - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

5563 Pats Pt, Winter Park, FL 32792

Luxury | Walk-in closets | On-site laundry

3 beds

2 baths

$2,570

House for rent

Available Jul 20

Top amenities
Ceiling Fan
Garage Parking
On-Site Laundry
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1839 Blaine Ter - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

1839 Blaine Ter, Winter Park, FL 32792

Luxury | Walk-in closets | Outdoor space

3 beds

2.5 baths

$2,520

House for rent

Available Jul 31

3439 Allston Ln - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

3439 Allston Ln, Winter Park, FL 32792

Luxury | Walk-in closets | Outdoor space

3 beds

2.5 baths

$2,470

House for rent

Available Aug 7

Top amenities
High Ceilings
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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

$2,570

Winter Park

$2,520

Winter Park

$2,470

Winter Park

5219 Ardmore Dr - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

5219 Ardmore Dr, Goldenrod, FL 32792

Luxury | Swimming pool | Outdoor space

4 beds

2 baths

$2,830

House for rent

Available Jul 17

Top amenities
Garage Parking
High Ceilings
6748 Ebans Bnd - Photo 1 of 1

4d ago

Our team has verified this company

Verified

6748 Ebans Bnd, Azalea Park, FL 32807

Luxury | Walk-in closets | Outdoor space

3 beds

2 baths

$2,630

$2,245

Price drop

House for rent

Available Jul 21

Top amenities
Ceiling Fan
Garage Parking
1345 Bridlebrook Dr - Photo 1 of 1

4d ago

Our team has verified this company

Verified

1345 Bridlebrook Dr, Casselberry, FL 32707

Luxury | Walk-in closets | Outdoor space

2 beds

2 baths

$2,225

House for rent

Available Jan 22

Top amenities
High Ceilings
3313 Hamlet Loop - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

3313 Hamlet Loop, Winter Park, FL 32792

Luxury | Walk-in closets | Swimming pool

3 beds

2.5 baths

$2,555

House for rent

Available Jun 23

Top amenities
Ceiling Fan
High Ceilings
3314 Calcutta Ave - Photo 1 of 1

1d ago

Our team has verified this company

Verified

3314 Calcutta Ave, Orlando, FL 32817

Luxury | Swimming pool | On-site laundry

3 beds

2 baths

$2,695

$2,500

Price drop

House for rent

Available Jul 14

Top amenities
On-Site Laundry
On-Site Management
3651 Oak Vista Ln - Photo 1 of 1

1d ago

Our team has verified this company

Verified

3651 Oak Vista Ln, Winter Park, FL 32792

Luxury | Swimming pool | On-site laundry

3 beds

2.5 baths

$2,800

$2,590

Price drop

House for rent

Available Jul 20

Top amenities
On-Site Laundry
On-Site Management
372 Fairgreen Pl - Photo 1 of 1

1d ago

Our team has verified this company

Verified

372 Fairgreen Pl, Casselberry, FL 32707

Luxury | Swimming pool | On-site laundry

3 beds

2 baths

$2,910

$2,550

Price drop

House for rent

Available Jul 1

Top amenities
On-Site Laundry
On-Site Management
2313 Dunbury Ct - Photo 1 of 1

19h ago

Our team has verified this company

Verified

2313 Dunbury Ct Winter Park, FL 32792

2313 Dunbury Ct, Winter Park, FL 32792

Luxury | Outdoor space | Garage parking

3 beds

2 baths

$2,395

House for rent

Available May 21

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611 Hewett Dr - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

611 Hewett Dr, Azalea Park, FL 32807

Luxury | Swimming pool | On-site laundry

4 beds

2 baths

$2,200

$2,075

Price drop

House for rent

Available Apr 30

Top amenities
On-Site Laundry
On-Site Management
3628 Datura Ct - Photo 1 of 1

19h ago

Our team has verified this company

Verified

3628 Datura Ct Winter Park, FL 32792

3628 Datura Ct, Goldenrod, FL 32792

Luxury

5 beds

2 baths

$2,395

House for rent

Available Jul 3

504 Saint Dunstan Way - Photo 1 of 1

9h ago

Our team has verified this company

Verified

504 Saint Dunstan Way, Winter Park, FL 32792

Luxury | Swimming pool | On-site laundry

3 beds

2 baths

$2,725

$2,505

Price drop

House for rent

Available Jun 26

Top amenities
On-Site Laundry
On-Site Management
Listings within 10 miles
7032 Carna Ct #NA - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

$2,600 - 5 Bedroom 2 Bathroom House In Orlando With Pool, pavers backyard, and Solar Panels $2,600

7032 Carna Ct #NA, Azalea Park, FL 32807

Luxury | Swimming pool | In-unit laundry

5 beds

2 baths

$2,599

House for rent

Available Jul 6

Top amenities
Air Conditioning
Dishwasher
In-Unit Laundry
On-Site Laundry
Swimming Pool
3510 Buffam Pl - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

3510 Buffam Pl, Casselberry, FL 32707

Luxury | Walk-in closets | On-site laundry

3 beds

2 baths

$2,785

$2,635

Price drop

House for rent

Available Jul 20

Top amenities
Ceiling Fan
Garage Parking
On-Site Laundry
429 Notre Dame Dr - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

429 Notre Dame Dr, Altamonte Springs, FL 32714

Luxury | Swimming pool | On-site laundry

3 beds

2 baths

$2,400

House for rent

Available Aug 17

Top amenities
On-Site Laundry
On-Site Management
3621 Sutton Dr - Photo 1 of 1

19h ago

Our team has verified this company

Verified

3621 Sutton Dr Orlando, FL 32808

3621 Sutton Dr, Lockhart, FL 32810

Luxury | Outdoor space | Garage parking

3 beds

2 baths

$2,195

$2,095

Price drop

House for rent

Available May 22

Showing 1 - 25 of 25 results
Home > House Rentals in Winter Park > Winter Park Luxury Houses For Rent
Updated: June 27, 2026

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Pet friendly houses in Winter Park, FL16 rentals

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Discover luxury Winter Park, FL houses for rent

🌇Available luxury house rentals25 houses
⭐Popular amenities, ,
🍽With dishwasher
❄️With air conditioning
🚗With garage parking
🍃With outdoor space
🏠With photos