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Best Luxury Houses for Rent in Winter Park FL

9 Rentals Available

2721 E Marks St

2721 E Marks St, Orlando, FL 32803
1 / 5
3 Beds, 2 Baths, 1,569 sq ft

$5,800

Total Monthly Price

Total Monthly Price New

Prices include all required monthly fees.

Furnished Fireplace
3227 N Orange Ave

3227 N Orange Ave, Orlando, FL 32803
1 / 20
3 Beds

$3,400

Pets Allowed Hardwood Floors Fireplace Security System
438 Lakeview Ave

438 Lakeview Ave, Winter Park, FL 32789
1 / 5
2 Beds, 1 Bath, 1,250 sq ft

$3,200

Pets Allowed Waterfront
1001 Nottingham St

1001 Nottingham St, Orlando, FL 32803
1 / 5
3 Beds, 2 Baths, 2,276 sq ft

$3,300

Pets Allowed
$3,795

1667 Mizell Ave, Winter Park, FL 32789

3 Beds | 3 Baths | 1,715 sq ft
$3,600

2252 Howard Dr, Winter Park, FL 32789

3 Beds | 2 Baths | 1,406 sq ft
$3,499

2497 Waving Moss Wy, Winter Park, FL 32792

3 Beds | 2.5 Baths | 1,790 sq ft
$9,500

660 Osceola Ave, Winter Park, FL 32789

3 Beds | 3.5 Baths | 2,714 sq ft
$3,500

2916 Westchester Ave, Orlando, FL 32803

3 Beds | 2 Baths | 1,824 sq ft
More Rentals Near Winter Park, FL

We found 25 more rentals that closely match your search.
3644 Becontree Pl

3644 Becontree Pl, Oviedo, FL 32765
1 / 20
3 Beds

$2,820

Total Monthly Price

Total Monthly Price New

Prices include all required monthly fees.
2152 Palm Crest Dr

2152 Palm Crest Dr, Apopka, FL 32712
1 / 20
3 Beds

$2,999

Dogs Allowed Pool Hardwood Floors Fireplace Fenced Lot Security System
481 Nadeau Way

481 Nadeau Way, Apopka, FL 32712
1 / 17
3 Beds

$2,810

Pets Allowed
4326 Blonigen Ave

4326 Blonigen Ave, Orlando, FL 32812
1 / 19
3 Beds

$3,450

Pets Allowed Furnished Fenced Lot Security System
7508 Carolyn Ave

7508 Carolyn Ave, Orlando, FL 32807
1 / 18
3 Beds

$3,600

Pets Allowed Furnished
7652 Clubhouse Estates Dr

7652 Clubhouse Estates Dr, Orlando, FL 32819
1 / 15
3 Beds

$3,245

Pets Allowed
7013 Hiawassee Overlook Dr

7013 Hiawassee Overlook Dr, Orlando, FL 32835
3 Beds

$3,280

Pets Allowed
2417 Myrtle Ave

2417 Myrtle Ave, Sanford, FL 32771
1 / 12
3 Beds

$2,600

Pets Allowed Fenced Lot
800 Maxwell St

800 Maxwell St, Orlando, FL 32804
1 / 20
2 Beds

$2,950

Furnished Hardwood Floors Fenced Lot Security System
644 E Hillcrest St

644 E Hillcrest St, Altamonte Springs, FL 32701
1 / 16
3 Beds

$2,505

Pets Allowed
2006 Williams Ave

2006 Williams Ave, Sanford, FL 32771
1 / 20
3 Beds

$2,995

Pets Allowed
833 N Fern Creek Ave

833 N Fern Creek Ave, Orlando, FL 32803
1 / 5
3 Beds, 3 Baths, 1,772 sq ft

$3,600

Pets Allowed
2804 Pewter Mist Ct

2804 Pewter Mist Ct, Oviedo, FL 32765

For Rent

By Owner
1 / 10
3 Beds, 2.5 Baths, 2,178 sq ft

$2,700

Total Monthly Price
12 Month Lease

Total Monthly Price New

Prices include all required monthly fees.

Patio Attic
1093 Kelly Creek Cir

1093 Kelly Creek Cir, Oviedo, FL 32765

For Rent

By Owner
1 / 18
3 Beds, 3 Baths, 1,800 sq ft

$2,800

Total Monthly Price
12 Month Lease

Total Monthly Price New

Prices include all required monthly fees.
10441 Coconut Grove Ln

10441 Coconut Grove Ln, Orlando, FL 32825

For Rent

By Owner
Studio, 1 Bath, 450 sq ft

$2,920

Total Monthly Price
2 Month Lease

Total Monthly Price New

Prices include all required monthly fees.
3319 Florene Dr

3319 Florene Dr, Orlando, FL 32806

For Rent

By Owner
1 / 25
3 Beds, 2 Baths, 2,450 sq ft

$5,500

Total Monthly Price
1 Month Lease

Total Monthly Price New

Prices include all required monthly fees.

Pool Furnished
8644 Sandberry Blvd

8644 Sandberry Blvd, Orlando, FL 32819
1 / 5
3 Beds, 2 Baths, 1,620 sq ft

$3,750

Pets Allowed Pool Furnished
1500 E Ridgewood St

1500 E Ridgewood St, Orlando, FL 32803
1 / 5
2 Beds, 2 Baths, 1,826 sq ft

$3,200

Pets Allowed
486 Lady Palm St

486 Lady Palm St, Apopka, FL 32703
1 / 5
3 Beds, 2.5 Baths, 2,147 sq ft

$2,700

Pets Allowed
1620 Park Lake St

1620 Park Lake St, Orlando, FL 32803
1 / 5
2 Beds, 1 Bath, 1,014 sq ft

$3,000

Fireplace
8413 Shady Glen Dr

8413 Shady Glen Dr, Orlando, FL 32819
1 / 5
3 Beds, 2.5 Baths, 1,952 sq ft

$3,300

Pool
$3,250

1455 Catherine St, Orlando, FL 32801

3 Beds | 2.5 Baths | 1,942 sq ft
2600 S Crystal Lake Dr

2600 S Crystal Lake Dr, Orlando, FL 32806
1 / 5
2 Beds, 1 Bath, 782 sq ft

$2,800

Pets Allowed Furnished
2165 Ridgewood St

2165 Ridgewood St, Orlando, FL 32803
1 / 5
3 Beds, 2.5 Baths, 1,910 sq ft

$3,075

Pets Allowed
7964 Waterfield Ave

7964 Waterfield Ave, Orlando, FL 32832
1 / 5
3 Beds, 2 Baths, 2,233 sq ft

$3,800

Furnished

Houses Florida Orange County Winter Park

Winter Park, FL Luxury Homes for Rent

Experience the finer side of living when you find a luxury home for rent in Winter Park, FL. From granite countertops and soaring ceilings to rich hardwood floors, Winter Park luxury houses provide all the upscale details you’re looking for. With 9 luxury rentals across the city, you’ll find a wide range of high-end homes to choose from. Start exploring Winter Park’s luxury home listings discover the perfect rental that fits your taste.

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