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Best Luxury Houses for Rent in Winter Park FL

10 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
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
503 Kilshore Ln

503 Kilshore Ln, Winter Park, FL 32789
1 / 5
2 Beds, 1 Bath, 1,125 sq ft

$2,250

Pets Allowed
814 Malone Dr

814 Malone Dr, Orlando, FL 32810
1 / 5
2 Beds, 2 Baths, 1,211 sq ft

$2,650

Pets Allowed
$3,995

1667 Mizell Ave, Winter Park, FL 32789

3 Beds | 3 Baths | 1,715 sq ft
$2,250

1671 Dale Ave, Winter Park, FL 32789

2 Beds | 1 Bath | 1,131 sq ft
$3,700

2335 Coldstream Dr, Winter Park, FL 32792

3 Beds | 2 Baths | 1,466 sq ft
$3,995

3400 Golfview Blvd, Orlando, FL 32804

3 Beds | 2.5 Baths | 1,900 sq ft
$4,000

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.
138 Pine Isle Dr

138 Pine Isle Dr, Sanford, FL 32773
1 / 20
3 Beds

$2,600

Total Monthly Price

Total Monthly Price New

Prices include all required monthly fees.
4713 Windsor Ave

4713 Windsor Ave, Orlando, FL 32819
1 / 5
3 Beds, 2 Baths, 1,619 sq ft

$3,500

Total Monthly Price

Total Monthly Price New

Prices include all required monthly fees.

Patio Gated Fireplace Security System
644 E Hillcrest St

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

$2,505

Pets Allowed
1197 W Lakeview Cir

1197 W Lakeview Cir, Altamonte Springs, FL 32714
1 / 16
3 Beds

$2,475

Pets Allowed Pool
1226 Creekbottom Cir

1226 Creekbottom Cir, Orlando, FL 32825
3 Beds

$3,850

Pets Allowed Vaulted Ceiling Double Vanities
800 Maxwell St

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

$3,200

Furnished Hardwood Floors Fenced Lot Security System
1460 Travertine Terrace

1460 Travertine Terrace, Sanford, FL 32771
1 / 20
3 Beds

$2,469

Pets Allowed Pool Patio Fitness Center
1118 Overdale St

1118 Overdale St, Orlando, FL 32825
1 / 16
3 Beds

$3,900

Pets Allowed Pool Furnished Fenced Lot Security System
7652 Clubhouse Estates Dr

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

$3,245

Pets Allowed
2173 Martingale Pl

2173 Martingale Pl, Oviedo, FL 32765
1 / 20
3 Beds

$2,900

Pets Allowed Pool Hardwood Floors Fireplace Fenced Lot
7013 Hiawassee Overlook Dr

7013 Hiawassee Overlook Dr, Orlando, FL 32835
3 Beds

$3,280

Pets Allowed
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.
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
5350 Arpana Dr

5350 Arpana Dr, Orlando, FL 32839
1 / 5
3 Beds, 2 Baths, 1,480 sq ft

$4,500

Pool Furnished
342 Lady Palm St

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

$2,650

Pets Allowed
1081 Lake Weldona Dr

1081 Lake Weldona Dr, Orlando, FL 32806
1 / 5
3 Beds, 2 Baths, 1,561 sq ft

$3,650
106 Lake Dr

106 Lake Dr, Oviedo, FL 32765
1 / 5
3 Beds, 2 Baths, 2,294 sq ft

$3,350
11987 Globe St

11987 Globe St, Orlando, FL 32832
1 / 5
3 Beds, 2 Baths, 1,698 sq ft

$3,400
407 E Crystal Lake St

407 E Crystal Lake St, Orlando, FL 32806
1 / 5
3 Beds, 2 Baths, 1,370 sq ft

$3,200

Pets Allowed Pool
1507 Carillon Park Dr

1507 Carillon Park Dr, Oviedo, FL 32765
1 / 5
3 Beds, 2.5 Baths, 2,286 sq ft

$3,500

Pets Allowed Pool Waterfront
803 Glen Arden Way

803 Glen Arden Way, Altamonte Springs, FL 32701
1 / 5
3 Beds, 2 Baths, 1,855 sq ft

$2,400

Pets Allowed Fireplace
5278 Dove Tree St

5278 Dove Tree St, Orlando, FL 32811
1 / 5
3 Beds, 2 Baths, 1,774 sq ft

$3,200

Pets Allowed
7284 Hawksnest Blvd

7284 Hawksnest Blvd, Orlando, FL 32835
1 / 5
3 Beds, 2.5 Baths, 2,451 sq ft

$3,449

Dogs Allowed Pool
2165 Ridgewood St

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

$3,500
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 10 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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