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Best Luxury Houses for Rent in Winter Park FL

8 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
220 Overlook Rd

220 Overlook Rd, Winter Park, FL 32789
1 / 5
2 Beds, 2 Baths, 1,393 sq ft

$3,600

Fireplace
865 S Pennsylvania Ave

865 S Pennsylvania Ave, Winter Park, FL 32789
2 Beds, 1 Bath, 1,000 sq ft

$2,650

Pets Allowed Fireplace
3707 Pelican Ln

3707 Pelican Ln, Orlando, FL 32803
1 / 5
3 Beds, 2 Baths, 1,947 sq ft

$3,250

Pets Allowed Pool Fireplace
4461 Trapp Ln

4461 Trapp Ln, Orlando, FL 32814
1 / 5
3 Beds, 2 Baths, 1,709 sq ft

$4,500

Fireplace
$3,500

2011 Meeting Pl, Orlando, FL 32814

3 Beds | 3.5 Baths | 2,064 sq ft
$4,450

4478 Twinview Ln, Orlando, FL 32814

3 Beds | 2.5 Baths | 2,614 sq ft
$3,450

1594 Common Way Rd, Orlando, FL 32814

3 Beds | 2 Baths | 1,495 sq ft
More Rentals Near Winter Park, FL

We found 25 more rentals that closely match your search.
1091 Summer Stone Loop

1091 Summer Stone Loop, Apopka, FL 32703
1 / 20
3 Beds

$2,775

Total Monthly Price

Total Monthly Price New

Prices include all required monthly fees.
2453 Sweetaire Ct

2453 Sweetaire Ct, Apopka, FL 32712
1 / 20
3 Beds

$2,600

Pets Allowed Pool Fenced Lot Smoke Free Vaulted Ceiling
2600 S Crystal Lake Dr

2600 S Crystal Lake Dr, Orlando, FL 32806
1 / 20
2 Beds

$2,800

Pets Allowed Furnished Fenced Lot Security System
1118 Overdale St

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

$3,200

Pets Allowed Pool Furnished Fenced Lot Security System
1614 Ferris Ave

1614 Ferris Ave, Orlando, FL 32803
1 / 18
3 Beds

$3,445

Pets Allowed Furnished
872 Fairview Ave

872 Fairview Ave, Altamonte Springs, FL 32701
3 Beds

$2,649

Pets Allowed
8014 Winpine Ct

8014 Winpine Ct, Orlando, FL 32819
1 / 20
3 Beds

$3,300

Pets Allowed
402 E Springtree Way

402 E Springtree Way, Lake Mary, FL 32746
1 / 17
2 Beds

$2,445

Pets Allowed Hardwood Floors Yard Fireplace Fenced Lot Vaulted Ceiling
226 White Dogwood Ln

226 White Dogwood Ln, Ocoee, FL 34761
1 / 16
3 Beds

$2,695

Pets Allowed
3169 Floral Way E

3169 Floral Way E, Apopka, FL 32703
1 / 20
3 Beds

$2,890

Pets Allowed Patio Walk-In Closets
805 Panical Dr

805 Panical Dr, Apopka, FL 32703
3 Beds

$2,590

Pets Allowed
2600 S Crystal Lake Dr

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

$3,150

Pets Allowed Furnished
607 Hattaway Dr

607 Hattaway Dr, Altamonte Springs, FL 32701
1 / 5
3 Beds, 2 Baths, 1,746 sq ft

$2,900

Pets Allowed Fireplace
1614-1614 Ferris Ave

1614-1614 Ferris Ave, Orlando, FL 32803
1 / 5
3 Beds, 1 Bath, 1,000 sq ft

$3,480

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
9957 Oak Quarry Dr

9957 Oak Quarry Dr, Orlando, FL 32832
1 / 5
3 Beds, 2 Baths, 2,395 sq ft

$4,100

Pool Waterfront
10656 Billings St

10656 Billings St, Orlando, FL 32832
1 / 5
3 Beds, 3 Baths, 2,798 sq ft

$3,995

Pets Allowed Pool
13321 Camborne Pl

13321 Camborne Pl, Orlando, FL 32832
1 / 5
3 Beds, 2 Baths, 1,920 sq ft

$3,200

Pets Allowed
1054 Wilks Ave

1054 Wilks Ave, Orlando, FL 32809
1 / 5
3 Beds, 2.5 Baths, 2,250 sq ft

$3,600

Pets Allowed
3585 Ventura Club Cir

3585 Ventura Club Cir, Orlando, FL 32822
1 / 5
3 Beds, 2.5 Baths, 2,074 sq ft

$3,100

Fireplace
7423 Elsworth Ct

7423 Elsworth Ct, Orlando, FL 32819
1 / 5
3 Beds, 2 Baths, 1,667 sq ft

$3,075
902 Grand Hilltop Dr

902 Grand Hilltop Dr, Apopka, FL 32703
1 / 5
3 Beds, 2 Baths, 1,792 sq ft

$2,700
7332 Mardell Ct

7332 Mardell Ct, Orlando, FL 32835
3 Beds, 2.5 Baths, 2,112 sq ft

$3,200

Pets Allowed Pool
5837 Wooden Pine Dr

5837 Wooden Pine Dr, Orlando, FL 32829
1 / 5
3 Beds, 2 Baths, 2,144 sq ft

$3,200

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 8 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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