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Luxury Houses for Rent in Winter Park, FL

25 rentals available

1020 Minnesota Ave #1 - Photo 1 of 1

10h ago

Luxury townhouse for rent in Winter Park

Residential Lease, WINTER PARK, FL

1020 Minnesota Ave #1, Winter Park, FL 32789

Luxury | In-unit laundry | Garage parking

3 beds

2.5 baths

$3,800

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
850 N Phelps Ave - Photo 1 of 1

1d ago

Luxury house for rent in Winter Park

850 N Phelps Ave, Winter Park, FL 32789

Luxury | Outdoor space | Garage parking

2 beds

2 baths

$2,908

Price dropped $100Total Monthly Price. The price shown includes base rent and all known required monthly fees, based on information provided by the property.
173 Lewfield Cir #1 - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Park

173 Lewfield Cir #1, Winter Park, FL 32792

Luxury | In-unit laundry | On-site management

1 bed

1 bath

$1,400

Additional fees apply. The price shown reflects base rent. Based on information provided by the property, additional fees may apply, but no required monthly charges have been confirmed. See all fees for details.
343 Harris Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

343 Harris Ave, Winter Park, FL 32789

Luxury | In-unit laundry | Outdoor space

3 beds

2 baths

$4,500

Price dropped $200Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
2417 Lafayette Ave - Photo 1 of 1
New construction

5d+ ago

Luxury house for rent in Winter Park

Residential Lease, WINTER PARK, FL

2417 Lafayette Ave, Winter Park, FL 32789

Luxury | Walk-in closets | Swimming pool

4 beds

3 baths

$10,000

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
1981 Blue Ridge Rd - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Residential Lease, WINTER PARK, FL

1981 Blue Ridge Rd, Winter Park, FL 32789

Luxury | Walk-in closets | In-unit laundry

5 beds

2 baths

$5,995

Price dropped $500Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.

Nearby rental good for eco-living

Nearby rental good for pet owners

1029 Wading Waters Cir #NA - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

$6,300 - 5 Bedroom 4.5 Bathroom House In Winter Park With Great Amenities

1029 Wading Waters Cir #NA, Winter Park, FL 32792

Luxury | Walk-in closets | Swimming pool

5 beds

4.5 baths

$6,000

Additional fees apply. The price shown reflects base rent. Based on information provided by the property, additional fees may apply, but no required monthly charges have been confirmed. See all fees for details.
2712 Goldenrod Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Residential Lease, WINTER PARK, FL

2712 Goldenrod Dr, Winter Park, FL 32792

Luxury | Outdoor space | Garage parking

3 beds

2 baths

$4,500

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
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741 Minnesota Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Spacious 3-Bedroom, 4-Bath Home for Rent in Winter Park, FL | WiFi Included + Private Community Pool

741 Minnesota Ave, Winter Park, FL 32789

Luxury | Balcony | Walk-in closets

3 beds

3.5 baths

$3,995

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
800 W Canton Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Residential Lease, WINTER PARK, FL

800 W Canton Ave, Winter Park, FL 32789

Luxury | In-unit laundry | On-site laundry

2 beds

1 bath

$2,500

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
2056 Wood Thrush Ln - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Residential Lease, WINTER PARK, FL

2056 Wood Thrush Ln, Winter Park, FL 32792

Luxury | Walk-in closets | Swimming pool

4 beds

3 baths

$5,500

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.

Find sweet deals near Winter Park

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

1368 Hibiscus Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Residential Lease, WINTER PARK, FL

1368 Hibiscus Ave, Winter Park, FL 32789

Luxury | Balcony | Walk-in closets

4 beds

2.5 baths

$7,250

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
1442 Palm Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Park

Residential Lease, WINTER PARK, FL

1442 Palm Ave, Winter Park, FL 32789

Luxury | Walk-in closets | Swimming pool

5 beds

6 baths

$9,900

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
400 Talquin Ct - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

400 Talquin Ct, Azalea Park, FL 32807

Luxury | Walk-in closets | Deck

3 beds

2 baths

$2,040

Price dropped $125Total Monthly Price. The price shown includes base rent and all known required monthly fees, based on information provided by the property.
5592 Garden Grove Cir - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

5592 Garden Grove Cir, Goldenrod, FL 32792

Luxury | Walk-in closets | Outdoor space

3 beds

2 baths

$2,535

Total Monthly Price. The price shown includes base rent and all known required monthly fees, based on information provided by the property.
3028 Dikewood Ct - Photo 1 of 1

4d ago

Our team has verified this company

Verified

3028 Dikewood Ct, Winter Park, FL 32792

Luxury | Walk-in closets | Outdoor space

3 beds

2 baths

$2,740

Total Monthly Price. The price shown includes base rent and all known required monthly fees, based on information provided by the property.
5025 Goldenrod Place Rd - Photo 1 of 1

17h ago

Our team has verified this company

Verified

5025 Goldenrod Place Rd, Goldenrod, FL 32792

Luxury | Walk-in closets | On-site laundry

3 beds

2 baths

$2,320

Price dropped $220Total Monthly Price. The price shown includes base rent and all known required monthly fees, based on information provided by the property.
143 Spoonhour Dr - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

143 Spoonhour Dr, Casselberry, FL 32707

Luxury | Walk-in closets | Outdoor space

3 beds

2 baths

$2,310

Price dropped $980Total Monthly Price. The price shown includes base rent and all known required monthly fees, based on information provided by the property.
1348 Benevolent St - Photo 1 of 1

3d ago

Our team has verified this company

Verified

1348 Benevolent St, Maitland, FL 32751

Luxury | Balcony | Walk-in closets

3 beds

2.5 baths

$2,575

Price dropped $955Total Monthly Price. The price shown includes base rent and all known required monthly fees, based on information provided by the property.
3650 Jonquil Ln - Photo 1 of 1

3d ago

Our team has verified this company

Verified

3650 Jonquil Ln, Winter Park, FL 32792

Luxury | Balcony | Swimming pool

3 beds

2 baths

$2,786

Total Monthly Price. The price shown includes base rent and all known required monthly fees, based on information provided by the property.
2217 Sussex Rd - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

2217 Sussex Rd, Winter Park, FL 32792

Luxury | Swimming pool | In-unit laundry

4 beds

2 baths

$3,400

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
Listings within 10 miles
236 Afton Sq #308 - Photo 1 of 1

5d+ ago

Luxury house for rent in Altamonte Springs

236 Afton Sq #308, Altamonte Springs, FL 32714

Luxury | Swimming pool | Outdoor space

1 bed

1 bath

$1,295

Fees may apply. The price shown reflects base rent. Complete fee information is not available from the property, so additional fees may increase the total monthly cost.
4342 Cloverleaf Pl - Photo 1 of 1

17h ago

Our team has verified this company

Verified

4342 Cloverleaf Pl, Casselberry, FL 32707

Luxury | Outdoor space | Garage parking

3 beds

2 baths

$2,545

Price dropped $230Total Monthly Price. The price shown includes base rent and all known required monthly fees, based on information provided by the property.
3762 Peaceful Pl - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

3762 Peaceful Pl, Lockhart, FL 32810

Luxury | On-site laundry | Outdoor space

3 beds

2 baths

$2,075

Price dropped $130Total Monthly Price. The price shown includes base rent and all known required monthly fees, based on information provided by the property.
3638 Okeechobee Cir - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

3638 Okeechobee Cir, Casselberry, FL 32707

Luxury | Walk-in closets | Outdoor space

3 beds

2 baths

$2,235

Price dropped $155Total Monthly Price. The price shown includes base rent and all known required monthly fees, based on information provided by the property.
Showing 1 - 25 of 25 results
Home > House Rentals in Winter Park > Winter Park Luxury Houses For Rent
Updated: November 11, 2026

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Discover luxury Winter Park, FL houses for rent

🌇Available luxury house rentals25 houses
⭐Popular amenities, ,
❄️With air conditioning
🚗With garage parking
🏠With photos