Deals & Discount Filters
Apartments for Rent in Winter Park, FL
1,831 Rentals
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3 BEDS, 2 BATHS$2,200 -
3 BEDS, 2 BATHS$3,4001817 Loch Berry Rd
1817 Loch Berry Rd, Winter Park, FL 32789 -
3 BEDS, 3 BATHS$2,495
7542 Cranes Creek Ct
7542 Cranes Creek Ct, Winter Park, FL 32792 -
8 BEDS, 6 BATHS$16,550
1860 Vía Contessa
1860 Vía Contessa, Winter Park, FL 32789 -
1 BED, 1 BATH$1,050
525 S Lakemont Ave
525 S Lakemont Ave, Winter Park, FL 32792 -
4 BEDS, 3 BATHS$4,995
1525 Palmer Ave
1525 Palmer Ave, Winter Park, FL 32789 -
1 BED, 1 BATH$1,125
139 Scottsdale Square
139 Scottsdale Square, Winter Park, FL 32792 -
1 BED, 1 BATH$1,300
Stylish Remodeled 1BR Condo with Pool & Low HOA – Ideal Winter Park Investment Unit N-10C
3060 George Mason Ave, Winter Park, FL 32792 -
2 BEDS, 2.5 BATHS$1,425
3007 George Mason Ave Unit H
3007 George Mason Ave, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,750
650 Trinidad Ct
650 Trinidad Ct, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,399
1502 Michigan Ave
1502 Michigan Ave, Winter Park, FL 32789 -
3 BEDS, 2 BATHS$2,099
2111 Biscayne Dr
2111 Biscayne Dr, Winter Park, FL 32789 -
1 BED, 1 BATH$1,300
3044 Antique Oaks Cir Unit 178
3044 Antique Oaks Cir, Winter Park, FL 32792 -
2 BEDS, 2.5 BATHS$1,500
7431 Glen Oaks Way Unit 89
7431 Glen Oaks Way, Winter Park, FL 32792 -
2 BEDS, 1.5 BATHS$1,895
200 St Andrews Blvd Unit 2903
200 St Andrews Blvd, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,700
Excellent location Unit 4968
4968 Tangerine Ave, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,740
Rent Special: Receive $100 in rent credit for the first three months with a 12-month lease!
7429 Daniel Webster Dr, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,295
2183 Crandon Ave Unit 1
2183 Crandon Ave, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,395
3011 George Mason Ave Unit 3B
3011 George Mason Ave, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,495
3651 N Goldenrod Rd Unit C204
3651 N Goldenrod Rd, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,129
3651 N Goldenrod Rd
3651 N Goldenrod Rd, Winter Park, FL 32792 -
1 BED, 1 BATH$1,050
2326 Wellington Blvd
2326 Wellington Blvd, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,500
2/2, updated, 1st floor condo, in Winter Park
101 Lewfield Cir, Winter Park, FL 32792 -
3 BEDS, 1 BATH$1,850
REMODELED 3 BEDROOM / 1 BATH / CARPORT (WINTER PARK!)
931 Cypress Ave, Winter Park, FL 32789 -
4 BEDS, 3.5 BATHS$3,850
Winter Park home in a Gated Community
1402 Lone Feather Trail, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,575
2 Bedroom/2 Bathroom 2nd Floor Unit at Lancelot Unit C205
3651 N Goldenrod Rd, Winter Park, FL 32792 -
1 BED, 1 BATH$1,325
Beautiful 1/1 Wood Floors Condo for Rent in Winter Park Unit 6
2905 Antique Oaks Cir, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,599
Beautiful Remodeled Winter Park 2/2 Condo for Rent in Front of Full Sail. Unit 132
3020 Antique Oaks Cir, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$3,250
Winter Park Charmer
2862 Kings Deer Rd, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,690
Cozy 2 bed 2 bath in Winter Park
211 Stefanik Rd, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$1,850
Well maintained townhome in Winter Park
2349 Inagua Way, Winter Park, FL 32792 -
20 BEDS, 2 BATHS$1,575
Beautiful Winter Park 2/2 Condo on the first floor x Rent in front of Full Sail ! Unit 71
2936 Antique Oaks Cir, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$2,350
Fully Remodeled Winter Park Home
7323 Antietam Ct W, Winter Park, FL 32792 -
4 BEDS, 4.25 BATHS$25,000
281 Shell Point E
281 Shell Point E, Maitland, FL 32751 -
2 BEDS, 2 BATHS$4,200
206 Quayside Cir Unit 103
206 Quayside Cir, Maitland, FL 32751 -
3 BEDS, 2.5 BATHS$2,275
824 Town Cir
824 Town Cir, Maitland, FL 32751 -
1 BED, 1 BATH$1,150
452 Banyon Tree Cir Unit 106
452 Banyon Tree Cir, Maitland, FL 32751 -
2 BEDS, 1 BATH$1,350
496 Banyon Tree Cir
496 Banyon Tree Cir, Maitland, FL 32751 -
3 BEDS, 2 BATHS$2,495
2501 Oberlin Ave
2501 Oberlin Ave, Orlando, FL 32804 -
3 BEDS, 3 BATHS$2,200
1718 Gulfview Dr Unit 429 B
1718 Gulfview Dr, Maitland, FL 32751 -
4 BEDS, 2 BATHS$2,700
724 Forest Glen Ct
724 Forest Glen Ct, Maitland, FL 32751
Showing 42 of 280 results, Page 6 of 7
Winter Park at a Glance
Renting in Winter Park
Average Rental Rates and Apartment Sizes
- Apartment Type Average Sq Ft Average Rent
- Studio 539 Sq Ft $1,381 / mo
- 1 Bedroom 707 Sq Ft $1,437 / mo
- 2 Bedrooms 1,019 Sq Ft $1,752 / mo
- 3 Bedrooms 1,273 Sq Ft $1,998 / mo
- 4 Bedrooms 1,506 Sq Ft $1,540 / mo
Top Budget-Friendly Neighborhoods in Winter Park
(For 1 bedroom apartments)- Neighborhoods Average Sq Ft Average Rent
- Four Seasons 590 Sq Ft $1,348/mo
- Winter Park Pines Merrie Oaks 590 Sq Ft $1,348/mo
- Winter Park Woods 763 Sq Ft $1,379/mo
- Winter Park Pines 669 Sq Ft $1,428/mo
- Eastbrook 747 Sq Ft $1,432/mo
- Laurel Springs 741 Sq Ft $1,434/mo
- Lake Howell 747 Sq Ft $1,520/mo
- Villas of Casselberry 764 Sq Ft $1,537/mo
- Windward Square 784 Sq Ft $1,552/mo
- Glenmoor 706 Sq Ft $1,552/mo
Average Rent in Nearby Cities
(For 1 bedroom apartments)- Cities Average Rent
- Winter Park $1,591/mo
- Maitland $1,747/mo
- Fern Park $1,298/mo
- Eatonville $875/mo
- Casselberry $1,741/mo
- Longwood $1,695/mo
- Altamonte Springs $1,599/mo
- Orlando $1,650/mo
- Pine Castle $1,294/mo
Getting Around Winter Park
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Note: Based on community-supplied data and independent market research. Subject to change without notice.