4 BEDS, 3 BATHS
$3,490
Deals & Discount Filters
Apartments for Rent in Winter Park, FL
1,912 Rentals
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1 BED, 1 BATH$9992517 Caper Ln Unit 203
2517 Caper Ln, Maitland, FL 32751 -
2 BEDS, 1.5 BATHS$1,495
5517 Decatur St
5517 Decatur St, Orlando, FL 32807 -
1 BED, 1 BATH$1,785
1140 S Orlando Ave Unit E2
1140 S Orlando Ave, Maitland, FL 32751 -
1 BED, 1 BATH$1,900
2510 Boyd Ave
2510 Boyd Ave, Orlando, FL 32803 -
2 BEDS, 1 BATH$1,700
2515 Formosa Ave
2515 Formosa Ave, Orlando, FL 32804 -
3 BEDS, 2.5 BATHS$1,950
1162 Carmel Cir Unit 100
1162 Carmel Cir, Casselberry, FL 32707 -
3 BEDS, 2.5 BATHS$5,400
1510 Lake Baldwin Ln
1510 Lake Baldwin Ln, Orlando, FL 32814 -
3 BEDS, 2 BATHS$3,750
4351 Anson Ln Unit 205
4351 Anson Ln, Orlando, FL 32814 -
1 BED, 1 BATH$1,200
2517 Caper Ln Unit 205
2517 Caper Ln, Maitland, FL 32751 -
2 BEDS, 2 BATHS$2,850
206 Quayside Cir Unit 503
206 Quayside Cir, Maitland, FL 32751 -
3 BEDS, 2 BATHS$1,845
514 Carver Blvd
514 Carver Blvd, Orlando, FL 32810 -
1 BED, 1 BATH$1,975
1550 Lake Baldwin Ln Unit C
1550 Lake Baldwin Ln, Orlando, FL 32814 -
4 BEDS, 2 BATHS$3,500
2120 Deloraine Trail
2120 Deloraine Trail, Maitland, FL 32751 -
1 BED, 1 BATH$1,200
421 E Kennedy Blvd
421 E Kennedy Blvd, Eatonville, FL 32751 -
5 BEDS, 3 BATHS$3,040
2900 N Mills Ave
2900 N Mills Ave, Orlando, FL 32803 -
STUDIO, 1 BATH$1,600
1420 Lake Baldwin Ln
1420 Lake Baldwin Ln, Orlando, FL 32814 -
2 BEDS, 1 BATH$1,600
492 Banyon Tree Cir Unit 206
492 Banyon Tree Cir, Maitland, FL 32751 -
2 BEDS, 2 BATHS$1,575FOR RENT! Beautiful 2/2 Winter Park Pool View Condo in front of Full Sail! Unit 12
2911 Antique Oaks Cir, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$2,3953146 Dwarf Pine Ave
3146 Dwarf Pine Ave, Winter Park, FL 32792 -
1 BED, 1 BATH$1,650
? Beautiful and move-in ready condo!
1695 Lee Rd, Winter Park, FL 32789 -
2 BEDS, 2 BATHS$1,550
COMING SOON! 5/1/26 2/2 Upgraded Condo in Winter Park**
7722 Country Pl, Winter Park, FL 32792 -
2 BEDS, 1.5 BATHS$1,499
200 St Andrews Blvd
200 St Andrews Blvd, Winter Park, FL 32792 -
5 BEDS, 4 BATHS$3,800
SPACIOUS Two Story Beautiful 5/4 Home in The Enclave At Aloma!
7993 Pleasant Pine Cir, 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$2,550
Beautiful 2 bedroom, 2 bath Condo located in Winter Park
110 Killarney Bay Ct, Winter Park, FL 32789 -
1 BED, 1 BATH$1,200
One bedroom apt 7 or 12 months furnish or unfurnished. Apartamento disponible amueblado o sin mue...
3075 Aaron Burr 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 -
3 BEDS, 3 BATHS$3,995
1667 Mizell Ave
1667 Mizell Ave, Winter Park, FL 32789 -
1 BED, 1 BATH$1,325
Stunning 1/1 Condo remodeled for Rent in front of Full Sail Winter Park! Unit 89
2948 Antique Oaks Cir, Winter Park, FL 32792 -
2 BEDS, 1 BATH$1,450
1ST MONTH RENT FREE 2 Bed 1 Bath 2nd Floor Unit With Balcony In Desirable Area Winter Park Sectio... Unit # D211
1695 Lee Rd, Winter Park, FL 32789 -
3 BEDS, 2.5 BATHS$2,500
Winter Park Townhome
252 Balfour Dr, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,527
Beautiful Remodeled Winter Park 2/2 Condo for Rent in Front of Full Sail. Unit 132
3020 Antique Oaks Cir, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,575
Gorgeous first floor 2/2 condo x Rent @ Winter Park in front of Full Sail! Unit 65
2936 Antique Oaks Cir, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,725
Townhouse in Winter Park 2/2
609 Montego Bay Ct, Winter Park, FL 32792 -
3 BEDS, 2.5 BATHS$1,950
7454 Wynnewood Square
7454 Wynnewood Square, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$1,800
1695 Lee Rd
1695 Lee Rd, Winter Park, FL 32789 -
3 BEDS, 3 BATHS$2,400
7542 Cranes Creek Ct
7542 Cranes Creek Ct, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$3,475
Fabulous & Furnished in Winter Park!
1850 Whitehall Dr, Winter Park, FL 32789 -
3 BEDS, 2 BATHS$1,950
3050 Autumn Ct
3050 Autumn Ct, Winter Park, FL 32792 -
3 BEDS, 2.5 BATHS$2,400
7503 Aloma Pines Ct
7503 Aloma Pines Ct, Winter Park, FL 32792 -
3 BEDS, 2.5 BATHS$2,650
1777 Indiana Ave
1777 Indiana Ave, Winter Park, FL 32789
Showing 42 of 255 results, Page 5 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 535 Sq Ft $1,377 / mo
- 1 Bedroom 706 Sq Ft $1,441 / mo
- 2 Bedrooms 1,021 Sq Ft $1,760 / mo
- 3 Bedrooms 1,273 Sq Ft $2,042 / mo
- 4 Bedrooms 1,506 Sq Ft $1,775 / mo
Top Budget-Friendly Neighborhoods in Winter Park
(For 1 bedroom apartments)- Neighborhoods Average Sq Ft Average Rent
- Laurel Springs 718 Sq Ft $1,389/mo
- Winter Park Pines 712 Sq Ft $1,395/mo
- Winter Park Woods 757 Sq Ft $1,401/mo
- Whisperwood 712 Sq Ft $1,414/mo
- Eastbrook 753 Sq Ft $1,458/mo
- Glenmoor 724 Sq Ft $1,525/mo
- Cedarwood Village 665 Sq Ft $1,531/mo
- Winter Park Estates 720 Sq Ft $1,542/mo
- Lake Howell 749 Sq Ft $1,552/mo
- Georgetown Estates 740 Sq Ft $1,565/mo
Average Rent in Nearby Cities
(For 1 bedroom apartments)- Cities Average Rent
- Winter Park $1,573/mo
- Maitland $1,772/mo
- Fern Park $1,302/mo
- Eatonville $990/mo
- Casselberry $1,674/mo
- Longwood $1,687/mo
- Altamonte Springs $1,597/mo
- Orlando $1,653/mo
Education
Data provided by GreatSchools.org 2025 © 2025. All rights reserved.
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Note: Based on community-supplied data and independent market research. Subject to change without notice.