2 BEDS, 2 BATHS
$2,200
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Two Bedroom Condos for Rent in Winter Park
39 Rentals
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2 BEDS, 2 BATHS$2,3004240 Jack Frost Ct Unit 4410
4240 Jack Frost Ct, Naples, FL 34112 -
2 BEDS, 2 BATHS$3,200
4010 Ice Castle Way Unit 7
4010 Ice Castle Way, Naples, FL 34112 -
2 BEDS, 2 BATHS$5,100
83 Glades Blvd Unit 3
83 Glades Blvd, Naples, FL 34112 -
2 BEDS, 2 BATHS$2,200
1470 Green Valley Cir Unit 301
1470 Green Valley Cir, Naples, FL 34104 -
2 BEDS, 2 BATHS$1,800
1470 Green Valley Cir Unit 303
1470 Green Valley Cir, Naples, FL 34104 -
2 BEDS, 2 BATHS$1,650
3511 Antarctic Cir Unit 2406
3511 Antarctic Cir, Naples, FL 34112 -
2 BEDS, 2 BATHS$1,850
4261 Jack Frost Ct Unit 4707
4261 Jack Frost Ct, Naples, FL 34112 -
2 BEDS, 2 BATHS$1,800
1460 Green Valley Cir Unit 403
1460 Green Valley Cir, Naples, FL 34104 -
2 BEDS, 1 BATH$1,500
3325 Arpt Rd S Unit L5
3325 Arpt Rd S, Naples, FL 34105 -
2 BEDS, 2 BATHS$5,200
306 Palm Dr Unit 412
306 Palm Dr, Naples, FL 34112 -
2 BEDS, 2 BATHS$5,000
51 Glades Blvd Unit 2
51 Glades Blvd, Naples, FL 34112 -
2 BEDS, 1 BATH$1,750
3325 Arpt Rd S Unit F2
3325 Arpt Rd S, Naples, FL 34105 -
2 BEDS, 2 BATHS$2,150
4100 Looking Glass Ln Unit 3008
4100 Looking Glass Ln, Naples, FL 34112 -
2 BEDS, 1 BATH$1,450
3325 Arpt Rd S Unit Q3
3325 Arpt Rd S, Naples, FL 34105 -
2 BEDS, 2 BATHS$2,700
3676 Arctic Cir Unit 112
3676 Arctic Cir, Naples, FL 34112 -
2 BEDS, 2 BATHS$1,800
1390 Green Valley Cir Unit 1103
1390 Green Valley Cir, Naples, FL 34104 -
2 BEDS, 2 BATHS$1,850
4270 Jack Frost Ct Unit 5
4270 Jack Frost Ct, Naples, FL 34112 -
2 BEDS, 1 BATH$1,700
3325 Arpt Rd S Unit H4
3325 Arpt Rd S, Naples, FL 34105 -
2 BEDS, 2 BATHS$1,800
1420 Green Valley Cir Unit 802
1420 Green Valley Cir, Naples, FL 34104 -
2 BEDS, 2 BATHS$2,500
150 Round Key Cir Unit G-15
150 Round Key Cir, Naples, FL 34112 -
2 BEDS, 2 BATHS$2,250
4060 Ice Castle Way Unit 3
4060 Ice Castle Way, Naples, FL 34112 -
2 BEDS, 1 BATH$1,665
3325 Arpt Rd S Unit R3
3325 Arpt Rd S, Naples, FL 34105 -
2 BEDS, 2 BATHS$3,500
4230 Jack Frost Ct Unit 7
4230 Jack Frost Ct, Naples, FL 34112 -
2 BEDS, 2 BATHS$2,400
4031 Ice Castle Way Unit 3303
4031 Ice Castle Way, Naples, FL 34112 -
2 BEDS, 2 BATHS$4,000
4775 Lakewood Blvd
4775 Lakewood Blvd, Naples, FL 34112 -
2 BEDS, 2 BATHS$5,000
360 Palm Dr Unit 474
360 Palm Dr, Naples, FL 34112 -
2 BEDS, 2 BATHS$5,000
348 Tern Dr Unit #4
348 Tern Dr, Naples, FL 34112 -
2 BEDS, 2 BATHS$4,000
385 Palm Dr Unit 1732
385 Palm Dr, Naples, FL 34112 -
2 BEDS, 2 BATHS$3,300
4210 Looking Glass Ln Unit 4210
4210 Looking Glass Ln, Naples, FL 34112 -
2 BEDS, 2 BATHS$4,200
3608 Arctic Cir Unit 514
3608 Arctic Cir, Naples, FL 34112 -
2 BEDS, 2 BATHS$5,000
30 Glades Blvd Unit 1473
30 Glades Blvd, Naples, FL 34112 -
2 BEDS, 2 BATHS$3,500
3400 Frosty Way Unit 5
3400 Frosty Way, Naples, FL 34112 -
2 BEDS, 2 BATHS$1,950
4130 Looking Glass Ln Unit 6
4130 Looking Glass Ln, Naples, FL 34112 -
2 BEDS, 2 BATHS$5,000
34 Glades Blvd Unit 1461
34 Glades Blvd, Naples, FL 34112 -
2 BEDS, 2 BATHS$2,1004011 Ice Castle Way Unit 3507
4011 Ice Castle Way, Naples, FL 34112 -
2 BEDS, 2 BATHS$1,8954011 Ice Castle Way Unit 7
4011 Ice Castle Way, Naples, FL 34112 -
2 BEDS, 1 BATH$1,550ANNUAL RENTAL - 2 BED/1 BATH IN POINCIANA
3325 Arpt Rd S, Naples, FL 34105 -
2 BEDS, 1 BATH$1,650
ANNUAL RENTAL - POINCIANA-2 BED / 1 BATH
3325 Arpt Rd S, Naples, FL 34105
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Clear All FiltersNaples at a Glance
Winter Park Neighborhood in Naples, FL
So you're looking for the perfect two-bedroom condo for rent in Winter Park. With great rent specials, price drops, and the best values in the city, Apartment Finder offers a wide selection of spacious two-bedroom condos that will fit your lifestyle and budget. The larger layout and versatile living spaces in two-bedroom rentals provide ample room for individuals, couples, or even small families in Winter Park.
With the shared cost of rent, two-bedroom condos offer great value for the space you get. A two-bedroom rental has practical benefits even if you're not searching with roommates. Experience the advantages of having an extra bedroom, whether for a home office, guest room, or added storage space. The flexibility of a second bedroom allows you to personalize your home and adapt to changing needs. Enjoy a larger living area, multiple closets, and potentially additional amenities like in-unit laundry. Choose any of these 39 two-bedroom condos for rent to view floor plans, see photos, and get more information on amenities and availability.
Top Budget-Friendly Neighborhoods in Naples
(For 1 bedroom apartments)- Neighborhoods Average Sq Ft Average Rent
- Kensington Park 751 Sq Ft $1,803/mo
- Grey Oaks 696 Sq Ft $1,827/mo
- Golden Gate 775 Sq Ft $1,935/mo
- Briarwood-Maplewood 797 Sq Ft $1,982/mo
- Wyndemere 768 Sq Ft $1,994/mo
- Rural Estates 797 Sq Ft $2,010/mo
- East Naples 781 Sq Ft $2,148/mo
- Naples Manor 786 Sq Ft $2,160/mo
- Urban Estates 811 Sq Ft $2,199/mo
- Moorings Park-Hawks Ridge 688 Sq Ft $2,303/mo
Discover the cheapest neighborhoods in Naples
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About Our Deals
Apartment Finder utilizes the industry's largest and most complete database of real-time rents and availabilities to help you find an amazing deal on your next rental.
Price Drop
Apartment communities change their rental rates often - sometimes multiple times a day. We track the changes and keep you up to date when a rental rate decreases.
Best Value
"Best value" units are located in buildings rated three stars or higher. We label apartment rentals that are priced significantly less than similar high-quality units nearby.
Rent Specials
Apartment communities regularly advertise deals for new residents. Whether it's a move-in special or a free tv, we locate the rentals that offer a little something extra when you sign your lease.
Note: Based on community-supplied data and independent market research. Subject to change without notice.