No results were found that match your criteria.
Showing all results in Windward Square - Winter Park, FL.
Luxury Apartments for Rent in Windward Square
-
Price Drop. $250 Off1 BED$1,399+2 BEDS$1,649+3 BEDS$1,899+
-
1 BED$1,528+2 BEDS$1,739+3 BEDS$1,928+
Stonecastle Apartment Homes
2015 New Stonecastle Ter, Winter Park, FL 32792 -
-
3 BEDS, 2.5 BATHS$2,700
2749 Bright Bird Ln
2749 Bright Bird Ln, Winter Park, FL 32792 -
3 BEDS, 2.5 BATHS$2,550
1943 Canny Cv
1943 Canny Cv, Winter Park, FL 32792 -
3 BEDS, 2.5 BATHS$2,750
2748 Bright Bird Ln
2748 Bright Bird Ln, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,850
3019 Casselwood St
3019 Casselwood St, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$2,100
3050 Autumn Ct
3050 Autumn Ct, Winter Park, FL 32792 -
3 BEDS, 2.5 BATHS$3,500
2774 Bright Bird Ln
2774 Bright Bird Ln, Winter Park, FL 32792 -
3 BEDS, 2.5 BATHS$3,500
Luxury furnished 3-Bed in Winter Park
2774 Bright Bird Ln, Winter Park, FL 32792
Winter Park at a Glance
Windward Square Neighborhood in Winter Park, FL
Browse 10 luxury apartments for rent in Windward Square and live next to some of the city's top destinations, including parks, museums, and theaters right at your doorstep. Windward Square luxury apartments offer some of the best amenities available, like high ceilings, upgraded appliances, quartz or granite countertops, and high-end lighting. Other upscale features often included are chef’s kitchens, spa-like bathrooms, spacious living areas, and fantastic views.
When you rent a luxury apartment, you will likely have access to some perks and features, such as a swimming pool, courtyard, fitness center, or even a spa or on-site lounge. Since luxury communities are designed to elevate residents' living experience, you might find additional services such as concierge, housekeeping, or laundry service. Luxury apartments in Windward Square offer the ideal blend of comfort, style, and convenience. Indulge in the amenities and features at home or enjoy easy access to some of the city’s finest restaurants, shops, and entertainment.
Top Budget-Friendly Neighborhoods in Winter Park
(For 1 bedroom apartments)- Neighborhoods Average Sq Ft Average Rent
- Winter Park Woods 767 Sq Ft $1,451/mo
- Eastbrook 720 Sq Ft $1,481/mo
- Cedarwood Village 642 Sq Ft $1,486/mo
- Winter Park Pines 707 Sq Ft $1,495/mo
- Four Seasons 640 Sq Ft $1,512/mo
- Winter Park Pines Merrie Oaks 640 Sq Ft $1,512/mo
- Albert Lee Ridge 768 Sq Ft $1,581/mo
- Lake Howell 726 Sq Ft $1,601/mo
- Winter Park Estates 692 Sq Ft $1,632/mo
- Windward Square 779 Sq Ft $1,648/mo
Getting Around Winter Park
Education
Data provided by GreatSchools.org 2025 © 2025. All rights reserved.
Select Bedrooms
Specialty Housing
Choose by Amenities
Submitting Request
Thank You
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.