
Deals & Discount Filters
Apartments for Rent in Winter Park, FL with a Swimming Pool
1,736 Rentals
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1 BED$1,295+2 BEDS$1,535+3 BEDS$1,945+
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1 BED$1,532+2 BEDS$1,787+3 BEDS$1,928+
Stonecastle Apartment Homes
2015 New Stonecastle Ter, Winter Park, FL 32792 -
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1 BED$1,526+2 BEDS$1,417+3 BEDS$2,024+
Atlas at Winter Park
3733 N Goldenrod Rd, Winter Park, FL 32792 -
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1 BED$1,232+2 BEDS$1,282+3 BEDS$1,723+
Venue At Winter Park
5 Autumn Breeze Way, Winter Park, FL 32792 -
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1 BED$1,207+2 BEDS$1,479+3 BEDS$1,900+
Village Park Senior
550 W Denning Dr, Winter Park, FL 32789 -
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1 BED$1,250+2 BEDS$1,550+3 BEDS$1,800+
Park Apartments
7528 Park Promenade Dr, Winter Park, FL 32792 -
STUDIO$1,032+1 BED$1,067+2 BEDS$1,246+3 BEDS$1,261+
Carlton Arms of Winter Park
300 Jamestown Dr, Winter Park, FL 32792 -
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STUDIO$1,804+1 BED$1,899+2 BEDS$2,284+3 BEDS$3,064+
Enders Place at Baldwin Park
4220 New Broad St, Orlando, FL 32814 -
1 BED, 1 BATH$1,100
7345 Daniel Webster Dr Unit D
7345 Daniel Webster Dr, Winter Park, FL 32792 -
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1 BED, 1 BATH$2,100
2892 Lincroft Ave Unit Baldwin Park lakefront
2892 Lincroft Ave, Orlando, FL 32814 -
Rent Special
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1 BED, 1 BATH$1,100
456 Banyon Tree Cir Unit 102
456 Banyon Tree Cir, Maitland, FL 32751 -
1 BED$1,074+2 BEDS$1,274+3 BEDS$1,495+
Sumerset Apartments
1051 Lee Rd, Orlando, FL 32810 -
STUDIO$900+1 BED$1,050+2 BEDS$1,200+3 BEDS$1,600+
Kingswood Apartments
1101 Lee Rd, Orlando, FL 32810 -
2 BEDS, 2.5 BATHS$1,925
7296 Daniel Webster Dr Unit 1
7296 Daniel Webster Dr, Winter Park, FL 32792 -
Rent Special
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5 BEDS, 5 BATHS$8,650
2851 Dorell Ave
2851 Dorell Ave, Orlando, FL 32814 -
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2 BEDS, 1 BATH$1,975
851 Miles Ave Unit 8
851 Miles Ave, Winter Park, FL 32789 -
4 BEDS, 3 BATHS$5,050
2627 Verona Trail
2627 Verona Trail, Winter Park, FL 32789 -
4 BEDS, 3 BATHS$4,000
1289 Heavenly Cove
1289 Heavenly Cove, Winter Park, FL 32792 -
2 BEDS, 1.5 BATHS$1,690
222 E Yale St Unit 222
222 E Yale St, Orlando, FL 32804 -
4 BEDS, 2.5 BATHS$4,900
2952 De Brocy Way
2952 De Brocy Way, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,595
115 Scottsdale Square
115 Scottsdale Square, Winter Park, FL 32792 -
4 BEDS, 2.5 BATHS$3,995
2514 Tuscarora Trail
2514 Tuscarora Trail, Maitland, FL 32751 -
3 BEDS, 2.25 BATHS$3,450
1308 Lake Baldwin Ln
1308 Lake Baldwin Ln, Orlando, FL 32814 -
1 BED$1,306+2 BEDS$1,686+
Alvista Winter Park
3935 Sutton Place Blvd, Winter Park, FL 32792 -
2 BEDS$1,849
The Fisher Apartments | Modern 1 & 2 Bedro...
2001 Glenridge Way, Winter Park, FL 32792 -
1 BED$1,410+2 BEDS$1,680+
Whisper Lake Apartments
3250 Whisper Lake Ln, Winter Park, FL 32792 -
1 BED$1,763+2 BEDS$2,326+3 BEDS$2,636+
Village at Baldwin Park
2055 Lake Baldwin Ln, Orlando, FL 32814 -
1 BED$1,574+2 BEDS$1,689+3 BEDS$2,311+
The Q at Maitland
430 E Packwood Ave, Maitland, FL 32751
Showing 42 of 83 results, Page 2 of 2
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Clear All FiltersWinter Park at a Glance
Renting in Winter Park
Average Rental Rates and Apartment Sizes
- Apartment Type Average Sq Ft Average Rent
- Studio 538 Sq Ft $1,405 / mo
- 1 Bedroom 708 Sq Ft $1,495 / mo
- 2 Bedrooms 1,019 Sq Ft $1,769 / mo
- 3 Bedrooms 1,271 Sq Ft $2,019 / mo
- 4 Bedrooms 1,506 Sq Ft $1,526 / mo
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
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About Our Deals
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Note: Based on community-supplied data and independent market research. Subject to change without notice.