Luxury Apartments for Rent in Winter Park, FL
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1 bd $1,930+3 bd $3,498+Base rent4.0 (6)940 W. Canton Avenue, Winter Park, FL 32789Apply online • Pet friendly • Parking
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Only 1 unit left5 bd $5,300Base rent433 Carolina Ave., Winter Park, FL 327893Apply online • Pet friendly -
2 bd $2,300Base rent981 Aragon Ave., Winter Park, FL 32789Apply online • Pet friendly
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Studio $1,344+1 bd $1,449+2 bd $1,555+Base rent4.0 (21)1701 Lee Road, Winter Park, FL 32789Apply online • Pet friendly • Fitness center
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2 bd $1,995Base rentUnits 1,2,3,4, Winter Park, FL 32792Pet friendly
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3 bd $2,795Base rent951 Harmon Ave., Winter Park, FL 32789Pet friendly -
3 bd $9,500Base rent147 S Interlachen Ave, Winter Park, FL 32789Pet friendly • Pool • Dishwasher
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1 bd $2,7954 bd $5,500Base rent690 Osceola Ave, Winter Park, FL 32789Pet friendly • Pool • Dishwasher
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More Rentals Near Winter Park, FL
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1 bd $1,923+2 bd $2,491+3 bd $3,127+Base rent4.5 (15)4460 Lower Park Road, Orlando, FL 32814Apply online • Pet friendly • Parking
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1 bd $1,977+2 bd $2,468+Base rent4.5 (9)190 Independence Lane, Maitland, FL 32751Apply online • Pet friendly • Parking
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1 bd $1,780+2 bd $2,038+3 bd $3,023+Base rent4.5 (19)955 N Orlando Ave, Maitland, FL 32751Apply online • Pet friendly • Pool
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Studio $1,846+1 bd $2,288+2 bd $2,416+Base rent4.0 (2)1305 Morgan Stanley Ave, Winter Park, FL 32789Apply online • Pet friendly • Parking
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Studio $1,585+1 bd $1,695+2 bd $2,365+Base rent4.5 (31)741 Clay Street, Winter Park, FL 32789Apply online • Pet friendly • Parking
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1 bd $1,372+2 bd $1,658+Base rent4.5 (7)3250 Bishop Park Dr, Winter Park, FL 32792Apply online • Pet friendly • Fitness center
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Studio $2,268+1 bd $2,403+2 bd $3,022+Base rent5.0 (2)2050 Jake Street, Orlando, FL 32814Apply online • Pet friendly • Fitness center
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Studio $1,552+1 bd $1,872+2 bd $2,288+Base rent4.0 (13)1874 Harmon Avenue, Winter Park, FL 32789Apply online • Pet friendly
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1 bd $1,805+2 bd $2,355+3 bd $3,445+Base rent4.0 (49)4688 New Broad Street, Orlando, FL 32814Apply online • Pet friendly • Parking
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Studio $1,730+1 bd $1,965+2 bd $2,421+Total monthly cost4.0 (2)2680 North Orange, Orlando, FL 32804Apply online • Pet friendly • Fitness center
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Studio $2,019+1 bd $1,720+2 bd $2,150+Base rent4.0 (13)2650 Dade Avenue, Orlando, FL 32804Apply online • Pet friendly • Parking
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1 bd $1,805+2 bd $2,136+3 bd $2,595+Base rent4.5 (24)9264 Moss Preserve Pkwy., Orlando, FL 32832Apply online • Pet friendly • Air conditioner
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1 bd $1,375+2 bd $1,599+3 bd $2,075+Base rent4.0 (92)1166 Pointe Newport Terrace Drive, Casselberry, FL 32707Apply online • Pet friendly • Fitness center
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1 bd $1,291+2 bd $1,699+Base rent4.5 (23)3935 Sutton Place Blvd, Winter Park, FL 32792Apply online • Pet friendly • Fitness center
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3 bd $3,550Base rent1704 North Shore Terrace, Orlando, FL 32804Apply online • Pet friendly
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Studio $1,905+1 bd $1,905+2 bd $2,550+Base rent4.5 (2)601 Trelago Way, Maitland, FL 32751Apply online • Pet friendly • Parking
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Ask for pricing4.5 (7)4220 New Broad Street, Orlando, FL 32814Pet friendly • Washer/Dryer
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Frequently asked questions
What is the price of a luxury apartment in Winter Park, FL?
The price range for a luxury apartment in Winter Park, FL is between $1,139 and $10,500.
How many luxury rentals are available in Winter Park, FL on RentCafe?
There are 21 luxury rentals available on RentCafe. Prices and availability in Winter Park, FL were last updated on 30 Jun 2026.
What is the average size of a luxury apartment in Winter Park, FL?
The average Winter Park, FL luxury apartment size is 1,360 sq. ft.
What are the advantages of renting a luxury apartment in Winter Park, FL?
Renting a luxury apartment in Winter Park, FL comes with many amenities, more space and central locations.
What are the downsides of renting a luxury apartment in Winter Park, FL?
Luxury apartments tend to be more expensive and have higher utility bills.
Renting a luxury apartment in Winter Park, FL
Here at RentCafe we appreciate the finer things in life and know that small things make big differences. So, when it comes to luxury apartments we are doing our utmost to bring you a selection of the best apartments in Winter Park, FL and we try to provide solutions for every pocket. Just starting your career and you’re on the lookout for luxury studio apartments to move in alone, close to everything loud and bustling the city has to offer? Or you’re searching for luxury townhomes in quieter areas with playgrounds, where you want to raise a family but still make commuting feel like a breeze? There are 25 properties in Winter Park, FL with an average size of 1,243 Sqft, so we’ve got your back whether you are on the search for small or large apartments.
Choosing between high rise apartments
We know that in today’s market finding the perfectly furnished, modern home among all the high rise apartments available might seem overwhelming. There are just so many interiors styled differently and so many buildings to choose from. And it’s not just about the interior. You’re shopping for amenities too: a fitness center or a spa, a yoga studio or a pool could all be deal breakers. After weeks of intense searching one apartment complex looks just like the other. That’s why we are providing detailed information including photos, floorplan and a straight to the point list of the amenities offered, so no guesswork is required. We also know that finding cheap luxury apartments sounds impossible, but the average price for listings in Winter Park, FL is $3,601 and the lowest monthly rents start at $1,291, so you may be able to find some deals on luxury after all.