Tap here to try the Rental Assistant! ×
Save This Search

Apartments for Rent in Winter Park, FL under $2100
204 Rentals Available

  • Top Rated for Location
    Mail Center at Maitland City Centre, Maitland Roof top pool at Maitland City Centre, Maitland, FL
    Today

    190 Independence Lane, Maitland, FL 32751
    14 Units available
    1 BED $1,936+
    2 BEDS $2,020+
    Property reviews
    5/5 Anonymous on Mar 20, 2024

    4 years here now. It's generally quiet but with activities in the area every now and then. Good places to eat around. Grocery and drugstore nearby. Lakes to walk around in the area. Excellent gym, mingle room, mail room. Property is maintained but there are some things that are not doen quickly.

    5/5 Dawn L. on Mar 9, 2023

    We found this lovely home 2 years ago. It has everything going for it. We are within walking distance of anything we want to do. We walk daily around the neighborhood.. Lake Lily, Lake Catherine, & Lake Sybelia, Also, There are many fine eateries to choose from. Our favorite is Francesco’s. Literally a half block away from our home. The beautiful City Hall and grounds are just across the street as is the Post Office. During the Christmas Holidays the huge trees in this park area are beautifully lit. We just walk out onto our patio to enjoy them. We also see the fireworks in splendid fashion when they are lit. It’s like we have our own private showing. There is a church and a library that we also use. Not to mention Publix is a short walk away. We literally do not need a car. On the occasion we do, we use Uber. The staff here are second to none. They truly treat us like we matter. They go above and beyond ( especially Courtney). Tho only downside is the fire hall is nearby. If they get a call at night they seem to wait to turn on the sirens until they get. To 17/92. P. S. There is a Starbucks in the building!! Need I say more!! Check them out. It’s legit.

  • Top Rated for Location
    a kitchen with stainless steel appliances and a granite counter top a blue and white bedroom with a bed and a window at Azul Baldwin Park, Orlando, Florida
    Today

    4460 Lower Park Road, Orlando, FL 32814
    3 Units available
    1 BED $1,787+
    Property reviews
    5/5 Anonymous on Dec 1, 2023

    safe and comfortableplace to leave with a bunch o green areas

    5/5 Cesar E. on Oct 1, 2023

    I am pleased to live here, with a great community office service

  • Top Rated for Location
    3 BR Apartments in Maitland, FL - Parker at Maitland Station - Modern Kitchen with Wood Vinyl Plank Flooring, Large Cooking Island with Stool Seating, Pendant Light, Granite Countertops, White Shaker-Style Cabinetry, Stainless Steel Appliances, and White Subway Tile Backsplash 1 BR Apartments in Maitland, FL - Parker at Maitland - Furnished Bedroom with Carpeted Floor, Large Bed, Ceiling Fan, Framed Art, Wooden Nightstand with Lamp, and Attached Bathroom
    Today

    955 N Orlando Ave, Maitland, FL 32751
    Available
    1 BED $1,766+
    2 BEDS Ask for Pricing
    Property reviews
    5/5 Anonymous on Dec 1, 2023

    Happy with our living situation here and

    5/5 Anonymous on Oct 3, 2023

    I have been living at the Parker at Maitland Station for seven months and what liked most is the friendliness of the staff, the cleanliness of the common areas, the timely maintenance service and my apartment is beautiful. Of course I recommend living in the Parker for everything mentioned above; besides this having the train station just a stone's throw away is a plus.

  • Today

    2650 Dade Ave, Orlando, FL 32804
    Available
    Studio $1,698
    1 BED $1,784
    2 BEDS $2,096
    Overview

    Uncover an energetic atmosphere, perfect for balancing your lifestyle and your work style. At The Ivy Residences at Health Village, you'll be able to find a studio, one-, two- and three-bedroom apartments featuring modern architecture, room to breathe, and luxury amenities to unwind. Our apartments' contemporary style and height have been a catalyst for significant changes within the Health Village. The Ivy has the ideal location near everything: the Hospital, SunRail, College Park, Winter Park, Loch Haven Park, Mills Park, Ivanhoe Row, and Mills/50 District.

    Amenities
    • Pets Allowed
  • Top Rated for Location
    a kitchen with black appliances and wooden cabinets our apartments offer a spacious bedroom with a king sized bed
    1 day ago

    541 Oak Reserve Lane, Winter Park, FL 32792
    1 Unit available
    1 BED $1,450
    2 BEDS $1,600
    3 BEDS $2,000
    Property reviews
    5/5 Anonymous on Apr 3, 2022

    It’s a nice complex.

    4.5/5 Anonymous on Oct 3, 2021

    Been so happy since we moved here

  • Today

    3250 Whisper Lake Lane, Winter Park, FL 32792
    17 Units available
    1 BED $1,510
    2 BEDS $1,710+
    Overview

    Experience the beauty and adventure of Whisper Lake Apartments located in historic Winter Park, Florida and surrounded by interconnected lakes. Catch sight of the countless upgraded features, contemporary finishes, and unique layouts that our apartments have to offer. Enjoy lakeside living at its finest, surrounded by awe-inspiring views in a tranquil environment with all the best in location and comfort. Turn the key to discover convenience draping over every square foot of your modern one or two-bedroom home. From the sun-drenched living areas and fully equipped kitchens to spa-like bathrooms and expansive patios/balconies, everything was designed to cater to the carefree life you’ve always wished to be yours. What’s more, air conditioner systems, washer/dryer connections, and ceiling fans are also part of the deal. Read More + Beyond the doors of our Winter Park apartments, you will be close to Full Sail Academy, Rollins College, and UCF, and also encounter a myriad of recreational spaces and scenic views, serving as nature's serene background. Swim your worries away in the Olympic-inspired pool, perfect your tan at the sundeck, or toast some buns on the grill at the BBQ island. Catch up on work emails or school projects at the technology/business center while sipping a cup of fresh brew from the complimentary coffee bar. Since Whisper Lake makes it so easy to retreat from the business of everyday life, take a little workout break, and head to the 24-hour fitness center or the CrossFit Park to reach your goals. Enjoy sunny days on the sports courts, nurturing your competitive senses, regardless of whether it’s racquetball, tennis, basketball, or sand volleyball. Other on-site amenities include maintenance and management services, laundry facilities, boat/RV parking options, and a car wash area. Make the right move – reach out today to schedule a tour!

    Amenities
    • Air Conditioner
    • Public Transportation
    • Pets Allowed
  • Resident Rated
    Living Room With Kitchen View at Newport Colony Apartment Homes, Florida, 32707 Swimming Pool With Relaxing Sundecks at Newport Colony Apartment Homes, Casselberry, 32707
    Today

    1166 Pointe Newport Terrace Drive, Casselberry, FL 32707
    11 Units available
    1 BED $1,225+
    2 BEDS $1,610+
    3 BEDS $1,960
    Property reviews
    5/5 Kayla R. on Apr 1, 2024

    I just hit the 1 year mark living at Newport Colony Apartments. Orlando is a tough market for affordability, but people are always shocked at the price I pay for rent when they see where I live. The whole complex is littered with huge old trees, mostly oak, and the whole place feels welcoming, cozy, inviting, clean and safe. It’s walking distance to a huge park, skate rink, gas stations, bars, and grocery stores. Eli at the front office is always super friendly and helpful, and has gone above and beyond from the first tour we took to my renewal now and everything inbetween. The rest of the staff, including the rare occasion I’ve had maintenance come to fix something, have also always been kind and professional. It’s a 10 minute drive for work, and the screened in porch with washer dryer in unit feel like luxeries on top of everything else. Over all I highly recommend it.

    5/5 Dale M. on Feb 2, 2024

    Over 21 years what more can I say to date the Manager Adam and his staff are excellent as well as the maintenance supervisor and his crew. Any problems I ever had they were taken care of in a reasonable length of time. An fortunately not many to the point my apartment has never been upgraded with relativity nothing only carpet cleaned yearly. I am 85 and hopefully & now on only social security and hope all the money I always paid on time will be considered in that I am no longer employed and hope to spend the rest of my days here...I could have paid off a condo if I hadn't remain I am also retired law enforcement and assist in security when they request me to as well as on my own and to neighbors come to me for advice or help. I have always recommended Newport Colony and a few are here due to my doing so...thank you

  • 1 day ago

    1512 Indiana Avenue, Winter Park, FL 32789
    1 BED $1,500
  • Today

    550 N. Denning Drive, Winter Park, FL 32789
    Income Restricted
    1 BED $999+
    2 BEDS $1,199+
    3 BEDS $2,099
  • Today

    1305 Morgan Stanley Ave, Winter Park, FL 32789
    Studio $1,892+
    1 BED $1,943+
  • 1 day ago

    3045 Aloma Avenue, Winter Park, FL 32792
    1 BED $1,745+
  • Today

    190 Independence Lane, Maitland, FL 32751
    1 BED $1,936+
    2 BEDS $2,020+
  • Too many options, too little time? Take a quiz and let us do the search for you
  • Today

    741 Clay Street, Winter Park, FL 32789
    Studio $1,640+
    1 BED $1,810+
  • Today

    430 East Packwood Ave, Maitland, FL 32751
    1 BED $1,926+
    2 BEDS $2,082+
  • Today

    3250 Bishop Park Dr, Winter Park, FL 32792
    1 BED $1,330+
    2 BEDS $1,735+
  • Today

    1874 Harmon Avenue, Winter Park, FL 32789
    Studio $1,516+
    1 BED $1,809+
  • Today

    4460 Lower Park Road, Orlando, FL 32814
    1 BED $1,787+
  • Today

    4688 New Broad Street, Orlando, FL 32814
    1 BED $1,755+
  • Interactive banner bedroom
    How many bedrooms are you
    looking for?
  • Today

    525 Sybelia Pkwy, Maitland, FL 32751
    Income Restricted
    1 BED $1,091
    2 BEDS $1,286
  • Today

    2680 North Orange, Orlando, FL 32804
    Studio $1,667+
    1 BED $1,775+
    2 BEDS Ask for Pricing
  • Today

    4220 New Broad Street, Orlando, FL 32814
    1 BED $1,663+
    2 BEDS $1,786+
  • Today

    955 N Orlando Ave, Maitland, FL 32751
    1 BED $1,766+
    2 BEDS Ask for Pricing
  • Today

    5800 Auvers Blvd, Orlando, FL 32807
    1 BED $1,400+
    2 BEDS $1,554+
    3 BEDS $1,987+
  • Today

    4000 Maguire Blvd, Orlando, FL 32803
    1 BED $1,760+
    2 BEDS $2,055+
  • Today

    9264 Moss Preserve Pkwy., Orlando, FL 32832
    Studio $1,695+
    1 BED $1,810+
3-22-city

Popular searches Average rent Renters guide Demographics

Getting around in Winter Park, FL

25 /100
Car-Dependent
32 /100
Some Transit
31 /100
Somewhat Bikeable
Walk Score®: 25, Transit Score®: 32, Bike Score®: 31

Frequently asked questions

When were prices and availability in Winter Park, FL last updated?

Prices and availability in Winter Park, FL were last updated on 20 Jun 2024.

What are the best apartments in Winter Park, FL?

The best apartments in Winter Park, FL are: Paseo at Winter Park Village, Indiana Ave. Triplex, 1055 S Kentucky Ave, 1833 Pineview Circle Winter Park, FL 32792 and San Jose Apartments.

What type of rental buildings are in Winter Park, FL?

In Winter Park, 33% of the residents are renting compared to 67% owning a home, according to data from the U.S. Census Bureau. Large-scale apartment buildings with more than 50 units represent 25% of Winter Park’s rentals, 50% are small-scale complexes with under 50 units, and 25% are single-family rentals.