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Short Term Rentals in Winter Park, FL

Short Term Rentals in Winter Park, FL. 382 Rentals Available
382 Rentals Available
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  • A living room with a white sofa and a wooden coffee table.
    Rent specials New units available
    Ask for pricing
    Verified Listing

    4.0 (15)
    1701 Lee Road, Winter Park, FL 32789
    Apply online • Pet friendly

  • More Rentals Near Winter Park, FL

  • A living room with a yellow sofa and a fireplace.
    Rent specials New units available
    Studio $1,199+
    2 bd $1,599+
    Base rent
    Verified Listing

    5.0 (21)
    7975 Canada Ave, Orlando, FL 32819
    Apply online • Pet friendly • Fitness center
  • A living room with blue chairs and a fireplace.
    Rent specials New units available
    1 bd $1,325+
    2 bd $1,595
    Total monthly cost
    Verified Listing

    3250 Whisper Lake Ln, Winter Park, FL 32792
    Apply online • Pet friendly • Air conditioner
  • a living room with furniture and a ceiling fan
    Rent specials New units available
    1 bd $1,425+
    2 bd $1,369+
    3 bd $1,599+
    Total monthly cost
    Verified Listing

    9201 Nelson Park Cir, Orlando, FL 32817
    Apply online • Pet friendly • Fitness center
  • a living room with a couch and a glass table
    Rent specials 20 units available
    1 bd $1,250+
    2 bd $1,525
    Total monthly cost
    Verified Listing

    1800 West 1St Street, Sanford, FL 32771
    Apply online • Pet friendly • In unit laundry
  • a living room with a couch and a ceiling fan
    Rent specials 37 units available
    1 bd $1,575+
    2 bd $1,899+
    3 bd $2,179+
    Total monthly cost
    Verified Listing

    14200 Colonial Grand Blvd, Orlando, FL 32837
    Apply online • Pet friendly • Dishwasher
  • the living room and dining room of a home with a table and chairs
    Rent specials
    1 bd $1,295+
    2 bd $1,495+
    3 bd $2,025
    Base rent
    Verified Listing

    4.5 (5)
    541 Oak Reserve Lane, Winter Park, FL 32792
    Pet friendly • Parking • Fitness center
  • A living room with a grey couch and a television.
    6 units available
    Studio $1,954+
    1 bd $2,430+
    2 bd $2,943+
    Base rent
    Verified Listing

    4.5 (2)
    295 NE Ivanhoe Blvd., Orlando, FL 32804
    Apply online • Pet friendly
  • a living room with couches and chairs and a pool
    Rent specials New units available
    1 bd $1,361+
    2 bd $1,459+
    Base rent
    Verified Listing

    4.0 (36)
    3207 Rosebud Lane, Winter Park, FL 32792
    Apply online • Pet friendly
  • A living room with blue chairs and a television.
    Rent specials New units available
    Studio $1,158+
    1 bd $1,200+
    2 bd $1,299+
    Base rent
    Verified Listing

    4.0 (1)
    828 Orienta Ave, Altamonte Springs, FL 32701
    Apply online • Pet friendly
  • A white couch with a black and white patterned pillow sits in a bright living room.
    10 units available
    1 bd $1,210+
    2 bd $1,580
    3 bd $1,985
    Base rent
    Verified Listing

    4.5 (22)
    400 Sandpiper Lane, Casselberry, FL 32707
    Apply online • Pet friendly
  • A modern living room with a dining table and chairs.
    Rent specials New units available
    1 bd $1,010+
    2 bd $1,290+
    Base rent
    Verified Listing

    4.0 (35)
    5175 Cinderlane Parkway, Orlando, FL 32808
    Apply online • Pet friendly
  • a living room with a couch and a coffee table
    Rent specials New units available
    1 bd $1,800+
    2 bd $1,787+
    3 bd $2,428+
    Base rent
    Verified Listing

    4.5 (105)
    2590 Greenhill Way, Oviedo, FL 32765
    Apply online • Pet friendly
  • an open kitchen and living room with a table
    Rent specials New units available
    Studio $1,333+
    1 bd $1,316+
    2 bd $1,599+
    Base rent
    Verified Listing

    4.0 (4)
    5789 Bent Pine Drive, #102, Orlando, FL 32822
    Apply online • Pet friendly
  • a living room with a couch and a table
    Rent specials
    2 bd $1,559
    Base rent
    Verified Listing

    318 Monks Ct, Lake Mary, FL 32746
    Apply online • Pet friendly
  • a living room with a couch and a ceiling fan
    Rent specials
    1 bd $1,773+
    2 bd $2,246+
    Base rent
    Verified Listing

    4.0 (98)
    6350 Vineland Rd., Orlando, FL 32819
    Apply online • Pet friendly
  • a living room with a couch and a table
    Rent specials New units available
    1 bd $1,514+
    2 bd $1,728+
    3 bd $1,964+
    Base rent
    Verified Listing

    4.5 (244)
    2415 Treasure Landing Pkwy, Ocoee, FL 34761
    Apply online • Pet friendly
  • A large house with a pool in the middle of a water body surrounded by greenery.
    Only 1 unit left
    1 bd $1,545+
    Base rent
    Verified Listing

    5.0 (700)
    100 Arbor Lakes Circle, Sanford, FL 32771
    Apply online • Pet friendly
  • a living room with two couches and a fireplace
    Rent specials 8 units available
    1 bd $1,806+
    2 bd $2,169+
    3 bd $2,612+
    Base rent
    Verified Listing

    4.5 (35)
    7650 Lower Gateway Loop, Orlando, FL 32827
    Apply online • Pet friendly
  • a living room with a couch and chairs and a table
    New units available 27 units available
    Studio $1,595+
    1 bd $1,617+
    2 bd $1,903+
    Base rent
    Verified Listing

    4.5 (198)
    6801 Integra Cove Blvd, Orlando, FL 32821
    Apply online • Pet friendly
  • an open living room with a white couch and a tv
    Rent specials New units available
    Studio $1,736+
    1 bd $1,963+
    2 bd $2,414+
    Base rent
    Verified Listing

    4.5 (25)
    7010 Lake Nona Blvd, Orlando, FL 32827
    Apply online • Pet friendly
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Frequently asked questions

What is the price of a short-term rental in Winter Park, FL?

The price range for a short-term rental in Winter Park, FL is between $1,330 and $2,231.

How many short-term rentals are available in Winter Park, FL on RentCafe?

There are 18 short-term rentals available on RentCafe. Prices and availability in Winter Park, FL were last updated on 6 Jun 2026.

What is the average size of a short-term rental in Winter Park, FL?

The average Winter Park, FL short-term rental size is 859 sq. ft..

What are the advantages of renting a short-term rental in Winter Park, FL?

Short-term rentals offer flexibility and are ideal for temporary stays or transitional periods.

What are the downsides of renting a short-term rental in Winter Park, FL?

Short-term rentals typically cost more per month and may have limited availability.