Vacation rentals in Winter Park

Find and book unique accommodations on Airbnb

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Popular amenities for Winter Park vacation rentals

Stay near Winter Park's top sights

Orlando Science Center124 locals recommend
Orlando Museum of Art58 locals recommend
Harry P. Leu Gardens83 locals recommend

Quick stats about vacation rentals in Winter Park

  • Total rentals

    380 properties

  • Total number of reviews

    19K reviews

  • Family-friendly rentals

    180 properties are a good fit for families

  • Pet-friendly rentals

    120 properties allow pets

  • Rentals with a pool

    110 properties have a pool

  • Rentals with dedicated workspaces

    210 properties have a dedicated workspace

Frequently Asked Questions

  • Where should I stay in Winter Park?

    Make yourself at home in Winter Park by choosing from our most frequently booked neighborhoods. We have over 1,540 vacation rentals in North Orange, over 2,010 vacation rentals in Baldwin Park, and over 1,080 vacation rentals in Lake Formosa.

  • Are there vacation rentals with a dedicated workspace in Winter Park?

    Yes! Work meets play with ease at over 210 vacation rentals in Winter Park featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Winter Park?

    Four-legged friends are welcome in Winter Park. Choose from more than 120 vacation rentals for guests traveling with pets.

  • Are there Winter Park vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 110 vacation homes with pools in Winter Park, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in condo rentals in Winter Park?

    Experience the best of Winter Park with our condo rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there family-friendly vacation rentals in Winter Park?

    Winter Park has more than 180 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Winter Park have a gym?

    Absolutely! We offer over 10 house rentals with a gym in Winter Park. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Winter Park have a bbq area?

    Absolutely! We offer over 30 house rentals with a bbq area in Winter Park. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Winter Park have self check-in?

    Absolutely! We offer over 40 house rentals with self check-in in Winter Park. Enjoy a tailored experience with all the comforts you desire.

  • Do private suite rentals in Winter Park have wifi?

    Absolutely! We offer over 20 private suite rentals with wifi in Winter Park. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Orange County
  5. Winter Park