Vacation rentals in Winter Park

Book unique vacation rentals, houses, and more on Airbnb

0 of 0 items showing
1 of 3 pages

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 1,990 vacation rentals in Baldwin Park, over 1,050 vacation rentals in Lake Formosa, and over 1,510 vacation rentals in North Orange.

  • 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.

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

    Experience the best of Winter Park with our apartment rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget 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.

  • Do guesthouse rentals in Winter Park have wifi?

    Absolutely! We offer over 30 guesthouse rentals with wifi 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 apartment rentals in Winter Park have a gym?

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

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

    Yes! Dive into the perfect getaway at one of over 30 apartment rentals with pools in Winter Park, available on Airbnb. Make a splash and soak up the sun in style!

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

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

  • What are the most popular amenities for Condo Rentals in Winter Park?

    Enhance your stay in our Condo Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

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