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Vacation rentals in Winter Park

Book unique vacation rentals, houses, and more on Airbnb

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Popular amenities for Winter Park vacation rentals

Stay near Winter Park's top sights

Orlando Science Center289 locals recommend
Orlando Museum of Art215 locals recommend
Harry P. Leu Gardens197 locals recommend
Scenic Boat Tour160 locals recommend
Prato124 locals recommend
East End Market111 locals recommend

Other great vacation rentals in Winter Park

Superhost
Home in Kissimmee
5 out of 5 average rating, 3 reviews

Dream vacation, near Disney

ChrisRating, 5 stars3 weeks ago
What an incredible stay we had at Rosario's place! We even extended 2 extra nights. Rosario was responsive, helpful, and so kind - she even left a birthday balloon and some treats for my mom's birthday! The house was impeccable and they were great about everything, from changing dates to heating the pool, and keeping it clean, and the pool was a perfect balmy respite. The next time we're in town (and we will be, this is our old neighborhood!), we will definitely try to book here again. Can't wait to come back!
Superhost
Home in Davenport
4.76 out of 5 average rating, 68 reviews

Vacation home

JaniquaRating, 5 stars3 weeks ago
Me and my Family enjoyed our days there! Miguel was very friendly and nice and welcome us to a little welcome gift I mean who dosen’t love chocolate
Guest favorite
Townhouse in Kissimmee
4.94 out of 5 average rating, 116 reviews

Meriggiare! Perfect for Disney Vacation! FREE WiFi

ShanaRating, 5 stars2 weeks ago
Wonderful stay for my birthday. the girls surprised me with this air bnb and it was wonderful. from the privacy to the cleanliness I loved it and hope to book with you again in the near VERY NEAR FUTURE
Guest favorite
Home in Davenport
5 out of 5 average rating, 5 reviews

New! Windsor Island Resort with pool by Disney 03

IrynaRating, 5 stars15 months ago
Nice house with good layout of rooms. It is very convenient to come with children as there is a lot of entertainment on the territory of the complex. I also liked the themed design of the rooms. Overall, this is a good house for a large and friendly company.
Guest favorite
Condo in Kissimmee
4.9 out of 5 average rating, 120 reviews

D-Gated Resort-5 miles to Disney-2 FREE Water Park

LauraRating, 5 stars1 week ago
My husband and I stayed In james apartment with our two children. This was a return trip for us having stayed previously in 2019. We enjoyed our stay just as much this time around. My son and husband are big Star Wars fans so loved the theming of the apartment. Everything was really well maintained and amenities were great. We enjoyed using the clubhouse as well. The location is perfect for visiting all the Disney parks and universal, everything was around a twenty minute drive. James was responsive and helpful to all queries, we hope to return one day soon!
Guest favorite
Cabin in Orlando
4.9 out of 5 average rating, 119 reviews

The Moose Cabin, Luxury Stay

DavidRating, 5 stars2 weeks ago
First time staying in the area, this spot was perfect for us to come and go from. Clean and well laid out... Great spot to rest between park!! Thank you!
Superhost
Home in Four Corners
4.88 out of 5 average rating, 16 reviews

DisneyVacationHomeLazyRiver9021

SharonRating, 5 stars1 week ago
This beautiful home worked well for our family…4 couples and 3 small children. Pool and hot tub were great and clean! The house was large and we had a ton of fun! The host was super responsive every time we sent a message. We would definitely come back to this house and would highly recommend it!
Guest favorite
Home in Orlando
4.91 out of 5 average rating, 35 reviews

Relaxing four bedroom getaway built 4 long stays

Mirtha MRating, 5 stars1 month ago
Edwin's house is beautiful, clean, and well-decorated. The rooms are spacious, and the bathrooms (for me, the most important thing) are very nice, clean, and recently remodeled. Edwin was very helpful, always available to help if we needed anything. Overall, I have no complaints. The house was close to the conference venue I attended, and I really liked his house. In fact, I highly recommend it and would return any time..thank you Edwin!

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 1,050 vacation rentals in Lake Formosa, over 1,990 vacation rentals in Baldwin Park, 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.

  • 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 townhouse rentals in Winter Park?

    Experience the best of Winter Park with our townhouse 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.

  • 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 apartment rentals in Winter Park have self check-in?

    Absolutely! We offer over 20 apartment rentals with self check-in in Winter Park. Enjoy a tailored experience with all the comforts you desire.

  • 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.

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

    Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with a bbq area, over 50 homes with self check-in, over 10 homes with a gym, 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