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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 Center120 locals recommend
Orlando Museum of Art57 locals recommend
Harry P. Leu Gardens81 locals recommend
Scenic Boat Tour56 locals recommend
Prato34 locals recommend
East End Market38 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 stars1 month 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 stars1 month 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 stars3 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 stars16 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
Townhouse in Kissimmee
4.94 out of 5 average rating, 188 reviews

Beautiful family home near all attractions.

ShannonRating, 5 stars2 weeks ago
Had a lovely stay, really enjoyed the heated pool and hot tubs. The place was very comfortable and had what we needed. The area was nice and quiet. Appreciated the restaurant recommendations and couple of water bottles which were just what we needed when our flight in had gotten delayed. Would definitely recommend!
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 stars3 weeks 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, 121 reviews

The Moose Cabin, Luxury Stay

YaritzaRating, 5 stars2 weeks ago
We came here for one night right after a Disney park and felt right at home! Such a nice tiny home! It was a quick and easy check in for us!
Superhost
Home in Four Corners
4.88 out of 5 average rating, 16 reviews

DisneyVacationHomeLazyRiver9021

SharonRating, 5 stars3 weeks 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!

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 bungalow rentals in Winter Park?

    Experience the best of Winter Park with our bungalow 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.

  • 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.

  • 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 50 house rentals with self check-in in Winter Park. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Winter Park have wifi?

    Absolutely! We offer over 10 condo rentals with wifi 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.

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