
Vacation rentals in Winter Park
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Top-rated vacation rentals in Winter Park
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Winter Park vacation rentals
Other great vacation rentals in Winter Park

Dream vacation, near Disney
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!

Vacation home
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

Meriggiare! Perfect for Disney Vacation! FREE WiFi
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

New! Windsor Island Resort with pool by Disney 03
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.

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

The Moose Cabin, Luxury Stay
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!

DisneyVacationHomeLazyRiver9021
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!

Relaxing four bedroom getaway built 4 long stays
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.
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- Fitness-friendly rentals Winter Park
- Rentals with outdoor seating Winter Park
- Rentals with a patio Winter Park
- Family-friendly rentals Winter Park
- Rentals with a hot tub Winter Park
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- Universal Studios Florida
- Orange County Convention Center
- Old Town Kissimmee
- Universal's Volcano Bay
- Reunion Resort Golf Courses - Palmer & Watson
- Discovery Cove
- Disney's Animal Kingdom Theme Park
- Disney Springs
- SeaWorld Orlando
- Cocoa Beach Pier
- Daytona International Speedway
- ESPN Wide World of Sports
- Reunion West
- Amway Center
- Universal Orlando Resort
- ChampionsGate Golf Club
- Kissimmee Lakefront Park
- Universal's Islands of Adventure
- Epcot
- Disney's Hollywood Studios
- Blue Spring State Park
- Magic Kingdom Park
- Harry Potter and the Escape from Gringotts™
- ICON Park
- Things to do Winter Park
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- Family travel hub Tips and inspiration
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- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes