
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

Lovely Winter Park Home close to Hospitals !
Property was just as described. Very easy communication with the owner. We were very comfortable there and enjoyed our time. Very handy location. Would definitely stay there again. Thank you for hosting us.

Winter Park Guest Suite near UCF/FullSail/Rollins!
Grear stay!!! We were extremely surprised when we walked in the door. It was exactly as the photographs. The airbnb was very clean. We did encounter a few flies in the airbnb but my son was able to get rid of them. I texted the hosts and they responded right away. They were apologetic and assured me that it had never happened before and would look into it. The very next day, they sent someone to try to figure out the problem. I believe it was because the garbage bin was next to the airbnb. Once it was moved over to the other side, we did not experience anymore flies. The airbnb was closed to Full Sail University, where my son did a one week summer program. It was also very close to grocery stores and restaurants. I was able to buy groceries and at times get them delivered. I was able to cook in there two range burner which was my number one reason for staying at an airbnb instead of a hotel. The airb had the pots, pans, and dishes. I did not rent a car and the Uber service was great.

SEEN ON TV! Private Resort, Nintendo-theme Game Rm
Caitlin was incredibly responsive whenever we had a question about anything. The house was incredible, they took so much time and money making all the amenities and details first class. Everything was explained in easy to read pamphlets that described everything. The game room was a big hit, and of course the bbq and pool area, and my family absolutely loved it. Everyone was raving at how nice a place the house was. I highly recommend staying here if you can, I would definitely rent again if we’re ever back in the area.

NEW! ☀Bungalow+Patio+FirePit! Close to Everything!
Overall our stay was great! The only snag was the place hadn’t been cleaned when we arrived due to a booking/communication error. Greg immediately responded and had cleaners there within the hour. Once It was cleaned the place was immaculate and our stay was peaceful - exactly what we were looking for!

Charming Bungalow in Winter Park
Loved the stay at this place! The instructions were clear on how to get to the parking and the large kitchen island was a great gathering spot. This house had more than enough space for what our needs were. Host was very responsive. Thank you for having us!

Amazing New Pool House!
We had an excellent stay in David and Nadia's pool house. Nadia was very responsive, friendly, and proactive host and made sure our visit went smoothly. The place matched the photos and description perfectly -- it's a real gem! The pool house itself is modern, attractive, and comfortable with everything you need for a comfortable stay. The shared backyard is such a lovely place to spend time. We especially enjoyed the pool and putting green. Overall we had a great trip and would happily stay there again.

Walk To Bike Trail, Baldwin Lake
We had a very comfortable stay. Michelle’s has a charming place close to a lovely park where we took several walks. Also the restaurants in the area are very good.

Balfour Villa
Wonderful stay at the little gem of an apartment! Clean, great location and the beds were awesome! (Great nights sleep!) Loved the easy walk to Starbucks and CVS too! The pool looked awesome but it rained during our trip so we were not able to take advantage of the outdoor space. Thanks for a lovely weekend!
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.
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