Search Vacation Homes in Winter Springs

Check prices for these dates

In two weeks

In one month

In two months

In three months

Vacation Homes in Winter Springs

Our top choices for Winter Springs vacation homes

"Hosts were wondeful. Nice quiet neighborhood. Our favorite part was definitely the pool. "

$171 nightly

Sep 29 - Sep 30

Total with taxes and fees

"Great spot for our convention at Orange County Convention Center. Easy walk and lots of restaurants close by. Townhouse was great. "

3 outdoor pools, a heated pool, pool umbrellas, sun loungers

"Excellent "

$365 nightly

Sep 19 - Sep 20

Total with taxes and fees

"Very nice place. Very clean. Would stay again"

$125 nightly

Sep 19 - Sep 20

Total with taxes and fees

"This was a beautiful home!"

"This property is beautiful. The location, the amenities were all well kept and a joy for my family. I’ve stayed at many other places but this one was by far the best. "

"Pretty decent property it was big the washer came in handy!"

"We had a 5 day stay here and it was nothing short of great! The house was very clean and exceeded all expectations. Julianna was fantastic with communication and even allowed us to come a few hours early! Highly recommend this place for any vacation!"

Smart TV, DVD player, books, video library

"Nice property and furnishings. Quiet and well kept area. Spacious rooms and deck & screened porch is a big plus. Location was perfect for us and would stay again! "

"GREAT STAY"

$346 nightly

Sep 22 - Sep 23

Total with taxes and fees

"Thank you nice place"

"overall stay was great. Kids enjoyed pool."

"We had a nice stay in this home. Would stay here again,"

"Very cute and quiet place to stay! The property manager is super sweet and great with communication! I would certainly stay here again!"

"The house is quite cozy and friendly with so many great additions, it has great charm and the owners clearly put a lot of love in effort in the place which shows.Ww celebrated my best friend birthday and the pool was quite a highlight, great many of laughs and good vibes were shared and this place really improved all of that, a great rental overall , and we’ll be sure to look out for others from these owners "

$430 nightly

Sep 24 - Sep 25

Total with taxes and fees

"This is our second time booking and our stay was just as great as the first time. Great Location and a Great Host. I look forward to booking again soon"

"Very accommodating."

"Excellent stay. Host was super accomodating and communicative. Only a few minor things like the keypad not working and the pool door being a little annoying are the negatives but these are super minor. Would stay again for sure."

"Property was clean and exactly how it was pictured, complete with snacks and all the amenities needed. Pool was great, too! Communication with host was great as well! "

View all properties