Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Cabins
Chalets
Condos
Hotels
Homes
Lodges
Studios
Townhomes
Barns
Boats
Bungalows
Castles
Cottages
Estates
Farmhouses
Villas
Yachts

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Winter Park Vacation Home Rentals(94)

94 Results
$600 - $1,450
per night
2 - 5 night minimum stay
  • 5 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 18
2 - 5 night minimum stay
(30)
$299 - $1,199
per night
2 - 6 night minimum stay
  • 6 BR,
  • 4 BA,
  • Sleeps 20
2 - 6 night minimum stay
(17)
  • 4 BR,
  • 3 BA,
  • Sleeps 20
2 - 5 night minimum stay
(23)
  • 4 BR,
  • 3 BA,
  • 2 HF BA,
  • Sleeps 20
2 - 6 night minimum stay
(4)
$275 - $640
per night
3 - 5 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 12
3 - 5 night minimum stay
(20)
$400 - $1,200
per night
2 - 4 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 13
2 - 4 night minimum stay
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 12
$382 - $1,634
per night
4 - 5 night minimum stay
  • 5 BR,
  • 6 BA,
  • Sleeps 17
4 - 5 night minimum stay
(3)
$900 - $2,800
per night
5 - 6 night minimum stay
  • 6 BR,
  • 5 BA,
  • Sleeps 20
5 - 6 night minimum stay
$375 - $600
per night
3 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 14
3 night minimum stay
(11)
$100 - $313
per night
1 - 3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
1 - 3 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
1 - 3 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 6
1 - 3 night minimum stay
  • 2 BR,
  • 3 BA,
  • Sleeps 10
1 - 3 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
1 - 3 night minimum stay
  • 1 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
1 - 3 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 6
1 - 3 night minimum stay
$900 - $1,750
per night
2 - 5 night minimum stay
  • 8 BR,
  • 8 BA,
  • 1 HF BA,
  • Sleeps 25
2 - 5 night minimum stay
(12)
  • 6 BR,
  • 3 BA,
  • Sleeps 14
2 - 4 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 4 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
(10)
  • 4 BR,
  • 2 BA,
  • Sleeps 10
3 night minimum stay
1 Review
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 4 night minimum stay
$295 - $995
per night
1 - 5 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 18
1 - 5 night minimum stay
1 Review
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
2 - 4 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
1 - 3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
1 - 3 night minimum stay
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 14
2 - 5 night minimum stay
(33)
$499 - $1,248
per night
2 - 4 night minimum stay
  • 9 BR,
  • 9 BA,
  • Sleeps 30
2 - 4 night minimum stay
1 Review
  • 5 BR,
  • 3 BA,
  • Sleeps 16
3 - 5 night minimum stay
(11)
Advertisement
 

Recent Winter Park Reviews

243 Leland Creek Circle - Labor Day Visit

4 of 5
Rating Details: I was more than satisfied with the condition of the vacation rental. I was very happy with the location. The vacation rental was spotless. The property manager was very helpful. Overall, I recommend this vacation rental. Reviewer Comments: Four couples were up for the Labor Day weekend to enjoy golfing and winter park activities. The house was great! Clean upon arrival. Everything worked great in the house except for the washing machine, was not working upon arrival. The only complaint we had about the house is there were no clothes hangers in the closets.
  • Submitted: Sep 18, 2014
  • Stayed: Aug 2014

Beautiful and Great Location, Wonderful for Groups!

5 of 5
We escaped up to Winter Park for the 4th this year and had a wonderful stay at this house. The owners were quick to get back with us when we first contacted them as well as accommodating when we requested to check in early. The house felt so comfortable that we felt like we were in our home! We have 3 small children so the upstairs was perfect for us and the beds were extremely comfortable. We also had a set of grandparents with us and the room above the garage was a perfect space for them as it was private, comfortable, and they had their own area to disappear when they wanted to. The location was fantastic for us as we were close to mountain biking, bike paths into town and to the recreation center where we swam, hiking trails, and the rodeo. The house was filled with all the comforts of home and we never had to run to the store to get anything like you usually do when renting a place! All this and I could see the fireworks perfectly from the room above the garage while my 9 month old was asleep soundly in the other part of the house. Thank you for sharing your home with us, it was beautiful, fresh, and very family friendly. We will be back in the winter to enjoy it all over again!
  • Submitted: Jul 7, 2014
  • Stayed: Jul 2014

I highly recommend this house towards anyone looking to have a fun interment getaway.

5 of 5
We had an amazing weekend getaway. The house had all new appliances, it was very clean, and extremely roomy. We had a ton of fun and the hot but was great too! I want to thank the owner Aaron for his hospitality. If we needed anything he was willing to help out. His customer service was over the top. Fast reply on email, willing to work with us and great follow up. I highly recommend this house to any one that is wanting to enjoy a wonderful getaway.
  • Submitted: May 5, 2014
  • Stayed: May 2014