Vacation Rentals in Winter Park

Start comparing over 640 rentals in Winter Park and book at the best price!

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Popular Accommodations in Winter Park

from
$139
per night

Apartment for 12 people, with balcony
12 pers., 3 bedrooms, 1,668ft², 1.5mi to skiing
4.2
(15 reviews)

from
$481
per night

Vacation rental for 10 people, with jacuzzi and balcony
10 pers., 4 bedrooms, 1,991ft², 600yd to skiing
3.2
(2 reviews)

from
$155
per night

Apartment for 9 people, with balcony
9 pers., 2 bedrooms, 1,152ft², 2.7mi to skiing
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Vacation rentals with free cancellation
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from
$337
per night

Apartment for 10 people, with jacuzzi and balcony
10 pers., 4 bedrooms, 2.8mi to skiingFREE cancellation
5.0

from
$377
per night

Vacation rental for 9 people, with jacuzzi
9 pers., 4 bedrooms, 2.7mi to skiingFREE cancellation
4.7
(4 reviews)

from
$487
per night

Vacation rental for 10 people, with jacuzzi
10 pers., 4 bedrooms, 1.5mi to skiingFREE cancellation
5.0
(21 reviews)
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Vacation Rentals in Winter Park
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from
$210
per night

Apartment for 8 people, with pool and jacuzzi
8 pers., 3 bedrooms, 2.8mi to skiing
5.0

from
$206
per night

Apartment for 6 people, with garden and jacuzzi
6 pers., 3 bedrooms, 1,292ft², 2mi to skiing

from
$572
per night

Vacation rental for 14 people, with jacuzzi
14 pers., 5 bedrooms, 2,293ft², 600yd to skiing
3.7
(8 reviews)

from
$181
per night

Apartment for 6 people, with jacuzzi and balcony as well as pool
6 pers., 2 bedrooms, 797ft², 2.1mi to skiing
5.0

from
$261
per night

Vacation rental for 10 people, with balcony and jacuzzi
10 pers., 3 bedrooms, 2,185ft², 1.7mi to skiing
5.0
(20 reviews)

from
$248
per night

Apartment for 9 people, with terrace
9 pers., 3 bedrooms, 1,281ft², 2.2mi to skiing
4.9
(20 reviews)
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Pet-friendly Vacation Rentals
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from
$210
per night

Apartment for 7 people, with terrace and jacuzzi as well as pool, with pets
7 pers., 2 bedrooms, 1,184ft², 2.2mi to skiing
4.6
(3 reviews)

from
$175
per night

Apartment for 8 people, with pool and terrace as well as jacuzzi, with pets
8 pers., 2 bedrooms, 2.2mi to skiing
4.7
(13 reviews)

from
$579
per night

Vacation rental for 13 people, with jacuzzi, with pets
13 pers., 5 bedrooms, 2.1mi to skiing
5.0
(2 reviews)
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Vacation Rentals with Pool
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from
$1,007
per night

Apartment for 8 people, with terrace and pool
8 pers., 2 bedrooms, 100yd to skiing
4.2
(20 reviews)

from
$193
per night

Apartment for 8 people, with pool and balcony as well as jacuzzi
8 pers., 2 bedrooms, 1,292ft², 2.2mi to skiing
5.0
(8 reviews)

from
$1,185
per night

Vacation rental for 10 people, with balcony and jacuzzi as well as pool
10 pers., 4 bedrooms, 600yd to skiingFREE cancellation
4.7
(20 reviews)
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Vacation Rentals with Internet
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from
$263
per night

Vacation rental for 9 people, with jacuzzi and balcony
9 pers., 3 bedrooms, 1,991ft², 600yd to skiing
4.4
(8 reviews)

from
$314
per night

Apartment for 8 people, with terrace and jacuzzi
8 pers., 2 bedrooms, 1,324ft², 2.7mi to skiing
4.3
(5 reviews)

from
$500
per night

Vacation rental for 10 people, with jacuzzi and garden
10 pers., 3 bedrooms, 1,916ft², 950yd to skiing
3.3
(10 reviews)
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Find Vacation Rentals in Winter Park

Map

Most popular in Winter Park

Internet 47
Balcony/Terrace 42
TV 46
Air conditioning 22
Parking 45
Washing machine 35
View 19
Jacuzzi 36
Heating 42

Prices and availability

Prices

May
June
July
August
September
$495
Apr 03 - Apr 10
$413 per night
Apr 10 - Apr 17
$374 per night
Apr 17 - Apr 24
$376 per night
Apr 24 - May 01
$412 per night
May 01 - May 08
$408 per night
May 08 - May 15
$301 per night
May 15 - May 22
$315 per night
May 22 - May 29
$376 per night
May 29 - Jun 05
$413 per night
Jun 05 - Jun 12
$409 per night
Jun 12 - Jun 19
$401 per night
Jun 19 - Jun 26
$425 per night
Jun 26 - Jul 03
$440 per night
Jul 03 - Jul 10
$419 per night
Jul 10 - Jul 17
$411 per night
Jul 17 - Jul 24
$426 per night
Jul 24 - Jul 31
$446 per night
Jul 31 - Aug 07
$445 per night
Aug 07 - Aug 14
$430 per night
Aug 14 - Aug 21
$373 per night
Aug 21 - Aug 28
$319 per night
Aug 28 - Sep 04
$466 per night
Sep 04 - Sep 11
$495 per night
Sep 11 - Sep 18
$396 per night
Average price per week

Availabilities

May
June
July
August
September
82 %
Apr 03 - Apr 10
28 %
Apr 10 - Apr 17
50 %
Apr 17 - Apr 24
60 %
Apr 24 - May 01
69 %
May 01 - May 08
78 %
May 08 - May 15
78 %
May 15 - May 22
76 %
May 22 - May 29
78 %
May 29 - Jun 05
78 %
Jun 05 - Jun 12
69 %
Jun 12 - Jun 19
76 %
Jun 19 - Jun 26
80 %
Jun 26 - Jul 03
69 %
Jul 03 - Jul 10
65 %
Jul 10 - Jul 17
56 %
Jul 17 - Jul 24
52 %
Jul 24 - Jul 31
60 %
Jul 31 - Aug 07
67 %
Aug 07 - Aug 14
76 %
Aug 14 - Aug 21
69 %
Aug 21 - Aug 28
73 %
Aug 28 - Sep 04
80 %
Sep 04 - Sep 11
82 %
Sep 11 - Sep 18
80 %
Percentage of available rentals

FAQs: Vacation Rentals in Winter Park

How much did it cost for a vacation rental in Winter Park in 2020, the first year impacted by the corona crisis?

At an average cost of $386.30 per night, Winter Park lies at the upper end of the price range for vacation rentals in the USA.

During which months can you find the best price for vacation rentals in Winter Park?

Travelers who want to save as much as possible visit Winter Park in June, May, and October, the cheapest months of the year, with average prices of $329.21, $333.28, and $341.26 per night, respectively, based on data collected in 2020.

When does the price of vacation rentals in Winter Park go up the most?

Analyzing the data from 2020, we found that costs per night for accommodation here are usually higher, on average, during the months of March ($487.52), January ($470.5), and February ($455.62).

Is Winter Park a good location for a last-minute getaway?

It is better to plan ahead in Winter Park as only 29% of the accommodations remain free throughout the year, according to our 2020 data.

What are the best months for a spontaneous getaway?

In 2020, the months with the largest number of properties available of the year in Winter Park were June, October and November, with average availabilities of 48.75%, 41.8%, and 41.5%, respectively.

Which months is it more difficult to find available vacation rentals?

The months with the lowest properties available in Winter Park are, in order, February, January, and March with respective average availability figures of 4%, 8.5%, and 16.25%, based on data collected in 2020.

Are there many rentals in Winter Park?

We have 880 rentals for you in Winter Park, provided by our 4 local and international partners.

Holidu compares hundreds of websites to find your perfect holiday rental for the best price.

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