Vacation Rentals in Winter Park

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Vacation house
Vacation apartment
Pool
Internet
Balcony/Terrace
4.0
& up
4.5
& up

Popular Accommodations in Winter Park
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from
$506
per night

Vacation rental for 14 people, with jacuzzi
14 pers., 5 bedrooms, 2,293ft², 200yd to skiing
FREE cancellation
5.0
(2 reviews)

from
$176
per night

Vacation rental for 4 people, with jacuzzi and balcony
4 pers., 1 bedroom, 657ft², 70yd to skiing
FREE cancellation
5.0
(20 reviews)

from
$217
per night

Vacation rental for 6 people, with jacuzzi
6 pers., 2 bedrooms, 872ft², 20yd to skiing
FREE cancellation
5.0
(20 reviews)
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Vacation Rentals in Winter Park
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from
$81
per night

Vacation rental for 4 people, with sauna and balcony as well as pool and jacuzzi
4 pers., 441ft², 10yd to skiing
FREE cancellation
5.0
(20 reviews)

from
$155
per night

Vacation rental for 8 people, with jacuzzi and balcony, child-friendly
8 pers., 2 bedrooms, 1,195ft², 2mi to skiing
FREE cancellation
4.7
(20 reviews)

from
$294
per night

Vacation rental for 8 people, with jacuzzi
8 pers., 3 bedrooms, 850yd to skiing
FREE cancellation
4.9
(13 reviews)

from
$110
per night

Vacation rental for 10 people, with balcony and pool as well as sauna and jacuzzi
10 pers., 2 bedrooms, 2mi to skiing
FREE cancellation
4.5
(12 reviews)

from
$162
per night

Vacation rental for 4 people, with jacuzzi, child-friendly
4 pers., 100yd to skiing
FREE cancellation
4.1
(15 reviews)

from
$89
per night

Vacation rental for 4 people, with terrace and view as well as pool
4 pers., 409ft², 30yd to skiing
FREE cancellation
3.8
(26 reviews)
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Pet-friendly Vacation Rentals
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from
$267
per night

Vacation rental for 8 people, with balcony and jacuzzi as well as pool, with pets
8 pers., 3 bedrooms, 1,496ft², 2.2mi to skiing
FREE cancellation
5.0
(16 reviews)

from
$160
per night

Log cabin for 8 people, with pets
8 pers., 2 bedrooms, 1,421ft², 1.7mi to skiing
4.2
(20 reviews)

from
$266
per night

Vacation rental for 10 people, with pool and view as well as terrace and sauna, with pets
10 pers., 3 bedrooms, 2.7mi to skiing
2.5
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Vacation Rentals with Pool
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from
$107
per night

Vacation rental for 8 people, with balcony and jacuzzi as well as pool and sauna
8 pers., 2 bedrooms, 1,055ft², 2.7mi to skiing
FREE cancellation
4.8
(20 reviews)

from
$108
per night

Vacation rental for 4 people, with pool and jacuzzi
4 pers., 441ft², 100yd to skiing
FREE cancellation
5.0
(5 reviews)

from
$255
per night

Vacation rental for 7 people, with pool and jacuzzi, child-friendly
7 pers., 2 bedrooms, 1,195ft², 2.1mi to skiing
FREE cancellation
5.0
(20 reviews)
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Vacation Rentals with Internet
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from
$121
per night

Vacation rental for 5 people, with balcony and jacuzzi as well as sauna
5 pers., 1 bedroom, 700ft², 80yd to skiing
FREE cancellation
4.4
(6 reviews)

from
$343
per night

Vacation rental for 9 people, with jacuzzi and balcony, child-friendly
9 pers., 3 bedrooms, 2,347ft², 650yd to skiing
FREE cancellation
5.0

from
$168
per night

Vacation rental for 5 people, with balcony and jacuzzi
5 pers., 1 bedroom, 20yd to skiing
FREE cancellation
5.0
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Vacation Rentals with Air Conditioning
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from
$146
per night

Vacation rental for 4 people, with sauna and pool as well as balcony
4 pers., 1 bedroom, 200yd to skiing
FREE cancellation
5.0
(3 reviews)

from
$390
per night

Vacation rental for 8 people, with jacuzzi and balcony, child-friendly
8 pers., 3 bedrooms, 1,475ft², 2.7mi to skiing
FREE cancellation
5.0
(2 reviews)

from
$279
per night

Vacation rental for 11 people, with balcony and jacuzzi
11 pers., 3 bedrooms, 2,099ft², 2.5mi to skiing
FREE cancellation
4.7
(20 reviews)
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Find Vacation Rentals in Winter Park

Map

Most popular in Winter Park

Pool 164
Internet 402
Balcony/Terrace 298
TV 397
Parking 391
Washing machine 351

Other property types in Winter Park that might be interesting:

Prices and availability

Prices

September
October
November
December
January
$797
Aug 07 - Aug 14
$438 per night
Aug 14 - Aug 21
$421 per night
Aug 21 - Aug 28
$377 per night
Aug 28 - Sep 04
$422 per night
Sep 04 - Sep 11
$459 per night
Sep 11 - Sep 18
$433 per night
Sep 18 - Sep 25
$409 per night
Sep 25 - Oct 02
$438 per night
Oct 02 - Oct 09
$429 per night
Oct 09 - Oct 16
$435 per night
Oct 16 - Oct 23
$481 per night
Oct 23 - Oct 30
$464 per night
Oct 30 - Nov 06
$459 per night
Nov 06 - Nov 13
$485 per night
Nov 13 - Nov 20
$515 per night
Nov 20 - Nov 27
$557 per night
Nov 27 - Dec 04
$636 per night
Dec 04 - Dec 11
$699 per night
Dec 11 - Dec 18
$641 per night
Dec 18 - Dec 25
$599 per night
Dec 25 - Jan 01
$711 per night
Jan 01 - Jan 08
$797 per night
Jan 08 - Jan 15
$635 per night
Jan 15 - Jan 22
$450 per night
Average price per week

Availabilities

September
October
November
December
January
83 %
Aug 07 - Aug 14
7 %
Aug 14 - Aug 21
9 %
Aug 21 - Aug 28
13 %
Aug 28 - Sep 04
10 %
Sep 04 - Sep 11
55 %
Sep 11 - Sep 18
67 %
Sep 18 - Sep 25
65 %
Sep 25 - Oct 02
68 %
Oct 02 - Oct 09
75 %
Oct 09 - Oct 16
80 %
Oct 16 - Oct 23
80 %
Oct 23 - Oct 30
82 %
Oct 30 - Nov 06
83 %
Nov 06 - Nov 13
83 %
Nov 13 - Nov 20
82 %
Nov 20 - Nov 27
74 %
Nov 27 - Dec 04
76 %
Dec 04 - Dec 11
76 %
Dec 11 - Dec 18
71 %
Dec 18 - Dec 25
56 %
Dec 25 - Jan 01
44 %
Jan 01 - Jan 08
57 %
Jan 08 - Jan 15
66 %
Jan 15 - Jan 22
64 %
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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