Vacation Rentals in Winter Park (FL)

Start comparing over 9 rentals in Winter Park (FL) and book at the best price!

Search millions of vacation rentals
+
Compare over 1500 websites
=
Find your perfect vacation rental at the best price

Find offers

Free cancellation
Vacation house
Vacation apartment
4.0
& up
4.5
& up

Popular Accommodations in Winter Park (FL)
show all

from
$285
per night

Vacation rental for 8 people, with view and garden as well as sauna and pool, with pets
8 pers., 3 bedrooms
FREE cancellation
5.0

from
$179
per night

Vacation rental for 5 people, with garden
5 pers., 2 bedrooms
4.9
(4 reviews)

from
$115
per night

Vacation rental for 4 people, with terrace, with pets
4 pers., 2 bedrooms
5.0
show all

Vacation Rentals in Winter Park (FL)
show all

from
$99
per night

Vacation rental for 2 people, with view and terrace as well as lake view
2 pers., 1 bedroom
4.4
(72 reviews)

from
$241
per night

Vacation rental for 2 people, with garden
2 pers., 1 bedroom, 205ft²
4.9
(27 reviews)

from
$93
per night

Vacation rental for 4 people, with pool
4 pers., 1 bedroom
4.3
(23 reviews)

from
$93
per night

Guesthouse for 4 people, with terrace
4 pers., 2 bedrooms
FREE cancellation
4.7
(23 reviews)

from
$54
per night

Guesthouse for 2 people, with garden, child-friendly
2 pers., 1 bedroom
4.8
(16 reviews)

from
$75
per night

Apartmenthotel for 4 people, with pool and balcony
4 pers., 1 bedroom
3.9
(139 reviews)
show all

Find Vacation Rentals in Winter Park (FL)

Map

Prices and availability

Prices

August
September
October
November
December
$594
Jul 17 - Jul 24
$264 per night
Jul 24 - Jul 31
$292 per night
Jul 31 - Aug 07
$310 per night
Aug 07 - Aug 14
$312 per night
Aug 14 - Aug 21
$326 per night
Aug 21 - Aug 28
$312 per night
Aug 28 - Sep 04
$323 per night
Sep 04 - Sep 11
$339 per night
Sep 11 - Sep 18
$333 per night
Sep 18 - Sep 25
$335 per night
Sep 25 - Oct 02
$312 per night
Oct 02 - Oct 09
$261 per night
Oct 09 - Oct 16
$259 per night
Oct 16 - Oct 23
$322 per night
Oct 23 - Oct 30
$409 per night
Oct 30 - Nov 06
$459 per night
Nov 06 - Nov 13
$594 per night
Nov 13 - Nov 20
$582 per night
Nov 20 - Nov 27
$332 per night
Nov 27 - Dec 04
$356 per night
Dec 04 - Dec 11
$432 per night
Dec 11 - Dec 18
$318 per night
Dec 18 - Dec 25
$325 per night
Dec 25 - Jan 01
$341 per night
Average price per week

Availabilities

August
September
October
November
December
0 %
Jul 17 - Jul 24
0 %
Jul 24 - Jul 31
0 %
Jul 31 - Aug 07
0 %
Aug 07 - Aug 14
0 %
Aug 14 - Aug 21
0 %
Aug 21 - Aug 28
0 %
Aug 28 - Sep 04
0 %
Sep 04 - Sep 11
0 %
Sep 11 - Sep 18
0 %
Sep 18 - Sep 25
0 %
Sep 25 - Oct 02
0 %
Oct 02 - Oct 09
0 %
Oct 09 - Oct 16
0 %
Oct 16 - Oct 23
0 %
Oct 23 - Oct 30
0 %
Oct 30 - Nov 06
0 %
Nov 06 - Nov 13
0 %
Nov 13 - Nov 20
0 %
Nov 20 - Nov 27
0 %
Nov 27 - Dec 04
0 %
Dec 04 - Dec 11
0 %
Dec 11 - Dec 18
0 %
Dec 18 - Dec 25
0 %
Dec 25 - Jan 01
0 %
Percentage of available rentals

FAQs: Vacation Rentals in Winter Park (FL)

How much did it cost for a vacation rental in Winter Park in 2020, during the corona crisis?

We can see from our data that Winter Park has an average price of $349.42 per night, a relatively high one for a city in the USA.

What time of year offers, on average, the best vacation rental prices in Winter Park?

If you want to save the maximum during your visit to Winter Park, travel in March ($264.23 per night on average), February ($272.33), or December ($278.43), to find the lowest prices for the whole year.

In which months is it more expensive to rent a vacation rental in Winter Park?

In 2020, the month that showed the highest annual average prices in Winter Park was June, with an average price of $474.61 per night. This was followed by July, with an average of $461.06, and August, with $381.61.

Is it necessary to plan a trip to Winter Park well in advance?

We recommend you to book in advance in Winter Park as only 11% of the properties remain available throughout the year, according to our 2020 data.

Which months offer the highest availability?

The months when it's the easiest to find free accommodation in Winter Park are April (the average amount of properties that are available reached 23% of the total in 2020), June (20.5%), and May (18%).

When are there fewer vacation rental options available in Winter Park?

The months with the lowest properties available in Winter Park are, in order, March, December, and February. March is usually fully booked with respective average availability figures for December and February at 3%, and 3.75%, based on data collected in 2020.

How many vacation rentals does Holidu have in Winter Park?

Even though Holidu combines the inventories of 2 different partners, we have found 10 properties in Winter Park, so make sure you book yours now!

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

Booking.com Vacation Rentals in Winter Park (FL)Booking.com Vacation Rentals in Winter Park (FL)HomeAway Vacation Rentals in Winter Park (FL)HomeAway Vacation Rentals in Winter Park (FL)FeWo-direkt Vacation Rentals in Winter Park (FL)FeWo-direkt Vacation Rentals in Winter Park (FL)Vrbo Vacation Rentals in Winter Park (FL)Vrbo Vacation Rentals in Winter Park (FL)HRS Vacation Rentals in Winter Park (FL)HRS Vacation Rentals in Winter Park (FL)Abritel Vacation Rentals in Winter Park (FL)Abritel Vacation Rentals in Winter Park (FL)Airbnb Vacation Rentals in Winter Park (FL)Airbnb Vacation Rentals in Winter Park (FL)
  1. Vacation Rentals
  2. USA
  3. Florida
  4. Central Florida
  5. Winter Park (FL)