Vacation Rentals in Winter Park (FL)

Start comparing over 40 rentals in Winter Park (FL) and book at the best price!

Find offers

Vacation housesBarnsPrivate poolInternet

8.0

Vacation rentals in Winter Park (FL)

Vacation rental for 4 people, with yard and terrace in Winter Park (FL)

Winter Park (FL), Orange County (FL)

10.0

Vacation rental for 4 people, with yard and terrace

Free cancellation

from $344 per night

Vacation rental for 4 people in Winter Park (FL)

Winter Park (FL), Orange County (FL)

9.8

Vacation rental for 4 people

Free cancellation

from $95 per night

Vacation rental for 4 people, with terrace and yard in Winter Park (FL)

Winter Park (FL), Orange County (FL)

9.7

Vacation rental for 4 people, with terrace and yard

Free cancellation

from $175 per night

Winter Park (FL), Orange County (FL)

Vacation rental for 4 people, with terrace

Free cancellation

from $430 per night

Vacation rentals in city center

Vacation rental for 5 people in Winter Park (FL)

Winter Park (FL), Orange County (FL)

9.9

Vacation rental for 5 people

Free cancellation

from $159 per night

Winter Park (FL), Orange County (FL)

Vacation rental for 4 people, with yard and pool, with pets

Free cancellation

from $125 per night

Vacation rental for 4 people, with pool and yard in Winter Park (FL)

Winter Park (FL), Orange County (FL)

10.0

Vacation rental for 4 people, with pool and yard

Free cancellation

from $143 per night

Vacation rental for 4 people, with yard and pool as well as terrace, with pets in Winter Park (FL)

Winter Park (FL), Orange County (FL)

10.0

Vacation rental for 4 people, with yard and pool as well as terrace, with pets

Free cancellation

from $148 per night

Vacation rentals with free cancellation

Vacation rental for 5 people, with yard in Winter Park (FL)

Winter Park (FL), Orange County (FL)

9.7

Vacation rental for 5 people, with yard

Free cancellation

from $284 per night

Vacation rental for 5 people, with yard and hot tub as well as terrace in Winter Park (FL)

Winter Park (FL), Orange County (FL)

10.0

Vacation rental for 5 people, with yard and hot tub as well as terrace

Free cancellation

from $159 per night

Vacation rental for 4 people, with pool and balcony as well as yard in Winter Park (FL)

Winter Park (FL), Orange County (FL)

8.0

Vacation rental for 4 people, with pool and balcony as well as yard

Free cancellation

from $174 per night

Vacation rental for 4 people, with yard and terrace as well as pool, with pets in Winter Park (FL)

Winter Park (FL), Orange County (FL)

10.0

Vacation rental for 4 people, with yard and terrace as well as pool, with pets

Free cancellation

from $119 per night

Vacation Rentals with Pool

Winter Park (FL), Orange County (FL)

Vacation rental for 4 people, with pool, with pets

Free cancellation

from $135 per night

Winter Park (FL), Orange County (FL)

Vacation rental for 4 people, with yard and pool as well as balcony

Free cancellation

from $188 per night

Vacation rental for 6 people, with pool and yard as well as balcony in Winter Park (FL)

Winter Park (FL), Orange County (FL)

10.0

Vacation rental for 6 people, with pool and yard as well as balcony

Free cancellation

from $245 per night

Winter Park (FL), Orange County (FL)

Vacation rental for 6 people

Free cancellation

from $270 per night

Vacation rentals with pets allowed

Winter Park (FL), Orange County (FL)

Vacation rental for 2 people, with balcony and pool, with pets

Free cancellation

from $367 per night

Vacation rental for 4 people, with yard in Winter Park (FL)

Winter Park (FL), Orange County (FL)

9.8

Vacation rental for 4 people, with yard

Free cancellation

from $247 per night

Winter Park (FL), Orange County (FL)

10.0

Vacation rental for 4 people

Free cancellation

from $123 per night

Vacation rental for 4 people, with pool and terrace in Winter Park (FL)

Winter Park (FL), Orange County (FL)

9.3

Vacation rental for 4 people, with pool and terrace

Free cancellation

from $142 per night

Find Vacation Rentals in Winter Park (FL)

Prices and availability

Current Vacation rental prices Winter Park (FL)

$239for 17 May - 24 May

$301 annual average

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Feb

Average price per week

Current vacation rental availability Winter Park (FL)

3%for 17 May - 24 May

9% annual average

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Feb

Percentage of available rentals

FAQs: Vacation Rentals in Winter Park (FL)

How much does it cost to book a vacation rental in Winter Park?

Last year, rentals in this destination had an annual average price of around $305 per night.

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

According to our most recent data, the months at the lowest possible cost in Winter Park are January, April and May, with average prices of $252, $254, and $256, respectively.

When are vacation rentals more expensive in Winter Park?

Analyzing the data from last year, we found that costs per night for accommodation here are usually higher, on average, during the months of November ($437), December ($337), and September ($325).

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

In order to not have problems finding accommodation in Winter Park, it is necessary to be proactive as 94% of rentals are usually booked, according to last year's data.

When are more vacation rentals available?

The months that offer the most accommodation options are, on average, August (with an availability of 19%), January (13%), and October (8%), according to the trends observed in the prior year.