Vacation Rentals in Winter Park (FL)

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

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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 $348 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

Winter Park (FL), Orange County (FL)

9.7

Vacation rental for 4 people, with yard and terrace

Free cancellation

from $175 per night

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 rentals in city center

Winter Park (FL), Orange County (FL)

Vacation rental for 4 people, with terrace

Free cancellation

from $429 per night

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 $127 per night

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

Winter Park (FL), Orange County (FL)

10.0

Vacation rental for 4 people, with yard and pool

Free cancellation

from $145 per night

Vacation rentals with free cancellation

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

Winter Park (FL), Orange County (FL)

10.0

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

Free cancellation

from $159 per night

Winter Park (FL), Orange County (FL)

Vacation rental for 4 people, with pool, with pets

Free cancellation

from $137 per night

Winter Park (FL), Orange County (FL)

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

Free cancellation

from $191 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 $150 per night

Vacation Rentals with Pool

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 $176 per night

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

Winter Park (FL), Orange County (FL)

10.0

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

Free cancellation

from $120 per night

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

Winter Park (FL), Orange County (FL)

10.0

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

Free cancellation

from $245 per night

Winter Park (FL), Orange County (FL)

Vacation rental for 6 people

Free cancellation

from $274 per night

Vacation rentals with pets allowed

Winter Park (FL), Orange County (FL)

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

Free cancellation

from $371 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 $246 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 $144 per night

Winter Park (FL), Orange County (FL)

10.0

Vacation rental for 4 people

Free cancellation

from $125 per night

Find Vacation Rentals in Winter Park (FL)

Prices and availability

Current Vacation rental prices Winter Park (FL)

$355for 31 May - 7 Jun

$298 annual average

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Feb

Mar

Average price per week

Current vacation rental availability Winter Park (FL)

3%for 31 May - 7 Jun

9% annual average

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Feb

Mar

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.