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 apartmentsVacation housesPrivate poolPool

8.0

Vacation Rentals in Winter Park (FL)

Vacation rental for 4 people, with yard and terrace

3 bedrooms

10.0

(58 reviews)

from $352 / nightFREE cancellation

Vacation rental for 4 people

2 bedrooms

9.8

(34 reviews)

from $126 / nightFREE cancellation

Vacation rental for 4 people, with terrace and yard

2 bedrooms

9.7

(26 reviews)

from $175 / nightFREE cancellation

Vacation rental for 5 people, with yard

2 bedrooms

9.7

(28 reviews)

from $284 / nightFREE cancellation

Vacation rentals with free cancellation

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

2 bedrooms

10.0

(18 reviews)

from $158 / nightFREE cancellation

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

2 bedrooms

from $126 / nightFREE cancellation

Vacation rental for 4 people, with pool, with pets

2 bedrooms

from $133 / nightFREE cancellation

Vacation rental for 4 people, with terrace

2 bedrooms

from $430 / nightFREE cancellation

Vacation Rentals with Pool

Pool

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

2 bedrooms

from $183 / nightFREE cancellation

Pool

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

2 bedrooms

10.0

from $156 / nightFREE cancellation

Pool

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

2 bedrooms

10.0

from $148 / nightFREE cancellation

Pool

Vacation rental for 4 people

2 bedrooms

10.0

(4 reviews)

from $107 / nightFREE cancellation

Vacation Rentals with Yard

Yard

Vacation rental for 6 people, with terrace and yard

2 bedrooms

9.5

(12 reviews)

from $216 / nightFREE cancellation

Yard

Vacation rental for 6 people, with hot tub and yard as well as terrace

3 bedrooms

10.0

(16 reviews)

from $197 / nightFREE cancellation

Yard

Vacation rental for 6 people, with terrace and yard

3 bedrooms

9.3

(18 reviews)

from $252 / nightFREE cancellation

Yard

Vacation rental for 8 people, with yard and terrace

4 bedrooms

8.9

(7 reviews)

from $318 / nightFREE cancellation

Vacation rentals with pets allowed

Pets allowed

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

1 bedroom

from $581 / nightFREE cancellation

Pets allowed

Vacation rental for 4 people, with terrace and pool

2 bedrooms

9.3

(3 reviews)

from $158 / nightFREE cancellation

Pets allowed

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

2 bedrooms

8.0

from $168 / nightFREE cancellation

Pets allowed

Vacation rental for 4 people, with yard

2 bedrooms

10.0

(8 reviews)

from $247 / nightFREE cancellation

Find Vacation Rentals in Winter Park (FL)

Prices and availability

Current Vacation rental prices Winter Park (FL)

$429for 28 Dec - 4 Jan

$318 annual average

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Average price per week

Current vacation rental availability Winter Park (FL)

3%for 28 Dec - 4 Jan

5% annual average

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

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.