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)

Hotel for 2 people, with pool

1 bedroom

from $377 / nightFREE cancellation

Vacation rental for 4 people, with terrace and yard

2 bedrooms

10.0

(34 reviews)

from $189 / nightFREE cancellation

Vacation rental for 4 people, with terrace and pool

2 bedrooms

9.3

(3 reviews)

from $142 / nightFREE cancellation

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

2 bedrooms

9.9

(15 reviews)

from $207 / nightFREE cancellation

Vacation rentals with free cancellation

Vacation rental for 4 people, with yard and terrace

2 bedrooms

9.9

(35 reviews)

from $350 / nightFREE cancellation

Vacation rental for 4 people, with terrace and yard

2 bedrooms

10.0

(2 reviews)

from $317 / nightFREE cancellation

Vacation rental for 4 people, with terrace and yard

2 bedrooms

9.7

(24 reviews)

from $175 / nightFREE cancellation

Vacation rental for 4 people, with pool and balcony

2 bedrooms

10.0

(3 reviews)

from $140 / nightFREE cancellation

Vacation rentals in city center

Vacation rental for 4 people, with yard

2 bedrooms

10.0

(8 reviews)

from $231 / nightFREE cancellation

Vacation rental for 5 people, with terrace and yard

2 bedrooms

9.9

(20 reviews)

from $142 / nightFREE cancellation

Vacation rental for 5 people

2 bedrooms

9.9

(21 reviews)

from $165 / nightFREE cancellation

Vacation rental for 12 people, with yard and terrace

4 bedrooms

10.0

(15 reviews)

from $402 / nightFREE cancellation

Vacation rentals with pets allowed

Pets allowed

Vacation rental for 4 people, with pool, with pets

2 bedrooms

from $142 / nightFREE cancellation

Pets allowed

Vacation rental for 6 people, with yard and terrace

2 bedrooms

9.8

(8 reviews)

from $222 / nightFREE cancellation

Pets allowed

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

2 bedrooms

from $183 / nightFREE cancellation

Pets allowed

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

2 bedrooms

from $132 / nightFREE cancellation

Vacation Rentals with Pool

Pool

Vacation rental for 2 people, with pool and balcony

1 bedroom

10.0

from $137 / nightFREE cancellation

Pool

Vacation rental for 2 people, with pool and balcony as well as yard

1 bedroom

10.0

from $137 / nightFREE cancellation

Pool

Vacation rental for 6 people

3 bedrooms

from $192 / nightFREE cancellation

Pool

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

2 bedrooms

10.0

from $121 / nightFREE cancellation

Find Vacation Rentals in Winter Park (FL)

Best Vacation Rentals in Winter Park (FL)

Guests agree: these stays are highly rated for location, cleanliness, and more.

Vacation Rental for 4 Guests in Winter Park (fl), Orange County (fl)

Vacation Rental for 4 Guests in Winter Park (fl), Orange County (fl), Picture 1

Vacation Rental for 4 Guests in Winter Park (fl), Orange County (fl), Picture 2

Vacation Rental for 4 Guests in Winter Park (fl), Orange County (fl), Picture 3

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Winter Park (fl), Orange County (fl)

Vacation Rental • 1173 ft² • 2 Bedrooms

Winter Park (fl), Orange County (fl)

Location!!! Beautifully appointed 2 bedroom, 2 bath second floor apartment overlooking a beautiful pool area with balcony. Just three blocks to Park Ave and two blocks to the Winter Park Village! Many great restaurants and shops are within walking distance as well as parks and stadium seating movie theater. 10' ceilings, beautiful acacia wood flooring with high-end appliances and fixtures throughout. Huge flat screen tv with cable and Netflix connection. Wifi connected. Very comfortable furniture and bedding. Clean! There are four bikes for you to use and the pool area contains heated pool,...

from $183 / night

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Vacation Rental for 5 Guests in Winter Park (fl), Orange County (fl)

Vacation Rental for 5 Guests in Winter Park (fl), Orange County (fl), Picture 1

Vacation Rental for 5 Guests in Winter Park (fl), Orange County (fl), Picture 2

Vacation Rental for 5 Guests in Winter Park (fl), Orange County (fl), Picture 3

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Winter Park (fl), Orange County (fl)

Vacation Rental • 990 ft² • 2 Bedrooms

Winter Park (fl), Orange County (fl)

9.9

(20 reviews)

Furnished Mid Century Modern Short/Long term rental located in charming Olde Winter Park. Two bedrooms and one and half baths. Steps from shopping and restaurants and less than a mile from Park Ave with it's famous museums, parks, shops and dining. This home is complete with authentic mid century modern furnishings, comfortable bedding, mid century couches and chairs, new linens, two televisions (includes cable tv), central heat and air, new landscaping, irrigation and yard maintenance provided, fenced back yard, dishwasher, disposal, washer, dryer, and a fully stocked kitchen, including ap...

from $142 / night

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Winter Park (fl), Orange County (fl)

Vacation Rental • 4 Guests • 2 Bedrooms

Winter Park (fl), Orange County (fl)

9.8

(32 reviews)

Private 2 bedroom guest suite with its own entry and a separate sitting room. Tandem bedroom include 1 queen sized bed and bunk beds. Easily sleeping 4. We are located very close to downtown Winter Park and steps off Park Ave. Museums, restaurants, golf and shopping are all within walking distance. There is a dedicated desk/work area for corporate guest. Designed to feel like home away from home we want to make sure your stay with us is enjoyable.

from $106 / night

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Prices and availability

Current Vacation rental prices Winter Park (FL)

$328for 3 Aug - 10 Aug

$318 annual average

Aug

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Dec

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Average price per week

Current vacation rental availability Winter Park (FL)

3%for 3 Aug - 10 Aug

8% annual average

Aug

Sep

Oct

Nov

Dec

Jan

Feb

Mar

Apr

May

Jun

Jul

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.