Vacation Rentals in Winter Park (FL)

Vacation Rentals in Winter Park (FL)

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

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
Vacation Rental for 4 Guests in Winter Park (fl), Orange County (fl), Picture 4
more...
Winter Park (fl), Orange County (fl)
Vacation Rental • 1345 ft² • 2 Bedrooms
9.9
(15 reviews)
2 bedroom 2 bath, 1350 sqft detached homeFamily friendly layout with master bedroom suite, shared bedroom (2 twin beds), main living room furnished with a coastal feel. Master bedroom has a Westin Heavenly Mattress. Twin Mattresses are Twin XL, one is the Serta CF 3000 Plush Hybrid and the other is the Serta CF 3000 Medium Hybrid. Kitchen with modern conveniences: all top line stainless steel appliances stove top, oven, dishwasher, fridge. Granite countertops and marble floors. Sunroom is set up with breakfast/coffee area and a plush lounging sofa for quiet relaxing reading. The entry way h...
from $154 / night
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
Vacation Rental for 5 Guests in Winter Park (fl), Orange County (fl), Picture 4
more...
Winter Park (fl), Orange County (fl)
Vacation Rental • 990 ft² • 2 Bedrooms
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 $124 / night
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
Vacation Rental for 4 Guests in Winter Park (fl), Orange County (fl), Picture 4
more...
Winter Park (fl), Orange County (fl)
Vacation Rental • 1173 ft² • 2 Bedrooms
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 $159 / night

Prices and availability

Current Vacation rental prices Winter Park (FL)

$317for 22 Jun - 29 Jun
$320 annual average
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
Average price per week

Current vacation rental availability Winter Park (FL)

6%for 22 Jun - 29 Jun
7% annual average
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
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.

How many vacation rentals are there in Winter Park?

Holidu has 60 vacation rentals in Winter Park, provided by 2 different partners.

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

500+ more