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 Rentals in Winter Park (FL)
1 bedroom
from $331 / nightFREE cancellation
2 bedrooms
9.3
2 bedrooms
10.0
2 bedrooms
9.9
Vacation rentals with free cancellation
2 bedrooms
9.9
2 bedrooms
9.7
2 bedrooms
10.0
2 bedrooms
10.0
Vacation rentals in city center
2 bedrooms
10.0
2 bedrooms
9.9
2 bedrooms
9.9
4 bedrooms
10.0
Vacation rentals with pets allowed
Pets allowed
2 bedrooms
from $107 / nightFREE cancellation
Pets allowed
2 bedrooms
from $122 / nightFREE cancellation
Pets allowed
2 bedrooms
9.8
Pets allowed
2 bedrooms
from $159 / nightFREE cancellationVacation Rentals with Pool
Pool
1 bedroom
10.0
Pool
1 bedroom
10.0
Pool
2 bedrooms
from $130 / nightFREE cancellation
Pool
2 bedrooms
10.0
Find Vacation Rentals in Winter Park (FL)
Best Vacation Rentals in Winter Park (FL)
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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 $159 / night
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Winter Park (fl), Orange County (fl)
Vacation Rental • 1625 ft² • 3 Bedrooms
Winter Park (fl), Orange County (fl)
9.8
Our home has high quality furniture, linens, cookware and tableware for your family dinners. There are large and small appliances (including airfryer) to help with preparation. Enjoy a fully-furnished 3 bedrooms, 2 baths, 1600 square-foot, single-story house in the heart of Winter Park, a wonderful town that is adjacent to Orlando and that is home to an array of restaurants, galleries, museums, up-scale shops, businesses, professional offices, parks, lakes and hiking and biking trails. Rollins College is just minutes away from the house by car. Address: 1827 Mizell Ave. (Between Lakemont an...
from $133 / night
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Winter Park (fl), Orange County (fl)
Vacation Rental • 990 ft² • 2 Bedrooms
Winter Park (fl), Orange County (fl)
9.9
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 $122 / night
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Prices and availability
Current Vacation rental prices Winter Park (FL)
$268for 27 Apr - 4 May
$308 annual averageMay
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Average price per week
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.
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