Find offers
Vacation Rentals in Winter Park (FL)
1 bedroom
10.0
1 bedroom
10.0
1 bedroom
from $316 / night
1 bedroom
from $83 / nightFREE cancellationVacation rentals with free cancellation
2 bedrooms
from $108 / nightFREE cancellation
2 bedrooms
10.0
2 bedrooms
from $132 / nightFREE cancellation
2 bedrooms
from $127 / nightFREE cancellationVacation rentals with pets allowed
Pets allowed
2 bedrooms
9.3
Pets allowed
2 bedrooms
9.9
Pets allowed
2 bedrooms
10.0
Pets allowed
2 bedrooms
10.0
Vacation Rentals with Pool
Pool
2 bedrooms
10.0
Pool
2 bedrooms
10.0
Pool
2 bedrooms
from $157 / nightFREE cancellation
Pool
3 bedrooms
from $202 / nightFREE cancellationVacation Rentals with Yard
Yard
2 bedrooms
9.7
Yard
2 bedrooms
10.0
Yard
2 bedrooms
9.9
Yard
2 bedrooms
9.6
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.
more...
Winter Park (fl), Orange County (fl)
Vacation Rental • 990 ft² • 2 Bedrooms
Winter Park (fl), Orange County (fl)
10.0
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 $123 / night
View offer
more...
Winter Park (fl), Orange County (fl)
Vacation Rental • 1625 ft² • 3 Bedrooms
Winter Park (fl), Orange County (fl)
9.8
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 and Phelps)Our house has high quality furniture, linens, cookware and tableware, large and small appliances; hardwood or tile flooring in most rooms; a large fenced backyard with ...
from $134 / night
View offer
more...
Winter Park (fl), Orange County (fl)
Vacation Rental • 1345 ft² • 2 Bedrooms
Winter Park (fl), Orange County (fl)
9.9
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 $163 / night
View offer
Prices and availability
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.
Most popular in Winter Park (FL)
Holidu compares hundreds of websites to find your perfect holiday rental for the best price.
500+ more
- Vacation Rentals
- USA
- Florida
- Central Florida
- Winter Park (FL)