The average price of a 7-day trip to Winter Park is $1,997 for a solo traveler, $3,587 for a couple, and $6,724 for a family of 4. Winter Park hotels range from $57 to $262 per night with an average of $54, while most vacation rentals will cost $120 to $380 per night for the entire home. Average worldwide flight costs to Executive Airport (ORL) are between $593 and $2,224 per person for economy flights and $1,861 to $6,979 for first class. Depending on activities, we recommend budgeting $51 to $73 per person per day for transportation and enjoying local restaurants.

See below for average, budget, and luxury trip costs. You can also look up flight costs from your airport for more tailored flight pricing.

 

 

The Cheapest Times to Visit Winter Park, FL, US

On average, these will be the cheapest dates to fly to ORL and stay in a Winter Park hotel:

  • January 1st to April 1st
  • October 22nd to November 11th

The absolute cheapest time to take a vacation in Winter Park is usually late January.

 

Average Winter Park Trip Costs

Average Solo Traveler

The average cost for one person to visit Winter Park for a week is $1,304-$3,162($186-$452 per day)

Food, Travel, and Sightseeing: $51 to $73 per day for one person’s daily expenses

Flights: $557 to $1,979 for economy

Lodging: $89 to $112 per night for one 2 or 3-star hotel room

or $65 to $79 per night for a 1-bed vacation rental

Average Couple’s Trip

The average cost for a couple to visit Winter Park for a week is $2,290-$6,142($327-$877 per day)

Food, Travel, and Sightseeing: $102 to $146 per day for two people’s daily expenses

Flights: $1,114 to $3,958 for economy

Lodging: $89 to $112 per night for one 2 or 3-star hotel room

or $65 to $79 per night for a 1-bed vacation rental

Average Family Vacation

The average cost for 4 people to visit Winter Park for a week is $4,280-$11,304($611-$1,615 per day)

Food, Travel, and Sightseeing: $204 to $292 per day for four people’s daily expenses

Flights: $2,228 to $7,916 for economy

Lodging: $178 to $224 per night for two 2 or 3-star hotel rooms

or $104 to $119 per night for a 2-bed vacation rental

Traveling Cheap to Winter Park

How cheap can you make a vacation to Winter Park? The cheapest trip to Winter Park is about $119 per person per day for travelers willing to take standby flights, deal with inconvenience, and otherwise limit travel expenses. About 2% of rentals are available in the $0 to $100 range for an entire place, and vacation rentals can be booked for as low as $20 per night. These inexpensive rentals must be booked as early as possible and may not be in the most desirable areas. 1-star hotels are more likely to be available, with rooms starting at around $46.

Even cheaper trips are possible depending on where you live and whether you can drive. Check the cheapest times to fly for more saving ideas.

Budget Solo Traveler

The lowest cost for one person to visit Winter Park for a week is $831-$2,647($119-$378 per day)

Food, Travel, and Sightseeing: $22 to $44 per day for one person’s daily expenses

Flights: $557 to $1,979 for economy

Lodging: $46 to $57 per night for one 1-star hotel room

or $20 to $60 per night for a 1-bed vacation rental

Budget Couple’s Trip

The lowest cost for a couple to visit Winter Park for a week is $1,542-$4,934($220-$705 per day)

Food, Travel, and Sightseeing: $44 to $88 per day for two people’s daily expenses

Flights: $1,114 to $3,958 for economy

Lodging: $46 to $57 per night for one 1-star hotel room

or $20 to $60 per night for a 1-bed vacation rental

Budget Family Vacation

The lowest cost for 4 people to visit Winter Park for a week is $3,036-$9,832($434-$1,405 per day)

Food, Travel, and Sightseeing: $88 to $176 per day for four people’s daily expenses

Flights: $2,228 to $7,916 for economy

Lodging: $92 to $114 per night for two 1-star hotel rooms

or $32 to $84 per night for a 2-bed vacation rental

Overall it is harder to travel to Winter Park cheaply.

The Cost of a Luxury Winter Park Trip

There is no true ceiling on the cost of a luxury trip, so our estimates are based on what most people do in Winter Park.

Luxury Solo Traveler

The high-end price for one person to visit Winter Park for a week is $2,966-$10,252($424-$1,465 per day)

Food, Travel, and Sightseeing: $97 to $146 per day for one person’s daily expenses

Flights: $1,159 to $5,126 for first class

Lodging: $188 to $262 per night for one 4 or 5-star hotel room

or $380 to $684 per night for a preferred vacation rental

Luxury Couple’s Trip

The high-end price for a couple to visit Winter Park for a week is $4,804-$16,400($686-$2,343 per day)

Food, Travel, and Sightseeing: $194 to $292 per day for two people’s daily expenses

Flights: $2,318 to $10,252 for first class

Lodging: $188 to $262 per night for one 4 or 5-star hotel room

or $380 to $684 per night for a preferred vacation rental

Luxury Family Vacation

The high-end price for 4 people to visit Winter Park for a week is $9,608-$30,340($1,373-$4,334 per day)

Food, Travel, and Sightseeing: $388 to $584 per day for four people’s daily expenses

Flights: $4,636 to $20,504 for first class

Lodging: $376 to $524 per night for two 4 or 5-star hotel rooms

or $608 to $958 per night for a preferred vacation rental

 

Winter Park Hotel Prices

The cost of staying in Winter Park is higher than the average city. On average hotels are less expensive than vacation rentals. Luxury vacation rentals are more expensive in Winter Park due to very high property costs. The graphs below show how much cost can vary depending on the type of experience you’re looking for.

Winter Park Lodging Cost by Star Status

The average price for the class of hotel is on the (y) axis. The hotel class (out of 5 stars) is on the (x) axis.

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Hotel Price

Prices are based on Winter Park hotel averages and may not reflect current prices. In some cases, we extrapolate prices to estimate costs, and hotels with your desired star rating may not be available.

Vacation Rental Prices

The percent of vacation rentals in the price range is on the left (y) axis. Price range is on the bottom (x) axis.

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Percent of rentals

There are a healthy amount of vacation rentals serving all budgets in Winter Park.

 

Flight Costs to Winter Park

Averaging flights around the world, prices go from a high of $2,224 average in early to mid May to a low of $593 in late January. Median flight price is $727. These prices are based on millions of flights. For Winter Park our data includes 792 originating airports, and several airlines. The area has much more variance in price compared with other locations. Flying to Winter Park from an airport like Lester B. Pearson International (YYZ) in Toronto (Canada) for an average $1,970 trip fare will obviously cost a lot more than from an airport like Leipzig Halle (LEJ) in Leipzig (Germany) at an average of just $520.

 

Average Flight Cost by Season

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Worldwide Flight Prices

Average Flight Cost by Day of Week

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Departure Day Prices

 

The cheapest day to fly in is typically Monday. Click here to see data for the cost of flights from your airport. In Winter Park, the difference between the cheapest and the most expensive week is about $1,631, so you can easily save about 275% simply by using our free flight guides and booking in advance.

 

Daily Expenses Budget

Daily vacation expenses vary more based on what you’re interested in doing. A fine dining restaurant with drinks around Winter Park can easily cost $330 per person or more, while a standard nice meal might be about $22 per person. Private tours can cost $653 per day, but self-guided tours to see the outdoor sights can be free. Costs vary wildly, so recommendations are made based on the cost of living and averages we see for this type of vacation.

 

 

Other Winter Park Guides