The average price of a 7-day trip to Wailea is $3,143 for a solo traveler, $5,645 for a couple, and $10,582 for a family of 4. Wailea hotels range from $157 to $625 per night with an average of $398, while most vacation rentals will cost $340 to $1000 per night for the entire home. Average worldwide flight costs to Kahului Airport (OGG) are between $929 and $1,500 per person for economy flights and $2,915 to $4,707 for first class. Depending on activities, we recommend budgeting $103 to $229 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 Wailea, HI, US

On average, these will be the cheapest dates to fly to OGG and stay in a Wailea hotel:

  • January 8th to March 4th
  • April 16th to April 29th
  • August 20th to December 9th (except the week of November 19th)

The absolute cheapest time to take a vacation in Wailea is usually early September.

 

Average Wailea Trip Costs

Average Solo Traveler

The average cost for one person to visit Wailea for a week is $2,182-$4,555($312-$651 per day)

Food, Travel, and Sightseeing: $103 to $229 per day for one person’s daily expenses

Flights: $513 to $1,290 for economy

Lodging: $158 to $250 per night for one 2 or 3-star hotel room

or $227 to $277 per night for a 1-bed vacation rental

Average Couple’s Trip

The average cost for a couple to visit Wailea for a week is $4,248-$7,868($607-$1,124 per day)

Food, Travel, and Sightseeing: $206 to $458 per day for two people’s daily expenses

Flights: $1,026 to $2,580 for economy

Lodging: $158 to $250 per night for one 2 or 3-star hotel room

or $227 to $277 per night for a 1-bed vacation rental

Average Family Vacation

The average cost for 4 people to visit Wailea for a week is $6,832-$14,572($976-$2,082 per day)

Food, Travel, and Sightseeing: $412 to $916 per day for four people’s daily expenses

Flights: $2,052 to $5,160 for economy

Lodging: $316 to $500 per night for two 2 or 3-star hotel rooms

or $363 to $443 per night for a 2-bed vacation rental

Traveling Cheap to Wailea

How cheap can you make a vacation to Wailea? The cheapest trip to Wailea is about $247 per person per day for travelers willing to take standby flights, deal with inconvenience, and otherwise limit travel expenses. About 0% of rentals are available in the $0 to $100 range for an entire place, and vacation rentals can be booked for as low as $160 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 $133.

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 Wailea for a week is $1,731-$3,330($247-$476 per day)

Food, Travel, and Sightseeing: $60 to $120 per day for one person’s daily expenses

Flights: $513 to $1,290 for economy

Lodging: $133 to $157 per night for one 1-star hotel room

or $160 to $200 per night for a 1-bed vacation rental

Budget Couple’s Trip

The lowest cost for a couple to visit Wailea for a week is $2,664-$5,460($381-$780 per day)

Food, Travel, and Sightseeing: $120 to $240 per day for two people’s daily expenses

Flights: $1,026 to $2,580 for economy

Lodging: $133 to $157 per night for one 1-star hotel room

or $160 to $200 per night for a 1-bed vacation rental

Budget Family Vacation

The lowest cost for 4 people to visit Wailea for a week is $5,076-$10,404($725-$1,486 per day)

Food, Travel, and Sightseeing: $240 to $480 per day for four people’s daily expenses

Flights: $2,052 to $5,160 for economy

Lodging: $266 to $314 per night for two 1-star hotel rooms

or $224 to $300 per night for a 2-bed vacation rental

Overall it is very difficult to travel to Wailea cheaply.

The Cost of a Luxury Wailea Trip

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

Luxury Solo Traveler

The high-end price for one person to visit Wailea for a week is $6,560-$16,980($937-$2,426 per day)

Food, Travel, and Sightseeing: $196 to $412 per day for one person’s daily expenses

Flights: $1,462 to $2,696 for first class

Lodging: $621 to $625 per night for one 4 or 5-star hotel room

or $1,000 to $1,900 per night for a preferred vacation rental

Luxury Couple’s Trip

The high-end price for a couple to visit Wailea for a week is $9,394-$22,560($1,342-$3,223 per day)

Food, Travel, and Sightseeing: $392 to $824 per day for two people’s daily expenses

Flights: $2,924 to $5,392 for first class

Lodging: $621 to $625 per night for one 4 or 5-star hotel room

or $1,000 to $1,900 per night for a preferred vacation rental

Luxury Family Vacation

The high-end price for 4 people to visit Wailea for a week is $18,788-$39,420($2,684-$5,631 per day)

Food, Travel, and Sightseeing: $784 to $1,648 per day for four people’s daily expenses

Flights: $5,848 to $10,784 for first class

Lodging: $1,242 to $1,250 per night for two 4 or 5-star hotel rooms

or $1,500 to $2,850 per night for a preferred vacation rental

 

Wailea Hotel Prices

The cost of staying in Wailea is much higher than the average city. On average hotels are less expensive than vacation rentals. Luxury vacation rentals are more expensive in Wailea 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.

Wailea 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 Wailea 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 Wailea.

 

Flight Costs to Wailea

Averaging flights around the world, prices go from a high of $1,500 average in late December to a low of $929 in early September. Median flight price is $901. These prices are based on millions of flights. For Wailea our data includes 431 originating airports, and 106 airlines. The area has more variance in price compared with other locations. Flying to Wailea from an airport like Shevchenko (SCO) in Aktau (Kazakhstan) for an average $7,753 trip fare will obviously cost a lot more than from an airport like Hana (HNM) in Hana, HI (the United States) at an average of just $96.

 

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
Return Day Prices

 

The cheapest day to fly in is typically Tuesday, and the cheapest day to fly back is usually Tuesday. Click here to see data for the cost of flights from your airport. In Wailea, the difference between the cheapest and the most expensive week is about $571, so you can easily save about 62% 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 Wailea can easily cost $900 per person or more, while a standard nice meal might be about $60 per person. Private tours can cost $1798 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 Wailea Guides