A Travel Price Comparison for United States of America Key West vs. Kailua-Kona for Vacations, Tours, and Honeymoons

Should you visit Key West or Kailua-Kona?

Which is cheaper to visit? Which is more expensive for vacation?

Should I visit Key West or Kailua-Kona? This is a common question asked by many travelers. By figuring out which city has activities that align with your interests along with knowing which is more affordable, you'll understand where you can get more bang for your buck. So, let's dive into the details and the data, which all comes from actual travelers.

Where Should I go: Key West or Kailua-Kona?

Key West

Key West is both a city and an island as well as the southern most Florida Key. It is also the southern most city in the continental United States. The island is only about four miles long and one mile wide. The total land mass covers just 4.2 square miles. The most famous street in town is Duval Street, which runs just 1.1 miles from the Gulf of Mexico to the Atlantic Ocean. There are 14 blocks. The size of the island doubled during the 1950s when many of the salt ponds along the eastern side of the island were filled in.

Kailua-Kona

Kailua Kona, or Kona, as it is commonly referred, is the largest city on the western side of the Big Island of Hawaii. It's a popular destination for sport fishing, snorkeling, and its beautiful sunsets. Kona is protected by the mountains so it receives very little rain annually and has about 300 days of sunshine every year. The closest airport is Kona International Airport at Keahole, which receives flights from the mainland United States, Canada, as well as Honolulu and other islands. Once in town, you can walk around Kona, but if you hope to explore anywhere else on the Big Island you will need a car. To take full advantage of your Hawaiian vacation it really is recommended that you rent a car for at least a few days while you're on the island.

For some great organized tour ideas, see The Best One-Week (7-Day) Tours from Los Angeles, The Best One-Week (7-Day) Tours from New York City, The Best 2-Week Tours from New York City, and The Best 2-Week Tours from Anchorage.


Which place is cheaper, Kailua-Kona or Key West?

These are the overall average travel costs for the two destinations.

The average daily cost (per person) in Key West is $551, while the average daily cost in Kailua-Kona is $231. These costs include accommodation (assuming double occupancy, so the traveler is sharing the room), food, transportation, and entertainment. While every person is different, these costs are an average of past travelers in each destination. What follows is a categorical breakdown of travel costs for Key West and Kailua-Kona in more detail.



Accommodation
  • Accommodation Hotel or hostel for one person
    Key West $132
    Kailua-Kona $141
  • Accommodation Typical double-occupancy room
    Key West $264
    Kailua-Kona $282
Compare Hotels in Key West and Kailua-Kona

Looking for a hotel in Key West or Kailua-Kona? Prices vary by location, date, season, and the level of luxury. See below for options and compare which is best for your budget and travel style.

Hotels in Key West


Hotels in Kailua-Kona


Kayak helps you find the best prices for hotels, flights, and rental cars for destinations around the world. Compare prices for multiple destinations when planning your next trip.


Our Analysis
We've analyzed the average and typical hotel prices based on guest reviews, star ratings, and hotel amenities here: Key West Hotel Prices and Kailua-Kona Hotel Prices.

Local Transportation
  • Local Transportation Taxis, local buses, subway, etc.
    Key West $51
    Kailua-Kona $45
Typical Local Transportation Prices in Key West

Below are a few samples from actual travelers for transportation costs in Key West:


  • Rental Car for One Day
    $38

Hired Cars and Shuttles in Key West

Some specific examples of transportation prices in Key West:

  • Private Transfer from Key West Int Airport to Key West Port: $38
  • Private Transfer from Key West Cruise Port to Key West hotels: $38
  • Key West Int Airport (EYW) to Key West - Arrival Private Transfer: $64
  • Key West to Key West Airport (EYW) - Departure Private Transfer: $64
  • Key West hotels to Key West Int Airport (EYW) Departure Transfer: $64
  • Marathon/ Key Largo to Fort Lauderdale Airport(FLL) - Departure Private Transfer: $109
  • Key West Airport (EYW) to Key West - Round-Trip Private Transfer: $129
  • Key West Int Airport (EYW) to Key West hotels Round-Trip Transfer: $129
  • Private Arrival Transfer from Key West Airport EYW: $144

Typical Local Transportation Prices in Kailua-Kona

Some typical examples of transportation costs in Kailua-Kona are as follows:


  • Rental Car for One Day
    $35

Is it cheaper to fly into Key West or Kailua-Kona?

Prices for flights to both Kailua-Kona and Key West change regularly based on dates and travel demand. We suggest you find the best prices for your next trip on Kayak, because you can compare the cost of flights across multiple airlines for your prefered dates.





Food
  • Food Meals for one day
    Key West $385
    Kailua-Kona $58

Food Tours and Cooking Classes in Key West

Also, here are some specific examples of food and dining related activities in Key West.

  • Sunset Dinner Cruise with Open Bar & Live Music: $81
  • Key West Sunset Cruise: Dinner and Drinks Included: $93
  • Southernmost Food & Cultural Walking Tour by Key West Food Tours: $93
  • Historic Seaport Food & Walking Tour by Key West Food Tours: $93
  • Old Town Secret Food Tour: $107
  • Sunset Sail Full Bar, Live Music & Dinner & Early Morning Snorkeling: $160
  • Snorkeling, Sunset Dinner Cruise & Open Bar: $200

Typical Food Prices in Kailua-Kona

Some typical examples of dining costs in Kailua-Kona are as follows:


  • Buffet Breakfast for Two
    $53

Entertainment
  • Entertainment Entrance tickets, shows, etc.
    Key West $33
    Kailua-Kona $40

Tours and Activities in Key West

Some specific costs of activities, tours, and entrance tickets for Key West are as follows:

  • Self-guided old town treasures walking tour: $6.99
  • Key West's Self Guided Ghost Walking Tours Smartphone Navigated on WalknTours: $7.75
  • Florida Keys: Self-Guided Walking Tour: $8.49
  • Audio Tours to Walk, Bike, or Drive in Key West: $9.99
  • Cruise Through Key West's Black History Audio Tour: $11
  • Easy Stroll (or Bike) Through Downtown Key West Audio Tour: $11
  • Key West’s Old Town Treasures: A Self-Guided Audio Tour: $15
  • Florida: Key West Overseas Highway Self-Driving Tour: $15
  • Mel Fisher Maritime Museum Admission Ticket: $18
  • Key West Shipwreck Treasure Museum Tickets: $19
  • Key West Shipwreck Treasure Museum Admission Ticket: $19
  • Key West Aquarium Admission Ticket: $23

Typical Entertainment Prices in Kailua-Kona

Some typical examples of activities, tours, and entrance ticket prices in Kailua-Kona are as follows:


  • Diving with Manta Rays for Two
    $162
  • Body Board Rental (1 Day)
    $12
  • 1 Day Kayak Rental
    $47
  • 2 Tank Morning Scuba Dive
    $115

Tours and Activities in Kailua-Kona

Some specific costs of activities, tours, and entrance tickets for Kailua-Kona are as follows:

  • From Kona-Volcanoes & waterfall tour in a small group: $295

Alcohol
  • Alcohol Drinks for one day
    Key West $16
    Kailua-Kona $15

Sample the Local Flavors in Key West

Also in Key West, these are the prices for nightlife and alcohol related activities from various tour providers:

  • Haunted Pub Crawl Walking Tour: $30
  • Key West Haunted Pub Crawl and Ghost Tour with Free T-Shirt: $32
  • Bone Island Haunted Pub Crawl: $32
  • 2.5-Hour Duval Street Pub Crawl: $43


When we compare the travel costs of actual travelers between Key West and Kailua-Kona, we can see that Key West is more expensive. And not only is Kailua-Kona much less expensive, but it is actually a significantly cheaper destination. So, traveling to Kailua-Kona would let you spend less money overall. Or, you could decide to spend more money in Kailua-Kona and be able to afford a more luxurious travel style by staying in nicer hotels, eating at more expensive restaurants, taking tours, and experiencing more activities. The same level of travel in Key West would naturally cost you much more money, so you would probably want to keep your budget a little tighter in Key West than you might in Kailua-Kona.

If you're trying to decide if either of these two destinations are within your price range, also see Is Key West Expensive? and Is Kailua-Kona Expensive?.


Which is Bigger, Key West or Kailua-Kona?

Key West has a larger population, and is about 2 times larger than the population of Kailua-Kona. When comparing the sizes of Key West and Kailua-Kona, keep in mind that a larger population does not always imply the destination has more attractions or better activities. So, always research the type of place that you want to visit along with the activities and attractions that interest you.


When is the best time to visit Key West or Kailua-Kona?

Both destinations experience a temperate climate with four distinct seasons. And since both cities are in the northern hemisphere, summer is in July and winter is in January.

Should I visit Key West or Kailua-Kona in the Summer?

Both Kailua-Kona and Key West are popular destinations to visit in the summer with plenty of activities. Many travelers come to Key West for the beaches, snorkeling, the small town charm, and the family-friendly experiences.

In July, Key West is generally a little warmer than Kailua-Kona. Daily temperatures in Key West average around 84°F (29°C), and Kailua-Kona fluctuates around 78°F (25°C).

The sun comes out a lot this time of the year in Key West. Key West usually receives more sunshine than Kailua-Kona during summer. Key West gets 328 hours of sunny skies, while Kailua-Kona receives 169 hours of full sun in the summer.

In July, Key West usually receives more rain than Kailua-Kona. Key West gets 3.3 inches (83 mm) of rain, while Kailua-Kona receives 2.3 inches (58 mm) of rain each month for the summer.


  • Summer Average Temperatures July
    Key West 84°F (29°C) 
    Kailua-Kona 78°F (25°C)

Should I visit Key West or Kailua-Kona in the Autumn?

Both Kailua-Kona and Key West during the autumn are popular places to visit. Many visitors come to Key West in the autumn for the shopping scene, the small town atmosphere, and the natural beauty of the area.

Key West is around the same temperature as Kailua-Kona in the autumn. The daily temperature in Key West averages around 80°F (27°C) in October, and Kailua-Kona fluctuates around 78°F (26°C).

It's quite sunny in Key West. In the autumn, Key West often gets more sunshine than Kailua-Kona. Key West gets 258 hours of sunny skies this time of year, while Kailua-Kona receives 138 hours of full sun.

It rains a lot this time of the year in Key West. Key West usually gets more rain in October than Kailua-Kona. Key West gets 5.1 inches (129 mm) of rain, while Kailua-Kona receives 1.6 inches (41 mm) of rain this time of the year. Keep in mind that June to November is the hurricane season in Key West.


  • Autumn Average Temperatures October
    Key West 80°F (27°C) 
    Kailua-Kona 78°F (26°C)

Should I visit Key West or Kailua-Kona in the Winter?

The winter attracts plenty of travelers to both Key West and Kailua-Kona. Most visitors come to Key West for the shopping scene and the cuisine during these months.

In the winter, Key West is around the same temperature as Kailua-Kona. Typically, the winter temperatures in Key West in January average around 70°F (21°C), and Kailua-Kona averages at about 74°F (23°C).

In Key West, it's very sunny this time of the year. Key West usually receives more sunshine than Kailua-Kona during winter. Key West gets 252 hours of sunny skies, while Kailua-Kona receives 158 hours of full sun in the winter.

Kailua-Kona receives a lot of rain in the winter. In January, Key West usually receives less rain than Kailua-Kona. Key West gets 1.7 inches (43 mm) of rain, while Kailua-Kona receives 3.9 inches (100 mm) of rain each month for the winter.


  • Winter Average Temperatures January
    Key West 70°F (21°C) 
    Kailua-Kona 74°F (23°C)

Should I visit Key West or Kailua-Kona in the Spring?

The spring brings many poeple to Key West as well as Kailua-Kona. The spring months attract visitors to Key West because of the beaches, the small town charm, and the natural beauty.

In April, Key West is generally around the same temperature as Kailua-Kona. Daily temperatures in Key West average around 77°F (25°C), and Kailua-Kona fluctuates around 74°F (24°C).

People are often attracted to the plentiful sunshine in Key West this time of the year. In the spring, Key West often gets more sunshine than Kailua-Kona. Key West gets 326 hours of sunny skies this time of year, while Kailua-Kona receives 134 hours of full sun.

Key West usually gets less rain in April than Kailua-Kona. Key West gets 0.8 inches (21 mm) of rain, while Kailua-Kona receives 3 inches (76 mm) of rain this time of the year. Also, June to November in Key West is the hurricane season.


  • Spring Average Temperatures April
    Key West 77°F (25°C) 
    Kailua-Kona 74°F (24°C)

Typical Weather for Kailua-Kona and Key West

Key West Kailua-Kona
Temp (°C) Rain (mm) Temp (°C) Rain (mm)
Jan 70°F (21°C) 1.7 inches (43 mm) 74°F (23°C) 3.9 inches (100 mm)
Feb 71°F (21°C) 1.4 inches (36 mm) 73°F (23°C) 3.2 inches (82 mm)
Mar 74°F (23°C) 1.7 inches (42 mm) 74°F (23°C) 4.4 inches (111 mm)
Apr 77°F (25°C) 0.8 inches (21 mm) 74°F (24°C) 3 inches (76 mm)
May 81°F (27°C) 2.7 inches (68 mm) 76°F (24°C) 1.6 inches (40 mm)
Jun 83°F (28°C) 4.5 inches (114 mm) 77°F (25°C) 1.8 inches (47 mm)
Jul 84°F (29°C) 3.3 inches (83 mm) 78°F (25°C) 2.3 inches (58 mm)
Aug 84°F (29°C) 3.9 inches (98 mm) 78°F (26°C) 1.9 inches (49 mm)
Sep 83°F (29°C) 5.7 inches (144 mm) 79°F (26°C) 1.1 inches (29 mm)
Oct 80°F (27°C) 5.1 inches (129 mm) 78°F (26°C) 1.6 inches (41 mm)
Nov 76°F (24°C) 2 inches (50 mm) 76°F (25°C) 3.3 inches (85 mm)
Dec 72°F (22°C) 1.4 inches (35 mm) 74°F (24°C) 3.4 inches (87 mm)