A Travel Price Comparison for Families, Couples, and Backpackers Grand Cayman vs. Key West for Vacations, Tours, and Honeymoons

Should you visit Grand Cayman or Key West?

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

Which city should you visit? Read on to compare the activities as well as the prices of travel for Grand Cayman and Key West. We'll break down costs for accommodation, food, transportation and more to help you learn more about these two destinations. Then, you can figure out if either of these two places are accessible based on your travel budget, schedule, and interests. So, let's dig into it.

Where Should I go: Grand Cayman or Key West?

Grand Cayman

When people think of the Cayman Islands, they typically think of offshore bank accounts and sunny, cruise ship ports. Grand Cayman has more to offer travelers than a playground for the wealthy or a short stopover for cruise passengers. This tropical island is the largest of the three Cayman Islands, it is a shopper's heaven, a center for global finance and an ideal vacation spot.

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.

For some great organized tour ideas, see The Best Train & Rail Tours in United States of America, and The Best Sightseeing Tours in United States of America.


Which place is cheaper, Key West or Grand Cayman?

These are the overall average travel costs for the two destinations. These travel costs come from the actual spending of real travelers.

The average daily cost (per person) in Grand Cayman is $242, while the average daily cost in Key West is $247. 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 Grand Cayman and Key West in more detail.



Accommodation
  • Accommodation Hotel or hostel for one person
    Grand Cayman $149
    Key West $132
  • Accommodation Typical double-occupancy room
    Grand Cayman $298
    Key West $264
Compare Hotels in Grand Cayman and Key West

Looking for a hotel in Grand Cayman or Key West? 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 Grand Cayman


Hotels in Key West


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: Grand Cayman Hotel Prices and Key West Hotel Prices.

Local Transportation
  • Local Transportation Taxis, local buses, subway, etc.
    Grand Cayman $31
    Key West $51

Hired Cars and Shuttles in Grand Cayman

Also for Grand Cayman, here are a few examples of actual transportation services:

  • Airport Transfer to West Bay Accommodations (GCM)-Round Trip: $88
  • Owen Roberts Airport GCM to George Town-Arrival Private Transfer: $150
  • Owen Roberts Airport (GCM) to George Town Cruise Port - Arrival Private Transfer: $150

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 hotels to Key West Cruise Port: $112
  • Private Transfer from Key West Port to Key West Airport (EYW): $111
  • Private Transfer from Key West Cruise Port to Key West hotels: $112
  • Private Transfer from Key West Airport (EYW) to Key West Port: $111
  • Private Arrival Transfer from Key West Airport EYW: $144
  • One Way Airport Transfer Service: $54
  • Key West to Key West Airport (EYW) - Departure Private Transfer: $153
  • Key West Airport (EYW) to Key West - Arrival Private Transfer: $153

Is it cheaper to fly into Grand Cayman or Key West?

Prices for flights to both Key West and Grand Cayman 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
    Grand Cayman $67
    Key West $81

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: $74
  • Cooking Show Chef Demonstration with Meal: $81
  • Southernmost Food & Cultural Walking Tour by Key West Food Tours: $90
  • Key West Cooking Show Chef Demonstration with Meal: $91
  • Key West Sunset Cruise: Dinner, Live Music & Drinks Included: $93
  • Secret Walking Food Tour: $115
  • Key West Sunset Buffet Dinner Cruise with Open Bar and Live Music: $120

Entertainment
  • Entertainment Entrance tickets, shows, etc.
    Grand Cayman $41
    Key West $33

Tours and Activities in Grand Cayman

For Grand Cayman, here are a few prices for actual activities, tours, and tickets provided by various companies:

  • Diamonds and Cocktails a Shopping Experience in Grand Cayman: $10
  • Bling and Beverages Cayman Jewelry Shopping Experience: $22
  • Fun Family StingrayCity Adventure.: $55
  • Stingray City Catamaran Sunset Tour: $59
  • Stingray City Catamaran Sunset Tour: $59
  • 4 Stops Tour: Stingray, Snorkeling, Starfish & 7 Mile Beach: $60
  • Stingray City and Starfish Experience with Coral Reef Snorkeling: $62
  • Cayman Best Stingray City Reef Snorkel and Starfish Point Tour: $63
  • Stingray City Sandbar Experience: $65
  • 3 Stop Boat Tour Stingray City Coral Gardens and Starfish Point: $65
  • Oculus Glass Bottom Boat Tour: $66
  • Stingrays and Starfish Point Tour: $70

Tours and Activities in Key West

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

  • 2 Hour Key West Mini Catamaran Eco Tour: $285
  • 2 Hour Mangrove Maze Kayak Tour in Key West: $65
  • Cruisin Tikis Marathon - Sunset Tiki Cruise: $89
  • Day Sailing Adventure in the Florida Marine Sanctuary: $120
  • Day in Key West - Private SUV Tour From Miami: $1,300
  • Florida Key West Self-Guided Walking Audio Tour: $9.99
  • Florida Keys Nature & History Tour from Key West: $119
  • Florida Keys: Aquarium Encounters Day Tour with Lunch: $182
  • Florida Keys: Dolphin Research Center Day Tour with Lunch: $182
  • Florida Keys: Up The Keys Nature Tour: $128
  • From Dolphin Watching Tour with Lunch & Drinks: $150
  • From Sandbar Cruise with Lunch and Open Bar (18+): $151

Alcohol
  • Alcohol Drinks for one day
    Grand Cayman $13
    Key West $16
Typical Alcohol Prices in Grand Cayman

Below are a few samples from actual travelers for alcohol and nightlife costs in Grand Cayman:


  • Beer
    $4.96

Sample the Local Flavors in Grand Cayman

Here are a few nightlife and alcohol tours and activities from local tour providers in Grand Cayman:

  • Cayman Spirits Co. Distillery Tour Pass Ticket Only: $24
  • Distillery Tour with Gin Tasting: $75
  • Cayman Art and Wine Tour: $150

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:

  • A Spectacular Bar Crawl in Key West: $15
  • Bone Island Haunted Pub Crawl: $32
  • Key West Haunted Pub Crawl Walking Tour: $35
  • Haunted Pub Crawl Walking Tour: $35
  • Key West Spirits and Haunted Pub Crawl: $36
  • Original Key West Pub Crawl: The Best Bars with Free T-Shirt: $43
  • 2.5-Hour Duval Street Pub Crawl: $43


When comparing the travel costs between Grand Cayman and Key West, we can see that Key West is more expensive. However, the two cities are actually relatively comparable in price, as the difference is somewhat minimal. Generally, this means that you could travel with generally the same travel style and level of luxury in each place. Even though Grand Cayman is in Caribbean Islands and Key West is in North America, both of these destinations have relatively similar prices of travel. Generally, the levels of luxury and expenses are the same for these cities even though they are geographically far apart.

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


Which is Bigger, Grand Cayman or Key West?

Grand Cayman has a larger population, and is about 19% larger than the population of Key West. When comparing the sizes of Grand Cayman and Key West, 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 Grand Cayman or Key West?

Key West has a temperate climate with four distinct seasons, but Grand Cayman experiences a warm climate with fairly sunny weather most of the year.

Should I visit Grand Cayman or Key West in the Summer?

The summer brings many poeple to Grand Cayman as well as Key West. Grand Cayman attracts visitors year-round for its warm weather and sunny climate. Additionally, many travelers come to Key West for the beaches, snorkeling, the small town charm, and the family-friendly experiences.

In July, Grand Cayman is generally around the same temperature as Key West. Daily temperatures in Grand Cayman average around 28°C (83°F), and Key West fluctuates around 84°F (29°C).

Grand Cayman receives a lot of rain in the summer. Grand Cayman usually gets more rain in July than Key West. Grand Cayman gets 179 mm (7 in) of rain, while Key West receives 3.3 inches (83 mm) of rain this time of the year.


  • Summer Average Temperatures July
    Grand Cayman 28°C (83°F) 
    Key West 84°F (29°C)

Should I visit Grand Cayman or Key West in the Autumn?

Both Key West and Grand Cayman are popular destinations to visit in the autumn with plenty of activities. The warm climate attracts visitors to Grand Cayman throughout the year. Also, many visitors come to Key West in the autumn for the shopping scene, the small town atmosphere, and the natural beauty of the area.

Grand Cayman is around the same temperature as Key West in the autumn. The daily temperature in Grand Cayman averages around 27°C (81°F) in October, and Key West fluctuates around 80°F (27°C).

It rains a lot this time of the year in Key West. It's quite rainy in Grand Cayman. In October, Grand Cayman usually receives more rain than Key West. Grand Cayman gets 238 mm (9.4 in) of rain, while Key West receives 5.1 inches (129 mm) of rain each month for the autumn. The hurricane season in Key West is June to November.


  • Autumn Average Temperatures October
    Grand Cayman 27°C (81°F) 
    Key West 80°F (27°C)

Should I visit Grand Cayman or Key West in the Winter?

Both Key West and Grand Cayman during the winter are popular places to visit. Plenty of visitors come to Grand Cayman because of the warm climate and sunshine that lasts throughout the year. Also, most visitors come to Key West for the shopping scene and the cuisine during these months.

In the winter, Grand Cayman is a little warmer than Key West. Typically, the winter temperatures in Grand Cayman in January average around 24°C (76°F), and Key West averages at about 70°F (21°C).

Grand Cayman usually gets more rain in January than Key West. Grand Cayman gets 58 mm (2.3 in) of rain, while Key West receives 1.7 inches (43 mm) of rain this time of the year.


  • Winter Average Temperatures January
    Grand Cayman 24°C (76°F) 
    Key West 70°F (21°C)

Should I visit Grand Cayman or Key West in the Spring?

The spring attracts plenty of travelers to both Grand Cayman and Key West. Warm weather and sunshine bring visitors to Grand Cayman year-round. Also, the spring months attract visitors to Key West because of the beaches, the small town charm, and the natural beauty.

In April, Grand Cayman is generally around the same temperature as Key West. Daily temperatures in Grand Cayman average around 26°C (79°F), and Key West fluctuates around 77°F (25°C).

In April, Grand Cayman usually receives more rain than Key West. Grand Cayman gets 48 mm (1.9 in) of rain, while Key West receives 0.8 inches (21 mm) of rain each month for the spring. June to November is the hurricane season in Key West.


  • Spring Average Temperatures April
    Grand Cayman 26°C (79°F) 
    Key West 77°F (25°C)

Typical Weather for Key West and Grand Cayman

Grand Cayman Key West
Temp (°C) Rain (mm) Temp (°C) Rain (mm)
Jan 24°C (76°F) 58 mm (2.3 in) 70°F (21°C) 1.7 inches (43 mm)
Feb 24°C (76°F) 51 mm (2 in) 71°F (21°C) 1.4 inches (36 mm)
Mar 25°C (77°F) 31 mm (1.2 in) 74°F (23°C) 1.7 inches (42 mm)
Apr 26°C (79°F) 48 mm (1.9 in) 77°F (25°C) 0.8 inches (21 mm)
May 27°C (81°F) 131 mm (5.1 in) 81°F (27°C) 2.7 inches (68 mm)
Jun 28°C (82°F) 183 mm (7.2 in) 83°F (28°C) 4.5 inches (114 mm)
Jul 28°C (83°F) 179 mm (7 in) 84°F (29°C) 3.3 inches (83 mm)
Aug 28°C (82°F) 172 mm (6.8 in) 84°F (29°C) 3.9 inches (98 mm)
Sep 28°C (82°F) 212 mm (8.3 in) 83°F (29°C) 5.7 inches (144 mm)
Oct 27°C (81°F) 238 mm (9.4 in) 80°F (27°C) 5.1 inches (129 mm)
Nov 26°C (79°F) 141 mm (5.6 in) 76°F (24°C) 2 inches (50 mm)
Dec 25°C (78°F) 57 mm (2.3 in) 72°F (22°C) 1.4 inches (35 mm)