Grassy Key Vacations from ￥329,299

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The Latest Grassy Key Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Pelican Hotel

Pelican Hotel

4 out of 5
South Beach
Price was ￥491,784, price is now ￥329,299 per person
￥329,299
per person
Mar 13 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
9.2/10 Wonderful! (394 reviews)
Beautiful room. Perfect location on south beach.

Reviewed on Jan 8, 2026

EAST Miami

EAST Miami

5 out of 5
Brickell
Save 100% on your flight
Price was ￥718,096, price is now ￥469,766 per person
￥469,766
per person
Mar 13 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
9.2/10 Wonderful! (3,553 reviews)
My wife and I stayed at east hotel from December 30th to January 2nd. This past holiday season. The staff were very professional and helpful friendly. From the architecture to the interiors, as well as the staff experience.This hotel is top quality as far as i'm concerned. Our stay was fantastic. The amenities were great. The room was big. The bed was big and very comfortable. The shower was big.The balcony was great. Sugar and the tea room are both located on the roof of this hotel. They are a total vibe. Sugar is just a great place to hang out and enjoy miami. The tier room is amazing.The food is amazing.The music was amazing top notch experience. Super vibi place, write in brickle, which is alive all the time with people. The restaurants in that area are killer. The indoor outdoor mall is right there. It's a great spot period

Reviewed on Jan 8, 2026

Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
Mid Beach
Save 100% on your flight
Price was ￥897,345, price is now ￥622,072 per person
￥622,072
per person
Mar 13 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8.2/10 Very Good! (7,303 reviews)
It was really nice just make sure you have quite a bit of money the whole thing is expensive

Reviewed on Jan 9, 2026

Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Mid Beach
Price was ￥511,508, price is now ￥358,914 per person
￥358,914
per person
Mar 13 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8/10 Very Good! (1,120 reviews)
Front desk staff was not very helpful. Even before the stay, I called to ask some questions. They were not helpful and lacked interest when asking basic questions (i.e. parking at the hotel). Also, there was a clump of hair in the bed upon check in. I wish I could attach the photo.

Reviewed on Jan 3, 2026

Nomada Residences

Nomada Residences

4 out of 5
Northeast Miami
Price was ￥492,368, price is now ￥352,374 per person
￥352,374
per person
Mar 13 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
9.2/10 Wonderful! (548 reviews)
Amazing, gorgeous and beautiful and spotless.

Reviewed on Jan 8, 2026

Find the Best Grassy Key Vacation Packages

Grassy Key Hotel Deals

Rainbow Bend Resort

Rainbow Bend Resort

2.5 out of 5
57784 Overseas Hwy Marathon FL
Fully refundableReserve now, pay when you stay
The price is ￥16,142 per night from Jan 12 to Jan 13
￥16,142
￥25,220 total
Jan 12 - Jan 13
includes taxes & fees
8/10 Very Good! (806 reviews)
I never made it to the hot tub. If we stay again I hope to make it. Very roomie rooms.

Reviewed on Jan 8, 2026

Rainbow Bend Resort
Grassy Flats Resort & Beach Club

Grassy Flats Resort & Beach Club

2.5 out of 5
58182 Overseas Hwy Marathon FL
Fully refundableReserve now, pay when you stay
The price is ￥47,468 per night from Jan 12 to Jan 13
￥47,468
￥53,402 total
Jan 12 - Jan 13
includes taxes & fees
9.4/10 Exceptional! (366 reviews)
Beautiful resort, felt like a deserted island. Perfect to set! Staff was very friendly and helpful. Really enjoyed our quick getaway!!

Reviewed on Jan 5, 2026

Grassy Flats Resort & Beach Club
Gulf View Waterfront Resort

Gulf View Waterfront Resort

2.5 out of 5
58743 OVERSEAS HWY Marathon FL
8.4/10 Very Good! (535 reviews)
Maria at the front desk was so nice and welcoming, letting me look around the property before deciding to making my booking decision. I got there an hour bedorw check in and she allowed me to gonin my room early. She even suggested a nearby place to eat. The room was neat and had a fully stocked ...

Reviewed on Dec 16, 2025

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Gulf View Waterfront Resort
See all 2,291 properties in Grassy Key
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Discover the most popular places to visit in Grassy Key

Sombrero Beach which includes a beach and general coastal views

Sombrero Beach

Play beach games; go swimming, kayaking or snorkeling; and lounge in the sun at one of Marathon’s most visited beaches.

Sombrero Beach
Seven Mile Bridge showing general coastal views and a bridge

Seven Mile Bridge

Walk, jog, cycle or drive across one of the longest bridges in North America to take in the scenic ocean views it provides.

Seven Mile Bridge

What to do in Grassy Key

Thumbs up!

Mangroves and Manatees - Guided Kayak Eco Tour

￥10,803
per adult
96% of travellers recommend
Mangroves and Manatees - Guided Kayak Eco Tour
Marathon: Rhum Runner Aqua Park Adventure

Marathon: Rhum Runner Aqua Park Adventure

￥5,890
per adult
Marathon: Rhum Runner Aqua Park Adventure
Our sailboat is named Chao Lay. The boat has completed one complete circumnavigation of the globe crossing the Atlantic, Pacific, and Indian Oceans.

Day Sailing Adventure in the Florida Marine Sanctuary

￥15,500
per adult
100% of travellers recommend
Day Sailing Adventure in the Florida Marine Sanctuary
See all activities in Grassy Key

Frequently asked questions

Can I cancel my flight booking to Grassy Key due to COVID-19?
If you've yet to book your tickets, check the terms and conditions of the airfare you're considering. If you've already locked in your flight to Grassy Key, make use of our Customer Service Portal. It has information that will help you work out which COVID-19 policies apply to your reservation and provide you with the next steps.
What's the best way to find cheap flights to Grassy Key that have flexible change policies?
By using our nifty "No change fee" filter, that's how. Just type in your travel details, click "Search," then check the box underneath the "Flexible change policies" heading (to the left of your screen). Expedia makes it easy to find flexible and affordable tickets to Grassy Key.
What are some of the general tips for travelers to Grassy Key during the COVID-19 outbreak?
The COVID-19 pandemic has triggered substantial changes to the way we travel. If you're planning a trip to Grassy Key, these tips will help you navigate travel's newest challenges:
  • Investigate if any travel restrictions apply to your origin and destination before booking anything. Also check if there are any conditions you'll need to follow on arrival, such as proof of a negative COVID-19 test.
  • When you pass through airport screening, keep your face mask on. You will be required to lower it briefly to verify your identity. Anyone refusing to wear a mask may face civil penalties and may also be denied boarding.
  • Rather than handing a TSA employee your boarding pass, position it directly on the reader yourself. When that's done, hold it up for inspection.
  • You are now allowed to take one container of hand sanitizer up to 12 oz (350 ml) in your carry-on baggage. This will need to be removed for X-ray scanning.
  • Remove items from your pockets, such as your wallet, coins and keys, and put them in your carry-on instead of the bins. This will reduce handling during the screening process.
  • Transport any food items in a clear plastic bag and also place them in a screening bin. Keeping your food separate from your carry-on means it's less likely a TSA officer will need to open your bag for inspection.

Which airlines fly to Grassy Key?
Delta runs flights into or near Grassy Key, including 191 that land at Key West Intl. Airport (EYW) each month. Work out your vacation dates and then reserve your ticket early to score the best deal.
How can I find cheap tickets to Grassy Key?
For an amazing deal to Grassy Key, book well ahead of time. Also think about using Expedia's "flexible dates" feature above your search results. This will show you the cheapest prices for nearby days. In the last seven days, was the best price for a flight to Grassy Key.
How much is a flight to Grassy Key?
One-way flights taking off from () sold for just in the last seven days. During this time, the cost of a return ticket to Grassy Key ranged between and . If you spot a bargain ticket, book ASAP — these prices don't stick around for long.
What are the most popular airports to fly into in Grassy Key?
Pack your suitcase and fly into Key West Intl. Airport (EYW), Grassy Key's leading flight hub. Book a ticket on one of the 1119 flights that touch down at this favorite destination every month.
When is the cheapest time to fly to Grassy Key?
Try to leave earlier in the week to score the best deal to Grassy Key. Tuesday is usually the most affordable day to fly, with Monday a close second. Saturday often has the costliest ticket prices. This is because many travelers like to start their vacation on a weekend.
How much is a plane ticket to Grassy Key?
In the last seven days, plane fares to Grassy Key ranged from to .
Which airlines with flights to Grassy Key employ COVID-19 cleanliness policies?
In an effort to minimize contact between passengers and flight crew during the ongoing pandemic, many airlines have taken physical distancing and other strategies to the skies. A great example of these are:
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.
  • Frontier Airlines - this airline is known for electrostatic cleaning and conducting passenger temperature checks.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.