Grassy Key Vacations from ￥347,906

Book a Hotel + Flight or Car together to unlock savings

Photo by Monica Ferro

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥45,448 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Grassy Key Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was ￥483,567, price is now ￥347,906 per person
￥347,906
per person
Apr 29 - May 5
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
Loved the location, room was nice, bathroom very small, very friendly staff, slow service at restaurant in the morning. Will go back

Reviewed on Feb 24, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was ￥5,577,227, price is now ￥2,720,360 per person
￥2,720,360
per person
Apr 29 - May 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8/10 Very Good! (1 review)
Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Mid Beach
Price was ￥596,394, price is now ￥405,922 per person
￥405,922
per person
Apr 29 - May 5
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8/10 Very Good! (1,120 reviews)
Staff are great but the bed and pillows were uncomfortable. Especially the pillows they are horrible. I had to use a towel as my pillow. Other hotels have feather pillows that are far more comfortable. It would be nice to have a choice. For this reason we won’t return. It’s too bad because everything else was nice.

Reviewed on Feb 19, 2026

The Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
Price was ￥486,183, price is now ￥353,314 per person
￥353,314
per person
Apr 29 - May 5
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8.2/10 Very Good! (1,491 reviews)
It was perfect. It was right across from the beach lots of shops lots of restaurants lovely area.

Reviewed on Feb 24, 2026

President Hotel

President Hotel

3.5 out of 5
South Beach
Price was ￥484,422, price is now ￥352,580 per person
￥352,580
per person
Apr 29 - May 5
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8.4/10 Very Good! (1,775 reviews)
Staff was very friendly and great locations. The rooms were decent for the price but did have a mild funky aroma. I guess that can expected when you are in such a humid hot environment..

Reviewed on Feb 24, 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 ￥27,021 per night from Mar 1 to Mar 2
￥27,021
￥37,357 total
Mar 1 - Mar 2
includes taxes & fees
8.2/10 Very Good! (864 reviews)
Walls were thin and had adjoining doors. could hear people in the other room breathe. Felt like we had no privacy. TV only worked half the time. Paid in full before arrival. Then when I got there they tried to run my card for $187 and then again when I left for $215. Both were declined because I ...

Reviewed on Feb 24, 2026

Rainbow Bend Resort
Grassy Flats Resort & Beach Club

Grassy Flats Resort & Beach Club

2.5 out of 5
58182 Overseas Hwy Marathon FL
The price is ￥54,098 per night from Mar 8 to Mar 9
￥54,098
￥68,283 total
Mar 8 - Mar 9
includes taxes & fees
9.4/10 Exceptional! (406 reviews)
When we checked in we were upgraded to a fantastic room. The views at this resort are incredible. The staff was so friendly and welcoming and the onsite restaurant was the best.

Reviewed on Feb 24, 2026

Grassy Flats Resort & Beach Club
Gulf View Waterfront Resort

Gulf View Waterfront Resort

2.5 out of 5
58743 OVERSEAS HWY Marathon FL
8.6/10 Excellent! (551 reviews)
The bathroom was extremely small including a shower that was minute. The electricity in the bathroom flickered on and off. Amenities were barely existent. It took 4 days for the “heated” pool to warm up to be useable. No maid service ALL week. We had to go to the laundry room to get fresh towels. ...

Reviewed on Feb 15, 2026

Get rates
Gulf View Waterfront Resort
See all 2,301 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

4.5/5(417 reviews)

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

4.5/5(830 reviews)

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

￥10,680
per adult
96% of travellers recommend
Mangroves and Manatees - Guided Kayak Eco Tour
Sunset Cruise

Sunset Cruise

￥13,391
per adult
Sunset Cruise
Marathon: Rhum Runner Aqua Park Adventure

Marathon: Rhum Runner Aqua Park Adventure

￥5,823
per adult
Marathon: Rhum Runner Aqua Park Adventure
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.

Explore a world of travel with Expedia

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