Grassy Key Holidays

Photo by Monica Ferro

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Top Flight + Hotel Deals in Grassy Key

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 €2,028, price is now €1,043 per person
€1,043
per person
28 Feb - 7 Mar
found 1 day ago
Return direct flight included
Dublin (DUB) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
I had a wondeful time at this hotel (1/20-1/24/2026). The staff was polite, friendly and always ready to help. Room was clean and stylish exacly like the photo. The location is perfect: quiet and peaceful. And the same time not far from popular places. I really enjoyed my stay and would definitely recommend this hotel to others.

Reviewed on 26 Jan 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 €29,610, price is now €14,339 per person
€14,339
per person
28 Feb - 7 Mar
found 1 day ago
Return direct flight included
Dublin (DUB) to Miami (MIA)
8/10 Very Good! (1 review)
President Hotel

President Hotel

3.5 out of 5
South Beach
Price was €2,133, price is now €1,190 per person
€1,190
per person
28 Feb - 7 Mar
found 1 day ago
Return direct flight included
Dublin (DUB) to Miami (MIA)
8.4/10 Very Good! (1,775 reviews)
Great hotel with great breakfast

Reviewed on 26 Jan 2026

President Hotel Villa

President Hotel Villa

3.5 out of 5
South Beach
Price was €2,133, price is now €1,190 per person
€1,190
per person
28 Feb - 7 Mar
found 1 day ago
Return direct flight included
Dublin (DUB) to Miami (MIA)
8.2/10 Very Good! (997 reviews)
We had a great stay at President Hotel Villa and stayed in a Deluxe Room. The room was clean, bright, and very comfortable. I want to give special thanks to Henry at the front desk — his service was outstanding. He was incredibly kind, caring, and attentive, and truly made us feel welcome. It’s rare to meet someone who cares so genuinely about guests. Breakfast was included, the price was very fair, and the location is perfect. The hotel is close to the beach but on the second line, which makes it quiet and peaceful. The nearby beach is also very nice. We really enjoyed our stay and would happily come back again.

Reviewed on 21 Jan 2026

The Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
Price was €1,821, price is now €1,052 per person
€1,052
per person
28 Feb - 7 Mar
found 1 day ago
Return direct flight included
Dublin (DUB) to Miami (MIA)
8.2/10 Very Good! (1,491 reviews)
Everything was great!

Reviewed on 26 Jan 2026

Top hotels in Grassy Key

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 €163 per night from 5 Feb to 6 Feb
€163
5 Feb - 6 Feb
includes taxes & fees
8/10 Very Good! (823 reviews)
Great Location Staff was Friendly Would stay there again

Reviewed on 22 Jan 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 €429 per night from 28 Jan to 29 Jan
€429
28 Jan - 29 Jan
includes taxes & fees
9.4/10 Exceptional! (378 reviews)
Staff was very kind. Room was clean beautiful views

Reviewed on 20 Jan 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! (542 reviews)
room appeared very clean. Staff had left the facility before we arrived.

Reviewed on 22 Jan 2026

Get rates
Gulf View Waterfront Resort
See all 2,298 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.

Popular places to visit

Sombrero Beach showing 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
Coco Plum Beach, Florida Keys

Coco Plum Beach

Why not spend a lazy afternoon at Coco Plum Beach during your trip to Marathon? Discover the area's beautiful sunsets or seek out its jogging trails.

Coco Plum Beach

What to do in Grassy Key

Thumbs up!

Mangroves and Manatees - Guided Kayak Eco Tour

€59
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

€32
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

€85
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 travellers 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 holiday 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 favourite 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 travellers like to start their holiday 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.