Grassy Key Trip

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Photo by Monica Ferro

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Top Grassy Key Flight + Hotel Deals

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

The Penguin Hotel

3.5 out of 5
South Beach
Price was ₹156,678, price is now ₹109,195 per person
₹109,195
per person
30 Dec - 2 Jan
found 1 day ago
Return direct flight included
Chicago (MDW) to Miami (MIA)
16.4/10 Exceptional! (1,491 reviews)
The area was very colourful and convenient to be around.

Reviewed on 17 Nov 2025

The Shelborne By Proper, a Member of Design Hotels

The Shelborne By Proper, a Member of Design Hotels

4 out of 5
South Beach
Save 100% on your flight
Price was ₹309,690, price is now ₹177,925 per person
₹177,925
per person
30 Dec - 2 Jan
found 1 day ago
Return direct flight included
Chicago (MDW) to Miami (MIA)
18.8/10 Exceptional! (56 reviews)
Staff super friendly and welcoming and helpful, room ready

Reviewed on 16 Nov 2025

President Hotel

President Hotel

3.5 out of 5
South Beach
Price was ₹157,017, price is now ₹109,354 per person
₹109,354
per person
30 Dec - 2 Jan
found 1 day ago
Return direct flight included
Chicago (MDW) to Miami (MIA)
16.8/10 Exceptional! (1,775 reviews)
Very clean and updated. Good price. Great location!!! Other than the bed there was only a small desk and desk chair and one luggage rack. No other places to put suitcases to open them other than the bed. There was also no comfy chair to sit in to read. If you wanted to sit down there was only the small desk chair and the bed. The elevator was also very small (3 person) so during busy times it took forever to get a lift to room or to lobby. The breakfast was really good but area was very crowded. Coffee should have been out in lobby so you could get a cup before breakfast. That would also remove it from adding to the crowding in the small diningroom. The outside dining area in back had pigeons. Not real sanitary for eating in.

Reviewed on 16 Nov 2025

72 Park - Miami Beach by Nomada

72 Park - Miami Beach by Nomada

4.5 out of 5
North Beach
Price was ₹195,346, price is now ₹140,350 per person
₹140,350
per person
30 Dec - 2 Jan
found 1 day ago
Return direct flight included
Chicago (MDW) to Miami (MIA)
8.8/10 Excellent! (64 reviews)
Room was so well prepared VIEW WAS AMAZING, STAFF was COURTEOUS and ATTENTIVE

Reviewed on 16 Nov 2025

Park Central South Beach

Park Central South Beach

4 out of 5
South Beach
Price was ₹169,890, price is now ₹127,614 per person
₹127,614
per person
30 Dec - 2 Jan
found 1 day ago
Return direct flight included
Chicago (MDW) to Miami (MIA)
17.2/10 Exceptional! (385 reviews)
Wonderful Stay every time I come to Miami I will be there just to stay at this hotel.

Reviewed on 18 Nov 2025

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 ₹6,696 per night from 20 Nov to 21 Nov
₹6,696
₹11,522 total
20 Nov - 21 Nov
includes taxes & fees
8/10 Very Good! (763 reviews)
Great, has a kitchen in the room. Very comfortable. The beach is very nice. But you can't swim, water is too low, and don't feel safety. We enjoyed any way, very peaceful place.

Reviewed on 14 Nov 2025

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 ₹18,226 per night from 14 Dec to 15 Dec
₹18,226
₹20,504 total
14 Dec - 15 Dec
includes taxes & fees
9.4/10 Exceptional! (336 reviews)
My expectations for Grassy Flats was so high. It is a beautiful setting and the rooms are wonderful with excellent service from all staff . I would have rated excellent had it been for a few details . I was unaware when I booked months back that the rooftop bar and Rhum House Restaurant would only ...

Reviewed on 15 Nov 2025

Grassy Flats Resort & Beach Club
Gulf View Waterfront Resort

Gulf View Waterfront Resort

2.5 out of 5
58743 OVERSEAS HWY Marathon FL
The price is ₹8,879 per night from 23 Nov to 24 Nov
₹8,879
₹9,989 total
23 Nov - 24 Nov
includes taxes & fees
8.4/10 Very Good! (512 reviews)
Spotless room, comfy, and check in so easy. Love the place definitely going back.

Reviewed on 3 Nov 2025

Gulf View Waterfront Resort
See all 2,319 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 featuring a sandy beach and general coastal views

Sombrero Beach

4.5/5(7 reviews)

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

Sombrero Beach
Curry Hammock State Park featuring a beach and kayaking or canoeing

Curry Hammock State Park

4.5/5(2 reviews)

Go camping near mangroves, bird-watching beneath a thick canopy or kayaking between the islands of this scenic state park in the Middle Keys.

Curry Hammock State Park
Crane Point Museum and Nature Center

Crane Point Museum and Nature Center

You can spend an afternoon exploring the galleries in Crane Point Museum and Nature Center in Marathon. Discover the area's beautiful sunsets or seek out its jogging trails.

Crane Point Museum and Nature Center

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.

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