Grassy Key Vacation Packages

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Top Grassy Key Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was CA $1,591, price is now CA $811 per person
CA $811
per person
Apr 10 - Apr 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
5.8/10 (311 reviews)
I stood in the multiple bed 1 bedroom everything was good beach right there pool and security where very friendly

Reviewed on Nov 12, 2025

Creekside Inn

Creekside Inn

2.5 out of 5
Price was CA $2,108, price is now CA $904 per person
CA $904
per person
Apr 10 - Apr 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8/10 Very Good! (1,004 reviews)
Room was clean, spacious with a wonderful canal view.

Reviewed on Jan 27, 2026

W South Beach

W South Beach

5 out of 5
South Beach
Price was CA $15,159, price is now CA $7,698 per person
CA $7,698
per person
Apr 29 - May 6
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
9.2/10 Wonderful! (1,002 reviews)
Clean rooms great service

Reviewed on Jan 29, 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 CA $26,470, price is now CA $14,654 per person
CA $14,654
per person
Apr 26 - May 1
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
8/10 Very Good! (1 review)
1 Hotel South Beach

1 Hotel South Beach

5 out of 5
South Beach
Price was CA $19,925, price is now CA $11,095 per person
CA $11,095
per person
Apr 29 - May 6
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
9.4/10 Exceptional! (1,365 reviews)
Amazing hotel. Beyond our expectations. Rooms are huge. Modern and stylish Lobby is fabulous as is the bars and restaurants You must stay here !!! Total wow

Reviewed on Jan 21, 2026

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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 CA $233 per night from Feb 9 to Feb 10
CA $233
CA $323 total
Feb 9 - Feb 10
includes taxes & fees
8/10 Very Good! (842 reviews)
Staff was great!! The Oceanside room was amazing and very comfortable well put together. The first room we had was not as great, Room 24, it has no natural light, no couch in the livingroom, no tv in the bedroom and unfortunately we were there on a record cold days, so weren’t really able to be outside ...

Reviewed on Feb 3, 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 CA $454 per night from Mar 8 to Mar 9
CA $454
CA $576 total
Mar 8 - Mar 9
includes taxes & fees
9.4/10 Exceptional! (386 reviews)
Exceptional services.

Reviewed on Feb 1, 2026

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 CA $356 per night from Feb 25 to Feb 26
CA $356
CA $400 total
Feb 25 - Feb 26
includes taxes & fees
8.4/10 Very Good! (547 reviews)
Easy checkin online. Easy access to unit. Very clean. A lot of great amenities on the property that we didnt get to use due to weather.

Reviewed on Jan 30, 2026

Gulf View Waterfront Resort
See all 2,303 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
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Discover the most popular places to visit in Grassy Key

Sombrero Beach featuring general coastal views and a sandy beach

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
Curry Hammock State Park which includes kayaking or canoeing and a sandy beach

Curry Hammock State Park

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

What to do in Grassy Key

Marathon: Rhum Runner Aqua Park Adventure

Marathon: Rhum Runner Aqua Park Adventure

CA $52
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

CA $167
per adult
100% of travellers recommend
Day Sailing Adventure in the Florida Marine Sanctuary
Sister snorkelers :)

Marathon: COMBO- Snorkel & Sandbar (Sombrero Reef)

CA $211
per adult
Marathon: COMBO- Snorkel & Sandbar (Sombrero Reef)
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.