Grassy Key Vacation Packages

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Top Grassy Key Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Creekside Inn

Creekside Inn

2.5 out of 5
Price was CA $3,045, price is now CA $1,418 per person
CA $1,418
per person
Apr 1 - Apr 8
found 22 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Miami (MIA)
8/10 Very Good! (1,004 reviews)
If you're looking for a super nice place to stay this is NOT that. It's an older hotel that serves It's purpose. Our room was very clean, AC was great, the bed & pillows are not comfortable but worked. The staff was extremely friendly. I would stay here again for a quick 2 night trip.

Reviewed on Feb 13, 2026

The Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
Price was CA $2,773, price is now CA $1,503 per person
CA $1,503
per person
Mar 20 - Mar 27
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.2/10 Very Good! (1,491 reviews)
Great location and I messed up our reservation dates and they graciously worked with me to change to the correct dates

Reviewed on Feb 14, 2026

President Hotel

President Hotel

3.5 out of 5
South Beach
Price was CA $2,673, price is now CA $1,460 per person
CA $1,460
per person
Mar 20 - Mar 27
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.4/10 Very Good! (1,775 reviews)
Clean room, good location, close to ocean. Room was in a side building with card security on elevator. Nothing fancy, but met our needs for a pre-cruise place. Lots of fun restaurants a stroll away.

Reviewed on Feb 14, 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 $18,108, price is now CA $9,985 per person
CA $9,985
per person
Apr 26 - Apr 30
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 $9,220, price is now CA $5,171 per person
CA $5,171
per person
Mar 20 - Mar 27
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
9.4/10 Exceptional! (1,365 reviews)
Room very nice but not very well designed. Bed and couch on a riser- not the floor- requiring a step up to get to each. Everytime you got up at night- a light would come on and stay on for 10 minutes. Safety so you don’t fall- but should we really have a bed on a riser? Found the light on disruptive to getting back to sleep. Very dark room- not well lit at all. No makeup mirror Slippery marble floor shower- ask for a rubber mat- which we finally got the day before our stay ended Great access to pool and beach Great service in hotel and beach Great service from the house car Very pleasant staff Mini bar beverages not cold- required ice to chill No ice machine- but they brought the ice to you if you called and requested Nice roof top pool but music was too loud to enjoy. Could not eat at Watr restaurant - roof top-due to the loud music Reserved a shower room to freshen up after check out our last day- but did not get one- had to use the gym for getting cleaned up for our flight- lot of disorganization around this entire situation. No one ever offered and explanation on what happened- did not have time to investigate- trying ti get to airport. Great location and vibe- we enjoyed our stay but would not stay here again.

Reviewed on Feb 11, 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 $335 per night from Feb 24 to Feb 25
CA $335
CA $438 total
Feb 24 - Feb 25
includes taxes & fees
8/10 Very Good! (850 reviews)
The rooms were very clean and the staff was amazing. The restaurant was absolutely wonderful. The staff there was fantastic and the food was fabulous!!!

Reviewed on Feb 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
The price is CA $445 per night from Feb 16 to Feb 17
CA $445
CA $565 total
Feb 16 - Feb 17
includes taxes & fees
9.4/10 Exceptional! (392 reviews)
We loved this resort. It is a great location as you can go anywhere to do things in the Keys in an hour or so. Our room was great, and the view from the patio looking through the palm trees was fantastic. The staff was friendly and helpful. The weather turned cold and we were not able to take advantage ...

Reviewed on Feb 9, 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! (550 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

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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.
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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 $51
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 $164
per adult
100% of travellers recommend
Day Sailing Adventure in the Florida Marine Sanctuary
Sister snorkelers :)

Marathon: COMBO- Snorkel & Sandbar (Sombrero Reef)

CA $210
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.