Grassy Key Vacation Packages

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Top Grassy Key Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Brickell Bay 3318

Brickell Bay 3318

3 out of 5
Brickell
Price was CA $2,516, price is now CA $980 per person
CA $980
per person
Jul 2 - Jul 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
No reviews
The W - Bayshore Unit 1003

The W - Bayshore Unit 1003

3 out of 5
East Fort Lauderdale
Price was CA $4,037, price is now CA $1,260 per person
CA $1,260
per person
Jul 1 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
6/10 (2 reviews)
Brickell Bay 3505

Brickell Bay 3505

3 out of 5
Brickell
Price was CA $3,751, price is now CA $1,300 per person
CA $1,300
per person
Jun 28 - Jul 4
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
9/10 Wonderful! (2 reviews)
The room was clean, there was a problem at the check out time as all the guest have the same check out and all the elevators collapse, it took us more than an hour to get down. The parking is really a problem as we had to go up almost 20 floors. Location is pretty good.

Reviewed on Apr 14, 2026

Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was CA $9,877, price is now CA $4,368 per person
CA $4,368
per person
Jul 11 - Jul 16
found 19 hours ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
5.8/10 (323 reviews)
Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great. It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it.

Reviewed on Feb 22, 2026

Creekside Inn

Creekside Inn

2.5 out of 5
Price was CA $1,955, price is now CA $1,059 per person
CA $1,059
per person
Jun 3 - Jun 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
7.8/10 Good! (1,007 reviews)
Not bad for a last-minute booking. Would consider staying here again. Near many restaurants and local adventures.

Reviewed on Apr 27, 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 $140 per night from May 3 to May 4
CA $140
CA $219 total
May 3 - May 4
includes taxes & fees
8.2/10 Very Good! (937 reviews)
Room was nice but not cleaned properly dirty towels hanging in the bathroom also shower itself was pretty dirty other than that the view was nice

Reviewed on Apr 27, 2026

Rainbow Bend Resort
Grassy Flats Resort & Beach Club

Grassy Flats Resort & Beach Club

4 out of 5
58182 Overseas Hwy Marathon FL
The price is CA $356 per night from May 28 to May 29
CA $356
CA $465 total
May 28 - May 29
includes taxes & fees
9.4/10 Exceptional! (435 reviews)
Great property, my only complaint was we had the same room with a couple we were traveling with and asked to be next to each other, they said they couldn't we had one room in between us even though nobody was in the other rooms. So Boo on you!!

Reviewed on Apr 21, 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 $269 per night from May 3 to May 4
CA $269
CA $302 total
May 3 - May 4
includes taxes & fees
8.4/10 Very Good! (567 reviews)
Room was clean, bed was comfortable. Not a great location for beaches/attractions but we were just passing through so it worked out.

Reviewed on Apr 23, 2026

Gulf View Waterfront Resort
See all 2,333 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
Family Vacations
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Discover the most popular places to visit in Grassy Key

Sombrero 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

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

Marathon: Rhum Runner Aqua Park Adventure

Marathon: Rhum Runner Aqua Park Adventure

CA $52
per adult
Marathon: Rhum Runner Aqua Park Adventure
Day Sailing Adventure in the Florida Marine Sanctuary

Day Sailing Adventure in the Florida Marine Sanctuary

CA $165
per adult
100% of travellers recommend
Day Sailing Adventure in the Florida Marine Sanctuary
Florida Keys Nature & History Tour from Key West

Florida Keys Nature & History Tour from Key West

CA $164
per adult
88% of travellers recommend
Florida Keys Nature & History Tour from Key West
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.