Grassy Key Vacation Packages

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Top Grassy Key Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Crosby Miami Worldcenter

The Crosby Miami Worldcenter

4 out of 5
Downtown Miami
Price was CA $2,071, price is now CA $1,287 per person
CA $1,287
per person
Jul 16 - Jul 23
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.2/10 Very Good! (194 reviews)
Extremely clean condo! Very pleased!

Reviewed on Jun 11, 2026

Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was CA $13,478, price is now CA $6,182 per person
CA $6,182
per person
Aug 16 - Aug 23
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
5.8/10 (324 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

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 $24,467, price is now CA $12,845 per person
CA $12,845
per person
Aug 21 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
8/10 Very Good! (1 review)
Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Mid Beach
Price was CA $4,215, price is now CA $2,472 per person
CA $2,472
per person
Jul 17 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8/10 Very Good! (1,145 reviews)
The property is excellent from every aspects. The staffs are so helpful and they put every effort to make our family trip enjoyable. I loved the breakfast buffet as it has all options for everyone. The food choices and quantities are also exceptional. The property is on the beach and easy access to the beach. Also, it is well secured and well lighted everywhere. I loved the fact it that it is little away from the south beach which is very loud. I don’t have much negative to say. I wish the property entry is little wider but they can’t do much about it. The lobby is wide and open. So that that covers it. Also, I wish they had more beach umbrellas as they run out fast. The swimming pool is little small and most of the time no music in the pool which some people would like. I loved this property and I may stay here again if I come to Miami.

Reviewed on Jun 9, 2026

The 27 Wynwood

The 27 Wynwood

4 out of 5
Wynwood Art District
Price was CA $2,492, price is now CA $1,548 per person
CA $1,548
per person
Jul 17 - Jul 24
found 18 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
10/10 Exceptional! (5 reviews)
Property is beautiful. The rooftop top pool is amazing. Everything is really close to the main street in wynwood. Will definitely be back.

Reviewed on Jun 5, 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 $133 per night from Jun 28 to Jun 29
CA $133
CA $212 total
Jun 28 - Jun 29
includes taxes & fees
8.2/10 Very Good! (994 reviews)
"I booked Rainbow Bend resort because it met the three requirements I was looking for: a small, oceanfront resort with a kitchen in-room. For those desires, it was a perfect fit! Unfortunately, the kayaks weren’t available when we wanted to use them because no staff was available to help us. And when ..."

Reviewed on Jun 10, 2026

Rainbow Bend Resort
Gulf View Waterfront Resort

Gulf View Waterfront Resort

2.5 out of 5
58743 OVERSEAS HWY Marathon FL
The price is CA $225 per night from Jun 15 to Jun 16
CA $225
CA $253 total
Jun 15 - Jun 16
includes taxes & fees
8.4/10 Very Good! (583 reviews)
"Todo"

Reviewed on Jun 2, 2026

Gulf View Waterfront Resort
Grassy Flats Resort & Beach Club

Grassy Flats Resort & Beach Club

4 out of 5
58182 Overseas Hwy Marathon FL
The price is CA $268 per night from Jun 15 to Jun 16
CA $268
CA $369 total
Jun 15 - Jun 16
includes taxes & fees
9.4/10 Exceptional! (456 reviews)
"Great location, beautiful room with sea view balcony. Would stay again"

Reviewed on Jun 12, 2026

Grassy Flats Resort & Beach Club
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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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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.