Grassy Key Vacation Packages

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Top Grassy Key Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Barcelona Studios Guesthouse

Barcelona Studios Guesthouse

2 out of 5
South Beach
Price was CA $845, price is now CA $517 per person
CA $517
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9.2/10 Wonderful! (89 reviews)
We had a good stay here!

Reviewed on Aug. 5, 2025

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 $23,847, price is now CA $11,049 per person
CA $11,049
per person
Oct 27 - Oct 31
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Miami (MIA)
8/10 Very Good! (1 review)
Park Central South Beach

Park Central South Beach

4 out of 5
South Beach
Price was CA $1,628, price is now CA $938 per person
CA $938
per person
Nov 11 - Nov 15
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
8.2/10 Very Good! (930 reviews)
Really nice location and staff. Valet service sucked.

Reviewed on Aug. 22, 2025

Barnacle Resort

Barnacle Resort

3 out of 5
Long Beach Estates
Price was CA $1,955, price is now CA $1,176 per person
CA $1,176
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
8.2/10 Very Good! (39 reviews)
Perfect place for a quiet getaway.

Reviewed on May 24, 2025

The Elser Hotel Miami

The Elser Hotel Miami

4 out of 5
Downtown Miami
Price was CA $1,651, price is now CA $994 per person
CA $994
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9/10 Wonderful! (3,057 reviews)
I love everything about this place!!

Reviewed on Aug. 21, 2025

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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 $142 per night from Sep 21 to Sep 22
CA $142
CA $223 total
Sep 21 - Sep 22
includes taxes & fees
8/10 Very Good! (724 reviews)
"Great"

Reviewed on Aug. 21, 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 CA $285 per night from Sep 1 to Sep 2
CA $285
CA $320 total
Sep 1 - Sep 2
includes taxes & fees
9.4/10 Exceptional! (307 reviews)
"The staff were friendly and very helpful. The room was beautiful, clean, and spacious. The view from our room was amazing. The resort is right on the water and offers a serene and tropical ambiance. Would highly recommend!"

Reviewed on Aug. 22, 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 CA $136 per night from Aug 24 to Aug 25
CA $136
CA $153 total
Aug 24 - Aug 25
includes taxes & fees
8.4/10 Very Good! (486 reviews)
"This is a fairly clean place. It has a great location to the water with jet ski rental at the property. The only real issue is the rooms are extremely noisy. We could here every step of the occupants above us and the highway noise was very loud in the room."

Reviewed on Jul. 18, 2025

Gulf View Waterfront Resort
See all 2,306 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
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Family 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

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

Florida Keys Nature & History Tour from Key West

Florida Keys Nature & History Tour from Key West

CA $150
per adult
88% of travellers recommend
Florida Keys Nature & History Tour from Key West
See all activities in Grassy Key

Frequently asked questions

How much does a Grassy Key vacation package cost?
Starting from just CA $517, a package is your portal to low-priced travel. Custom build your Grassy Key trip by selecting from our wide range of airfares, hotels and rental cars.
How do I get a cheap travel package to Grassy Key?
Search for flights that fit your schedule, add a hotel room to your booking and watch how much you save with a Grassy Key vacation package. It's that simple! From hotels and flights to activities and rental cars, Expedia is where your cheap getaway begins. And with over 550 air carriers and 1,000,000 hotels around the world to pick from, you'll never be short of choice.
Where should I stay in Grassy Key?
Close to the action. Many travelers like to book hotels within easy reach of top sights, like Dolphin Research Center, Curry Hammock State Park and Crawl Key.
What are the top hotels in Grassy Key?
Make a reservation at Gulf View Waterfront Resort. It's one of this neighborhood's most popular hotels. Another highly rated option in Grassy Key is Sun Outdoors Marathon.
How far in advance should I book my Grassy Key vacation?
It's difficult to pick the ideal time for airfares, but we normally say the earlier, the better. Many international flights on Expedia become available to compare up to a year in advance. If you can't book ahead, don't stress. Budget prices appear from time to time within a few weeks of departure dates.
What does an Expedia Grassy Key travel package include?
It all depends on what sort of escape you want to have. Grassy Key vacation deals can include hotels, flights and car rentals. You can mix and match to find the travel package that suits you. You can also add on experiences and activities after you've booked to get even bigger discounts.
What should I know before booking a Grassy Key travel package?
A package can be easier on the wallet than individually booking everything you need for your getaway. For example, bundle your hotels, flights and rental cars and save a tidy sum. No matter your vacation plans, there's sure to be a package within your budget.
Can I choose my airline with a Grassy Key Expedia vacation package?
With a vacation package, you're the boss. Whether you're looking to fly to Grassy Key in economy or first class, simply choose from the available airline options. Expedia has access to more than 550 partner airlines worldwide.
If I'm not able to travel, can I cancel my Grassy Key vacation package?
Whether it's your hotel, flight or rental car, you can cancel or change it. Locked in your Grassy Key vacation package in the last 24 hours? You may be able to make changes for free. For bookings made more than 24 hours ago, you may incur a fee from your hotel, airline or car rental company. For more information, take a look at our Customer Service Portal. We're here to help you every step of the way.

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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.