Grassy Key Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Grassy Key Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Bay Breeze Premium Apartments By Eskape Collection
CA $944
per person
Oct 20 - Oct 25
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
8.8/10 Excellent! (234 reviews)
Definitely 10/10 really spacious, clean nice size balcony,even had kitchen necessities. I’ll be rebooking when I revisit
Reviewed on Aug 12, 2026
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
CA $18,615
per person
Oct 18 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8/10 Very good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on Jun 22, 2016
1 Hotel South Beach
South Beach
CA $5,138
per person
Oct 18 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
9.4/10 Exceptional! (1,586 reviews)
Was a very good experience. The staff was very friendly and helpful with everything. Room was amazing!
Reviewed on Aug 15, 2026
Ready to book your vacation to Grassy Key?
Grassy Key Hotel Deals
Rainbow Bend Resort
57784 Overseas Hwy Marathon FL
Fully refundableReserve now, pay when you stay
CA $136
CA $216 total
Aug 31 - Sep 1
includes taxes & fees
8.2/10 Very good! (1,000 reviews)
"The only 5-star I know at Rainbow Bend, was for the receptionist/helper throughout the resort. Her name is Summer. My husband and I are pretty much laid back, so the positive things I noticed was the beautiful sand around the resort. Our bed was comfortable, breakfast was good, but don't expect the ..."
Reviewed on Aug 8, 2026
Grassy Flats Resort & Beach Club
58182 Overseas Hwy Marathon FL
CA $188
CA $278 total
Sep 14 - Sep 15
includes taxes & fees
9.4/10 Exceptional! (484 reviews)
"I’d say the property is boutique, Florida Keys chic. After being greeted by beautiful lush greenery and a small circular gravel driveway the building is straight up Key West style but bonus, it’s on Marathon. It’s on the beach with an intimate pool area and oversized wooden balconies. Exactly what ..."
Reviewed on Aug 14, 2026
Gulf View Waterfront Resort
58743 OVERSEAS HWY Marathon FL
CA $100
CA $113 total
Aug 16 - Aug 17
includes taxes & fees
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.
What to do in Grassy Key
Day Sailing Adventure in the Florida Marine Sanctuary
CA $168
per adult
100% of travellers recommend
Marathon Key FL: Snorkel Trips and Sunset Cruises
CA $97
per adult
Frequently asked questions
How much does a Grassy Key vacation package cost?
Starting from just CA $944, 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.
Explore a world of travel with Expedia
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- Flights from West Palm Beach (PBI) to Marathon (MTH)
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- Flights from Toronto (YTO) to Marathon (MTH)
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- Flights from Nashville (BNA) to Marathon (MTH)
- Flights from Detroit (DTW) to Marathon (MTH)
- Flights from Buffalo (BUF) to Marathon (MTH)
- Flights from Myrtle Beach (MYR) to Marathon (MTH)
- Flights from Fort Lauderdale (FLL) to Marathon (MTH)
- Flights from Vancouver (YVR) to Marathon (MTH)
- Flights from Miami (MIA) to Marathon (MTH)
- Flights from Lewisburg (LWB) to Marathon (MTH)
- Flights from Florida Keys Marathon
- Flights from Jacksonville (OAJ) to Marathon (MTH)
- Flights from Fort Pierce (FPR) to Marathon (MTH)
- Flights from Boston (BOS) to Marathon (MTH)
- Flights from Chicago (ORD) to Marathon (MTH)
- Flights from Seattle (SEA) to Marathon (MTH)
- Flights from Key West (EYW) to Marathon (MTH)
- Flights from Charleston (CRW) to Marathon (MTH)
- Flights from Knoxville (TYS) to Marathon (MTH)
- Flights from Baltimore (BWI) to Marathon (MTH)
- Flights to Grassy Key
- Flights from Orlando (ORL) to Marathon (MTH)
- Flights to Duck Key
- Flights from London (LON) to Marathon (MTH)
- Flights from Elmira (ELM) to Marathon (MTH)
- Flights from Chicago (MDW) to Marathon (MTH)
- Flights from Orlando (MCO) to Marathon (MTH)
- Flights from Destin (DSI) to Marathon (MTH)
- Flights from Brunswick (SSI) to Marathon (MTH)
- Flights from Newark Liberty Intl. Airport (EWR) to Marathon (MTH)
- Flights from Montreal (YUL) to Marathon (MTH)
- Flights from Wilmington (ILM) to Marathon (MTH)
- Flights to Marathon
- Harry S. Truman Little White House
- Fort East Martello Museum and Gallery
- Islamorada Vacations
- Anne's Beach
- Seven Mile Bridge
- Fort Zachary Taylor Historic State Park
- Sunset Park Beach
- Boca Chica Nude Beach
- Duval Street
- History of Diving Museum
- Marathon Vacations
- Clarence S. Higgs Memorial Beach Park
- Ernest F. Coe Visitor Center
- Baker's Cay Resort Beach
- Dagny Johnson Key Largo Hammock Botanical State Park
- Curry Hammock State Park
- Mallory Square
- Key West Vacations
- Calusa Beach
- Visit Duck Key
- Smathers Beach
- Visit Marathon
- Key Largo Vacations
- Sombrero Beach
- Southernmost Point
- Mel Fisher Maritime Museum
- Veterans Memorial Park & Beach
- South Beach
- Crane Point Museum and Nature Center
- Everglades National Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
