A dolphin swimming near a wooden dock and a tree branch in the water.
Photo by Monica Ferro
Open Photo by Monica Ferro

Grassy Key All inclusive Vacations

Book a Hotel + Flight or Car together to unlock savings

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    Save up to $2,000 when you book a flight and hotel together*
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Top All inclusive vacation packages in Grassy Key

Price found within the past 48 hours. Click for updated prices.
  • Jan 21 - Jan 24

    Cavalier Hotel South Beach + Flight

    South Beach
    3 nights
    3.5 star property
    8.6/10 - Excellent (1,003 reviews)
    Roundtrip • Boston (BOS) - Miami (MIA)
    BOS - FLL • Nonstop FLL - BOS • Nonstop
    $866
    $445
    per traveler
    found 1 day ago
    Cavalier Hotel South Beach
  • Dec 30 - Jan 5

    The Retreat Collection at 1 Hotel & Homes South Beach + Flight

    South Beach
    6 nights
    5.0 star property
    8.0/10 - 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 June 22, 2016
    Roundtrip • Boston (BOS) - Miami (MIA)
    BOS - MIA • Nonstop MIA - BOS • 1 stop
    $42,134
    $20,903
    per traveler
    found 1 day ago
    The Retreat Collection at 1 Hotel & Homes South Beach
  • Jan 16 - Jan 21

    501 First Studio Balcony by Palermo Home + Flight

    Downtown Miami
    5 nights
    2.0 star property
    Roundtrip • Boston (BOS) - Miami (MIA)
    BOS - FLL • Nonstop FLL - BOS • Nonstop
    $1,596
    $803
    per traveler
    found 1 day ago
    501 First Studio Balcony by Palermo Home
  • Dec 16 - Dec 19

    Avi Lux Stay + Flight

    East Fort Lauderdale
    3 nights
    4.5 star property
    7.6/10 - Good (10 reviews)
    "If you are looking for a quiet place to stay this suite is NOT recommended. You can hear motorcycles and racing cars at all hours of the night. Valet is $60 per night mandatory payment required upon check in for the entire length of your stay tips not included. This is not stated in the description prior to booking. BEWARE. "
    Reviewed August 28, 2025
    Roundtrip • Boston (BOS) - Miami (MIA)
    BOS - MIA • 1 stop MIA - BOS • 1 stop
    $1,178
    $629
    per traveler
    found 1 day ago
    Avi Lux Stay
  • Feb 1 - Feb 6

    Miami Vacation Rentals Downtown with Pool + Flight

    Downtown Miami
    5 nights
    4.5 star property
    Roundtrip • New York (EWR) - Miami (MIA)
    EWR - MIA • Nonstop MIA - EWR • Nonstop
    $2,237
    $1,198
    per traveler
    found 1 day ago
    Miami Vacation Rentals Downtown with Pool

What to do in Grassy Key

Top All inclusive Grassy Key Hotels

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 Grassy Key vacations: everything you need to know

Can I book a Grassy Key vacation with airfare and meals?

On an all-inclusive vacation, your mind and body can wander far from your wallet. Pay one simple price when you bundle your accommodation and airfare, and you avoid all those yucky bills after conversation-starting cocktails or decadent dinners.

How can I find Grassy Key all-inclusive vacations that are adults only?

All the best all-inclusive, all-adult vacations are a click of a filter or two away. Choose from great grown-up features. Say, a spa for a couple’s massage, a hot tub to soak away the stresses of the day, or a swim-up bar to get the party started.

How much is an all-inclusive trip to Grassy Key?

Affordable all-inclusive is yours, whatever your budget. Packages start tempting you from just $445. Prices and availability are subject to change. Additional terms may apply.

How can I book cheap all-inclusive trips to Grassy Key?

Whenever you book your travel, sorting by price and filtering by budget shows you what’s out there in your price range.

What are the benefits of all-inclusive Grassy Key vacations with airfare?

Create your dream getaway by bundling your flight and hotel and you get delightful deals and discounts. Add your car rental, too, and you save on all three.

What should I think about when I book an all-inclusive Grassy Key family vacation package?

With little tummies taken care of, you just need to put smiles on their faces. Easy! Book an all-inclusive vacation with a full-on water park or epic pools—or book your stay near the world’s biggest theme parks and attractions.

Why should I book an all-inclusive honeymoon package in Grassy Key?

You can start your married life how you mean to go on with an all-inclusive honeymoon package. Eat and drink to your heart’s content, waltz around in happy harmony, and have your fill of delights. Together, you can book up adventure excursions and return to a pool-side cabana for cocktails at sunset.

Can I book an all-inclusive Grassy Key package with free cancellation and/or flexible dates?

When you’re searching for your all-inclusive getaway, filter your results by payment option to find free cancellation and buy now, pay later options. That way, you can rebook without worry, should your plans change.

Why should I book an all-inclusive Grassy Key package vacation with Expedia?

Book amazing all-inclusive adventures, all in one place. Choose from a vast inventory of deals, adding every little extra to build your brilliant break in minutes.