Grassy Key Vacation Packages 2026 from $685

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The Latest Grassy Key vacation packages

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

President Hotel Villa

South Beach

Save 100% on your flight

$685

per person

Dec 3 - Dec 6

found 2 days ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (1,004 reviews)

I liked having a balcony but there was no view

Reviewed on Sep 24, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$9,688

per person

Nov 10 - Nov 15

found 1 day ago

Roundtrip flight included

Boston (BOS) 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

Pelican Hotel

South Beach

Save 100% on your flight

$1,025

per person

Nov 1 - Nov 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (506 reviews)

Resort Fee is something that we did not notice when we booked online through Expedia. We paid $45+tax extra per night. Also, there is Service fee $3 per person for Breakfast that is included.

Reviewed on Sep 22, 2026

Cavalier Hotel South Beach

South Beach

Save 100% on your flight

$1,211

per person

Nov 30 - Dec 6

found 2 days ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.6/10 Excellent! (1,005 reviews)

President Hotel

South Beach

Save 100% on your flight

$1,151

per person

Nov 30 - Dec 6

found 2 days ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.4/10 Very Good! (2,738 reviews)

Nice safe place to stay at. For the price it was a good decent stay that included two drinks and breakfast .

Reviewed on Sep 24, 2026

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What to do in Grassy Key

Sunset Cruise

$71

per adult

100% of travellers recommend

Marathon: Rhum Runner Aqua Park Adventure

$38

per adult

Day Sailing Adventure in the Florida Marine Sanctuary

$120

per adult

100% of travellers recommend

See all activities in Grassy Key

Grassy Key Hotel Deals

Rainbow Bend Resort

57784 Overseas Hwy Marathon FL

Fully refundableReserve now, pay when you stay

$149 nightly

$168 total

Sep 27 - Sep 28

Total with taxes and fees

8.2/10 Very Good! (1,000 reviews)

"The place is clean, and quaint. The staff is very helpful. Unfortunately, the sargassum was still pretty bad so the water was murky and smelled horrible. The pool was closed for maintenance, but we were allowed to use their Sister property. Breakfast was great!"

Reviewed on Sep 20, 2026

Gulf View Waterfront Resort

58743 OVERSEAS HWY Marathon FL

$84 nightly

$95 total

Sep 29 - Sep 30

Total with taxes and fees

8.4/10 Very Good! (622 reviews)

"Absolutely amazing. The property is well maintained and our time there was relaxing. Will definitely go back!"

Reviewed on Sep 24, 2026

Grassy Flats Resort & Beach Club

58182 Overseas Hwy Marathon FL

$237 nightly

$267 total

Oct 25 - Oct 26

Total with taxes and fees

See all 2,353 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.