
Grassy Key Vacations from $413
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The Latest Grassy Key vacation packages
Price found within the past 48 hours. Click for updated prices.


Bentley Hotel South Beach
South Beach
Price was $3,395, price is now $1,496 per person
$1,496
per person
Dec 31 - Jan 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
9.4/10 Exceptional! (390 reviews)
Beautifully renovated with great additional touches like Continental breakfast and champagne at 5:00
Reviewed on Nov 7, 2025



The Local House
South Beach
Price was $1,979, price is now $950 per person
$950
per person
Jan 14 - Jan 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (1,002 reviews)
Our room was spacious and clean with an incredible view. The rooftop pool and sitting areas were beautiful, and the staff was incredibly friendly and courteous.
Reviewed on Nov 5, 2025
Discover the most popular places to visit in Grassy Key

Sombrero Beach
4.5/5(417 reviews)
Play beach games; go swimming, kayaking or snorkeling; and lounge in the sun at one of Marathon’s most visited beaches.

Seven Mile Bridge
4.5/5(830 reviews)
Walk, jog, cycle or drive across one of the longest bridges in North America to take in the scenic ocean views it provides.

Vaca Key
4.5/5(39 reviews)
Commune with nature and explore the great outdoors at Vaca Key during your travels in Marathon. Stroll along the seaside or discover the area's beautiful sunsets.
What to do in Grassy Key

Marathon: Private Cable or Cable Kiteboarding Session
$177
per traveler

Marathon: Intro to Foilboarding Experience
$214
per traveler
Grassy Key Hotel Deals

Rainbow Bend Resort
57784 Overseas Hwy, Marathon, FL
Fully refundableReserve now, pay when you stay
$138 nightly
The price is $156 total per night from Nov 12 to Nov 13
$156 total
Nov 12 - Nov 13
Total with taxes and fees
8/10 Very Good! (758 reviews)
Room was clean !!great view and the manager was helpful. there doing a awesome job will definitely be going back and staying there
Reviewed on Nov 5, 2025

Grassy Flats Resort & Beach Club
58182 Overseas Hwy, Marathon, FL
Fully refundableReserve now, pay when you stay
$250 nightly
The price is $282 total per night from Dec 9 to Dec 10
$282 total
Dec 9 - Dec 10
Total with taxes and fees
9.4/10 Exceptional! (329 reviews)
Beautiful!! Gorgeous at night!
Reviewed on Nov 2, 2025

Gulf View Waterfront Resort
58743 OVERSEAS HWY, Marathon, FL
$143 nightly
The price is $161 total per night from Nov 13 to Nov 14
$161 total
Nov 13 - Nov 14
Total with taxes and fees
8.4/10 Very Good! (509 reviews)
Second time staying, very convenient for us
Reviewed on Oct 14, 2025
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.
Find the Best Grassy Key Vacation Packages
Grassy Key Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Miami Intl. Airport (MIA) |
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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.




















