Grassy Key Vacations from $563
Book a Hotel + Flight or Car together to unlock savings
Photo by Monica Ferro
The Latest Grassy Key vacation packages
Price found within the past 48 hours. Click for updated prices.
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 beautiful beaches or discover the area's beautiful sunsets.
What to do in Grassy Key
Day Sailing Adventure in the Florida Marine Sanctuary
$99
per adult
100% of travellers recommend
Marathon: Private Cable or Cable Kiteboarding Session
$177
per traveler
Grassy Key Hotel Deals
Rainbow Bend Resort
57784 Overseas Hwy Marathon FL
Fully refundableReserve now, pay when you stay
$132 nightly
The price is $149 total per night from Dec 21 to Dec 22
$149 total
Dec 21 - Dec 22
Total with taxes and fees
8/10 Very Good! (781 reviews)
Was greeted by Stacie and she was more than helpful. Room was clean,very friendly staff, nice beach area, breakfast was great. Pool was heated and clean loved the hot tub. I would definitely stay here the next time I am down in the keys.
Reviewed on Dec 15, 2025
Grassy Flats Resort & Beach Club
58182 Overseas Hwy Marathon FL
$377 nightly
The price is $424 total per night from Dec 20 to Dec 21
$424 total
Dec 20 - Dec 21
Total with taxes and fees
9.4/10 Exceptional! (355 reviews)
room clean staff friendly restaurant not opened 2 of 3 day stay and not informed at time of booking.
Reviewed on Dec 11, 2025
Gulf View Waterfront Resort
58743 OVERSEAS HWY Marathon FL
$114 nightly
The price is $129 total per night from Dec 21 to Dec 22
$129 total
Dec 21 - Dec 22
Total with taxes and fees
8.4/10 Very Good! (525 reviews)
yes
Reviewed on Dec 6, 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) |
More vacations you might like
Explore a world of travel with Expedia
- Hotels near Crawl Key
- Duck Key Hotels
- Hotels near Curry Hammock State Park
- Resorts in Duck Key
- Cheap Hotels in Duck Key
- Villas in Duck Key
- RV Parks in Duck Key
- 5 Star Hotels in Duck Key
- Houseboats in Duck Key
- Vacation Homes in Duck Key
- Hotels with Laundry Facilities in Duck Key
- Luxury Hotels in Duck Key
- Resorts & Hotels with Spas in Duck Key
- Cottages in Duck Key
- 4 Star Hotels in Duck Key
- Beach Hotels in Duck Key
- Condo Rentals in Duck Key
- All-inclusive Resorts in Duck Key
- Hotels with Tennis Courts in Duck Key
- Hotel Wedding Venues Hotels in Duck Key
- Family Hotels in Duck Key
- Golf Hotels in Duck Key
- Apartments in Duck Key
- Honeymoon Resorts & in Duck Key
- Hotels with Restaurants in Duck Key
- Pet-friendly Hotels in Duck Key
- Hilton Hotels in Duck Key
- Fishing Resorts & in Duck Key
- Hotels with Balconies in Duck Key
- Motels in Duck Key
- Hotels with Suites in Duck Key
- Romantic Hotels in Duck Key
- Hotels with Bars in Duck Key
- Hotels with Hot Tubs in Duck Key
- Hotels near Little Conch Key
- Cottages in Conch Key
- Conch Key Hotels
- Villas in Conch Key
- Resorts in Conch Key
- RV Parks in Conch Key
- Cabin Rentals in Conch Key
- Motels in Conch Key
- Pet-friendly Hotels in Conch Key
- Beach Hotels in Conch Key
- Houseboats in Conch Key
- Key Colony Beach Hotels
- Condo Rentals in Key Colony Beach
- Hotels near Coral Lagoon
- Oceanfront Hotels in Key Colony Beach
- Apartments in Key Colony Beach
- Cheap Hotels in Key Colony Beach
- Resorts & Hotels with Spas in Key Colony Beach
- Golf Hotels in Key Colony Beach
- Pet-friendly Hotels in Key Colony Beach
- Hilton Hotels in Key Colony Beach
- Hotel Wedding Venues Hotels in Key Colony Beach
- All-inclusive Resorts in Key Colony Beach
- Motels in Key Colony Beach
- Vacation Homes in Key Colony Beach
- Hotels with Tennis Courts in Key Colony Beach
- Beach Hotels in Key Colony Beach
- Family Hotels in Key Colony Beach
- Houseboats in Key Colony Beach
- Hotels with Suites in Key Colony Beach
- Flights to Duck Key
- Flights from Philadelphia to Duck Key
- Flights from Pittsburgh to Duck Key
- Flights from Raleigh to Duck Key
- Flights from Duck Key
- Flights from Cleveland to Duck Key
- Flights from Buffalo to Duck Key
- Flights from Indianapolis to Duck Key
- Flights to Conch Key
- Flights to Key Colony Beach
- Flights from Key Colony Beach
- Car rentals near Curry Hammock State Park
- Car rentals near Duck Key
- Hertz Rental Cars in Duck Key
- Budget Rental Cars in Duck Key
- Dollar Rent A Car Rental Cars in Duck Key
- Enterprise Rental Cars in Duck Key
- Hawk Rental Cars in Duck Key
- Car rentals near Key Colony Beach
- Enterprise Rental Cars in Key Colony Beach
- Avis Rental Cars in Key Colony Beach
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.