
Grassy Key Vacations from $391
Book a Hotel + Flight or Car together to unlock savings
Photo by Monica Ferro
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 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
- Rest easyPlan, book, and manage your trip all in one place
The Latest Grassy Key vacation packages
Price found within the past 48 hours. Click for updated prices.



Cavalier Hotel South Beach
South Beach
Price was $1,355, price is now $667 per person
$667
per person
Mar 12 - Mar 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
I had a wondeful time at this hotel (1/20-1/24/2026). The staff was polite, friendly and always ready to help. Room was clean and stylish exacly like the photo. The location is perfect: quiet and peaceful. And the same time not far from popular places.
I really enjoyed my stay and would definitely recommend this hotel to others.
Reviewed on Jan 26, 2026


Discover the most popular places to visit in Grassy Key

Sombrero Beach
Play beach games; go swimming, kayaking or snorkeling; and lounge in the sun at one of Marathon’s most visited beaches.

Seven Mile Bridge
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
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
$120
per adult
100% of travellers recommend

Marathon: Historic 7-Mile Bridge Sunset Cruise
$125
per adult
Grassy Key Hotel Deals

Rainbow Bend Resort
57784 Overseas Hwy Marathon FL
Fully refundableReserve now, pay when you stay
$178 nightly
The price is $201 total per night from Feb 1 to Feb 2
$201 total
Feb 1 - Feb 2
Total with taxes and fees
8/10 Very Good! (826 reviews)
It was beautiful, comfortable, and clean.
Reviewed on Jan 25, 2026

Grassy Flats Resort & Beach Club
58182 Overseas Hwy Marathon FL
Fully refundableReserve now, pay when you stay
$431 nightly
The price is $485 total per night from Feb 2 to Feb 3
$485 total
Feb 2 - Feb 3
Total with taxes and fees
9.4/10 Exceptional! (379 reviews)
The room was great and very clean with a spectacular view. The staff was extremely friendly and helpful. Housekeeping was great as well. We loved the pool area and beautiful views. We will definitely be back!
Reviewed on Jan 22, 2026

Gulf View Waterfront Resort
58743 OVERSEAS HWY Marathon FL
$206 nightly
The price is $232 total per night from Feb 1 to Feb 2
$232 total
Feb 1 - Feb 2
Total with taxes and fees
8.4/10 Very Good! (542 reviews)
room appeared very clean. Staff had left the facility before we arrived.
Reviewed on Jan 22, 2026
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.




















