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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Resorts in Grassy Key and around

Our top choices for Grassy Key resorts

Villas At Hawks Cay Resort
5 outdoor pools, pool cabanas (surcharge), pool umbrellas

Villas At Hawks Cay Resort

4.0 star property
8.6 out of 10, Excellent, (116)
"I loved my stay!"
Villas At Hawks Cay Resort
Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton
2 outdoor pools, pool umbrellas, pool loungers

Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton

4.0 star property
8.8 out of 10, Excellent, (1286)
"Great stay "
The price is €181
includes taxes & fees
28 Aug - 29 Aug
Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton
Lime Tree Bay Resort
Exterior

Lime Tree Bay Resort

3.5 star property
9.2 out of 10, Wonderful, (1093)
"This place was amazing for our 5 day stay. We will definitely be back in the future! "
Lime Tree Bay Resort
Matecumbe Resort
Private beach, white sand

Matecumbe Resort

2.0 star property
8.8 out of 10, Excellent, (70)
"Rooms where clean, cool, and comfortable. I will visit again."
The price is €112
includes taxes & fees
24 Aug - 25 Aug
Matecumbe Resort
2 BD/2BA VILLA WITH BOAT SLIP IN ISLAMORADA,FL
Beach

2 BD/2BA VILLA WITH BOAT SLIP IN ISLAMORADA,FL

9.0 out of 10, Wonderful, (2)
"We enjoyed our stay here, although units are older and do need some sprucing up.It was nice to have a beach onsite, as well as a heated pool, the use of (older) bikes and kayaks. We were only a few miles from the action of Islamorada, including restaurants, tourist attractions, shopping, breweries"
2 BD/2BA VILLA WITH BOAT SLIP IN ISLAMORADA,FL
Keys Villa
Property grounds

Keys Villa

10.0 out of 10, Exceptional, (7)
"Wonderful place to stay. It was quiet with a private beach. Just what we were looking for. "
Keys Villa
2 Bedrm / 2 Bath Private Beach Boat Dock Fishing Pier Pool Hot Tub Dream Vacay
Outdoor dining

2 Bedrm / 2 Bath Private Beach Boat Dock Fishing Pier Pool Hot Tub Dream Vacay

2 Bedrm / 2 Bath Private Beach Boat Dock Fishing Pier Pool Hot Tub Dream Vacay
Brand New Luxurious Oceanside Home - Free Dockage until Nov. 30!
Terrace/patio

Brand New Luxurious Oceanside Home - Free Dockage until Nov. 30!

Brand New Luxurious Oceanside Home - Free Dockage until Nov. 30!
Property No Longer Available
Beach

Property No Longer Available

Property No Longer Available
Situated just off the historic Florida Keys Overseas Highway.
Outdoor pool

Situated just off the historic Florida Keys Overseas Highway.

Situated just off the historic Florida Keys Overseas Highway.
JULY 4th Islamorada BEACH paradise - 2 Bedrooms Boat Slip Ramp Pier Pool Hot Tub
Beach nearby, sun-loungers, beach towels

JULY 4th Islamorada BEACH paradise - 2 Bedrooms Boat Slip Ramp Pier Pool Hot Tub

JULY 4th Islamorada BEACH paradise - 2 Bedrooms Boat Slip Ramp Pier Pool Hot Tub
On the water in Islamorada elevated detached unit!!!
Aerial view

On the water in Islamorada elevated detached unit!!!

On the water in Islamorada elevated detached unit!!!
Beautiful oceanfront resort located at mile marker 73.8
Outdoor pool

Beautiful oceanfront resort located at mile marker 73.8

Beautiful oceanfront resort located at mile marker 73.8
The Hammocks- Marathon Paradise
Marina

The Hammocks- Marathon Paradise

The Hammocks- Marathon Paradise
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.
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Top Grassy Key Hotel Reviews

Fairfield Inn & Suites by Marriott Marathon Florida Keys

Fairfield Inn & Suites by Marriott Marathon Florida Keys

10/10 Excellent
"Great hotel! Good location with lots of free parking. Staff were helpful and even let us keep the room for late check out without charging. Rooms were large and well appointed and very clean. The free breakfast was a great treat and a good selection in a lovely restaurant. The pool area was really lovely and we chilled out on the hammocks. "
Stacey 1-night trip
Posted 7 hours ago
Fairfield Inn & Suites by Marriott Marathon Florida Keys