Monroe County Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AED 5,000 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Monroe County Hotel Deals

Cheeca Lodge & Spa

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL
AED 509
AED 841 total
21 Sep - 22 Sep
includes taxes & fees
Cheeca Lodge & Spa
Chesapeake Beach Resort

Chesapeake Beach Resort

83409 Overseas Hwy Islamorada FL
Fully refundableReserve now, pay when you stay
AED 544
AED 818 total
21 Sep - 22 Sep
includes taxes & fees
9.2/10 Wonderful! (1,778 reviews)
"Nice pool, great breakfast with seating outside with nice views"

Reviewed on 19 September 2026

Chesapeake Beach Resort
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL
AED 587
AED 929 total
28 Sep - 29 Sep
includes taxes & fees
Southernmost Beach Resort and Guesthouses
See all 8,312 properties in Monroe County
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.

Stay near popular Monroe County attractions

A street with a pharmacy, a theater, and a yellow building.

Duval Street

9.2/10 (20,928 reviews)
With a visit to Duval Street, a favorite shopping spot in Key West, you can search for that perfect souvenir. Wander the seaside or discover the area's beautiful sunsets.
See properties
A beach with a pier extending into the ocean during sunset.

Florida Keys Beaches

8.4/10 (858 reviews)
Nothing says vacation like spending a carefree day at Florida Keys Beaches, a popular beach in Long Beach Estates.
See properties
A colorful monument with text indicating it is the Southernmost Point of the Continental U.S.A. in Key West, Florida.

Southernmost Point

8.8/10 (17,214 reviews)
You can find out about the history of Key West with a stop at Southernmost Point. Discover the area's lively bars and its lively festivals.
See properties
A sign reading "Welcome to Mallory Square" with an American flag, a red and white striped awning, and a statue of a man in a blue shirt and straw hat.

Mallory Square

9.2/10 (15,939 reviews)
You can find out about the history of Key West with a stop at Mallory Square. Stroll along the area's seaside or experience its lively festivals.
See properties
A sailboat named 'Soundwave' docked at a calm harbor with clear blue water, surrounded by a sandy beach and lush greenery.

Sombrero Beach

9.0/10 (2,464 reviews)
Why not spend a carefree afternoon at Sombrero Beach during your travels in Marathon? Stroll along the area's seaside, or simply savor its seafood restaurants.
See properties
A beach with white sand, palm trees, and a building in the background.

Smathers Beach

8.4/10 (8,320 reviews)
If a restful vacation is part of your travel plans, Smathers Beach might be the perfect place to seek out during your trip to Key West. Stroll along the seaside or discover the area's sunrises.
See properties
Fort Jefferson, a brick fort with arched windows and a flagpole.

Dry Tortugas National Park

8.8/10 (2,184 reviews)
Explore the great outdoors at Dry Tortugas National Park, a lovely green space in Key West. Amble around the area's seaside or seek out the biking trails.
See properties
A vintage typewriter on a wooden table with a notebook and pen beside it.

Ernest Hemingway Home and Museum

9.2/10 (8,543 reviews)
You can spend time studying the exhibits at Ernest Hemingway Home and Museum in Key West. Wander the area's seaside or simply enjoy one of its lively bars.
See properties

Explore a world of travel with Expedia