Monroe County Vacations

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Monroe County Hotel Deals

Cheeca Lodge & Spa

Cheeca Lodge & Spa

81801 Overseas Highway, Mile Marker 82 Islamorada FL
Fully refundableReserve now, pay when you stay
SAR 492
SAR 829 total
13 Oct - 14 Oct
includes taxes & fees
Cheeca Lodge & Spa
Margaritaville Beach House Key West

Margaritaville Beach House Key West

2001 South Roosevelt Blvd Key West FL
SAR 785
SAR 1,120 total
13 Oct - 14 Oct
includes taxes & fees
8.8/10 Excellent! (1,798 reviews)
"The staff was very receptive and friendly. I did not get the room I booked, I booked 2 bedroom room with 1 king and 2 queens and got a 3 queen room with no balcony. The one bedroom had no dressers or closet. The only closet for the whole group was in the shared bathroom that was approx. 18 inches ..."

Reviewed on 11 October 2026

Margaritaville Beach House Key West
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
SAR 470
SAR 740 total
13 Oct - 14 Oct
includes taxes & fees
Blue Flamingo Resort Key West
See all 8,246 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.
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A wooden signpost with city names and distances, a beach with umbrellas, and lounge chairs.

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.
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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.
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A beach with clear turquoise water, white sand, and palm trees.

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.
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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.
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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.
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A two-story colonial-style building with a balcony, surrounded by lush greenery and palm trees.

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.
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A coastal fortification with a staircase leading to a higher platform, overlooking the sea.

Fort Zachary Taylor Historic State Park

9.0/10 (4,544 reviews)
Enjoy a trip to Fort Zachary Taylor Historic State Park and popular activities like boating in Key West. Discover the area's beautiful sunsets, or seek out its biking trails.
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