Best Hotels in Monroe County for 2026

Our customers tell us that they can't get enough of the pool at Southernmost Beach Resort and Guesthouses. During your stay, you're just a quick walk from Duval Street. Features include 3 outdoor pools, 2 poolside bars and a full-service spa.

Our customers tell us that they can't get enough of the pool at Beachside Resort & Residences. During your stay, you're just a quick walk from Key West Tropical Forest and Botanical Garden. Free WiFi in public areas, a free area shuttle and 2 restaurants are available.

Our customers tell us that they can't get enough of the helpful staff at Cheeca Lodge & Spa. During your stay, you're just a quick walk from Matecumbe United Methodist Church. Free valet parking, 3 outdoor pools and 3 restaurants are available.

Our customers tell us that they can't get enough of the pool at Hawks Cay Resort. During your stay, you'll be close to Little Conch Key. Enjoy features like free WiFi in public areas, plus 3 outdoor pools and 4 restaurants.

Our customers tell us they can't get enough of Blue Flamingo Resort Key West's great location. During your stay, you'll be within walking distance of Regal Key West. Enjoy features like free WiFi in public areas and a free area shuttle, plus 2 outdoor pools. This property offers pet-friendly amenities, such as an off-lead area.

Our customers tell us they can't get enough of Isla Bella Beach Resort & Spa's great location. During your stay, you're just a quick walk from Vaca Key. Enjoy features like free WiFi in public areas, plus 5 outdoor pools and 2 bars.

The free breakfast at Chesapeake Beach Resort gets high marks from our customers. During your stay, you'll be within walking distance of History of Diving Museum. Enjoy features like free WiFi in public areas, plus 2 outdoor pools and a marina.

Our customers tell us they can't get enough of Margaritaville Beach House Key West's great beach location. During your stay, you'll be within walking distance of Clarence S. Higgs Memorial Beach Park. An outdoor pool, a restaurant and a 24-hour gym are available. This property offers pet-friendly amenities, such as food and water bowls.

Our customers tell us they can't get enough of Parrot Key Hotel & Villas's great location. During your stay, you'll be within walking distance of Regal Key West. Enjoy features like free WiFi in public areas and a free area shuttle, plus 4 outdoor pools.

Our customers tell us that they can't get enough of the helpful staff at Baker's Cay Resort Key Largo, Curio Collection by Hilton. During your stay, you'll be within walking distance of Bluefin Rock Harbor Marina. Enjoy features like 2 outdoor pools, 2 restaurants and 4 bars. This property offers pet-friendly amenities, such as food and water bowls.

Waterside Suites & Marina's great location gets high marks from our customers. During your stay, you're just a quick walk from John Pennekamp Coral Reef State Park. You'll find features such as free WiFi in public areas, plus an outdoor pool and a marina. This property offers pet-friendly amenities, such as food and water bowls.

The free breakfast at Ibis Bay Beach Resort gets good marks from our customers. During your stay, you're just a quick walk from Regal Key West. Enjoy features like free WiFi in public areas, plus an outdoor pool and a restaurant.

La Concha Key West, Autograph Collection's great location gets high marks from our customers. During your stay, you're just a quick walk from Duval Street. Free WiFi in public areas, 3 restaurants and 2 bars are available.

Our customers tell us they can't get enough of Havana Cabana at Key West 's great location. During your stay, you're just a quick walk from Regal Key West. You'll find features such as free WiFi in public areas and free self-parking, plus an outdoor pool. This property offers pet-friendly amenities, such as food and water bowls.

During your stay at Casa Marina Key West, Curio Collection by Hilton, you're just a quick walk from Florida Keys Beaches. You'll find features such as free WiFi in public areas, plus 2 outdoor pools and a full-service spa.