5 Best Hotels in Key West Historic District (2026)

Explore Key West Historic District Hotels: Rates from $270 per Night

Paradise Inn - Adult Exclusive
Hotel
819 Simonton Street, Downtown Key West, Key West, FL 33040, USA
• View on map
  • Oceanfront
    Oceanfront
  • Hot Tub
    Hot Tub
  • Pool
    Pool
  • Ocean View
    Ocean View
12 Baths398.26 ft²
8.6

Exceptional

748 reviews

$270
Average price / night
Check Availability
The Mermaid & The Alligator
Hotel
729 Truman Avenue, Downtown Key West, Key West, 33040, USA
• View on map
  • Oceanfront
    Oceanfront
  • Hot Tub
    Hot Tub
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
6 Baths251.16 ft²
9.2

Exceptional

158 reviews

$366
Average price / night
Check Availability
The Conch House Heritage Inn
Bed & Breakfast
• View on map
  • Oceanfront
    Oceanfront
  • Pool
    Pool
  • Ocean View
    Ocean View
  • Balcony/Terrace
    Balcony/Terrace
  • Price Dropped
    Price Dropped
  • Ocean View
7 Baths199.9 ft²
9.3

Exceptional

30 reviews

$307
Average price / night
Check Availability
Ella's Cottages - Key West Historic Inns
Hotel
811 Simonton Street, Downtown Key West, Key West, FL 33040, USA
• View on map
  • Fireplace/Heating
    Fireplace/Heating
  • Pool
    Pool
  • Balcony/Terrace
    Balcony/Terrace
  • View
    View
  • Price Dropped
    Price Dropped
  • Free Cancellation
6 Baths324.71 ft²
8.5

Exceptional

239 reviews

$404
Average price / night
Check Availability
Winslow's Bungalows - Key West Historic Inns
Hotel
725 Truman Avenue, Downtown Key West, Key West, FL 33040, USA
• View on map
  • Pool
    Pool
  • Balcony/Terrace
    Balcony/Terrace
  • View
    View
  • Pet Friendly
    Pet Friendly
11 Baths252.46 ft²
8.4

Exceptional

1229 reviews

$451
Average price / night
Check Availability

Compare the 5 Best Hotels in Key West Historic District (2026) – Addresses, Prices, Stars, Rating, and Review Count

Hotel Name Address Price ($)Star Rating Review Count Book
Paradise Inn - Adult Exclusive819 Simonton Street, Downtown Key West, Key West, FL 33040, USA27038.6748
The Mermaid & The Alligator729 Truman Avenue, Downtown Key West, Key West, 33040, USA36609.2158
Ella's Cottages - Key West Historic Inns811 Simonton Street, Downtown Key West, Key West, FL 33040, USA40438.5239
Winslow's Bungalows - Key West Historic Inns725 Truman Avenue, Downtown Key West, Key West, FL 33040, USA45148.41229

Note: The prices for each 5 Best Hotels in Key West Historic District (2026) do vary. This can be because of the number of people you are booking for, how far in advance you book and the season. The prices above are only meant as a rough estimate for comparison purposes. Click the buttons above (or click here>) to get the latest prices.

5 Best Hotels in Key West Historic District (2026) on the Map

refinedluxuryhotels.com logo
About
Nearby destinations
Popular destinations