La Pensione InnvsWestwinds Inn
Both properties are rated highly by expert reviewers. On balance, La Pensione Inn scores marginally higher than Westwinds Inn. La Pensione Inn comes in at #37 in Key West with endorsements from 3 sources such as Frommer's, Fodor's and DK Eyewitness.
La Pensione Inn Fodor's
 Fodor's Frommer's
 Frommer's DK Eyewitness
 DK Eyewitness
809 Truman Avenue, Key West, FL 33040
From $159/night
- Free Internet
- Free Breakfast
- Pool
- Free Parking
- Air Conditioning
- Breakfast included
 "Hospitality and period furnishings make this 1891 home, once owned by a cigar executive, a wonderful glimpse into Key West life in the late 19th century." Full review
 "This classic B&B, set in a stunning 1891 home, is a total charmer. The comfortable rooms all have air-conditioning, ceiling fans, and king-size beds." Full review
 "An adults-only B&B located in the 1891 home of a former cigar baron. The staff are knowledgeable and friendly." 
Westwinds Inn Fodor's
 Fodor's Frommer's
 Frommer's DK Eyewitness
 DK Eyewitness
914 Eaton Street, Key West, FL 33040
From $267/night
- Free Internet
- Free Breakfast
- Laundry Service
- Pool
- Multilingual
- Air Conditioning
 "This cluster of historic gingerbread-trimmed houses has individually decorated rooms that make you feel right at home." 
 "A close second to staying in your own private 19th-century, tin-roofed clapboard house is this tranquil inn, just 4 blocks from Duval Street in the historic seaport district." Full review
 "A charming 19th-century clapboard house that exudes tranquility, Westwinds is shaded by lime trees."