The Florida Keys Travel Guide

32 Hotels

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21

Pier House Resort & Spa

$$$$ | 1 Duval St.

This upscale resort, near Mallory Square in the heart of Old Town, offers a wide range of amenities, including... Read More

Pier House Resort & Spa

$$$$ | 1 Duval St.

This upscale resort, near Mallory Square in the heart of Old Town, offers a wide range of amenities, including... Read More

22

Santa Maria Suites

$$$$ | 1401 Simonton St.

It's odd to call this a hidden gem when it sits on a prominent corner just one block off Duval, but a concrete... Read More

Santa Maria Suites

$$$$ | 1401 Simonton St.

It's odd to call this a hidden gem when it sits on a prominent corner just one block off Duval, but a concrete... Read More

S 23

Simonton Court

$$$ | 320 Simonton St.

A small world all its own, this adults-only maze of accommodations and four swimming pools makes you feel deli... Read More

Simonton Court

$$$ | 320 Simonton St.

A small world all its own, this adults-only maze of accommodations and four swimming pools makes you feel deli... Read More

S 24

Southernmost Beach Resort

$$$ | 1319 Duval St.

Rooms at this hotel on the quiet end of Duval—a 20-minute walk from downtown—are modern and sophisticated, and... Read More

Southernmost Beach Resort

$$$ | 1319 Duval St.

Rooms at this hotel on the quiet end of Duval—a 20-minute walk from downtown—are modern and sophisticated, and... Read More

S 25

Southwinds Motel

$$ | 1321 Simonton St.

Operated by the same company as the ultra-high-end Santa Maria Suites, this motel-style property is a good-val... Read More

Southwinds Motel

$$ | 1321 Simonton St.

Operated by the same company as the ultra-high-end Santa Maria Suites, this motel-style property is a good-val... Read More

26

Speakeasy Inn

$ | 1117 Duval St.

During Prohibition, Raul Vasquez made this place popular by smuggling in rum from Cuba; today, its reputation... Read More

Speakeasy Inn

$ | 1117 Duval St.

During Prohibition, Raul Vasquez made this place popular by smuggling in rum from Cuba; today, its reputation... Read More

27

The Gardens Hotel

$$$$ | 526 Angela St.

Built in 1875, this gloriously shaded property was a labor of love from the get-go, and it covers a third of a... Read More

The Gardens Hotel

$$$$ | 526 Angela St.

Built in 1875, this gloriously shaded property was a labor of love from the get-go, and it covers a third of a... Read More

G 28

The Grand Maloney

$$$ | 529 Caroline St.

It took nearly two years to restore this property—dating from the late 19th century and named after Walter C.... Read More

The Grand Maloney

$$$ | 529 Caroline St.

It took nearly two years to restore this property—dating from the late 19th century and named after Walter C.... Read More

M 29

The Marker

$$$ | 200 William St.

The Marker is a welcome and luxurious option on the waterfront in Old Town, with conch-style architecture and... Read More

The Marker

$$$ | 200 William St.

The Marker is a welcome and luxurious option on the waterfront in Old Town, with conch-style architecture and... Read More

M 30

The Mermaid & the Alligator

$$ | 729 Truman Ave.

An enchanting combination of flora and fauna makes this 1904 Victorian house a welcoming retreat. The property... Read More

The Mermaid & the Alligator

$$ | 729 Truman Ave.

An enchanting combination of flora and fauna makes this 1904 Victorian house a welcoming retreat. The property... Read More

P 31

The Perry Hotel

$ | 7001 Shrimp Rd.

This industrial-chic stunner—where spacious, airy rooms juxtapose crisp white linens with furnishings and fixt... Read More

The Perry Hotel

$ | 7001 Shrimp Rd.

This industrial-chic stunner—where spacious, airy rooms juxtapose crisp white linens with furnishings and fixt... Read More

W 32

Winslow's Bungalows

$$$ | 725 Truman Ave.

Part of the Kimpton Hotel brand, this 1854, Grand Bahama–style house on the National Register of Historic Plac... Read More

Winslow's Bungalows

$$$ | 725 Truman Ave.

Part of the Kimpton Hotel brand, this 1854, Grand Bahama–style house on the National Register of Historic Plac... Read More

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