34 Hotels
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1
Sunset Key Cottages
$$$$ | 245 Front St.
Looking for a quiet, island getaway that will afford you pampering and privacy? Look no further. Read More
Sunset Key Cottages
$$$$ | 245 Front St.
Looking for a quiet, island getaway that will afford you pampering and privacy? Look no further. Read More
2
The Reach, A Waldorf Astoria Resort
$$$ | 1435 Simonton St.
You might never know it’s there unless you stumble to the quiet end of Duval and wander down a side street tha... Read More
The Reach, A Waldorf Astoria Resort
$$$ | 1435 Simonton St.
You might never know it’s there unless you stumble to the quiet end of Duval and wander down a side street tha... Read More
3
Casa Marina, A Waldorf-Astoria Resort
$$$ | 1500 Reynolds St.
If you’ve got the money, honey, this resort delivers. History buffs will relish in its storied past, and afflu... Read More
Casa Marina, A Waldorf-Astoria Resort
$$$ | 1500 Reynolds St.
If you’ve got the money, honey, this resort delivers. History buffs will relish in its storied past, and afflu... Read More
4
Pier House Resort and Spa
$$$$ | 1 Duval St.
Marrying the best of Key West culture with modern conveniences, The Pier House Resort & Spa is perched on the... Read More
Pier House Resort and Spa
$$$$ | 1 Duval St.
Marrying the best of Key West culture with modern conveniences, The Pier House Resort & Spa is perched on the... Read More
5
The Gardens Hotel
$$$$ | 526 Angela St.
Could this be the most luxurious hotel in all of Key West? Yes, indeed. Read More
The Gardens Hotel
$$$$ | 526 Angela St.
Could this be the most luxurious hotel in all of Key West? Yes, indeed. Read More
6
Margaritaville Key West Resort & Marina
$$$$ | 245 Front St.
The vibe isn’t "grapefruit and juicy fruit" yet at this former Westin-turned-Margaritaville, but the brand has... Read More
Margaritaville Key West Resort & Marina
$$$$ | 245 Front St.
The vibe isn’t "grapefruit and juicy fruit" yet at this former Westin-turned-Margaritaville, but the brand has... Read More
7
Ocean Key Resort & Spa
$$$$ | Zero Duval St.
Luxury can be fun, especially when it’s at the edge of everything Key West. Even if you’re more of a watcher t... Read More
Ocean Key Resort & Spa
$$$$ | Zero Duval St.
Luxury can be fun, especially when it’s at the edge of everything Key West. Even if you’re more of a watcher t... Read More
8
Santa Maria Suites
$$$$ | 1401 Simonton St.
Although it’s on a busy corner and adjacent to a popular sushi restaurant, you’d never know what luxury awaits... Read More
Santa Maria Suites
$$$$ | 1401 Simonton St.
Although it’s on a busy corner and adjacent to a popular sushi restaurant, you’d never know what luxury awaits... Read More
9
Key West Marriott Beachside Hotel
$$$$ | 3841 N. Roosevelt Blvd.
A whopping seven acres on the Gulf of Mexico, this is the place to stay if you love to earn your Marriott poin... Read More
Key West Marriott Beachside Hotel
$$$$ | 3841 N. Roosevelt Blvd.
A whopping seven acres on the Gulf of Mexico, this is the place to stay if you love to earn your Marriott poin... Read More
10
La Concha Hotel & Spa
$$$ | 430 Duval St.
Historic properties always have their quirks, and La Concha is no exception, but Read More
La Concha Hotel & Spa
$$$ | 430 Duval St.
Historic properties always have their quirks, and La Concha is no exception, but Read More
11
Merlin Guesthouse
$$ | 811 Simonton St.
Consider yourself lucky if you get a reservation in one of their 20 rooms, updated in comfortable Keys-style. Read More
Merlin Guesthouse
$$ | 811 Simonton St.
Consider yourself lucky if you get a reservation in one of their 20 rooms, updated in comfortable Keys-style. Read More
12
Speakeasy Inn
$ | 1117 Duval St.
Romantic and historic, this fully restored inn sits on the more-quiet end of popular Duval Street, and will no... Read More
Speakeasy Inn
$ | 1117 Duval St.
Romantic and historic, this fully restored inn sits on the more-quiet end of popular Duval Street, and will no... Read More
13
NYAH: Not Your Average Hotel
$$$ | 420 Margaret St.
Traveling for a girls’ getaway? Or a "mancation" with the bros? This is the affordable place to lay your head.... Read More
NYAH: Not Your Average Hotel
$$$ | 420 Margaret St.
Traveling for a girls’ getaway? Or a "mancation" with the bros? This is the affordable place to lay your head.... Read More
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14
Ambrosia Key West
$$$ | 615, 618, 622 Fleming St., Key West, Florida, 33040, USA
If you desire personal attention, a casual atmosphere, and a dollop of style, stay at these twin inns spread o... Read More
Ambrosia Key West
$$$ | 615, 618, 622 Fleming St., Key West, Florida, 33040, USA
If you desire personal attention, a casual atmosphere, and a dollop of style, stay at these twin inns spread o... Read More
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15
Angelina Guest House
$ | 302 Angela St., Key West, Florida, 33040, USA
In the heart of Old Town, this home away from home offers simple, clean, attractively priced accommodations. T... Read More
Angelina Guest House
$ | 302 Angela St., Key West, Florida, 33040, USA
In the heart of Old Town, this home away from home offers simple, clean, attractively priced accommodations. T... Read More
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16
Azul Key West
$$ | 907 Truman Ave., Key West, Florida, 33040, USA
The ultramodern—nearly minimalistic—redo of this classic circa-1903 Queen Anne mansion is a break from the sen... Read More
Azul Key West
$$ | 907 Truman Ave., Key West, Florida, 33040, USA
The ultramodern—nearly minimalistic—redo of this classic circa-1903 Queen Anne mansion is a break from the sen... Read More
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17
Best Western Key Ambassador Resort Inn
$$ | 3755 S. Roosevelt Blvd., Key West, Florida, 33040, USA
You know what to expect from this chain hotel: well-maintained rooms, predictable service, and competitive pri... Read More
Best Western Key Ambassador Resort Inn
$$ | 3755 S. Roosevelt Blvd., Key West, Florida, 33040, USA
You know what to expect from this chain hotel: well-maintained rooms, predictable service, and competitive pri... Read More
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18
Courtney's Place
$$ | 720 Whitmarsh La., off Petronia St., Key West, Florida, 33040, USA
If you like kids, cats, and dogs, you'll feel right at home in this collection of accommodations ranging from... Read More
Courtney's Place
$$ | 720 Whitmarsh La., off Petronia St., Key West, Florida, 33040, USA
If you like kids, cats, and dogs, you'll feel right at home in this collection of accommodations ranging from... Read More
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19
Eden House
$$ | 1015 Fleming St., Key West, Florida, 33040, USA
From the vintage metal rockers on the street-side porch to the old neon hotel sign in the lobby, this 1920s ra... Read More
Eden House
$$ | 1015 Fleming St., Key West, Florida, 33040, USA
From the vintage metal rockers on the street-side porch to the old neon hotel sign in the lobby, this 1920s ra... Read More
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20
Harborside Motel & Marina
$ | 903 Eisenhower Dr., Key West, Florida, 33040, USA
This little motel neatly packages three appealing characteristics—affordability, safety, and a pleasant locati... Read More
Harborside Motel & Marina
$ | 903 Eisenhower Dr., Key West, Florida, 33040, USA
This little motel neatly packages three appealing characteristics—affordability, safety, and a pleasant locati... Read More
