23 Hotels
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The Reach, A Waldorf Astoria Resort
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
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 Southernmost House
This Victorian beauty is perhaps the most photographed home in Key West, for good reason. It just oozes tropic... Read More
The Southernmost House
This Victorian beauty is perhaps the most photographed home in Key West, for good reason. It just oozes tropic... Read More
Parrot Key Resort
From the busy road, you can’t see much, just a long driveway leading to a resort that is nowhere near... Read More
Parrot Key Resort
From the busy road, you can’t see much, just a long driveway leading to a resort that is nowhere near... Read More
Deer Run Bed & Breakfast
Need serenity now? Find your way to this oceanfront B&B that not only will be good for your soul, it wi... Read More
Deer Run Bed & Breakfast
Need serenity now? Find your way to this oceanfront B&B that not only will be good for your soul, it wi... Read More
La Concha Hotel & Spa
Historic properties always have their quirks, and La Concha is no exception, but Read More
La Concha Hotel & Spa
Historic properties always have their quirks, and La Concha is no exception, but Read More
The Caribbean Resort
Many resorts tout that they are your "home away from home," but The Caribbean Resort delivers like few can. Re... Read More
The Caribbean Resort
Many resorts tout that they are your "home away from home," but The Caribbean Resort delivers like few can. Re... Read More
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7
Ambrosia Key West
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
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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8
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Nestled within a “hardwood hammock” (localese for uplands habitat where hardwood trees such as live oak grow)... Read More
Baker's Cay Resort Key Largo, Curio Collection by Hilton
Nestled within a “hardwood hammock” (localese for uplands habitat where hardwood trees such as live oak grow)... Read More
Casa Marina, Curio Collection by Hilton
This luxurious property is on the largest private beach in Key West, and it has the same richly appointed lobb... Read More
Casa Marina, Curio Collection by Hilton
This luxurious property is on the largest private beach in Key West, and it has the same richly appointed lobb... Read More
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10
Casa Morada
This relic from the 1950s has been restyled into a suave, design-forward, all-suites property with outdoor sho... Read More
Casa Morada
This relic from the 1950s has been restyled into a suave, design-forward, all-suites property with outdoor sho... Read More
Hawks Cay Resort
The 60-acre, Caribbean-style retreat with a full-service spa and six restaurants has plenty to keep the kids o... Read More
Hawks Cay Resort
The 60-acre, Caribbean-style retreat with a full-service spa and six restaurants has plenty to keep the kids o... Read More
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12
Island City House Hotel
A private garden with brick walkways, tropical plants, and a canopy of palms sets this convivial guesthouse ap... Read More
Island City House Hotel
A private garden with brick walkways, tropical plants, and a canopy of palms sets this convivial guesthouse ap... Read More
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13
La Siesta Resort & Marina
With 6 acres of oceanfront property, accommodations that range from studio units to a glamorous three-bedroom... Read More
La Siesta Resort & Marina
With 6 acres of oceanfront property, accommodations that range from studio units to a glamorous three-bedroom... Read More
M
14
Marquesa Hotel
In a town that prides itself on its laid-back luxury, this complex of four restored 1884 houses stands out. Gu... Read More
Marquesa Hotel
In a town that prides itself on its laid-back luxury, this complex of four restored 1884 houses stands out. Gu... Read More
NYAH: Not Your Average Hotel
From its charming white picket fence, it may look similar to other Victorian-style Key West B&Bs, but that’s w... Read More
NYAH: Not Your Average Hotel
From its charming white picket fence, it may look similar to other Victorian-style Key West B&Bs, but that’s w... Read More
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16
Playa Largo Resort & Spa, Autograph Collection
At this luxurious, 14-acre, bayfront retreat, you'll find one of the nicest beaches in the Keys, as well as wa... Read More
Playa Largo Resort & Spa, Autograph Collection
At this luxurious, 14-acre, bayfront retreat, you'll find one of the nicest beaches in the Keys, as well as wa... Read More
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17
Reefhouse Resort & Marina
Set on 17 acres overlooking Blackwater Sound, this hotel has been given a much-needed refresh, including the r... Read More
Reefhouse Resort & Marina
Set on 17 acres overlooking Blackwater Sound, this hotel has been given a much-needed refresh, including the r... Read More
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18
Simonton Court
A small world all its own, this adults-only maze of accommodations and four swimming pools makes you feel deli... Read More
Simonton Court
A small world all its own, this adults-only maze of accommodations and four swimming pools makes you feel deli... Read More
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19
Southernmost Beach Resort
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
Rooms at this hotel on the quiet end of Duval—a 20-minute walk from downtown—are modern and sophisticated, and... Read More
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20
The Grand Maloney
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
It took nearly two years to restore this property—dating from the late 19th century and named after Walter C.... Read More
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