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2 Rooms Left
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Solid
DEAL
Islander Resort
$243
94%
|
–
islamorada
was on HT
$319
Newly reimagined! Amazing location on the gorgeous beach – fitting that this spot is owned by an artist.
Also available in Florida Keys
Unavailable
Charming
DAILY DROP
Winslow's Bungalows - Key West Historic Inns
$173
92%
|
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Old Town Key West
was on HT
$399
Smack dab in the middle of historic Old Town, two blocks from Duval Street and half a mile from the beach.
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Unavailable
2 Rooms Left
Luxe
Cheeca Lodge & Spa
$255
94%
|
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Islamorada
was on HT
$322
Borrowable bikes, sea kayaks & paddleboats make the most of this scenic + explorable locale.
Unavailable
3 Rooms Left
Luxe
DEAL
Baker's Cay Resort Key Largo, Curio Collection by Hilton
$270
91%
|
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Key Largo
was on HT
$430
Two words: private beach. Snorkel, paddleboard, kayak, fish or just kick back and relax.
Unavailable
2 Rooms Left
Solid
DEAL
Parrot Key Hotel & Villas
$191
93%
|
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Key West
was on HT
$309
5 acres of tropical and sculpture gardens (might wanna LoJack your shades just in case…).
Unavailable
3 Rooms Left
Charming
DEAL
Fitch Lodge- Key West Historic Inns
$180
88%
|
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Old Town Key West
was on HT
$619
Situated in five conch-style buildings that just scream classic Key West, rooms are comfy and cozy.
Unavailable
Solid
DEAL
Banana Bay Resort & Marina
$141
90%
|
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Marathon
was on HT
$193
Rooms’ chilled-out, classically Floribbean ‘tude maxes the vaycay vibes.
Unavailable
Basic
Ocean Pointe Suites At Key Largo
$139
84%
|
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Tavernier
was on HT
$209
Each suite has unique decor, ranging from classic to kitsch.
Unavailable
Charming
DEAL
Winslow's Bungalows - Key West Historic Inns
$222
92%
|
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Old Town Key West
was on HT
$399
Smack dab in the middle of historic Old Town, two blocks from Duval Street and half a mile from the beach.
Unavailable
1 Room Left
Charming
The Duval House - Adults Only
$199
97%
|
–
Florida Keys
was on HT
$489
7 classic Caribbean-style houses behind a li’l front gate, complete with gazebo and 100-year-old Banyan tree, steps from the Duval Street action.
Unavailable
2 Rooms Left
Solid
Islander Bayside Villas & Boatslips
$234
96%
|
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Islamorada
was on HT
$399
Max the vacay vibes in your very own vintage-cool villa (bedecked with musts like a kitchen, tons of space & tropical ‘tude).
Unavailable
1 Room Left
Luxe
DEAL
Southernmost Beach Resort
$314
84%
|
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Key West- Upper Duval
was on HT
$548
Minutes from the beach, but why leave when you're right on the beach?
Unavailable
2 Rooms Left
Basic
Bayside Inn Key Largo
$145
90%
|
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Florida Keys
was on HT
$184
On a private stretch of sand overlooking the bay, plus a pool with views, swimming lagoon and fishing pier.
Unavailable
2 Rooms Left
Solid
Margaritaville Beach House Key West
$299
89%
|
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Key West
was on HT
$407
Yup, all rooms are spacious with Sweet Sleeper beds as deliciously comfortable as they sound.
Unavailable
1 Room Left
Basic
Knight's Key Suites
$128
100%
|
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Florida Keys
was on HT
$159
Gorgeous little getaway in Marathon with easy access to the bay and the ocean.
Unavailable
Solid
24 North Hotel
$198
88%
|
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Key West
was on HT
$252
Awesome outdoor pool with plenty of space. Kick back with a drink from the poolside bar.
Unavailable
1 Room Left
Luxe
DEAL
Reefhouse Resort and Marina
$270
89%
|
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Florida Keys
was on HT
$299
Primping, preening, and pampering to the max with onsite spa services.
Unavailable
1 Room Left
Basic
Parmer's Resort
$199
–
Summerland Key
was on HT
$244
Inviting residential setting puts you less than a half-hour from Key West and Marathon if you’re up for exploring. (But first, free breakfast!)
Unavailable
2 Rooms Left
Basic
Westwinds Inn
$302
85%
|
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Key West
The main house is a stately white-pillared affair, with smaller bungalows around the tropical gardens and pools.
Unavailable
Luxe
DEAL
Pier House Resort & Spa
$501
90%
|
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Key West
was on HT
$929
Jutting out into the water on a pier (surprise!), it has its very own slice of private beach.
Unavailable
Charming
DEAL
Lighthouse Hotel - Key West Historic Inns
$341
93%
|
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Old Town Key West
was on HT
$400
Prime central spot next to the Lighthouse Museum and across the street from the Ernest Hemingway Home.
Unavailable
1 Room Left
Luxe
DEAL
Casa Morada
$424
96%
|
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Islamorada
was on HT
$472
The hotel has its own private island, complete with a pool, secluded cabana, bar and, of course, stunning views.
Unavailable
1 Room Left
Charming
Island City House Hotel
$305
98%
|
–
Key West
Eclectic style covers it all from Caribbean to Victorian, with plenty of space to enjoy it.
Unavailable
1 Room Left
Luxe
Santa Maria Suites
$589
97%
|
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Key West
was on HT
$739
Classic Key West digs boasting contemporary-tropical decor in the rooms juxtaposed with the original, historic facade just a block off Duval.
Unavailable
2 Rooms Left
HighRoller
The Marker Key West Highroller
$9,999
–
Florida Keys
Over 1000 sq ft of stylish space to relax in, featuring chic decor, soothing hues and a plush, king-sized bed.
Sold Out
0 Rooms Left
Charming
Key West Bed and Breakfast
100%
|
–
Florida Keys
Adults only- Built in 1898 by Bahamian shipbuilders & decked out with cheerfully tropical tones, local artwork and all the mod cons you’ll need.
Sold Out
0 Rooms Left
Hip
Creekside Inn Islamorada
81%
|
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Tavernier
Maxin’ & relaxin’ by the canal (right outside!) is how we love to end our day.
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