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Unavailable
1 Room Left
Charming
DAILY DROP
Fitch Lodge
$156
88%
|
–
Old Town Key West
was on HT
$360
Situated in five conch-style buildings that just scream classic Key West, rooms are comfy and cozy.
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Unavailable
Solid
DEAL
Banana Bay Resort & Marina
$136
90%
|
–
Marathon
was on HT
$215
Rooms’ chilled-out, classically Floribbean ‘tude maxes the vaycay vibes.
Unavailable
1 Room Left
Solid
DEAL
Islander Bayside Villas & Boatslips
$225
95%
|
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Islamorada
was on HT
$388
Max the vacay vibes in your very own vintage-cool villa (bedecked with musts like a kitchen, tons of space & tropical ‘tude).
Unavailable
3 Rooms Left
Basic
DEAL
Hadley House
$153
89%
|
–
Florida Keys
was on HT
$169
Indoor/outdoor lobby lounge, plus an outdoor oceanfront(!) tiki bar. Get out of your beverage rut and order something bright blue or umbrella’d.
Unavailable
1 Room Left
Basic
Fisher Inn Resort & Marina
$157
92%
|
–
Florida Keys
was on HT
$179
Got a boat in tow? Fisher Inn is Islamorada’s only hotel with boat parking and a ramp. Brag accordingly.
Unavailable
Solid
DEAL
Skipjack Resort Suites & Marina
$187
87%
|
–
Florida Keys
was on HT
$248
All-suite escape complete with galley kitchens for whipping up whatever it is you like to whip up on vaycay.
Unavailable
2 Rooms Left
Basic
DEAL
La Siesta Resort & Villas
$267
92%
|
–
Islamorada
was on HT
$288
Nicknamed the intriguing (though redundant) ‘hidden hideaway of the Florida Keys,’ this place is on 6 blissful acres of private sugar sand beach.
Unavailable
2 Rooms Left
Luxe
DEAL
Baker's Cay Resort Key Largo, Curio Collection by Hilton
$351
91%
|
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Key Largo
was on HT
$570
Two words: private beach. Snorkel, paddleboard, kayak, fish or just kick back and relax.
Unavailable
Solid
DEAL
Islander Resort
$324
94%
|
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islamorada
was on HT
$359
Unbeatable location on the gorgeous beach – fitting that this spot is owned by an artist.
Unavailable
3 Rooms Left
Basic
Creekside Inn Islamorada
$138
82%
|
–
Tavernier
was on HT
$242
Maxin’ & relaxin’ by the canal (right outside!) is how we love to end our day.
Unavailable
1 Room Left
Luxe
DEAL
Reefhouse Resort and Marina
$289
88%
|
–
Florida Keys
was on HT
$339
Primping, preening, and pampering to the max with onsite spa services.
Unavailable
2 Rooms Left
Basic
Bayside Inn Key Largo
$199
89%
|
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Florida Keys
was on HT
$209
On a private stretch of sand overlooking the bay, plus a pool with views, swimming lagoon and fishing pier.
Unavailable
2 Rooms Left
Basic
DEAL
Ocean Pointe Suites At Key Largo
$189
85%
|
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Tavernier
was on HT
$267
Each suite has unique decor, ranging from classic to kitsch.
Unavailable
2 Rooms Left
Hip
DEAL
Amara Cay Resort
$336
93%
|
–
Islamorada
We’ll be in a hammock on the private beach all day (right after we Instagram it).
Unavailable
Solid
Holiday Inn Key Largo
$204
88%
|
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Key Largo
was on HT
$234
Don't go chasing waterfalls (unless they're in one of the two onsite pools — you should chase those).
Unavailable
Solid
Dove Creek Trademark Coll
$164
100%
|
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Florida Keys
was on HT
$202
Non-smoking rooms are a breath of fresh air.
Unavailable
Basic
Looe Key Resort
$224
33%
|
–
Florida Keys
Non-smoking rooms are a breath of fresh air.
Unavailable
1 Room Left
Charming
The Duval House - Adults Only
$219
97%
|
–
Florida Keys
was on HT
$439
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
1 Room Left
Charming
DEAL
Fitch Lodge
$200
88%
|
–
Old Town Key West
was on HT
$360
Situated in five conch-style buildings that just scream classic Key West, rooms are comfy and cozy.
Unavailable
2 Rooms Left
Charming
DEAL
Winslow’s Bungalows
$298
91%
|
–
Old Town Key West
was on HT
$580
Smack dab in the middle of historic Old Town, two blocks from Duval Street and half a mile from the beach.
Unavailable
Charming
Lighthouse Hotel - Key West Historic Inns
$299
94%
|
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Old Town Key West
was on HT
$380
Prime central spot next to the Lighthouse Museum and across the street from the Ernest Hemingway Home.
Unavailable
2 Rooms Left
Charming
DEAL
Ella’s Cottages
$315
92%
|
–
Old Town Key West
was on HT
$610
Close proximity to sweet sites like Ernest Hemingway's home, as well as Jimmy Buffet's (Margaritaville).
Unavailable
2 Rooms Left
Solid
DEAL
Margaritaville Beach House Key West
$342
90%
|
–
Key West
was on HT
$429
Yup, all rooms are spacious with Sweet Sleeper beds as deliciously comfortable as they sound.
Unavailable
Charming
DEAL
Ridley House - Key West Historic Inns
$342
94%
|
–
Old Town Key West
was on HT
$450
One block from Duval Street, walking (or stumbling) distance to plenty of restaurants and nightlife.
Unavailable
Solid
Parrot Key Hotel & Villas
$306
93%
|
–
Key West
was on HT
$413
5 acres of tropical and sculpture gardens (might wanna LoJack your shades just in case…).
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