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Unavailable
Charming
DAILY DROP
Lighthouse Hotel - Key West Historic Inns
$329
93%
|
–
Old Town Key West
was on HT
$799
Prime central spot next to the Lighthouse Museum and across the street from the Ernest Hemingway Home.
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Unavailable
Hip
DEAL
La Siesta Resort & Villas
$221
93%
|
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Islamorada
was on HT
$649
Nicknamed the intriguing (though redundant) ‘hidden hideaway of the Florida Keys,’ this place is on 6 blissful acres of private sugar sand beach.
Unavailable
3 Rooms Left
Luxe
Baker's Cay Resort Key Largo, Curio Collection by Hilton
$360
91%
|
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Key Largo
was on HT
$502
Two words: private beach. Snorkel, paddleboard, kayak, fish or just kick back and relax.
Unavailable
2 Rooms Left
Charming
DEAL
Winslow's Bungalows - Key West Historic Inns
$315
92%
|
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Old Town Key West
was on HT
$699
Smack dab in the middle of historic Old Town, two blocks from Duval Street and half a mile from the beach.
Unavailable
Hip
DEAL
Amara Cay Resort
$266
93%
|
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Islamorada
was on HT
$299
We’ll be in a hammock on the private beach all day (right after we Instagram it).
Unavailable
Solid
DEAL
Skipjack Resort Suites & Marina
$187
87%
|
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Florida Keys
was on HT
$216
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
Bayside Inn Key Largo
$184
90%
|
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Florida Keys
was on HT
$237
On a private stretch of sand overlooking the bay, plus a pool with views, swimming lagoon and fishing pier.
Unavailable
1 Room Left
Solid
DEAL
Islander Resort
$340
94%
|
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islamorada
was on HT
$815
Unbeatable location on the gorgeous beach – fitting that this spot is owned by an artist.
Unavailable
Solid
DEAL
Banana Bay Resort & Marina
$153
90%
|
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Marathon
was on HT
$170
Rooms’ chilled-out, classically Floribbean ‘tude maxes the vaycay vibes.
Unavailable
1 Room Left
Luxe
Reefhouse Resort and Marina
$429
89%
|
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Florida Keys
was on HT
$459
Primping, preening, and pampering to the max with onsite spa services.
Unavailable
Solid
Holiday Inn Key Largo
$239
88%
|
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Key Largo
was on HT
$275
Don't go chasing waterfalls (unless they're in one of the two onsite pools — you should chase those).
Unavailable
3 Rooms Left
Luxe
Cheeca Lodge & Spa
$465
94%
|
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Islamorada
was on HT
$759
Borrowable bikes, sea kayaks & paddleboats make the most of this scenic + explorable locale.
Unavailable
1 Room Left
Luxe
Casa Morada
$585
96%
|
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Islamorada
The hotel has its own private island, complete with a pool, secluded cabana, bar and, of course, stunning views.
Unavailable
Solid
Voco Sarasota
$289
–
Florida Keys
was on HT
$393
Whatever time you stumble in, the 24-hour front desk serves up service with a smile.
Unavailable
2 Rooms Left
Solid
Parrot Key Hotel & Villas
$316
93%
|
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Key West
was on HT
$449
5 acres of tropical and sculpture gardens (might wanna LoJack your shades just in case…).
Unavailable
Charming
Lighthouse Hotel - Key West Historic Inns
$423
93%
|
–
Old Town Key West
was on HT
$799
Prime central spot next to the Lighthouse Museum and across the street from the Ernest Hemingway Home.
Unavailable
Charming
Fitch Lodge- Key West Historic Inns
$324
88%
|
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Old Town Key West
was on HT
$532
Situated in five conch-style buildings that just scream classic Key West, rooms are comfy and cozy.
Unavailable
1 Room Left
Basic
Westwinds Inn
$324
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
Hip
The Gates Hotel Key West
$240
84%
|
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Key West
was on HT
$429
Partnership with a local distillery starts your stay with a rum cocktail welcome & continues the party at the pool bar.
Unavailable
2 Rooms Left
Solid
Margaritaville Beach House Key West
$515
90%
|
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Key West
Yup, all rooms are spacious with Sweet Sleeper beds as deliciously comfortable as they sound.
Unavailable
1 Room Left
Basic
Knight's Key Suites
$135
100%
|
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Florida Keys
Gorgeous little getaway in Marathon with easy access to the bay and the ocean.
Unavailable
Solid
Playa Largo Resort & Spa, Autograph Collection
$487
98%
|
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Key Largo
was on HT
$577
Onsite restaurants & bars galore, plus 24-hour room service at your beck and call.
Unavailable
Solid
Dove Creek Trademark Coll
$173
100%
|
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Florida Keys
was on HT
$191
Non-smoking rooms are a breath of fresh air.
Unavailable
2 Rooms Left
Hip
DEAL
Creekside Inn Islamorada
$237
81%
|
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Tavernier
was on HT
$297
Maxin’ & relaxin’ by the canal (right outside!) is how we love to end our day.
Unavailable
Basic
Looe Key Resort
$247
60%
|
–
Florida Keys
Non-smoking rooms are a breath of fresh air.
Unavailable
2 Rooms Left
Solid
DEAL
Islander Bayside Villas & Boatslips
$842
96%
|
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Islamorada
was on HT
$983
Max the vacay vibes in your very own vintage-cool villa (bedecked with musts like a kitchen, tons of space & tropical ‘tude).
Unavailable
Basic
DEAL
Fairfield Inn & Suites Homestead Florida City
$117
96%
|
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Florida City
was on HT
$139
To-dos include exploring the Everglades National Park, visiting an alligator farm, outlet shopping & more. Where to?
Unavailable
Basic
Holiday Inn Express Hotel & Suites Florida City
$119
83%
|
–
Florida City
was on HT
$169
Shopping, golfing, Everglades alligator spotting, Key Largo beaches – all nearby.
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