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Charming
DAILY DROP
Winslow's Bungalows - Key West Historic Inns
$617
$361
92%
|
–
Old Town Key West
per night
Includes fees
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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2 Rooms Left
Luxe
DEAL
Cheeca Lodge & Spa
$646
$381
93%
|
–
Islamorada
per night
Includes fees
Borrowable bikes, sea kayaks & paddleboats make the most of this scenic + explorable locale.
1 Room Left
Charming
The Duval House - Adults Only
$420
$201
97%
|
–
Florida Keys
per night
Includes fees
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.
Solid
DEAL
Faro Blanco Resort & Yacht Club
$424
$264
91%
|
–
Florida Keys
per night
Includes fees
In the mood for a leisurely lunch? Look no further than the hotel’s own eatery.
2 Rooms Left
Hip
DEAL
La Siesta Resort & Villas
$393
$329
92%
|
–
Islamorada
per night
Includes fees
Nicknamed the intriguing (though redundant) ‘hidden hideaway of the Florida Keys,’ this place is on 6 blissful acres of private sugar sand beach.
Solid
Three Waters Resort And Marina, Islamorada, A Tribute Portfolio Resort
$376
91%
|
–
Islamorada
per night
Includes fees
Relaxingly retro for a good ol' beachy days vibe.
2 Rooms Left
Basic
DEAL
Southwinds Motel
$311
$228
87%
|
–
Florida Keys
per night
Includes fees
Steps from Duval Street as well as the ocean, it's a perfect little motel in all its aquamarine glory.
Luxe
DEAL
Baker's Cay Resort Key Largo, Curio Collection by Hilton
$594
$540
91%
|
–
Key Largo
per night
Includes fees
Two words: private beach. Snorkel, paddleboard, kayak, fish or just kick back and relax.
Luxe
Reefhouse Resort and Marina
$316
89%
|
–
Florida Keys
per night
Includes fees
Primping, preening, and pampering to the max with onsite spa services.
2 Rooms Left
Solid
Parrot Key Hotel & Villas
$374
$295
93%
|
–
Key West
per night
Includes fees
5 acres of tropical and sculpture gardens (might wanna LoJack your shades just in case…).
Solid
DEAL
Skipjack Resort Suites & Marina
$276
$252
85%
|
–
Florida Keys
per night
Includes fees
All-suite escape complete with galley kitchens for whipping up whatever it is you like to whip up on vaycay.
Solid
Holiday Inn Key Largo
$267
$213
88%
|
–
Key Largo
per night
Includes taxes and fees
Don't go chasing waterfalls (unless they're in one of the two onsite pools — you should chase those).
1 Room Left
Luxe
DEAL
Casa Morada
$675
$482
96%
|
–
Islamorada
per night
Includes fees
The hotel has its own private island, complete with a pool, secluded cabana, bar and, of course, stunning views.
2 Rooms Left
Charming
Lighthouse Hotel - Key West Historic Inns
$509
$434
93%
|
–
Old Town Key West
per night
Includes fees
Prime central spot next to the Lighthouse Museum and across the street from the Ernest Hemingway Home.
Solid
Even Hotel Sweetwater Doral
$214
$169
–
Florida Keys
per night
Includes taxes and fees
Charming
DEAL
Winslow's Bungalows - Key West Historic Inns
$580
$464
92%
|
–
Old Town Key West
per night
Includes fees
Smack dab in the middle of historic Old Town, two blocks from Duval Street and half a mile from the beach.
1 Room Left
Charming
Fitch Lodge- Key West Historic Inns
$367
$329
88%
|
–
Old Town Key West
per night
Includes fees
Situated in five conch-style buildings that just scream classic Key West, rooms are comfy and cozy.
3 Rooms Left
Basic
Parmer's Resort
$267
–
Summerland Key
per night
Includes fees
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!)
1 Room Left
Basic
Knight's Key Suites
$235
$147
100%
|
–
Florida Keys
per night
Includes fees
Gorgeous little getaway in Marathon with easy access to the bay and the ocean.
Hip
Blue Flamingo Resort Key West
$303
$262
88%
|
–
Key West
per night
Includes fees
Awesome outdoor pool with plenty of space. Kick back with a drink from the poolside bar.
3 Rooms Left
Luxe
DEAL
Pier House Resort & Spa
$569
91%
|
–
Key West
per night
Includes fees
Jutting out into the water on a pier (surprise!), it has its very own slice of private beach.
1 Room Left
Charming
Coco Plum Inn
$408
97%
|
–
Florida Keys
per night
Includes fees
Gorgeous 19th century homes in the heart of Key West, steps from Duval Street.
1 Room Left
Luxe
H2O Suites
$1,023
$654
98%
|
–
Florida Keys
per night
Includes fees
Stunning modern décor throughout. Living room rocks a sofa and wet bar for an awesome getaway.
1 Room Left
Luxe
Santa Maria Suites
$787
95%
|
–
Key West
per night
Includes fees
Classic Key West digs boasting contemporary-tropical decor in the rooms juxtaposed with the original, historic facade just a block off Duval.
Basic
Best Western Hibiscus Motel
$502
–
Key West
per night
Includes taxes and fees
Courtyard pool confirms you have indeed arrived in Key West, lined with palms and loungers.
Luxe
DEAL
Amrit Ocean Resort & Residences
$828
$625
–
Florida City
per night
Includes fees
Get the night (or afternoon) started without leaving the onsite bar.
Basic
Holiday Inn Express Hotel & Suites Florida City
$215
$135
84%
|
–
Florida City
per night
Includes taxes and fees
Shopping, golfing, Everglades alligator spotting, Key Largo beaches – all nearby.
Solid
Residence Inn Coconut Creek
$214
$183
–
Florida City
per night
Includes fees
Unwind with a dip in the relaxing outdoor pool after the day's adventures.
Basic
TL Florida City/Homestead
$124
$109
95%
|
–
Florida City
per night
Includes taxes and fees
Practice your best Phelps impression at the pool.
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