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Charming
DAILY DROP
Winslow's Bungalows - Key West Historic Inns
92%
|
–
Old Town Key West
per night
Includes all 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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DAILY DROP
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Solid
DEAL
Faro Blanco Resort & Yacht Club
92%
|
–
Florida Keys
per night
Includes all fees
In the mood for a leisurely lunch? Look no further than the hotel’s own eatery.
1 room left
Luxe
DEAL
Cheeca Lodge & Spa
93%
|
–
Islamorada
per night
Includes all fees
Borrowable bikes, sea kayaks & paddleboats make the most of this scenic + explorable locale.
1 room left
Charming
DEAL
The Duval House - Adults Only
97%
|
–
Florida Keys
per night
Includes all 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.
2 rooms left
Hip
DEAL
Amara Cay Resort
93%
|
–
Islamorada
per night
Includes all fees
We’ll be in a hammock on the private beach all day (right after we Instagram it).
2 rooms left
Luxe
Casa Morada
96%
|
–
Islamorada
per night
Includes all fees
The hotel has its own private island, complete with a pool, secluded cabana, bar and, of course, stunning views.
1 room left
Solid
DEAL
Banana Bay Resort & Marina
90%
|
–
Marathon
per night
Includes all fees
Rooms’ chilled-out, classically Floribbean ‘tude maxes the vaycay vibes.
2 rooms left
Basic
Seashell Motel
88%
|
–
Florida Keys
per night
Includes all fees
Free parking means you're not stuck tracking down a spot.
1 room left
Solid
Silver Palms Inn & Historic Homes
100%
|
–
Florida Keys
per night
Includes all fees
Leave your car behind (free parking!) and rent one of the house bikes to truly get a lay of the land (and burn off some of that free breakfast).
1 room left
Hip
La Siesta Resort & Villas
93%
|
–
Islamorada
per night
Includes all fees
Nicknamed the intriguing (though redundant) ‘hidden hideaway of the Florida Keys,’ this place is on 6 blissful acres of private sugar sand beach.
1 room left
Luxe
DEAL
Baker's Cay Resort Key Largo, Curio Collection by Hilton
91%
|
–
Key Largo
per night
Includes all fees
Two words: private beach. Snorkel, paddleboard, kayak, fish or just kick back and relax.
Luxe
H2O Suites
98%
|
–
Florida Keys
per night
Includes all fees
Stunning modern décor throughout. Living room rocks a sofa and wet bar for an awesome getaway.
Charming
Fitch Lodge- Key West Historic Inns
88%
|
–
Old Town Key West
per night
Includes all fees
Situated in five conch-style buildings that just scream classic Key West, rooms are comfy and cozy.
Luxe
Reefhouse Resort and Marina
89%
|
–
Florida Keys
per night
Includes all fees
Primping, preening, and pampering to the max with onsite spa services.
Solid
DEAL
Skipjack Resort Suites & Marina
85%
|
–
Florida Keys
per night
Includes all fees
All-suite escape complete with galley kitchens for whipping up whatever it is you like to whip up on vaycay.
Solid
Three Waters Resort And Marina, Islamorada, A Tribute Portfolio Resort
91%
|
–
Islamorada
per night
Includes all fees
Relaxingly retro for a good ol' beachy days vibe.
Solid
Parrot Key Hotel & Villas
94%
|
–
Key West
per night
Includes all fees
5 acres of tropical and sculpture gardens (might wanna LoJack your shades just in case…).
1 room left
Charming
Winslow's Bungalows - Key West Historic Inns
92%
|
–
Old Town Key West
per night
Includes all fees
Smack dab in the middle of historic Old Town, two blocks from Duval Street and half a mile from the beach.
2 rooms left
Basic
The Pelican Key Largo Cottages
85%
|
–
Florida Keys
per night
Includes all fees
Tweet, post, pin and ‘gram with reckless abandon. Thank you, free WiFi.
1 room left
Luxe
Santa Maria Suites
95%
|
–
Key West
per night
Includes all fees
Classic Key West digs boasting contemporary-tropical decor in the rooms juxtaposed with the original, historic facade just a block off Duval.
Charming
Lighthouse Hotel - Key West Historic Inns
93%
|
–
Old Town Key West
per night
Includes all fees
Prime central spot next to the Lighthouse Museum and across the street from the Ernest Hemingway Home.
Basic
DEAL
Southwinds Motel
88%
|
–
Florida Keys
per night
Includes all fees
Steps from Duval Street as well as the ocean, it's a perfect little motel in all its aquamarine glory.
Basic
Best Western Hibiscus Motel
–
Key West
per night
Includes all fees
Courtyard pool confirms you have indeed arrived in Key West, lined with palms and loungers.
Solid
Holiday Inn Key Largo
88%
|
–
Key Largo
per night
Includes all fees
Don't go chasing waterfalls (unless they're in one of the two onsite pools — you should chase those).
Solid
Even Hotel Sweetwater Doral
75%
|
–
Florida Keys
per night
Includes all fees
1 room left
Basic
Knight's Key Suites
100%
|
–
Florida Keys
per night
Includes all fees
Gorgeous little getaway in Marathon with easy access to the bay and the ocean.
1 room left
Luxe
Pier House Resort & Spa
91%
|
–
Key West
per night
Includes all fees
Jutting out into the water on a pier (surprise!), it has its very own slice of private beach.
1 room left
Hip
Blue Flamingo Resort Key West
88%
|
–
Key West
per night
Includes all fees
Awesome outdoor pool with plenty of space. Kick back with a drink from the poolside bar.
1 room left
Basic
DEAL
Quality Inn Florida City - Gateway to the Keys
90%
|
–
Florida City
per night
Includes all fees
You know what’s nice to wake up to? Free breakfast, that’s what.
Basic
Super 8 Florida City/Gateway
84%
|
–
Florida City
per night
Includes all fees
Free breakfast to keep hanger at bay.
Basic
Holiday Inn Express Hotel & Suites Florida City
84%
|
–
Florida City
per night
Includes all fees
Shopping, golfing, Everglades alligator spotting, Key Largo beaches – all nearby.